Heterocyclyl pyridines as novel fungicides
Granted 27 Jan 2026 · 1 office action
Current assignee: Bayer Aktiengesellschaft · originally Bayer Corporation
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Inventors: Tomoki Tsuchiya, Dominique Loque, Anthony Millet, Vincent Thomas +3 · Examiner: Golam M Shameem · AU 1621 · TC 1600
Life of the application
8 dated eventsDescription
79 parts›CROSS REFERENCE TO RELATED APPLICATIONS
This application is a national stage application under 35 U.S.C. § 371 of International Application No. PCT/EP2021/064680, filed internationally on Jun. 1, 2021, which claims benefit of European Application No.: 20178203.4, filed Jun. 4, 2020.
The present invention relates to heterocyclyl pyridine compounds and the uses thereof for controlling phytopathogenic microorganisms such as phytopathogenic fungi. It also relates to processes and intermediates for preparing these compounds.
Numerous crop protection agents to combat or prevent microorganisms' infestations have been developed until now. However, the need remains for the development of new compounds as such, so as to provide compounds being effective against a broad spectrum of phytopathogenic microorganisms, such as fungi, having low toxicity, high selectivity or that can be used at low application rate whilst still allowing effective pest control. It may also be desired to have new compounds to prevent the emergence of resistances.
The present invention provides new compounds for controlling phytopathogenic microorganisms such as fungi which have advantages over known compounds and compositions in at least some of these aspects.
Heterocyclyl-substituted Pyridazines as fungicides are disclosed in WO 2020/127780.
›DETAILED DESCRIPTION · 1 of 78
Compounds of Formula (I)
The present invention relates to compounds of the formula (I):
wherein
A is O, S, C(═O), S(═O), S(═O) 2 , NR 1 or CR 2A R R2B ,
wherein R 1 is hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl or formyl,
wherein R 11 and R 12 are independently C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, R 13 and R 14 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 , wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 2 of 78
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino, wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents, R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
›DETAILED DESCRIPTION · 3 of 78
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
›DETAILED DESCRIPTION · 4 of 78
as well as N-oxides, salts, hydrates and hydrates of the salts and N-oxides thereof.
The present invention relates to a composition comprising at least one compound of formula (I) as defined herein and at least one agriculturally suitable auxiliary.
The present invention also relates to the use of a compound of formula (I) as defined herein or a composition as defined herein for controlling phytopathogenic fungi.
The present invention relates to a method for controlling phytopathogenic fungi which comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.
The present invention also relates to processes and intermediates for preparing compounds of formula (I).
Unless otherwise stated, the following definitions apply for the substituents and residues used throughout this specification and claims: The term “halogen” as used herein refers to fluorine, chlorine, bromine or iodine atom.
The term “methylidene” as used herein refers to a CH 2 group connected to a carbon atom via a double bond.
The term “halomethylidene” as used herein refers to a CX 2 group connected to a carbon atom via a double bond, wherein X is halogen.
The term “oxo” as used herein refers to an oxygen atom which is bound to a carbon atom or sulfur atom via a double bound.
The term “C 1 -C 6 -alkyl” as used herein refers to a saturated, branched or straight hydrocarbon chain having 1, 2, 3, 4, 5 or 6 carbon atoms. Examples of C 1 -C 6 -alkyl include but are not limited to methyl, ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), butyl (n-butyl), 1-methylpropyl (sec-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl (tert-butyl), pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl. Particularly, said hydrocarbon chain has 1, 2, 3 or 4 carbon atoms (“C 1 -C 4 -alkyl”), e.g. methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, iso-butyl or tert-butyl.
The term “C 1 -C 6 -haloalkyl” as used herein refers to a C 1 -C 6 -alkyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different. Examples of C 1 -C 6 -haloalkyl include but are not limited to chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl. Preferred are fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl and 1,1,1-trifluoroprop-2-yl.
The term “C 1 -C 6 -fluoroalkyl” as used herein refers to a C 1 -C 6 -alkyl group as defined above in which one or more hydrogen atoms are replaced with one or more fluorine atoms that may be the same or different. Examples of C 1 -C 6 -fluoroalkyl include but are not limited to monofluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 1,1-difluoroethyl, 2,2-difluoroethyl and 2,2,2-trifluoroethyl.
The term “C 1 -C 6 -alkylene” as used herein refers to a divalent C 1 -C 6 -alkyl group as defined herein. Examples of C 1 -C 6 -alkylene include but are not limited to methylene, ethylene, propyl-1,3-ene, propyl-1,2-ene, butyl-1,4-ene, butyl-1,3-ene, butyl-1,2-ene, 1,5-pentylene and 1,6-hexylene.
The terms “C 3 -C 8 -cycloalkyl” and “C 3 -C 8 -cycloalkyl-ring” as used herein refers to a saturated, monocyclic hydrocarbon ring containing 3, 4, 5, 6, 7 or 8 carbon atoms. Examples of C 3 -C 8 -cycloalkyl include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Particularly, said cycloalkyl has 3 to 6 carbon atoms.
The term “C 3 -C 8 -halocycloalkyl” as used herein refers to a saturated hydrocarbon ring system in which all of the ring members, which vary from 3 to 8, are carbon atoms and in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 2 -C 6 -alkenyl” as used herein refers to an unsaturated, branched or straight hydrocarbon chain having 2, 3, 4, 5 or 6 carbon atoms and comprising at least one double bond. Examples of C 2 -C 6 -alkenyl include but are not limited to ethenyl (or “vinyl”), prop-2-en-1-yl (or “allyl”), prop-1-en-1-yl, but-3-enyl, but-2-enyl, but-1-enyl, pent-4-enyl, pent-3-enyl, pent-2-enyl, pent-1-enyl, hex-5-enyl, hex-4-enyl, hex-3-enyl, hex-2-enyl, hex-1-enyl, prop-1-en-2-yl (or “isopropenyl”), 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methylprop-1-enyl, 1-methylprop-1-enyl, 3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methyl-but-3-enyl, 3-methylbut-2-enyl, 2-methylbut-2-enyl, 1-methylbut-2-enyl, 3-methylbut-1-enyl, 2-methylbut-1-enyl, 1-methylbut-1-enyl, 1,1-dimethylprop-2-enyl, 1-ethylprop-1-enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methylpent-4-enyl, 4-methylpent-3-enyl, 3-methylpent-3-enyl, 2-methylpent-3-enyl, 1-methylpent-3-enyl, 4-methylpent-2-enyl, 3-methylpent-2-enyl, 2-methylpent-2-enyl, 1-methylpent-2-enyl, 4-methylpent-1-enyl, 3-methyl-pent-1-enyl, 2-methylpent-1-enyl, 1-methylpent-1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-enyl, 3-ethylbut-2-enyl, 2-ethylbut-2-enyl, 1-ethylbut-2-enyl, 3-ethylbut-1-enyl, 2-ethylbut-1-enyl, 1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl, 1-iso-propylprop-2-enyl, 2-propylprop-1-enyl, 1-propylprop-1-enyl, 2-isopropylprop-1-enyl, 1-isopropylprop-1-enyl, 3,3-dimethylprop-1-enyl, 1-(1,1-dimethylethyl)ethenyl, buta-1,3-dienyl, penta-1,4-dienyl, hexa-1,5-dienyl or methylhexadienyl group.
›DETAILED DESCRIPTION · 5 of 78
The term “C 2 -C 6 -alkynyl” as used herein refers to a branched or straight hydrocarbon chain having 2, 3, 4, 5 or 6 carbon atoms and comprising at least one triple bond. Examples of C 2 -C 6 -alkynyl include but are not limited to ethynyl, prop-1-ynyl, prop-2-ynyl (or “propargyl”), but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1-ethylprop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methyl-pent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methyl-pent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1-ethylbut-3-ynyl, 1-ethylbut-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl or 3,3-dimethylbut-1-ynyl group.
The term “C 2 -C 6 -haloalkenyl” as used herein refers to a C 2 -C 6 -alkenyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 2 -C 6 -haloalkynyl” as used herein refers to a C 2 -C 6 -alkynyl group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 1 -C 6 -alkoxy” as used herein refers to a group of formula (C 1 -C 6 -alkyl)-O—, in which the term “C 1 -C 6 -alkyl” is as defined herein. Examples of C 1 -C 6 -alkoxy include but are not limited to methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethyl-ethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-tri-methylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy. This definition also applies to alkoxy as part of a composite substituent, for example alkoxyalkyl, alkoxyalkoxy, unless defined elsewhere.
The term “C 1 -C 6 -haloalkoxy” as used herein refers to a C 1 -C 6 -alkoxy group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different. Examples of C 1 -C 6 -haloalkoxy include but are not limited to chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoro-methoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoro-ethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy.
The term “C 1 -C 6 -hydroxyalkyl” as used herein refers to a C 1 -C 6 -alkyl group as defined above in which at least one hydrogen atom is replaced with a hydroxyl group. Examples of C 1 -C 6 -hydroxyalkyl include but are not limited to hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1,2-dihydroxyethyl, 3-hydroxy-propyl, 2-hydroxypropyl, 1-hydroxypropyl, 1-hydroxypropan-2-yl, 2-hydroxypropan-2-yl, 2,3-di-hydroxypropyl and 1,3-dihydroxypropan-2-yl.
The term “C 3 -C 8 -cycloalkoxy” as used herein refers to a monocyclic, saturated cycloalkoxy radical having 3 to 8 and preferably 3 to 6 carbon ring members, for example (but not limited to) cyclopropyloxy, cyclobutyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a composite substituent, for example cycloalkoxyalkyl, unless defined elsewhere.
The term “C 3 -C 8 -halocycloalkoxy” as used herein refers to a C 3 -C 8 -cycloalkoxy group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term C 2 -C 6 -alkenyloxy as used herein refers to a formula (C 2 -C 6 -alkenyl)-O—, in which the term “C 1 -C 6 -alkenyl” group is which the as defined herein. Examples of C 2 -C 6 -alkenyl include but are not limited to ethenyloxy (or “vinyloxy”), prop-2-en-1-yloxy (or “allyl”), prop-1-en-1-yloxy, but-3-enyloxy, but-2-enyloxy, but-1-enyloxy, pent-4-enyloxy, pent-3-enyloxy, pent-2-enyloxy, pent-1-enyloxy, hex-5-enyloxy, hex-4-enyloxy, hex-3-enyloxy, hex-2-enyloxy, hex-1-enyloxy, prop-1-en-2-yloxy (or “iso-propenyloxy”), 2-methylprop-2-enyloxy, 1-methylprop-2-enyloxy, 2-methylprop-1-enyloxy, 1-methyl-prop-1-enyloxy, 3-methylbut-3-enyloxy, 2-methylbut-3-enyloxy, 1-methylbut-3-enyloxy, 3-methylbut-2-enyloxy, 2-methylbut-2-enyloxy, 1-methylbut-2-enyloxy, 3-methylbut-1-enyloxy, 2-methylbut-1-enyloxy, 1-methylbut-1-enyloxy, 1,1-dimethylprop-2-enyloxy, 1-ethylprop-1-enyloxy, 1-propylvinyl-oxy, 1-isopropylvinyloxy, 4-methylpent-4-enyloxy, 3-methylpent-4-enyloxy, 2-methylpent-4-enyloxy, 1-methylpent-4-enyloxy, 4-methylpent-3-enyloxy, 3-methylpent-3-enyloxy, 2-methylpent-3-enyloxy, 1-methylpent-3-enyloxy, 4-methylpent-2-enyloxy, 3-methylpent-2-enyloxy, 2-methylpent-2-enyloxy, 1-methylpent-2-enyloxy, 4-methylpent-1-enyloxy, 3-methylpent-1-enyloxy, 2-methylpent-1-enyloxy, 1-methylpent-1-enyloxy, 3-ethylbut-3-enyloxy, 2-ethylbut-3-enyloxy, 1-ethylbut-3-enyloxy, 3-ethylbut-2-enyloxy, 2-ethylbut-2-enyloxy, 1-ethylbut-2-enyloxy, 3-ethylbut-1-enyloxy, 2-ethylbut-1-enyloxy, 1-ethylbut-1-enyloxy, 2-propylprop-2-enyloxy, 1-propylprop-2-enyloxy, 2-isopropylprop-2-enyloxy, 1-isopropylprop-2-enyloxy, 2-propylprop-1-enyloxy, 1-propylprop-1-enyloxy, 2-isopropyl-prop-1-enyloxy, 1-isopropylprop-1-enyloxy, 3,3-dimethylprop-1-enyloxy, 1-(1,1-dimethyl-ethyl)ethenyloxy, buta-1,3-dienyloxy, penta-1,4-dienyloxy, hexa-1,5-dienyloxy or methylhexadienyl-oxy group.
The term “C 2 -C 6 -haloalkenyloxy” as used herein refers to a (C 2 -C 6 -alkenyl)-O— group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
›DETAILED DESCRIPTION · 6 of 78
The term “C 2 -C 6 -alkenylene” as used herein refers to a divalent C 2 -C 6 -alkenyl group as defined herein. Examples of C 2 -C 6 -alkenylene include but are not limited to ethenylene, 1,3-propenylene, butenylene, pentenylene, hexenylene, heptenylene, octenylene, nonenylene, decenylene, undecenylene, dodecenylene, and the like.
The term “C 2 -C 6 -haloalkynyloxy” as used herein refers to a (C 2 -C 6 -alkynyl)-O— group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 1 -C 6 -alkylsulfanyl” as used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkyl)-S—, in which the term “C 1 -C 6 -alkyl” is as defined herein. Examples of C 1 -C 6 -alkylsulfanyl include but are not limited to methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, hexylsulfanyl group.
The term “C 1 -C 6 -haloalkylsulfanyl” as used herein refers to a C 1 -C 6 -alkylsulfanyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 3 -C 8 -cycloalkylsulfanyl” as used herein refers to a saturated, monovalent, monocylic hydrocarbon ring which contains 3, 4, 5, 6, 7 or 8 carbon atoms and which is bound to the skeleton via a sulfur atom. Examples of monocyclic C 3 -C 8 -cycloalkylsulfanyls include but are not limited to cyclopropylsulfanyl, cyclobutylsulfanyl, cyclopentylsulfanyl, cyclohexylsulfanyl, cycloheptylsulfanyl, or cyclooctylsulfanyl.
The term “C 1 -C 6 -alkylsulfinyl” as used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkyl)-S(═O)—, in which the term “C 1 -C 6 -alkyl” is as defined herein. Examples of C 1 -C 6 -alkylsulfinyl include but are not limited to saturated, straight-chain or branched alkylsulfinyl radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) C 1 -C 6 -alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentyl-sulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropyl-sulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-di-methylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
The term “C 1 -C 6 -haloalkylsulfinyl” as used herein refers to a C 1 -C 6 -alkylsulfinyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 3 -C 8 -cycloalkylsulfinyl” as used herein refers to a saturated, monovalent, monocylic hydrocarbon ring which contains 3, 4, 5, 6, 7 or 8 carbon atoms and which is bound to the skeleton via a —S(═O)-group. Examples of monocyclic C 3 -C 8 -cycloalkylsulfinyls include but are not limited to cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, cyclohexylsulfinyl, cycloheptylsulfinyl or cyclooctylsulfinyl.
The term “C 1 -C 6 -alkylsulfonyl” s used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkyl)-S(═O) 2 —, in which the term “C 1 -C 6 -alkyl” is as defined herein. Examples of C 1 -C 6 -alkylsulfonyl include but are not limited to methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methyl-ethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethyl-sulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropyl-sulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutyl-sulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethyl-butylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.
The term “C 1 -C 6 -haloalkylsulfonyl” as used herein refers to a C 1 -C 6 -alkylsulfonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 3 -C 8 -cycloalkylsulfonyl” as used herein refers to a saturated, monovalent, monocylic hydrocarbon ring which contains 3, 4, 5, 6, 7 or 8 carbon atoms and which is bound to the skeleton via a —S(═O) 2 -group. Examples of monocyclic C 3 -C 8 -cycloalkylsulfonyls include but are not limited to cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cycloheptylsulfonyl or cyclooctylsulfonyl.
The term “C 1 -C 6 -alkylcarbonyl” as used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkyl)-C(═O)—, in which the term “C 1 -C 6 -alkyl” is as defined herein.
The term “C 1 -C 6 -haloalkylcarbonyl” as used herein refers to a C 1 -C 6 -alkylcarbonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “C 1 -C 6 -alkylcarbonyloxy” as used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkyl)-C(═O)O—, in which the term “C 1 -C 6 -alkyl” is as defined herein.
The term “C 1 -C 6 -alkoxycarbonyl” as used herein refers to a saturated, linear or branched group of formula (C 1 -C 6 -alkoxy)-C(═O)—, in which the term “C 1 -C 6 -alkoxy” is as defined herein.
›DETAILED DESCRIPTION · 7 of 78
The term “C 1 -C 6 -haloalkoxycarbonyl” as used herein refers to a C 1 -C 6 -alkoxycarbonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.
The term “mono-(C 1 -C 6 -alkyl)amino” as used herein refers to an amino radical having one C 1 -C 6 -alkyl group as defined herein. Examples of mono-(C 1 -C 6 -alkyl)amino include but are not limited to Nmethyl-amino, N-ethylamino, N-isopropylamino, N-n-propylamino, N-isopropylamino and N-tert-butylamino.
The term “di-(C 1 -C 6 )-alkylamino” as used herein refers to an amino radical having two independently selected C 1 -C 6 -alkyl groups as defined herein. Examples of C 1 -C 6 -dialkylamino include but are not limited to N,N-dimethylamino, N,N-diethylamino, N,N-diisopropylamino, N-ethyl-N-methylamino, N-methyl-N-n-propylamino, N-isopropyl-N-n-propylamino and N-tert-butyl-N-methylamino.
The term “C 3 -C 12 -carbocyclyl” as used herein refers to a saturated or partially unsaturated hydrocarbon ring system in which all of the ring members, which vary from 3 to 12, are carbon atoms. The ring system may be monocyclic or polycyclic (fused, spiro or bridged). C 3 -C 12 -carbocyclyls include but are not limited to C 3 -C 12 -cycloalkyl (mono or bicyclic), C 3 -C 12 -cycloalkenyl (mono or bicyclic), bicylic system comprising an aryl (e.g. phenyl) fused to a monocyclic C 3 -C 8 -cycloalkyl (e.g. tetrahydronaphthalenyl, indanyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl), bicylic system comprising an aryl (e.g. phenyl) fused to a monocyclic C 3 -C 8 -cycloalkenyl (e.g. indenyl, dihydronaphthalenyl) and tricyclic system comprising a cyclopropyl connected through one carbon atom to a bicylic system comprising an aryl (e.g. phenyl) fused to a C 3 -C 8 -cycloalkyl or to a C 3 -C 8 -cycloalkenyl. The C 3 -C 12 -carbocyclyl can be attached to the parent molecular moiety through any carbon atom.
The term “C 3 -C 12 -cycloalkenyl” as used herein refers to an unsaturated, monovalent, mono- or bicylic hydrocarbon ring which contains 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12 carbon atoms and one or two double bonds. Examples of monocyclic C 3 -C 8 -cycloalkenyl group include but are not limited to cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl and cyclooctenyl group. Examples of bicyclic C 6 -C 12 -cycloalkenyl group include but are not limited to 3-bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[2.2.1]hept-2-enyl or bicyclo[2.2.2]oct-2-enyl.
The term “C 6 -C 14 -aryl” as used herein refers to an aromatic hydrocarbon ring system in which all of the ring members, which vary from 6 to 14, preferably from 6 to 10, are carbon atoms. The ring system may be monocyclic or fused polycyclic (e.g. bicyclic or tricyclic). Examples of aryl include but are not limited to phenyl, azulenyl and naphthyl.
The term “3- to 14-membered heterocyclyl” as used herein refers to a saturated or partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered ring system comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atoms, they are not directly adjacent. Heterocycles include but are not limited to 3- to 7-membered monocyclic heterocycles and 8- to 14-membered polycyclic (e.g. bicyclic or tricyclic) heterocycles. The 3- to 14-membered heterocycle can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle. Examples of saturated heterocycles include but are not limited to 3-membered ring such as oxiranyl, aziridinyl, 4-membered ring such as azetidinyl, oxetanyl, thietanyl, 5-membered ring such as tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, 6-membered ring such as piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, thiomorpholinyl or 7-membered ring such as oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Examples of unsaturated heterocycles include but are not limited to 5-membered ring such as dihydrofuranyl, 1,3-dioxolyl, dihydrothienyl, pyrrolinyl, dihydroimidazolyl, dihydropyrazolyl, isoxazolinyl, dihydrooxazolyl, dihydrothiazolyl or 6-membered ring such as pyranyl, thiopyranyl, thiazinyl and thiadiazinyl. Bicyclic heterocycles may consist of a monocyclic heteroaryl as defined herein fused to a monocyclic C 3 -C 8 -cycloalkyl, a monocyclic C 3 -C 8 -cycloalkenyl or a monocyclic heterocycle or may consist of a monocyclic heterocycle fused either to an aryl (e.g. phenyl), a C 3 -C 8 -cycloalkyl, a C 3 -C 8 -cycloalkenyl or a monocyclic heterocycle. When two monocyclic heterocycles or one monocyclic heterocycle and one monocyclic heteroaryl comprising nitrogen atoms are fused, nitrogen atom may be at the bridgehead (e.g. 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridinyl). Tricyclic hetero-cycles may consist of a monocyclic cycloalkyl connected through one common atom to a bicyclic heterocycle.
The terms “3- to 7-membered heterocyclyl” and “3- to 7-membered heterocyclyl-ring” as used herein refers to a saturated 3-, 4-, 5-, 6- or 7-membered ring system comprising 1 or 2 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. Examples include but are not limited to oxiranyl, aziridinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrofuranyl, 1,3-dioxolanyl, tetrahydrothienyl, pyrrolidinyl, pyrazolidinyl, imidazolidinyl, triazolidinyl, isoxazolidinyl, oxazolidinyl, oxadiazolidinyl, thiazolidinyl, isothiazolidinyl, thiadiazolidinyl, piperidinyl, hexahydropyridazinyl, hexahydropyrimidinyl, piperazinyl, triazinanyl, hexahydrotriazinyl, tetrahydropyranyl, dioxanyl, tetrahydrothiopyranyl, dithianyl, morpholinyl, 1,2-oxazinanyl, oxathianyl, thiomorpholinyl, oxepanyl, azepanyl, 1,4-diazepanyl and 1,4-oxazepanyl. Preferred 3- to 7-membered heterocyclyl are oxiranyl, aziridinyl, azetidinyl, oxetanyl, tetrahydrofuranyl, 1,3-dioxolanyl, pyrrolidinyl, piperidinyl, piperazinyl, tetrahydropyranyl, dioxanyl, morpholinyl and thiomorpholinyl.
›DETAILED DESCRIPTION · 8 of 78
The term “5- to 14-membered heteroaryl” as used herein refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. If the ring system contains more than one oxygen atom, they are not directly adjacent. Aromatic heterocycles include 5- or 6-membered monocyclic heteroaryls and 7- to 14-membered polycyclic (e.g. bicyclic or tricyclic) heteroaryls. The 5- to 14-membered heteroaryl can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.
The term “5- or 6-membered heteroaryl” as used herein refers to a 5- or 6-membered aromatic monocyclic ring system containing 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. Examples of 5-membered monocyclic heteroaryl include but are not limited to furyl (furanyl), thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, isoxazolyl, oxazolyl, oxadiazolyl, oxatriazolyl, isothiazolyl, thiazolyl, thiadiazolyl and thiatriazolyl. Examples of 6-membered monocyclic heteroaryl include but are not limited to pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl.
The term “7- to 14-membered heteroaryl” as used herein refers to a 7-, 8-, 9-, 10-, 11-, 12-, 13- or 14-membered aromatic polycyclic (e.g. bicyclic or tricyclic) ring system containing 1, 2 or 3 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. Bicyclic heteroaryls may consist of a monocyclic heteroaryl as defined herein fused to an aryl (e.g. phenyl) or to a monocyclic heteroaryl. Examples of bicyclic heteroaryls include but are not limited to 9-membered ring such as indolyl, indolizinyl, isoindolyl, benzimadozolyl, imidazopyridinyl, indazolyl, benzotriazolyl, purinyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl and benzisoxazolyl or 10-membered ring such as quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, pteridinal and benzodioxinyl. In 9- or 10-membered bicyclic heteroaryls comprising two fused 5- or 6-membered monocyclic heteroaryls, nitrogen atom may be at the bridgehead (e.g. imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl). Examples of tricyclic aromatic heterocyle include but are not limited to carbazolyl, acridinyl and phenazinyl.
The terms “C 3 -C 12 -carbocyclyloxy”, “C 3 -C 8 -cycloalkoxy”, “C 6 -C 14 -aryloxy”, “5- to 14-membered heteroaryloxy”, “3- to 14-membered heterocyclyloxy” as used herein designate a group of formula —O—R wherein R is respectively a C 3 -C 12 -carbocyclyl, a C 3 -C 8 -cycloalkyl, a C 6 -C 14 -aryl, a 5- to 14-membered heteroaryl or a 3- to 14-membered heterocyclyl group as defined herein.
The terms “C 3 -C 12 -carbocyclylsulfanyl”, “C 6 -C 14 -arylsulfanyl”, “5- to 14-membered heteroaryl-sulfanyl”, “3- to 14-membered heterocyclylsulfanyl” as used herein designate a group of formula —S—R wherein R is respectively a C 3 -C 12 -carbocyclyl, a C 6 -C 14 -aryl, a 5- to 14-membered heteroaryl or a 3- to 14-membered heterocyclyl group as defined herein.
The terms “C 3 -C 12 -carbocyclylsulfinyl”, “C 6 -C 14 -arylsulfinyl”, “5- to 14-membered heteroarylsulfinyl”, “3- to 14-membered heterocyclylsulfinyl” as used herein designate a group of formula —(S═O)—R wherein R is respectively a C 3 -C 12 -carbocyclyl, a C 6 -C 14 -aryl, a 5- to 14-membered heteroaryl or a 3- to 14-membered heterocyclyl group as defined herein.
The terms “C 3 -C 12 -carbocyclylsulfonyl”, “C 6 -C 14 -arylsulfonyl”, “5- to 14-membered heteroaryl-sulfonyl”, “3- to 14-membered heterocyclylsulfonyl” as used herein designate a group of formula —(S═O) 2 —R wherein R is respectively a C 3 -C 12 -carbocyclyl, a C 6 -C 14 -aryl, a 5- to 14-membered heteroaryl or a 3- to 14-membered heterocyclyl group as defined herein.
The term “leaving group” as used herein is to be understood as meaning a group which is displaced from a compound in a substitution or an elimination reaction, for example a halogen atom, a trifluoromethanesulphonate (“triflate”) group, alkoxy, methanesulphonate, p-toluenesulphonate, etc.
The terms “as described herein” and “as described above” when referring to a variable A, L, Q, T, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and m incorporates by reference the broad definition of the variable as well as preferred, more preferred, even more preferred definitions and most preferred, if any.
Not encompassed herein are compounds resulting from combinations which are against natural laws and which the person skilled in the art would therefore exclude based on his/her expert knowledge. For instance, ring structures having three or more adjacent oxygen atoms are excluded.
The compounds of formula (I) can suitably be in their free form, salt form, N-oxide form or solvate form (e.g. hydrate).
Depending on the nature of the substituents, the compound of formula (I) may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Where a compound can be present in two or more tautomer forms in equilibrium, reference to the compound by means of one tautomeric description is to be considered to include all tautomer forms.
Any of the compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. Geometric isomers by nature of substituents about a double bond or a ring may be present in cis (=Z-) or trans (=E-) form. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
Depending on the nature of the substituents, the compound of formula (I) may be present in the form of the free compound and/or a salt thereof, such as an agrochemically active salt.
›DETAILED DESCRIPTION · 9 of 78
Agrochemically active salts include acid addition salts of inorganic and organic acids well as salts of customary bases. Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated fatty acids having 6 to 20 carbon atoms, alkylsulphuric monoesters, alkylsulphonic acids (sulphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two phosphonic acid radicals), where the alkyl and aryl radicals may bear further substituents, for example p-toluenesulphonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
Solvates of the compounds of the invention or their salts are stoichiometric compositions of the compounds with solvents.
The compounds of the invention may exist in multiple crystalline and/or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.
The term “leaving group” as used herein is to be understood as meaning a group which is displaced from a compound in a substitution or an elimination reaction, for example a halogen atom, a trifluoromethanesulphonate (“triflate”) group, alkoxy, methanesulphonate, p-toluenesulphonate, etc.
The present invention relates to compounds of the formula (I), wherein
A is O, S, C(═O), S(═O), S(═O), NR 1 or CR 2A R R2B ,
wherein R 1 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 2A and R 2B are independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or R 2A and R 2B form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
m is 0, 1 or 2, T is hydrogen, hydroxyl, C 1 -C 6 -alkyl, —C(═O)R 11 , —C(═O)(OR 12 ), —C(═O)N(R 13 ) 2 , —S(═O)R 14 , —S(═O) 2 R 14 or —S(═O) 2 N(R 14 ) 2 ,
wherein R 11 and R 12 are independently C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, R 13 and R 14 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a
methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 10 of 78
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 )—, —C(═NR L8 )— or a group of formula
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 11 of 78
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 12 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
as well as salts, N-oxides, solvates and solvates of salts and N-oxides.
Preferably the present invention relates to compounds of formula (I), wherein
A is O, C(═O), NR 1 or CR 2A R R2B ,
wherein R 1 is hydrogen, C 1 -C 4 -alkyl or formyl, R 2A and R 2B are independently hydrogen, C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl,
m is 0, 1 or 2, T is hydrogen, or C 1 -C 4 -alkyl R 3 and R 4 are independently hydrogen, fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkylcarbonyloxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkyl is optionally substituted with one or two substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, oxo, methylidene, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
›DETAILED DESCRIPTION · 13 of 78
R 5 is hydrogen or C 1 -C 4 -alkyl,
wherein C 1 -C 4 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
L is a direct bond, C 1 -C 6 -alkylene or a group of formula
wherein
said C 1 -C 6 -alkylene is optionally substituted with one to three substituents L SA ,
# is the point of attachment to the heterocyclyl-moiety,
## is the point of attachment to R 6 ,
L 1 is a direct bond or C 1 -C 6 -alkylene,
L 2 is a direct bond or C 1 -C 6 -alkylene,
E is C 3 -C 8 -cycloalkyl or 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , and wherein L SA is independently fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl or C 3 -C 6 -halocycloalkyl, or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 6 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, L SC is independently fluoro, chloro, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
R 6 is C 5 -C 10 -carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C 5 -C 10 -carbocyclyloxy, phenoxy, naphthyloxy, 5- to 10-membered heteroaryloxy, 5- to 10-membered heterocyclyloxy, C 5 -C 10 -carbocyclylsulfanyl, phenylsulfanyl, naphthyl-sulfanyl, 5- to 10-membered heteroarylsulfanyl, 5- to 10-membered heterocyclylsulfanyl, C 1 -C 3 -alkoxy or C 1 -C 3 -haloalkoxy,
wherein C 1 -C 3 -alkoxy and C 1 -C 3 -haloalkoxy are substituted with one substituent selected from the group consisting of C 5 -C 10 -carbocyclyl, phenyl, naphthyl, 5- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 5 -C 10 -carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl in turn are optionally substituted with one to three R 6S substituents,
wherein C 5 -C 10 -carbocyclyl, phenyl, naphthyl, 5- to 10-membered heterocyclyl, 5- to 10-membered heteroaryl, C 5 -C 10 -carbocyclyloxy, phenoxy, naphthyloxy, 5- to 10-membered heteroaryloxy, 5- to 10-membered heterocyclyloxy, C 5 -C 10 -carbocyclylsulfanyl, phenylsulfanyl, naphthylsulfanyl, 5- to 10-membered heteroarylsulfanyl and 5- to 10-membered heterocyclyl-sulfanyl, are optionally substituted with one to three R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 3 -C 6 -cycloalkyl sulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, phenyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —C(═O)R 16 , —C(═O)(OR 17 ) or —C(═O)N(R 18 ) 2 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl and C 1 -C 4 -haloalkylsulfanyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy,
and wherein R 16 , R 17 and R 18 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
R 7 is hydrogen, halogen, cyano, hydroxyl, mercapto, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 3 -C 6 -cycloalkylsulfanyl, phenylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 3 -C 6 -cycloalkylsulfinyl, phenylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkylsulfonyl, phenylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 6 -cycloalkyl oxy, phenoxy, naphthyloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 6 -cycloalkylsulfanyl, phenylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 3 -C 6 -cycloalkylsulfinyl, phenylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkylsulfonyl, phenylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 6 -cycloalkyloxy, phenoxy, naphthyloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclyloxy, are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -halo-alkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl or C 3 -C 6 -cycloalkyl,
›DETAILED DESCRIPTION · 14 of 78
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 6 -cycloalkyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 4 -alkoxy,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halo-alkyl and C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl in turn are optionally substituted with one or two R 7Sa substituents, and wherein C 3 -C 6 -cycloalkyl in turn is optionally substituted with one or two R 7Sc substituents,
wherein R 7Sa is independently hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl or —Si(C 1 -C 4 -alkyl) 3 R 7Sc is independently fluoro, chloro, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 3 -C 6 -cycloalkyl,
R 8 is hydrogen, halogen, amino, hydroxyl, mercapto, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -haloalkenyloxy, C 2 -C 4 -alkynyloxy, C 2 -C 4 -haloalkynyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl 4- to 7-membered heterocyclyl, 5- to 6-membered heteroaryl, C 3 -C 6 -cycloalkyloxy, phenoxy 4- to 7-membered heterocyclyloxy, 5- or 6-membered heteroaryloxy, —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -haloalkenyloxy, C 2 -C 4 -alkynyloxy and C 2 -C 4 -haloalkynyloxy, are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl 4- to 7-membered heterocyclyl, 5- to 6-membered heteroaryl, C 3 -C 6 -cycloalkyloxy, phenoxy 4- to 7-membered heterocyclyloxy and 5- or 6-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein phenyl, naphthyl, C 5 -C 10 -carbocyclyl, 5- to 10-membered heterocyclyl or 5- to 10-membered heteroaryl are optionally substituted with one to three substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, nitro, formyl, carboxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, 5- or 6-membered heteroaryl, —O—C(═O)R 33 or —N(R 43 ) 2 ,
wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkyl-carbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -halo-alkoxycarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl and 3- to 7-membered heterocyclyl, said C 3 -C 6 -cycloalkyl, phenyl, 3- to 7-membered heterocyclyl and 5- or 6-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -haloalkoxycarbonyl and C 3 -C 6 -cycloalkyl, R 33 is C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl, R 43 is independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl or C 3 -C 8 -cycloalkyl,
as well as salts, hydrates and hydrates of the salts thereof.
Preferably the present invention also relates to compounds of formula (I), wherein
A is O, S, C(═O), S(═O), S(═O) 2 , NR 1 or CR 2A R R2B ,
wherein R 1 is hydrogen, C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 6 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 2A and R 2B are independently hydrogen, C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 6 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 15 of 78
m is 0, 1 or 2, T is hydrogen, C 1 -C 4 -alkyl, R 3 and R 4 are independently hydrogen, fluoro, chloro, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, oxo, methylidene, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 alkenyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, or
R 5 is hydrogen, hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkylsulfanyl,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 6 -alkylsulfanyl are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, oxo, methylidene, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 alkenyl, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
or R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 6 -cycloalkyl-ring, L is a direct bond, C 1 -C 6 -alkylene or a group of formula
wherein C 1 -C 3 -alkoxy and C 1 -C 3 -haloalkoxy are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl and 3- to 14-membered heterocyclylsulfanyl are optionally substituted with one to three R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 6 -cycloalkyl sulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —C(═O)(OR 17 ) and —C(═O)N(R 18 ) 2 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl and C 1 -C 6 -haloalkylsulfanyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halo-cycloalkyl and wherein C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -halo-alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, and wherein R 17 and R 18 are independently hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
wherein said C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl,
R 7 is hydrogen, halogen, cyano, hydroxyl, mercapto, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 3 -C 6 -cycloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 3 -C 6 -cycloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl-sulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
Wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 haloalkylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl and C 1 -C 4 -haloalkylsulfinyl are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkylsulfinyl, C 3 -C 6 -cycloalkylsulfonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl or C 3 -C 6 -cycloalkyl,
›DETAILED DESCRIPTION · 16 of 78
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 6 -cycloalkyl in turn is optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 -alkoxy, wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl and C 1 -C 4 -alkoxy in turn are optionally substituted with one to three R 7Sa substituents, R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -halo-alkyl and C 3 -C 6 -cycloalkyl,
wherein C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl in turn are optionally substituted with one or two R 7Sa substituents, and wherein C 3 -C 6 -cycloalkyl in turn is optionally substituted with one or two R 7Sc substituents,
wherein R 7Sa is independently hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 3 -C 6 -cycloalkyl, R 7Sc is independently fluoro, chloro, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy or C 3 -C 6 -cycloalkyl,
R 8 is hydrogen, halogen, amino, hydroxyl, mercapto, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -haloalkenyloxy, C 2 -C 4 -alkynyloxy, C 2 -C 4 -haloalkynyloxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl, naphthyl, 3- to 7-membered heterocyclyl, 5- or 6-membered heteroaryl, C 3 -C 6 -cycloalkyloxy, phenyloxy 3- to 7-membered heterocyclyloxy, 5- or 6-membered heteroaryloxy, —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 2 -C 4 -alkenyloxy, C 2 -C 4 -haloalkenyloxy, C 2 -C 4 -alkynyloxy and C 2 -C 4 -haloalkynyloxy are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, phenyl, naphthyl, 3- to 7-membered heterocyclyl, 5- or 6-membered heteroaryl, C 3 -C 6 -cycloalkyloxy, phenyloxy, 3- to 7-membered heterocyclyloxy and 5- or 6-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein phenyl, naphthyl, C 3 -C 10 -carbocyclyl, 5- to 10-membered heterocyclyl and 5- to 10-membered heteroaryl are optionally substituted with one to three substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, nitro, formyl, carboxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl, C 3 -C 6 -cycloalkyl, 3- to 7-membered heterocyclyl, phenyl, 5- or 6-membered heteroaryl,
wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -haloalkyl-carbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -halo-alkoxycarbonyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl and C 1 -C 4 -haloalkylsulfonyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl and 3- to 7-membered heterocyclyl, said C 3 -C 6 -cycloalkyl, 3- to 7-membered heterocyclyl, phenyl and 5- or 6-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxy-carbonyl, C 1 -C 4 -haloalkoxycarbonyl and C 3 -C 6 -cycloalkyl,
as well as salts, hydrates and hydrates of the salts thereof.
More preferably, the present invention relates to compounds of formula (I), wherein
A is O, C(═O), NR 1 or CR 2A R R2B ,
wherein R 1 is hydrogen, methyl or formyl, R 2A and R 2B are independently hydrogen,
m is 0, 1 or 2, T is hydrogen, R 3 and R 4 are independently hydrogen, fluoro, chloro, methyl, ethyl, methylcarbonyloxy, ethylcarbonyloxy cyclopropyl or cyclobutyl, R 5 is hydrogen methyl or ethyl, L is a direct bond, methylene or ethylene,
wherein said methylene or ethylene are optionally substituted with one or two substituents L SA , wherein L SA is fluoro or methyl, or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a cyclopropyl or cyclobutyl-ring,
R 6 is indanyl, tetrahydronaphthalenyl, indenyl, 1,2-dihydronaphthalenyl, spiro[cyclopropane-2,1′-indane]-1-yl, spiro[cyclopropane-2,1′-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF 2 -phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, tetrahydroquinolinyl, tetrahydrobenzothiophenyl, tetrahydrobenzofuranyl, tetrahydro-1,3-benzoxazolyl, tetrahydro-1,3-benzothiazolyl, tetrahydro-1H-benzimidazolyl, tetrahydro-1H-indazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl or isoquinolinyl,
›DETAILED DESCRIPTION · 17 of 78
wherein indanyl, tetrahydronaphthalenyl, indenyl, 1,2-dihydronaphthalenyl, spiro[cyclo-propane-2,1′-indane]-1-yl, spiro[cyclopropane-2,1′-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF 2 -phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, tetrahydroquinolinyl, tetrahydrobenzothiophenyl, tetrahydrobenzofuranyl, tetrahydro-1,3-benzoxazolyl, tetrahydro-1,3-benzothiazolyl, tetra-hydro-1H-benzimidazolyl, tetrahydro-1H-indazolyl, tetrahydro-2H-isoindolyl, tetrahydro-2-benzothiophenyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl and isoquinolinyl are optionally substituted with one to three R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -halo-alkenyl, C 2 -C 4 -alkynyl C 3 -C 6 -cycloalkyl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and —C(═O)R 16 ,
and wherein R 16 is C 1 -C 4 -alkyl,
R 7 is hydrogen, fluoro, chloro, cyano, hydroxyl, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, phenylsulfanyl, C 3 -C 6 -cycloalkyl, phenyl, pyridyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl or —N(R 20 ) 2 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one or two R 7Sa substituents, wherein phenylsulfanyl, C 3 -C 6 -cycloalkyl, phenyl, pyridyl, oxetanyl, pyrrolidinyl and tetrahydrofuranyl are optionally substituted with one or two R 7Sc substituents, and wherein R 20 is independently hydrogen or C 1 -C 4 -alkyl, R 7Sa is independently hydroxyl, methoxy, ethoxy, cyclopropyl, cyclobutyl or —Si(CH 3 ) 3 , R 7Sc is independently fluoro, chloro, hydroxyl, oxo, methyl, ethyl, difluoromethyl or tri-fluoromethyl,
R 8 is hydrogen, halogen, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoro-methoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, —N(R 30 ) 2 or —SR 31 ,
wherein C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy are optionally substituted with one or two R 8Sa substituents, wherein C 3 -C 6 -cycloalkyl and phenyl are optionally substituted with one or two R 8Sc substituents, and wherein R 30 is independently hydrogen, C 1 -C 4 -alkyl and C 2 -C 4 -alkenyl, R 31 is C 1 -C 4 -alkyl, and wherein R 8Sa is independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, R 8Sc is independently selected from the group consisting of halogen, oxo and C 1 -C 4 -alkyl,
R 9 is hydrogen, fluoro or chloro, Q is phenyl, naphthyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl, indanyl, tetrahydronaphthalenyl, dihydrobenzofuranyl, indenyl, dihydronaphthalenyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl or quinolinyl,
wherein phenyl, naphthyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl, indanyl, tetrahydronaphthalenyl, dihydrobenzofuranyl, indenyl, dihydronaphthalenyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, oxazolyl, thiazolyl, pyridinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl and quinolinyl, are optionally substituted with one to three substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, formyl, C 1 -C 4 -alkyl, difluoromethyl, trifluormethyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, difluoro-methoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylsulfanyl, difluoromethylsulfanyl, trifluoromethylsulfanyl, C 1 -C 4 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, phenyl, thienyl, furanyl, pyrrolyl, pyridyl, —O(C═O)R 33 and —N(R 43 ) 2 ,
wherein said C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylsulfanyl and C 1 -C 4 -alkylsulfonyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl, C 1 said C 3 -C 6 -cycloalkyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl, phenyl, thienyl, furanyl, pyrrolyl and pyridyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of halogen and C 1 -C 4 -alkyl, R 33 is C 1 -C 4 -alkyl, R 43 is independently hydrogen or C 1 -C 4 -alkyl,
as well as salts, hydrates and hydrates of the salts thereof.
Even more preferably the present invention relates to compounds of formula (I), wherein
A is O, m is 1, T is hydrogen, R 3 and R 4 are independently hydrogen, fluoro or C 1 -C 4 -alkyl, R 5 is hydrogen, L is a direct bond or C 1 -C 4 -alkylene,
wherein said C 1 -C 4 -alkylene is optionally substituted with one or two substituents L SA , L SA is fluoro, or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a cyclopropyl or cyclobutyl,
R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxinyl,
›DETAILED DESCRIPTION · 18 of 78
wherein indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxinyl are optionally substituted with one or two R 6S substituents, wherein R 6S is independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl,
R 7 is hydrogen, fluoro, chloro, cyano, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, cyclopropyl, cyclobutyl, oxetanyl, pyrrolidinyl or tetrahydrofuranyl, R 8 is hydrogen or fluoro, R 9 is hydrogen, Q is phenyl,
wherein phenyl is optionally substituted with one or two substituents Q S , wherein Q S is independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 alkenyl, C 2 -C 4 -alkynyl, cyclopropyl and cyclobutyl,
as well as salts, hydrates and hydrates of the salts thereof.
Not encompassed herein are compounds resulting from combinations which are against natural laws and which the person skilled in the art would therefore exclude based on his/her expert knowledge. For instance, ring structures having three or more adjacent oxygen atoms are excluded.
The compound of formula (I) can suitably be in its free form, salt form, N-oxides form or solvate form (e.g. hydrate).
Depending on the nature of the substituents, the compound of formula (I) may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Where a compound can be present in two or more tautomer forms in equilibrium, reference to the compound by means of one tautomeric description is to be considered to include all tautomer forms.
Any of the compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. Geometric isomers by nature of substituents about a double bond or a ring may be present in cis (=Z-) or trans (=E-) form. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.
Depending on the nature of the substituents, the compound of formula (I) may be present in the form of the free compound and/or a salt thereof, such as an agrochemically active salt.
Agrochemically active salts include acid addition salts of inorganic and organic acids well as salts of customary bases. Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated fatty acids having 6 to 20 carbon atoms, alkylsulphuric monoesters, alkylsulphonic acids (sulphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulphonic acids or aryldisulphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two sulphonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two phosphonic acid radicals), where the alkyl and aryl radicals may bear further substituents, for example p-toluenesulphonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.
Solvates of the compounds of the invention or their salts are stoichiometric compositions of the compounds with solvents.
The compounds of the invention may exist in multiple crystalline and/or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.
Preferably, A is O, C(═O), S(═O) 2 , NR 1 and CR 2A R 2B , wherein R 1 is hydrogen or C 1 -C 4 -alkyl and R 2A and R 2B are independently hydrogen, halogen or C 1 -C 4 -alkyl.
More preferably, A is O, NR 1 and CR 2A R 2B , wherein R 1 is hydrogen or C 1 -C 4 -alkyl and R 2A and R 2B are independently hydrogen, halogen or C 1 -C 4 -alkyl. Even more preferably, A is O.
Even more preferably, m is 1.
More preferably, T is hydrogen and C 1 -C 4 -alkyl.
More preferably, A is O, C(═O), NR 1 or CR 2A R R2B , wherein R 1 is hydrogen, methyl or formyl, and R 2A and R 2B are independently hydrogen.
Even more preferably, A is O, m is 1 and T is hydrogen.
Preferably, T is hydrogen and C 1 -C 4 -alkyl.
Preferably, R 3 and R 4 are independently hydrogen, fluorine, chlorine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl and C 3 -C 6 -cycloalkyl, or R 3 and R 4 form together with the carbon atom to which they are attached to a C 3 -C 6 -cycloalkyl-ring. More preferably, R 3 and R 4 are independently hydrogen, fluorine or C 1 -C 4 -alkyl.
Preferably R 5 is hydrogen, hydroxyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy. More preferably, R 5 is hydrogen.
Even more preferably, A is O, m is 1, T is hydrogen, R 3 and R 4 are independently hydrogen, fluorine or C 1 -C 4 -alkyl and R 5 is hydrogen.
Preferably, L is a direct bond, C 1 -C 6 -alkylene or a group of formula
wherein
said C 1 -C 6 -alkylene is optionally substituted with one to three substituents L SA ,
# is the point of attachment to the heterocyclyl-moiety,
## is the point of attachment to R 6 ,
L 1 is a direct bond or C 1 -C 6 -alkylene,
›DETAILED DESCRIPTION · 19 of 78
L 2 is a direct bond or C 1 -C 6 -alkylene,
E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC ,
L SA is independently halogen, hydroxyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl or 3- to 7-membered heterocyclyl,
or
two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 6 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
L Sc is independently halogen, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,
and/or
two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring.
Preferably, L is a direct bond C 1 -C 6 -alkylene or a group of formula
wherein
said C 1 -C 6 -alkylene is optionally substituted with one to three substituents L SA ,
# is the point of attachment to the heterocyclyl-moiety,
## is the point of attachment to R 6 ,
L 1 is a direct bond or C 1 -C 6 -alkylene,
L 2 is a direct bond or C 1 -C 6 -alkylene,
E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC ,
L SA is independently halogen, hydroxyl, C 1 -C 4 -alkoxy, C 3 -C 6 -cycloalkyl or 3- to 7-membered heterocyclyl,
or
two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 6 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
L Sc is independently halogen, hydroxyl, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 haloalkoxy,
and/or
two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring.
More preferably, L is a direct bond or C 1 -C 4 -alkylene,
wherein said C 1 -C 4 -alkylene is optionally substituted with one or two substituents L SA , L SA is fluoro, or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a cyclopropyl or cyclobutyl.
Even more preferably, L is a direct bond, methylene, monofluoromethylene or difluoromethylene. Preferably, R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 6 -C 14 -aryloxy, C 1 -C 3 -alkoxy substituted by a C 6 -C 14 -aryl or C 6 -C 14 -arylsulfanyl, wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 6 -C 14 -aryloxy, C 1 -C 3 -alkoxy substituted by a C 6 -C 14 -aryl and C 6 -C 14 -arylsulfanyl are optionally substituted with one to four substituents R 6S , wherein
R 6S is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —C(═O)(OR 17 ) and —C(═O)N(R 18 ) 2 , wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl and C 1 -C 6 -haloalkylsulfanyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, and wherein R 17 and R 18 are independently hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
wherein said C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl.
More preferably, R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indenyl, 1,2-dihydronaphthalenyl, spiro[cyclopropane-2,1′-indane]-1-yl, spiro[cyclopropane-2,1′-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF 2 -phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, 4,5,6,7-tetrahydrobenzofuranyl, 4,5,6,7-tetrahydro-1,3-benzoxazolyl, 4,5,6,7-tetrahydro-1,3-benzothiazolyl, 4,5,6,7-tetrahydro-1H-benzimidazolyl, 4,5,6,7-tetrahydro-1H-indazolyl, 4,5,6,7-tetra-hydro-2H-isoindolyl, 4,5,6,7-tetrahydro-2-benzothiophenyl, 5,6-dihydro-4H-cyclopenta[b]thiophenyl, 5,6-dihydro-4H-cyclopenta[d]thiazolyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridinyl, 6,7-dihydro-5H-thieno[3,2-b]pyranyl, spiro[chromane-3,1′-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1′-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridazinyl and pyrimidinyl, indolyl, benzimadazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[2,3-b]pyridin-3-yl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[3,2-b]pyrrol-6-yl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl or thieno[2,3-d]isothiazolyl, wherein indanyl, 1,2,3,4-tetrahydronaphthalenyl, bicyclo[4.2.0]octa-1,3,5-trienyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indenyl, 1,2-dihydronaphthalenyl, spiro[cyclopropane-2,1′-indane]-1-yl, spiro[cyclopropane-2,1′-tetralin]-1-yl, phenyl, naphthyl, phenoxy, benzyloxy, OCF 2 -phenyl, phenylsulfanyl, 3-dihydrobenzofuranyl, 2,3-dihydrobenzothiophenyl, indolinyl, 1,3-benzodioxolyl, 1,2,3,4-tetrahydroquinolinyl, chromanyl, isochromanyl, thiochromanyl, 2,3-dihydro-1,4-benzodioxinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, 5,6,7,8-tetrahydroquinolinyl, 4,5,6,7-tetrahydrobenzothiophenyl, 4,5,6,7-tetrahydrobenzofuranyl, 4,5,6,7-tetrahydro-1,3-benzoxazolyl, 4,5,6,7-tetrahydro-1,3-benzothiazolyl, 4,5,6,7-tetrahydro-1H-benzimidazolyl, 4,5,6,7-tetrahydro-1H-indazolyl, 4,5,6,7-tetra-hydro-2H-isoindolyl, 4,5,6,7-tetrahydro-2-benzothiophenyl, 5,6-dihydro-4H-cyclopenta[b]thiophenyl, 5,6-dihydro-4H-cyclopenta[d]thiazolyl, 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridinyl, 5,6,7,8-tetrahydroimidazo[1,2-a]pyridinyl, 6,7-dihydro-5H-thieno[3,2-b]pyranyl, spiro[chromane-3,1′-cyclopropane]-yl, spiro[7,8-dihydro-5H-quinoline-6,1′-cyclopropane]-yl, furanyl, thienyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, oxadiazolyl, thiazolyl, thiadiazolyl, pyridinyl, pyridazinyl and pyrimidinyl, indolyl, benzimadazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinoxalinyl, pyrrolo[2,3-b]pyridin-3-yl, imidazo[1,2-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[3,2-b]pyrrol-6-yl, thieno[3,2-b]thiophenyl, imidazo[2,1-b]oxazolyl, furo[2,3-d]isoxazolyl and thieno[2,3-d]isothiazolyl are optionally substituted with one to three substituents R 6S , wherein
›DETAILED DESCRIPTION · 20 of 78
R 6S is independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —C(═O)(OR 17 ) and —C(═O)N(R 18 ) 2 , wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl and C 1 -C 6 -haloalkylsulfanyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl, and wherein C 3 -C 6 -cycloalkylsulfanyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy,
and wherein R 17 and R 18 are independently hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl,
wherein said C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of fluoro, chloro, hydroxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 3 -C 6 -cycloalkyl and C 3 -C 6 -halocycloalkyl.
Even more preferably, R 6 is indanyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxinyl, thienyl or indolyl, wherein indanyl, phenyl, naphthyl, dihydrobenzofuranyl, dihydrobenzodioxinyl, thienyl and indolyl are optionally substituted with one or two R 6S substituents, wherein
R 6S is independently selected from the group consisting of fluoro, chloro, bromo, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl and pyrazolyl,
wherein said cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl and pyrazolyl are optionally substituted with one or two substituents independently selected from the group consisting of fluoro and methyl.
Likewise even more preferably, R 6 is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxinyl, wherein indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxinyl are optionally substituted with one or two R 6S substituents, wherein
R 6S is independently selected from the group consisting of fluoro, chloro, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl, pyrazolyl and pyridyl.
In a still even more preferred embodiment, R 6 is
wherein
§ 1 is the attachment to L,
R 6S1 and R 6S2 are independently hydrogen or R 6S ,
wherein R 6S is halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl and pyrazolyl,
wherein said C 3 -C 6 -cycloalkyl and pyrazolyl are optionally substituted with one or two substituents independently selected from the group consisting of halogen and C 1 -C 4 -alkyl,
with the proviso that at least one of R 6S1 and R 6S2 is different from hydrogen.
Non-limiting examples of suitable -L-R 6 groups include any of the -L-R 6 groups disclosed in column “-L-R 6 ” of Table 1.
Preferably R 7 is hydrogen, halogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 20 ) 2 , —C(═NR 21 )R 22 , —C(═O)(OR 21 ) or —C(═O)N(R 26 ) 2 , wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and C 1 -C 6 -haloalkylsulfonyl are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three R 7Sc substituents,
wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 3 -C 6 -cycloalkyl,
wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one or two substituents independently selected from the group consisting of halogen and C 1 -C 6 -alkyl,
R 21 is hydroxyl, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy, R 22 is hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, R 25 and R 26 are independently hydrogen or C 1 -C 6 -alkyl,
and wherein R 7Sa is independently cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxycarbonyl and phenyl, R 7Sc is independently halogen, hydroxyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy.
More preferably R 7 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl, —N(R 20 ) 2 , —C(═NR 21 )R 22 or —C(═O)(OR 25 ), wherein C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -hydroxyalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one or two R 7Sa substituents, wherein C 3 -C 6 -cycloalkyl, pyridinyl, imidazolyl, pyrazolyl, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, pyrrolidinyl, piperidinyl are optionally substituted with one or two R 7Sc substituents,
›DETAILED DESCRIPTION · 21 of 78
wherein R 20 is hydrogen, C 1 -C 4 -alkyl or C 3 -C 6 -cycloalkyl, R 21 is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 22 is C 1 -C 4 -alkyl, R 25 is hydrogen or C 1 -C 4 -alkyl,
and wherein
R 7Sa is independently C 1 -C 4 -alkoxy or phenyl, R 7Sc is independently halogen or C 1 -C 4 -alkyl.
Even more preferably R 7 is hydrogen, fluoro, chloro, cyano, hydroxyl, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, phenylsulfanyl, C 3 -C 6 -cycloalkyl, phenyl, pyridyl, oxetanyl, pyrrolidinyl, tetrahydrofuranyl or —N(R 20 ) 2 ,
wherein C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one or two R 7Sa substituents, wherein phenylsulfanyl, C 3 -C 6 -cycloalkyl, phenyl, pyridyl, oxetanyl, pyrrolidinyl and tetrahydrofuranyl are optionally substituted with one or two R 7Sc substituents, and wherein R 20 is independently hydrogen or C 1 -C 4 -alkyl, R 7Sa is independently hydroxyl, methoxy, ethoxy, cyclopropyl, cyclobutyl or —Si(CH 3 ) 3 , R 7Sc is independently fluoro, chloro, hydroxyl, oxo, methyl, ethyl, difluoromethyl or trifluoromethyl.
Likewise even more preferably R 7 is chloro, iodo, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, —N(R 20 ) 2 or —C(═NR 21 )R 22 ,
wherein C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl and C 2 -C 4 -alkynyl are optionally substituted with one or two R 7Sa substituents, wherein C 3 -C 6 -cycloalkyl is optionally substituted with one or two R 7Sc substituents, R 20 is hydrogen, cyclopropyl or cyclobutyl, R 21 is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, R 22 is C 1 -C 4 -alkyl, and wherein R 7Sa is independently C 1 -C 4 -alkoxy, R 7Sc is independently halogen.
Likewise even more preferably R 7 is chloro, iodo, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, methylcarbonyl, ethylcarbonyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, cyclopropyl, cyclobutyl, oxetanyl, tetrahydrofuranyl or pyrrolidinyl.
Non-limiting examples of suitable R 7 include any of the R 7 groups listed in column “R 7 ” of Table 1.
Preferably R 8 is hydrogen, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylsulfanyl, C 3 -C 6 -cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl, pyridinyl or —N(R 30 ) 2 ,
wherein said C 3 -C 6 -cycloalkyl, phenyl, oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, pyrazolyl, imidazolyl, thiazolyl and pyridinyl are optionally substituted with one or two R 8Sc substituents, R 30 is C 1 -C 6 -alkyl, R 8Sc is independently selected from the group consisting of halogen and C 1 -C 4 -alkyl.
Even more preferably R 8 is hydrogen or fluoro.
More preferably, R 8 is hydrogen, halogen, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, phenyl, —N(R 30 ) 2 or —SR 31 ,
wherein C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy are optionally substituted with one or two R 8Sa substituents, wherein C 3 -C 6 -cycloalkyl and phenyl are optionally substituted with one or two R 8Sc substituents, and wherein R 30 is independently hydrogen, C 1 -C 4 -alkyl and C 2 -C 4 -alkenyl, R 31 is C 1 -C 4 -alkyl, and wherein R 8Sa is independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkoxy, R 8Sc is independently selected from the group consisting of halogen, oxo and C 1 -C 4 -alkyl.
Even more R 7 is hydrogen, fluoro, chloro, cyano, hydroxyl, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, phenylsulfanyl, C 3 -C 6 -cycloalkyl, pyridyl, pyrrolidinyl, tetrahydrofuranyl or —N(R 20 ) 2 ,
wherein C 2 -C 4 -alkynyl is optionally substituted with one substituents —Si(CH 3 ) 3 , wherein phenylsulfanyl, phenyl and pyridyl are optionally substituted with one or two R 7Sc substituents, and wherein R 20 is independently hydrogen or C 1 -C 4 -alkyl, R 7Sc is independently fluoro, methyl, ethyl, difluoromethyl or trifluoromethyl, and R 8 is hydrogen, fluoro, iodo, C 1 -C 4 -alkyl, difluoromethyl, trifluoromethyl, C 1 -C 4 -alkoxy, difluoro-methoxy, trifluoromethoxy, C 3 -C 6 -cycloalkyl, phenyl, —N(R 30 ) 2 or —SR 31 , wherein C 1 -C 4 -alkoxy is optionally substituted with one substituents C 1 -C 4 -alkoxy, and wherein R 30 is independently hydrogen, C 1 -C 4 -alkyl and C 2 -C 4 -alkenyl, R 31 is C 1 -C 4 -alkyl.
Non-limiting examples of suitable R 8 include any of the R 8 groups listed in column “R 8 ” of Table 1.
Preferably Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl or thieno[2,3-d]thiazolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, indanyl, tetrahydronaphthalenyl, indenyl, dihydronaphthalenyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, dihydrobenzofuranyl, 1,3-dihydroisobenzofuranyl, indolinyl, 1,3-benzodioxolyl, chromanyl, dihydro-1,4-benzodioxinyl, [1,3]dioxolo[4,5-b]pyridinyl, tetrahydroquinolinyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, pyrrolyl, furanyl, thienyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, furo[3,2-b]pyridinyl, thieno[3,2-b]thiophenyl and thieno[2,3-d]thiazolyl are optionally substituted with one to four substituents Q S , wherein
›DETAILED DESCRIPTION · 22 of 78
Q S is independently selected from group consisting of halogen, cyano, nitro, hydroxyl, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 6 -cycloalkyl, oxetanyl and —N(R 43 ) 2 , wherein said C 3 -C 6 -cycloalkyl and oxetanyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of halogen, C 1 -C 4 -alkyl and C 1 -C 4 -haloalkyl, and wherein R 43 is hydrogen and C 1 -C 6 -alkyl.
More preferably Q is phenyl, naphthyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl, indanyl, dihydrobenzofuranyl, 1,3-benzodioxolyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, thienyl, pyridinyl or benzothiophenyl,
wherein phenyl, naphthyl, 3-bicyclo[4.2.0]octa-1,3,5-trienyl, indanyl, dihydrobenzofuranyl, 1,3-benzodioxolyl, 6,7-dihydro-5H-cyclopenta[b]pyridinyl, thienyl, pyridinyl and benzothiophenyl are optionally substituted with one or two substituents Q S , wherein
Q S is independently selected from the group consisting of halogen, cyano, formyl, C 1 -C 4 -alkyl, difluoromethyl, trifluormethyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, difluormethoxy, trifluormethoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylsulfanyl, difluoromethylsulfanyl, trifluormethylsulfanyl, C 1 -C 4 -alkylsulfonyl, C 3 -C 6 -cycloalkyl, oxetanyl, tetrahydrofuranyl, phenyl, pyridyl, —O(C═O)R 33 and —N(R 43 ) 2 ,
wherein said C 1 -C 4 -alkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkylsulfanyl and C 1 -C 4 -alkylsulfonyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of hydroxyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl, said C 3 -C 6 -cycloalkyl, oxetanyl, tetrahydrofuranyl, phenyl and pyridyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of halogen and C 1 -C 4 -alkyl, and wherein R 33 is C 1 -C 4 -alkyl, R 43 is independently hydrogen or C 1 -C 4 -alkyl.
Likewise more preferably Q is phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl or indolyl, wherein phenyl, naphthyl, bicyclo[4.2.0]octa-1(6),2,4-trienyl, benzodioxolyl, 2,3-dihydrobenzofuranyl, pyridinyl, thienyl and indolyl are optionally substituted with one to three substituents Q S , wherein
Q S is independently selected from the group consisting of halogen, cyano, nitro, formyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkynyl and C 3 -C 6 -cycloalkyl, wherein said C 3 -C 6 -cycloalkyl and oxetanyl are in turn optionally substituted with one or two substituents independently selected from the group consisting of fluoro or methyl.
Likewise even more preferably, Q is phenyl, wherein phenyl is substituted with one or two substituents Q S independently selected from the group consisting of halogen, cyano, nitro, formyl, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkynyl, cyclopropyl and cyclobutyl, wherein said cyclopropyl and cyclobutyl in turn are optionally substituted with one or two substituents independently selected from the group consisting of fluoro or methyl.
Still even more preferably Q is
wherein
§ 2 is the attachment to the oxygen atom,
Q S1 is hydrogen or fluoro,
Q S2 is hydrogen, fluoro, chloro, C 1 -C 4 -alkyl, trifluoromethyl, difluoromethyl, C 1 -C 4 -alkoxy, difluoromethoxy, trifluoromethoxy, C 2 -C 4 -alkynyl, cyclopropyl or cyclobutyl,
with the proviso that at least one of Q S1 and Q S2 is different from hydrogen.
Non-limiting examples of suitable Q include any of the Q groups listed in column “Q” of Table 1.
The above specified definitions of A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , L, m and Q (broad definition as well as preferred, more preferred, even more preferred definitions) can be combined in various manners. These combinations of definitions thus provide sub-classes of compounds according to the invention, such as for instance the ones disclosed below. They apply both to the end products and correspondingly to precursors and intermediates. In addition, individual definitions may not apply.
The present invention also relates to any compounds of formula (I) disclosed in Table 1.
The compounds of formula (I) may be used as fungicides (for controlling phytopathogenic fungi), in particular in methods for controlling phytopathogenic fungi which comprises the step of applying one or more compounds of formula (I) to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.
Processes for the Preparation of Compounds of Formula (I) and Intermediates
The present invention relates to processes for the preparation of compounds of formula (I) and their intermediates. Unless indicated otherwise, the radicals A, Q, T, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and m have the meanings given above for the compounds of formula (I). These definitions apply not only to the end products of formula (I) but also to all intermediates.
Compounds of formula (I-a) to (I-e) are various subsets of formula (I). Compounds of formula (I-a-1) to (I-a-3) are various subsets of formula (I-a). All substituents for formula (I-a) to (I-e) and (I-a-1) to (I-a-3) are as defined above for formula (I) unless otherwise noted.
The compounds of formula (I) can be prepared by various routes in analogy to known processes (see e.g. and references therein). Non-limiting examples of suitable processes are herein described.
A compound of formula (I) may be directly obtained by performing process A to G or may be obtained by conversion or derivatization of another compound of formula (I) prepared in accordance with the processes described herein. For instance, a compound of formula (I) can be converted into another compound of formula (I) by replacing one or more substituents of the starting compound of formula (I) by other substituents. Non-limiting examples of such conversion or derivatization are described below (processes H and I).
›DETAILED DESCRIPTION · 23 of 78
The processes described herein may be suitably performed using one or more inert organic solvents which is/are customary for the considered reaction. Suitable inert organic solvents can be chosen from the following: aliphatic, alicyclic or aromatic hydrocarbons (e.g. petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, ligroin, benzene, toluene, xylene or decalin), halogenated aliphatic, alicyclic or aromatic hydrocarbons (e.g. chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane), ethers (e.g. diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole), ketones (e.g. acetone, methyl ethyl ketone, methyl isopropyl ketone and methyl isobutyl ketone), esters (e.g. methyl acetate, ethyl acetate or butyl acetate), alcohols (e.g. methanol, ethanol, propanol, iso-propanol, butanol, tert-butanol), nitriles (e.g. acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile), amides (e.g. N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone, or hexamethyl-phosphoric triamide), sulfoxides (e.g. dimethyl sulfoxide) or sulfones (e.g. sulfolane), ureas (e.g. 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone) or any mixture thereof.
Some processes described herein may require or be optionally performed using one or more inorganic or organic bases which are customary for such reactions. Examples of suitable inorganic and organic bases include, but are not limited to, alkaline earth metal or alkali metal carbonates (e.g. sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate), alkali metal hydrides (e.g. sodium hydride), alkaline earth metal or alkali metal hydroxides (e.g. sodium hydroxide, calcium hydroxide, potassium hydroxide or other ammonium hydroxide derivatives), alkaline earth metal, alkali metal or ammonium fluorides (e.g. potassium fluoride, cesium fluoride or tetrabutylammonium fluoride), alkali metal or alkaline earth metal acetates (e.g. sodium acetate, lithium acetate, potassium acetate or calcium acetate), alkali metal alcoholates (e.g. potassium tert-butoxide or sodium tert-butoxide), alkali metal phosphates (e.g. tri-potassium phosphate), tertiary amines (e.g. trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dicyclohexylmethylamine, N,N-diisopropylethylamine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN), diazabicycloundecene (DBU), quinuclidine, 3-acetoxy-quinuclidine, guanidines or aromatic bases (e.g. pyridines, picolines, lutidines or collidines).
Some of the processes described herein may be optionally performed in the presence of a transition metal catalyst, such as a metal (e.g. copper or palladium) salt or complex, if appropriate in the presence of a ligand.
Suitable copper salts or complexes and their hydrates include, but are not limited to, copper metal, copper(I) iodide, copper(I) chloride, copper(I) bromide, copper(II) chloride, copper(II) bromide, copper(II) oxide, copper(I) oxide, copper(II) acetate, copper(I) acetate, copper(I) thiophene-2-carboxylate, copper(I) cyanide, copper(II) sulfate, copper(II) bis(2,2,6,6-tetramethyl-3,5-heptane-dionate), copper(II) trifluoromethanesulfonate, tetrakis(acetonitrile)copper(I) hexafluorophosphate, tetrakis(acetonitrile)-copper(I) tetrafluoroborate.
It is also possible to generate in situ a suitable copper complex in the reaction mixture by separate addition to the reaction of a copper salt and a ligand or salt, such as ethylenediamine, N,N-dimethylethylenediamine, N,N′-dimethylethylenediamine, rac-trans-1,2-diaminocyclohexane, rac-trans-N,N′-dimethylcyclohexane-1,2-diamine, 1,1′-binaphthyl-2,2′-diamine, N,N,N′,N′-tetramethylethylenediamine, proline, N,N-dimethylglycine, quinolin-8-ol, pyridine, 2-aminopyridine, 4-(dimethyl-amino)pyridine, 2,2′-bipyridyl, 2,6-di(2-pyridyl)pyridine, 2-picolinic acid, 2-(dimethylaminomethyl)-3-hydroxypyridine, 1,10-phenanthroline, 3,4,7,8-tetramethyl-1,10-phenanthroline, 2,9-dimethyl-1,10-phenanthroline, 4,7-dimethoxy-1,10-phenanthroline, N,N′-bis[(E)-pyridin-2-ylmethylidene]cyclo-hexane-1,2-diamine, N-[(E)-phenylmethylidene], N-[(E)-phenylmethylidene]-cyclohexanamine, 1,1,1-tris(hydroxymethyl)ethane, n-butylimidazol, ethylene glycol, 2,2,6,6-tetramethylheptane-3,5-dione, 2-(2,2-dimethylpropanoyl)cyclohexanone, acetylacetone, dibenzoylmethane, 2-(2-methyl-propanoyl)cyclohexanone, biphenyl-2-yl(di-tert-butyl)phosphane, ethylenebis-(diphenylphosphine), N,N-diethylsalicylamide, 2-hydroxybenzaldehyde oxime, oxo[(2,4,6-trimethylphenyl)amino]acetic acid or 1H-pyrrole-2-carboxylic acid.
Suitable palladium salts or complexes include, but are not limited to, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), tris(di-benzylideneacetone)dipalladium(0), bis(triphenylphosphine)palladium(II) dichloride, [1,1′-bis(di-phenylphosphino)ferrocene]dichloropalladium(II), bis(cinnamyl)dichlorodipalladium(II), bis(allyl)-di-chlorodipalladium(II) or [1,1′-Bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II).
It is also possible to generate a palladium complex in the reaction mixture by separate addition to the reaction of a palladium salt and a ligand or salt, such as triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphino)-2′-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2,6′-di-methoxybiphenyl, 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl, triphenyl-phosphine, tris-(o-tolyl)phosphine, sodium 3-(diphenylphosphino)benzenesulfonate, tris-(2-methoxy-phenyl)phosphine, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino) ethane, 1,4-bis(dicyclohexylphosphino)butane, 1,2-bis(dicyclohexylphosphino)-ethane, 2-(di-cyclohexylphosphino)-2′-(N,N-dimethylamino)-biphenyl, 1,1′-bis(diphenylphosphino)-ferrocene, (R)-(−)-1-[(S)-2-diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphine, tris-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine or 1,3-bis(2,4,6-trimethyl-phenyl)imidazolium chloride.
›DETAILED DESCRIPTION · 24 of 78
The appropriate catalyst and/or ligand may be chosen from commercial catalogues such as “Metal Catalysts for Organic Synthesis” by Strem Chemicals or from reviews (Chemical Society Reviews (2014), 43, 3525, Coordination Chemistry Reviews (2004), 248, 2337 and references therein).
Some of the processes described herein may be performed by metallo-photoredox catalysis according to methods reported in the literature (Nature chemistry review, (2017) 0052 and references therein; Science (2016) 352, 6291, 1304; Org. Lett. 2016, 18, 4012, J. Org. Chem 2016, 81, 6898; J. Am. Chem. Soc. 2016, 138, 12715, J. Am. Chem. Soc. 2016, 138, 13862; J. Am. Chem. Soc. 2016, 138, 8034; J. Org. Chem. 2016, 81, 12525, J. Org. Chem. 2015, 80, 7642). The process is then performed in the presence a photosensitizer, such as Ir and Ru complexes or organic dyes, and a metal catalyst such as Ni complexes. The reaction can be performed in the presence of a ligand and if appropriate in the presence of a base under irradiation with blue or white light.
Suitable photosensitizers include, but are not limited to, Ir(III) photocatalyst such as [Ir(dFCF 3 ppy) 2 (bpy)]PF 6 (dFCF 3 ppy=2-(2,4-difluorophenyl)-5-trifluoromethylpyridine, bpy=2,2′-bipyridine), [Ir(dFCF 3 ppy) 2 (dtbbpy)]PF 6 (dtbbpy=4,4′-di-tert-butyl-2,2′-bipyridine), Ir(ppy) 2 (dtbbpy)PF 6 (ppy=2-phenylpyridine), Ir(ppy) 2 (bpy)PF 6 , Ir(dFppy) 3 PF 6 (dFppy=2-(2,4-difluorophenyl)pyridine), fac-Ir(ppy) 3 , (Ir[diF(5-Me)ppy] 2 (tetraMePhen)PF 6 (diF(5-Me)ppy=2-(2,4-difluorophenyl)-5-methylpyridine, tetraMePhen=3,4,7,8-tetramethyl-1,10-phenanthroline), Ru(II) photocatalyst such as Ru(bpy) 3 Cl 2 or Ru(bpy) 3 (PF 6 ) 2 or organic dyes like 9-mesityl-10-acridinium perchlorate or tetrafluoroborate, or 2,4,5,6-tetra-9H-carbazol-9-yl-1,3-benzenedicarbonitrile, 9-fluorenone and 9,10-phenanthrenequinone.
Suitable nickel catalysts include, but are not limited to, bis(1,5-cyclooctadiene)nickel (0), nickel(II) chloride, nickel(II) bromide, nickel(II) iodide under their anhydrous or hydrate forms or as dimethoxyethane complexes, nickel(II) acetylacetonate, nickel(II) nitrate hexahydrate. These nickel catalysts can be used in combination with bipyridine ligand such as 2,2′-bipyridine, 4,4′-di-tert-butyl-2,2′-bipyridine, 4,4′-dimethoxy-2,2′-bipyridine, 4,4′-dimethyl-2,2′-bipyridine or phenantroline such as 1,10-phenanthroline, 4,7-dimethyl-1,10-phenantroline, 4,7-dimethoxy-1,10-phenantroline or diamines such as N,N,N′,N′-tetramethylethylenediamine or dione such as tetramethylheptanedione.
The processes described herein may be performed at temperature ranging from −105° C. to 250° C., preferably from −78° C. to 185° C.
The reaction time varies as a function of the scale of the reaction and of the reaction temperature, but is generally between a few minutes and 48 hours.
The processes described herein are generally performed under standard pressure. However, it is also possible to work under elevated or reduced pressure.
In the processes described herein, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the starting materials in a relatively large excess.
Processes for the Preparation of Compounds of Formula (I)
Process A
A compound of formula (I-a-1), wherein Q, L, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein
A is O or methylene, T is hydrogen, m is 1 or 2, may be prepared either when W is hydrogen, by treating the compound of formula (4) with a dehydrating agent, optionally in the presence of a base to obtain directly the compound of formula (I-a-1) or when W is an aminoprotecting group preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, by treating the compound of formula (4) with a dehydrating agent, optionally in the presence of a base, and then performing a deprotection step to obtain the compound of formula (I-a-1) as shown in scheme 1.
The compound of formula (I-a-1) may be obtained by treating a compound of formula (4a) with a dehydrating agent such as POCl 3 , P 2 O 5 or triflic anhydride, optionally in the presence of a base. Such methods to form oxadiazine rings are known and have been described in the literature (J. Med. Chem. 2017, 60, 2383-2400). The reaction may be performed in any customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichlorethane, ethers, such as diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; alcohols, such as ethanol or isopropanol.
When W represents an amino protecting group, step 3 is followed by an additional deprotection step using reaction conditions described in the literature (Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example a tert-butoxycarbonyl group can be removed in acidic medium such as hydrochloric acid or trifluoroacetic acid.
The compound of formula (I-a-1) may be obtained by treating a compound of formula (4b) with trifluoromethanesulfonic anhydride and triphenylphosphine oxide in any inert organic solvents such as dichloromethane (see e.g. J. Org. Chem. 2013, 78, 14, 7356-7361).
Compound of formula (4a), wherein Q, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and A is O, may be obtained by first reacting a compound of formula (1), wherein Q, R 7 , R 8 and R 9 are defined as above and
U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy, with an amine of formula (2), wherein m, L, R 3 , R 4 , R 5 and R 6 are defined as above and W is hydrogen or an aminoprotecting group, preferably tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, or a salt thereof, to provide a compound of formula (3), wherein m, W, Q, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, from which the phthalimide group of compound (3), wherein m, W, Q, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, is removed to provide a compound of formula (4a).
›DETAILED DESCRIPTION · 25 of 78
Reaction conditions to remove a phthalimide group are well known and have been reported in the literature (Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 1012-1014).
Compound of formula (4b), wherein Q, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and A is methylene, may be obtained by reacting a compound of formula (4a), wherein Q, L, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, with a base such as potassium tert-butoxide or triethylamine and trityl chloride. The reaction may be performed in any customary inert organic solvents such as dichloromethane.
Compounds of formula (1) can be prepared by one or more processes described herein (see processes J, K, L and M)
Amines of formula (2) may be prepared by process O described herein.
Compounds of formula (1) wherein U 1 is a hydroxyl group can be reacted with an amine of formula (2) in the presence of a condensing reagent by means of methods described in the literature (e.g. Tetrahedron 2005, 61, 10827-10852). Examples of suitable condensing reagents include, but are not limited to, halogenating reagents (e.g. phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride), dehydrating reagents (e.g. ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride), carbodiimides (e.g. N,N′-dicyclohexylcarbodiimide (DCC)) or other customary condensing (or peptide coupling) reagents (e.g. phosphorous pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), N,N′-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloro-methane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bromo-tripyrrolidinophosphoniumhexafluorophosphate or propanephosphonic anhydride (T3P).
Compounds of formula (1) wherein U 1 is a halogen atom can be reacted with an amine of formula (2) in the presence of an acid scavenger by means of well-known methods. Suitable acid scavengers include any inorganic and organic bases, as described herein, which are customary for such reactions. Preference is given to alkali metal carbonates, alkaline earth metal acetates, tertiary amines or aromatic bases.
Compounds of formula (1) wherein U 1 is a C 1 -C 6 -alkoxy group can be reacted with an excess of amine of formula (2), optionally in the presence of a Lewis acid such as trimethylaluminum.
Process B
A compound of formula (I-a-1), wherein Q, L, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein
A is O, T is hydrogen, m is 1 or 2, may be prepared by reacting a compound of formula (7), wherein m, A, L, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, X 1 is halogen, preferably bromo, with a compound of formula (8), wherein Q is defined as above, in the presence of a base (e.g. organic or inorganic base) and optionally in the presence of a suitable copper salt or complex, followed by a deprotection step if W is tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, as shown in scheme 2.
Compounds of formula (7), wherein m, A, L, T, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, may be prepared by reacting a compound of formula (5), wherein X 1 , R 7 , R 8 and R 9 are defined as above and
U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy, with an amine of formula (2), wherein m, A, L, W, R 3 , R 4 , R 5 and R 6 are defined as above, or a salt thereof, to obtain a compound of formula (6a), wherein m, A, L, T, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, and G is phthalimido, or a salt thereof, then removing the phthalimide group of compound (6a) to obtain a compound of formula (6b), wherein m, A, L, T, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, and G is hydrogen, which is then, when W is hydrogen, directly treated with a dehydrating agent, optionally in the presence of a base to obtain directly the compound of formula (7), or which is then, when W is an aminoprotecting group, treated with a dehydrating agent, optionally in the presence of a base, and finally deprotected to obtain the compound of formula (7), under the same conditions as described herein for process A.
The reaction of compound of formula (7) with a compound of formula (8) may be performed in the presence of a transition metal catalyst such as a copper salt or complex, and if appropriate in the presence of a ligand as described herein.
Compounds of formula (5) are commercially available or may be prepared by process J described herein.
Compounds of formula (8) are commercially available or may be obtained by conversion or derivatization of another compound of formula (8) in accordance to well-known methods.
Process C
A compound of formula (I-a-1), wherein Q, L, R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein
m is 1 or 2, A is O, T is hydrogen, R 5 is hydrogen, hydroxyl or C 1 -C 6 -alkoxy, may be prepared by adding a reducing agent under acidic conditions to a compound of formula (12), wherein m, Q, L, T, R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are defined as above, to provide a compound of formula (I-a-1), as shown in scheme 3.
Compounds of formula (12) may be cyclized under acidic conditions in the presence of a reducing agent such as sodium cyanoborohydride to provide a compound of formula (I-a-1). Reaction conditions to form oxadiazine rings with this methodology are known and have been described in the literature (Heterocycles 2016, 92, 2166-2200).
Compound of formula (12), wherein m, Q, T, L, R 3 , R 4 , R 6 , R 7 , R 8 and R 9 are defined as above, may be obtained by reacting a compound of formula (10), wherein Q, T, R 7 , R 8 and R 9 are defined as above, with a compound of formula (11), wherein m, L, R 3 , R 4 and R 6 are defined as above, in the presence of a base. Suitable bases are alkali metal hydrides such as sodium hydride, alkali metal carbonates such as potassium carbonate, alkali metal hydroxides such as potassium hydroxide, or phosphazene bases such as BEMP as described in the literature (Heterocycles 2016, 92, 2166-2200).
›DETAILED DESCRIPTION · 26 of 78
Compound of formula (10), wherein Q, R 7 , R 8 and R 9 are defined as above, may be obtained by reacting a compound of formula (9), wherein Q, R 7 , R 8 and R 9 are defined as above, with hydroxylamine or a salt thereof. Reaction conditions to perform such transformations are known and have been reported in the literature (WO2010/138600).
Compounds of formula (9) may be prepared by process N described herein.
Compounds of formula (11) are either commercially available or may be prepared by processes described in the literature (Eur. J. Med. Chem. 2014, 84, 302, Eur. J. Med. Chem. 2015, 100, 18-23, WO2017/031325).
Process D
A compound of formula (I-a-1), wherein Q, L, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and
m is 1 or 2, A is O, T is hydrogen, may be prepared by first reacting a compound of formula (1), wherein Q, R 7 , R 8 and R 9 are defined as above and U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy, with an amine of formula (13), wherein m, L, R 3 , R 4 , R 5 and R 6 are defined as above and E 1 is hydroxyl or halogen, W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, to provide a compound of formula (14), wherein m, E 1 , L, W, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and Q are defined as above, under the conditions as described in process A, which is then treated with a dehydrating agent followed by hydroxylamine (15) to form a compound of formula (16), wherein m, E 1 , L, Q, W, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and E 2 is hydroxyl, which is finally converted into a compound of formula (I-a-1) as shown in scheme 4.
When E 1 is hydroxyl a compound of formula (16) is converted into a compound of formula (I-a-1) using Mitsunobu reaction conditions known by the skilled person of the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and reference herein). When E 1 is halogen a compound of formula (16) is converted into a compound of formula (I-a-1) in the presence of a base.
When W represents an amino protecting group, Step 3 is followed by an additional deprotection step using reaction conditions described in the literature (Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194) to provide a compound of formula (I-a-1).
Aminoalcohols of formula (13-a, E 1 =hydroxyl) are commercially available or may be producible by methods described in the literature (Molecules, 9 (6), 405-426; 2004; WO2017203474). Compounds of formula (13-b, E 1 =halogen) can be obtained from the corresponding aminoalcohol by well-known methods.
Process E
A compound of formula (I-a-1), wherein Q, L, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and
m is 1 or 2, A is O, T is hydrogen, may be prepared by reacting a compound of formula (5), wherein R 7 , R 8 and R 9 are defined as above and X 1 is halogen, U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy, with an amine of formula (13), wherein m, L, R 3 , R 4 , R 5 and R 6 are defined as above and E 1 is hydroxyl or halogen, W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, to provide a compound of formula (17), wherein m, E 1 , L, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, under the conditions described in process A, which is then treated with a dehydrating agent followed by hydroxylamine (15) to form a compound of formula (18), wherein m, E 1 , L, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, which in the following is converted into compound of formula (7), wherein m, A, L, W, X 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, which is finally reacted with a compound of formula (8), wherein Q is defined as above, in the presence of a base (e.g. organic or inorganic base) and optionally in the presence of a suitable copper salt or complex to provide a compound of formula (I-a-1) as shown in scheme 5.
Step 3 is performed under Mitsunobu reaction conditions when E1 is hydroxy (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and reference herein), and in the presence of a base, when E 1 is halogen.
When W represents an amino protecting group, Step 3 is followed by an additional deprotection step using reaction conditions described in the literature (Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194) to provide a compound of formula (I-a-1).
Compounds of formula (5) are commercially available or may be prepared by process J described herein.
Process F
A compound of formula (I-a-2), wherein Q, R 3 , R 4 , R 5 , R 7 , R 8 and R 9 are defined as above and
A is O, L is a direct bond, T is hydrogen, m is 2, R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl or 5- or 6-membered heteroaryl,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted with one to four R 6S substituents, wherein R 6S is defined as above,
may be prepared by treating a compound of formula (9), wherein Q, R 7 , R 8 and R 9 are defined as above, with a hydroxylamine derivative (19), wherein R 3 , R 4 and R 5 are defined as above, in the presence of a suitable base as described herein to provide compound of formula (20), wherein Q, R 3 , R 4 , R 5 , R 7 , R 8 and R 9 are defined as above, which is then reacted with a reagent of formula (21), wherein R 6 is defined as above and X 2 is halogen, in the presence of a metal catalyst and a suitable ligand to provide a compound of formula (22), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above, which in the following is treated with iodine and phenylsilane to form a compound of formula (I-a-2) as shown in scheme 6.
Reagents of formula (19) are either commercially available or producible by processes described in the literature (WO2010/099279).
›DETAILED DESCRIPTION · 27 of 78
Reagents of formula (21) are commercially available or can be prepared by known processes. Compounds of formula (9) may be prepared by process N described herein.
Process G
A compound of formula (I-a-3), wherein L, Q, R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and
A is CR 2A R R2B ,
wherein R 2A and R 2B are independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or R 2A and R 2B form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
T is hydrogen, m is 0, may be prepared by reacting a compound of formula (1), wherein Q, R 7 , R 8 and R 9 are defined as above and U 1 is hydroxy or halogen, with a diamine of formula (23), wherein L, R 2A , R 2B , R 5 , R 6 are defined as above, as shown in scheme 7.
Process G can be performed in the presence of a dehydrating agent such as POCl 3 .
Diamines of formula (23) are commercially available or can be prepared by methods described in the literature (Eur. J. Med. Chem 1990, 25(1), 35-44; J. Org. Chem 2012, 77(9), 4375-4384; WO2009/003867).
Process H
A compound of formula (I-a), wherein m, L, Q, R 3 , R 4 , R 5 , R 6 , R 8 and R 9 are defined as above and
T is H, R 7a is hydrogen or chloro, may be converted by means of methods described in the literature into the corresponding compounds of formula (I-b), wherein m, L, Q, T, R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are defined as above and R 7b is hydrogen, iodo, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyl sulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 20 ) 2 or —C(═O)(OR 21 ),
Wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted as defined above,
or into a compound of formula (I-c), wherein m, L, Q, T, R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are defined as above and R 7c is nitro, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, —C(═NR 21 )R 22 , —C(═O)N(R 26 ) 2 , —S(═O)(═NR 28 )R 29 or —S(═O) 2 N(R 27 ) 2 ,
wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl and C 3 -C 8 -cycloalkylsulfonyl are optionally substituted as defined above,
in one or more steps as shown in scheme 8.
In process H, R 20 , R 21 , R 22 , R 25 , R 26 , R 27 , R 28 and R 29 are as disclosed herein.
Non-limiting examples of conversions performed in accordance with scheme 8 are provided below.
A compound of formula (I-a), wherein R 7a is halogen, can be converted into a compound of formula (I-b) wherein R 7b is cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 20 ) 2 or —C(═O)(OR 25 ) by transition metal catalyzed or metallo-photoredox catalyzed processes as described herein.
A compound of formula (I-b), wherein R 7b is C 2 -C 6 -alkenyl substituted by a C 1 -C 3 -alkoxy, can be converted into a compound of formula (I-c), wherein R 7c is C 1 -C 6 -alkylcarbonyl, by means of methods described in the literature (e.g. J. Org. Chem. 1993, 55, 3114).
The compound of formula (I-c), wherein R 7c is C 1 -C 6 -alkylcarbonyl, can be further converted into a compound of formula (I-c), wherein R 7c is —C(═NR 21 )—C 1 -C 6 -alkyl, by methods described in the literature (e.g. Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 655, 661, 667).
A compound of formula (I-c), wherein R 7c is C 1 -C 6 -alkylcarbonyl, can be further converted into a compound of formula (I-c), wherein R 7c is C 1 -C 6 -hydroxyalkyl, by classical functional group interconversion such as reductions of ketones to alcohols in the presence of NaBH 4 in methanol.
A compound of formula (I-c), wherein R 7c is C 1 -C 6 -hydroxyalkyl, can be further converted into a compound (I-c), wherein R 7c is C 1 -C 6 -fluoroalkyl, in the presence of a fluorinating agent. Non-limitative examples of fluorinating agents include sulfur fluorides such as sulfur tetrafluoride, diethyl-aminosulfurtrifluoride, morpholinosulfur trifluoride, bis(2-methoxyethyl)aminosulfur trifluoride, 2,2-difluoro-1,3-dimethylimidazolidine or 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride.
A compound of formula (I-a) can be prepared by one or more of the processes herein described.
›DETAILED DESCRIPTION · 28 of 78
Process I
A compound of formula (I-d), wherein m, L, Q, R 3 , R 4 , R 5 , R 6 and R 9 are defined as above and
R 7 is halogen, R 8a is halogen, T is H, may be converted by means of methods described in the literature to the corresponding compound of formula (I-e), wherein m, L, Q, T, R 3 , R 4 , R 5 , R 6 , R 7 and R 9 are defined as above and R 8b is cyano, amino, mercapto, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl, —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted as defined above,
in one or more steps as shown in scheme 9.
In process I, R 30 and R 31 are defined as above.
Non-limiting examples of conversions performed in accordance with scheme 12 are provided below.
A compound of formula (I-d), wherein R 8a is halogen, can be converted in a compound of formula (I-e), wherein R 8b is cyano, amino, mercapto, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl, —N(R 30 ) 2 or —SR 31 , in the presence of a base and optionally in the presence of a transition metal catalyst such as a metal salt or complex described herein, and if appropriate in the presence of a ligand in analogy to processes described in the literature (WO2008/151211; WO2000/050401; J. Org. Chem. 2005, 70, 1432-1437).
A compound of formula (I-e), wherein R 8b is —SR 31 , can be further converted into a compound of formula (I-a-8), wherein R 8b is —S(═O)R 31 or —S(═O) 2 R 31 , by reacting the starting compound of formula (I-a-8) with an oxidant such as hydrogen peroxide.
A compound of formula (I-d) can be prepared by one or more of the processes herein described.
Processes for the Preparation of a Compound of Formula (1)
A compound of formula (1) may be directly obtained by performing process J described below or may be obtained by conversion or derivatization of another compound of formula (1) prepared in accordance with the processes described herein. Compounds of formula (1-a)-(1-h) are various subsets of formula (1).
Process J
A compound of formula (1-a), wherein Q and R 9 are as defined above and
R 7 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy, R 8 is hydrogen, halogen or C 1 -C 6 -alkyl, U 1 is hydroxyl or C 1 -C 6 -alkoxy, may be prepared by reacting a compound of formula (5), wherein U 1 , R 7 , R 8 and R 9 are as defined above and X 1 is halogen, with a reagent of formula (8), wherein Q is as defined above, in the presence of a base and in the presence of suitable transition metal catalyst salts or complexes, if appropriate in the presence of a ligand as shown in scheme 10.
Compounds of formula (5) can be prepared by treating compounds of formula (24), wherein X 1 , R 7 , R 8 and R 9 are as defined above, with a base (e.g. nBuLi or LDA) and carbon dioxide or a reagent of formula (25), wherein
E 3 is halogen, cyano, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxycarbonyloxy, U 2 is C 1 -C 6 -alkoxy.
Compounds of formula (1-a), wherein U 1 is C 1 -C 6 -alkoxy, can be converted to compounds of formula (1-a), wherein U 1 is hydroxyl, by well-known functional group interconversion methods, for example by hydrolysis of an ester group with LiOH in THF/water.
Compounds of formula (1-a), wherein U 1 is hydroxyl, can be converted to compounds of formula (1-a), wherein U 1 is halogen, in the presence of halogenating agents by well-known methods. Suitable halogenating reagents include, but are not limited to, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride.
Compounds of formula (24) and (25) are commercially available.
Compounds of formula (8) are commercially available or may be obtained by conversion or derivatization of another compound of formula (8) in accordance to well-known methods.
Process K
A compound of formula (1-b), wherein Q, R 8 and R 9 are defined as above and
U 1 is C 1 -C 6 -alkoxy, R 7a is hydrogen or chloro, may be converted by means of known methods to the corresponding compounds of formula (1-c), wherein U 1 , Q, R 8 and R 9 are defined as above and R 7b is hydrogen, iodo, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 20 ) 2 or —C(═O)(OR 25 ),
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted as defined above,
›DETAILED DESCRIPTION · 29 of 78
or a compound of formula (1-d), wherein U 1 , Q, R 8 and R 9 are defined as above and R 7c is nitro, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, —C(═NR 21 )R 22 , —C(═O)N(R 26 ) 2 , —S(═O)(═NR 25 )R 29 or —S(═O) 2 N(R 27 ) 2 ,
wherein C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -fluoroalkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl and C 3 -C 8 -cycloalkylsulfonyl are optionally substituted as defined above,
in one or more steps as shown in scheme 11.
In process K, R 20 , R 21 , R 22 , R 25 , R 26 , R 27 , R 28 and R 29 are defined as above.
Non-limiting examples of conversion may be performed in accordance the description provided in process H.
The obtained compound of formula (1-c) and (1-d), wherein U 1 is C 1 -C 6 -alkoxy, can then be converted into compounds of formula (1-c) and (1-d), wherein U 1 is hydroxyl or halogen.
Examples of such conversion are described below.
Compounds of formula (1-b), (1-c) and (1-d), wherein U 1 is C 1 -C 6 -alkoxy, can be converted to compounds of formula (1-b), (1-c) and (1-d), wherein U 1 is hydroxyl, by well-known functional group interconversion methods, for example by hydrolysis of an ester group with LiOH in THF/water.
Compounds of formula (1-b), (1-c) and (1-d), wherein U 1 is hydroxyl, can then be further converted to compounds of formula (1-b), (1-c) and (1-d), wherein U 1 is halogen, in the presence of halogenating agents by well-known methods. Suitable halogenating reagents include, but are not limited to, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride.
Compounds of formula (1-b) can be prepared by one or more of the processes described herein.
Process L
A compound of formula (1-e), wherein Q, R 7 and R 9 are defined as above and
U 1 is C 1 -C 6 -alkoxy, may be converted by means of methods described in the literature to the corresponding compound of formula (1-f), wherein U 1 , Q, R 7 and R 9 are defined as above and R 8a is halogen or C 1 -C 6 -alkyl, or into a compound of formula (1-g), wherein U 1 , Q, R 7 and R 9 are defined as above and R 8b is cyano, amino, mercapto, hydroxyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl, —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted as defined above,
in one or more steps as shown in scheme 12.
In process L R 30 and R 31 are defined as above. Non-limiting examples of conversion may be performed in accordance the description provided in process I.
The obtained compound of formula (1-f) and (1-g), wherein U 1 is C 1 -C 6 -alkoxy can then be converted into compounds of formula (1-f) and (1-g), wherein U 1 is hydroxyl or halogen.
Compounds of formula (1-e), (1-f) and (1-g), wherein U 1 is C 1 -C 6 -alkoxy, can be converted into compounds of formula (1-e), (1-f) and (1-g), wherein U 1 is hydroxyl, by well-known functional group interconversion methods, for example by hydrolysis of an ester group with LiOH in THF/water.
Compounds of formula (1-e), (1-f) and (1-g), wherein U 1 is hydroxyl, can then be further converted into compounds of formula (1-e), (1-f) and (1-g), wherein U 1 is halogen in the presence of halogenating agents by well-known methods. Suitable halogenating reagents include, but are not limited to, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride.
Compounds (1-e) can be prepared by one or more of the processes described herein.
Process M
A compound of formula (1-h), wherein Q is defined as above and
R 7 is hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy or C 1 -C 6 -haloalkoxy, R 8 is hydrogen, halogen or C 1 -C 6 -alkyl, R 9 is halogen, U 1 is hydroxy or C 1 -C 6 -alkoxy, may be prepared by reacting a compound of formula (28), wherein Q, R 7 , R 8 and R 9 are defined as above, with carbon dioxide or a reagent of formula (25), wherein E 3 is halogen, cyano, C 1 -C 6 -alkoxy or C 1 -C 6 -alkoxycarbonyloxy, U 2 is C 1 -C 6 -alkoxy, as shown in scheme 13.
Compounds of formula (28) may be prepared by reacting compounds of formula (26), wherein R 7 , R 8 and R 9 are defined as above, with a reagent of formula (27), wherein
E 4 is a group of formula # —B(OR 46 ) 2
wherein # is the attachment to Q. R 46 is hydrogen or C 1 -C 6 -alkyl or both R 46 form together a —C(CH 3 ) 2 —C(CH 3 ) 2 -bridge,
in the presence of a base and in the presence of suitable transition metal catalyst salts or complexes, and if appropriate in the presence of a ligand as described herein in analogy to processes described in the literature (WO2009/044160; WO2016/040222).
The compounds of formula (1-h), wherein U 1 is C 1 -C 6 -alkoxy may be converted into compound of formula (1-h), wherein U 1 is hydroxyl or halogen, using the same conditions as described in process J.
›DETAILED DESCRIPTION · 30 of 78
Starting materials of formula (25), (26) and (27) are commercially available.
Process for the Preparation of Compound of Formula (9)
A compound of formula (9) may be obtained by performing process N described below or may be obtained by conversion or derivatization of another compound of formula (9-a) prepared in accordance with the processes described herein. Compounds of formula (9-a) and (9-b) are various subsets of formula (9).
Process N
A compound of formula (9-a), wherein Q and R 9 are defined as above and
X 3 is halogen, R 8 is hydrogen or C 1 -C 6 -alkyl, may be converted by means of methods described in the literature to the corresponding compounds (9-b), wherein Q, X 2 , R 8 and R 9 are defined as above and R 7 is halogen, hydroxyl, mercapto, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy or —N(R 20 ) 2 ,
Wherein C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy and 3- to 7-membered heterocyclyloxy are optionally substituted as defined above,
in one or more steps as shown in scheme 14.
In process N, R 20 is defined as above.
Compounds of formula (29) are commercially available or producible by processes described in the literature (WO2019/087129).
A compound of formula (29) may be converted according to Step 1 of Process N into a compound of formula (9-a) in the presence of a reagent of formula (8), wherein Q is defined as above, and a base (e.g. organic or inorganic base) as described herein.
Non-limiting examples of conversion of (9-a) to (9-b) may be performed in accordance to scheme 14.
For example, a compound of formula (9-a) can be further converted in a compound of formula (9-b), wherein R 7 is hydroxyl, mercapto, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy or —N(R 21 ) 2 , by treating the reacting compound of formula (9-a) with an oxygen, a sulfur or an amino based nucleophile.
A compound of formula (9-a) can be converted into a compound of formula (9-b), wherein R 7 is cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy or 3- to 7-membered heterocyclyloxy, by transition metal catalyzed or metallo-photoredox catalyzed processes as described herein.
Compounds of formula (8) are commercially available or may be obtained by conversion or derivatization of another compound of formula (8) in accordance to well-known methods.
Process for the Preparation of Compounds of Formula (2), (13-a) and (13-b)
Process O
A compound of formula (30) may be converted by means of methods described in the literature to the corresponding compounds (13-a) and (2) as shown in scheme 14.
The amino function of compound (30) may be first protected (W=tert-butoxycarbonyl, benzyl, allyl or 4-methoxyphenyl)methyl) in accordance with known methods to provide a compound of formula (13-a) (Greene's Protective Groups in organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194).
Subsequently, the compound of formula (13-a) may be converted by Step 2 of Process 0 into a compound of formula (2) using classical Mitsunobu reaction conditions known by the skilled person of the art (Strategic Applications of Named Reactions in Organic Synthesis; Laszlo Kurti, Barbara Czako; Elsevier; 2005; 294-295 and reference herein).
Compounds of formula (13-a) wherein E 1 is a hydroxyl may be converted to compounds of formula (13-b) wherein E 1 is a halogen in the presence of halogenating agents by well-known methods. Suitable halogenating reagents include, but are not limited to, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride.
Aminoalcohols of formula (30) are commercially available or may be producible by methods described in the literature (Molecules, 9 (6), 405-426; 2004, WO2017203474).
Process P
A compound of formula (I-a-1), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein
A is O,
T is hydrogen,
L is a direct bond,
m is 1 or 2,
may be prepared by a process comprising the steps of first placing a compound of formula (31) under oxidative condition to provide compound (32), which is then treated with a compound of formula (33a), wherein
R 6A is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted as described above,
under acidic conditions to form a compound of formula (I-a-1)
or
which is then treated with an halogenating reagent such as SOCl 2 and a compound of formula (33b), wherein
R 6B is C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclylsulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroarylsulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl,
›DETAILED DESCRIPTION · 31 of 78
wherein C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted as described above,
to form compounds of formula (I-a-1)
as shown in scheme 16.
The compound of formula (32) can be reacted with a compound of formula (33a) under acidic conditions to provide a compound of formula (I-a-1). Reaction conditions to form oxadiazine rings with this methodology are known and have been described in the literature (WO2017/031325).
Compounds of formula (32) can be obtained from a compound of formula (31) under oxidative conditions, for example in the presence of osmium trioxide and sodium periodate.
Compounds of formula (31) may be prepared by process F from a compound of formula (9) described herein.
Process Q
A compound of formula (I-i), wherein m, L, Q, T, R 3 , R 4 , R 5 , R 7 , R 8 and R 9 are defined as above and
R 6C is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxinyl,
wherein indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxinyl are optionally substituted with one or two R 6SC substituents, wherein R 6SC is halogen,
may be converted by means of methods described in the literature to the corresponding compound of formula (I-j), wherein m, L, Q, T, R 3 , R 4 , R 5 , R 7 , R 8 and R 9 are defined as above and R 6D is indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl or dihydrobenzodioxinyl,
wherein indanyl, 1,2,3,4-tetrahydronaphthalenyl, phenyl, naphthyl, dihydrobenzofuranyl and dihydrobenzodioxinyl are optionally substituted with one or two R 61D substituents, wherein R 6SD is independently selected from the group consisting cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 21 ) 2 or —C(═O)(OR 21 )
in one or more steps as shown in scheme 17.
In process Q, R 21 , R 21 , R 22 , R 25 , R 26 , R 27 , R 28 and R 29 are as disclosed herein.
Non-limiting examples of conversions performed in accordance with scheme 17 are provided below.
A compound of formula (I-i), wherein R 6SC is halogen, can be converted into a compound of formula (I-j) wherein R 6SD is cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 20 ) 2 or —C(═O)(OR 25 ) by transition metal catalyzed or metallo-photoredox catalyzed processes as described herein by methods known to the person skilled in the art.
A compound of formula (I-i) can be prepared by one or more of the processes herein described.
Process R
A compound of formula (I-a-1), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein
A is O, T is hydrogen, L is a direct bond, m is 1 or 2, a compound of formula (I-a-3), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein A is CR 1 R 2 T is hydrogen, L is a direct bond, m is 1 or 2, a compound of formula (I-a-4), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein A is C(═O) T is hydrogen, L is a direct bond, m is 1 or 2, or a compound of formula (I-a-5), wherein Q, R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are defined as above and wherein A is S(═O) 2 T is hydrogen, L is a direct bond, m is 1 or 2, can be prepared by a process comprising the steps of first treating a compound of formula (9), wherein Q, R 7 , R 8 and R 9 are defined as above, with an alkoxide to provide compound of formula (34), wherein Q, R 7 , R 8 and R 9 are defined as above and Y is C 1 -C 6 -alkyl, which is then reacted with an amine of formula (35a-1), (35a-2), (35a-3) or (35a-4) or a salt thereof respectively, wherein m, L, R 3 , R 4 , R 5 and R 6 are defined as above and E 1 is NH 2 —O— in compound of formula (35a-1), E 1 is NH 2 —CR 44 R 45 — in compound of formula (35a-2),
wherein R 44 and R 45 are hydrogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl or C 6 -C 14 -aryl, or R 44 and R 45 form together with the carbon atom to which they are attached, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
E 1 is NH 2 —C(═O)— in compound of formula (35a-3), E 1 is NH 2 —S(═O) 2 — in compound of formula (35a-4), and W is hydrogen or an amino protecting group to obtain a compound of formula (I-a-1), (I-a-3), (I-a-4) or (I-a-5) respectively, as shown in scheme 18.
The compound of formula (34) can be obtained by treating a compound of formula (9) with an alkoxide such as sodium methanolate or sodium ethanolate according to methods described in the literature (Heterocycles, 34, 1992, 929-935).
The compound of formula (34) is treated with a compound of formula (35-a-1), (35-a-2), (35-a-3) or (35-a-4) and cyclized under acidic conditions to form respectively a compound of formula (I-a-1), (I-a-3), (I-a-4) or (I-a-5). Reaction conditions to perform such transformations based on this methodology have been described in the literature (Heterocycles 2016, 92, 2166-2200).
Amines of formula (35-a-1), (35-a-2), (35-a-3) or (35-a-4) are either commercially available, or may be prepared by methods described in the literature (Molecules, 9 (6), 405-426; 2004, WO2017/203474; J. Med. Chem 1985, 28, 694-698; J. Med. Chem 2006, 49, 4333-4343) and by Process 0 of this invention.
›DETAILED DESCRIPTION · 32 of 78
Intermediates
The present invention also relates to intermediates for the preparation of compounds of formula (I).
Thus, the present invention relates to compounds of formula (1):
wherein
U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 33 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
Thus, the present invention also relates to compounds of formula (1):
wherein
U 1 is hydroxyl, halogen or C 1 -C 6 -alkoxy,
R 7 is halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
›DETAILED DESCRIPTION · 34 of 78
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl 6- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
The present invention also relates to compounds of formula (2):
wherein
m is 1,
A is O,
R 3 and R 4 are independently hydrogen, halogen or C 1 -C 6 -alkyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
The present invention also relates to compounds of formula (3):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
›DETAILED DESCRIPTION · 35 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl, wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents, wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 36 of 78
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 37 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
The present invention also relates to compounds of formula (3):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 38 of 78
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 39 of 78
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 40 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , —C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
The present invention also relates to compounds of formula (4):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 41 of 78
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 5 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 42 of 78
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 43 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
W represents hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
The present invention also relates to compounds of formula (4):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 44 of 78
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclylsulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 45 of 78
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 ) 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 46 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
W represents hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl.
The present invention also relates to compounds of formula (6a) and (6b):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 47 of 78
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 48 of 78
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 49 of 78
The present invention also relates to compounds of formula (6a) and (6b):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 50 of 78
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 ) 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to together a C 3 -C 8 -cycloalkyl,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
›DETAILED DESCRIPTION · 51 of 78
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
The present invention also relates to compounds of formula (7):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
›DETAILED DESCRIPTION · 52 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
›DETAILED DESCRIPTION · 53 of 78
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
The present invention also relates to compounds of formula (7):
wherein
m is 1 or 2,
A is O,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 54 of 78
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
›DETAILED DESCRIPTION · 55 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are bound to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
The present invention also relates to compounds of formula (9):
wherein
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
›DETAILED DESCRIPTION · 56 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
›DETAILED DESCRIPTION · 57 of 78
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
provided that the compound of formula (9) is not:
The present invention also relates to compounds of formula (9):
wherein
Q is C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl, 7- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl,
wherein C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl, 7- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 58 of 78
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
R 7 is, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
›DETAILED DESCRIPTION · 59 of 78
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
The present invention also relates to compounds of formula (10):
wherein
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 60 of 78
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
›DETAILED DESCRIPTION · 61 of 78
provided that at least one of R 7 and R 8 is different from hydrogen.
The present invention also relates to compounds of formula (10):
wherein
Q is C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl, 7- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl,
wherein C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl, 7- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S , wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents,
and
wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 62 of 78
The present invention also relates to compounds of formula (12):
wherein
m is 1 or 2,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 )—, —C(═NR L8 )— or a group of formula
wherein
said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA ,
# is the point of attachment to the heterocyclyl-moiety,
## is the point of attachment to R 6 ,
L 1 is a direct bond or C 1 -C 6 -alkylene,
L 2 is a direct bond or C 1 -C 6 -alkylene,
E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , and wherein R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, and/or two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, L SC is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, and/or two L SC substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
›DETAILED DESCRIPTION · 63 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
›DETAILED DESCRIPTION · 64 of 78
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
›DETAILED DESCRIPTION · 65 of 78
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl.
The present invention also relates to compounds of formula (12):
wherein
m is 1 or 2
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
›DETAILED DESCRIPTION · 66 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom from a C 3 -C 8 -cycloalkyl, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
›DETAILED DESCRIPTION · 67 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or
two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl,
wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl,
and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy,
›DETAILED DESCRIPTION · 68 of 78
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl.
The present invention also relates to compounds of formula (13):
wherein
m is 1,
L is methylidene or difluoromethylidene,
R 3 and R 4 are hydrogen,
R 5 is hydrogen,
R 6 is phenyl,
wherein phenyl is optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
The present invention also relates to compounds of formula (14):
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 69 of 78
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
›DETAILED DESCRIPTION · 70 of 78
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
The present invention also relates to compounds of formula (14):
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom from a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
›DETAILED DESCRIPTION · 71 of 78
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are bound to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
›DETAILED DESCRIPTION · 72 of 78
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
The present invention also relates to compounds of formula (16):
wherein
m is 1 or 2,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl-ring and 3- to 7-membered heterocyclyl-ring are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
›DETAILED DESCRIPTION · 73 of 78
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 21 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 6 -C 14 -arylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -aryl-sulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halo-cycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents R 7Sc ,
›DETAILED DESCRIPTION · 74 of 78
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino in turn are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl,
or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═O)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
The present invention also relates to compounds of formula (16):
wherein
m is 1 or 2,
R 3 and R 4 are independently hydrogen, halogen, cyano, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, 3- to 14-membered heterocyclyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 14-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
or
R 3 and R 4 form together with the carbon atom to which they are attached to a carbonyl, a methylidene, a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring,
wherein C 3 -C 8 -cycloalkyl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 75 of 78
R 5 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl or —O—Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylcarbonyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl and —O—Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl,
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 76 of 78
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 20 ) 2 , —C(═NR 21 )R 22 , —NR 23 C(═O)R 24 , —C(═O)(OR 25 ), —C(═O)N(R 26 ) 2 , —S(═O) 2 N(R 27 ) 2 or —S(═O)(═NR 28 )R 29 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 7Sa substituents, wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 5- or 6-membered heteroaryloxy, 3- to 7-membered heterocyclyloxy are optionally substituted with one to three R 7Sc substituents, and wherein R 20 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl are optionally substituted with one to three substituents R 7Sa , and wherein C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are optionally substituted with one to three substituents R 7Sc ,
R 21 and R 22 are independently hydroxyl, amino, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino or di-(C 1 -C 6 -alkyl)amino,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, mono-(C 1 -C 6 -alkyl)amino and di-(C 1 -C 6 -alkyl)amino are optionally substituted with one to three R 7Sa substituents,
R 23 , R 24 , R 25 , R 26 , R 27 , R 28 and R 29 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -halo-alkyl and C 3 -C 8 -cycloalkyl,
wherein C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl are optionally substituted with one to three R 7Sa substituents, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three R 7Sc substituents,
wherein R 7Sa is independently cyano, hydroxyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 6 -C 14 -aryl or 3- to 7-membered heterocyclyl, R 7Sc is independently halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, or two R 7Sc substituents C 1 -C 6 -alkyl that are attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring,
R 8 is selected from the group consisting of hydrogen, halogen, cyano, isocyano, amino, nitro, hydroxyl, mercapto, carboxyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy, 5- to 14-membered heteroaryloxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —N(R 30 ) 2 , —SR 31 , —S(═O)R 31 or —S(═O) 2 R 31 ,
wherein C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are optionally substituted with one to three R 8Sa substituents, wherein C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 8 -cycloalkyloxy, C 6 -C 14 -aryloxy, 3- to 14-membered heterocyclyloxy and 5- to 14-membered heteroaryloxy are optionally substituted with one to three R 8Sc substituents, and wherein R 30 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -halo-alkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 77 of 78
wherein C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl are optionally substituted with one to five substituents Q S wherein Q S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, formyl, carboxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , —O—C(═O)R 33 , —NR 34 C(═O)R 35 , —C(═)N(R 36 ) 2 , C(═S)R 37 , —C(═S)N(R 38 ) 2 , —C(═NR 39 )R 40 , —C(═NOR 41 )R 42 and —N(R 43 ) 2 ,
The present invention also relates to compounds of formula (17):
wherein C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl and C 1 -C 3 -alkylsulfonyl are substituted with one substituent selected from the group consisting of C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl,
wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents,
wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is independently selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyl-oxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkyl-sulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 ,
wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
and wherein R 15 is independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl,
wherein said C 1 -C 6 -alkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl,
R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, wherein said C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl,
›DETAILED DESCRIPTION · 78 of 78
R 7 is hydrogen, halogen, cyano, isocyano, hydroxyl, mercapto, nitro, amino, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -hydroxyalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkynyloxy, C 2 -C 6 -haloalkynyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 2 -C 6 -alkenylsulfanyl, C 2 -C 6 -alkynylsulfanyl, C 6 -C 14 -arylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkylsulfinyl, C 6 -C 14 -arylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 6 -C 14 -arylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, C 3 -C 8 -cycloalkyloxy, C 6
›Tables in the description — 71
| wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | R 2A and R 2B are independently hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl, | wherein C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, and wherein C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, oxo, methylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | or R 2A and R 2B form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, |
| m is 0, 1 or 2, | T is hydrogen, hydroxyl, C 1 -C 6 -alkyl, —C(═O)R 11 , —C(═O)(OR 12 ), —C(═O)N(R 13 ) 2 , —S(═O)R 14 , —S(═O) 2 R 14 or —S(═O) 2 N(R 14 ) 2 , |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L SC is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L SC substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 alkenyl and C 2 -C 4 -haloalkenyl in turn are optionally substituted with one or two R 8Sa substituents, said C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclylin turn are optionally substituted with one or two R 8Sc substituents, | R 31 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynylin turn are optionally substituted with one or two R 8Sa substituents, said C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one or two R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of hydroxyl, carboxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one or two substituents C 1 -C 4 -alkyl substituents that may be identical or different, | R 8Sc is independently selected from the group consisting of halogen, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 3 -C 8 -cycloalkyl, |
| R 9 is hydrogen, fluoro, chloro or methyl, | Q is phenyl, naphthyl, C 5 -C 10 -carbocyclyl, 5- to 10-membered heterocyclyl or 5- to 10-membered heteroaryl, |
| wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 alkenyl and C 2 -C 4 haloalkenyl in turn are optionally substituted with one or two R 8Sa substituents, said C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, naphthyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one or two R 8Sc substituents, | R 31 is C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl, C 2 -C 4 -haloalkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -alkynyl and C 2 -C 4 -haloalkynyl in turn are optionally substituted with one or two R 8Sa substituents, said C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, phenyl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one or two R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of hydroxyl, carboxyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -haloalkoxycarbonyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 4 -alkylsulfanyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylsulfonyl and, 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one or two substituents C 1 -C 6 -alkyl substituents that may be identical or different, | R 8Sc is independently selected from the group consisting of halogen, oxo, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 3 -C 6 -cycloalkyl, |
| R 9 is hydrogen or halogen, | Q is phenyl, naphthyl, C 3 -C 10 -carbocyclyl, 5- to 10-membered heterocyclyl or 5- to 10-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| provided that the compound of formula (1) is not: | |||||
| 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoro- | 2267344-96-5 | ||||
| methoxy)phenoxy]isonicotinic acid | |||||
| ethyl 2-cyclopropyl-3-fluoro-5-[2-methoxy-4- | 2267344-95-4 | ||||
| (trifluoromethoxy)phenoxy]isonicotinate | |||||
| 5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2- | 2267344-69-2 | ||||
| (trifluoromethyl)isonicotinic acid | |||||
| 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2- | 2267343-60-0 | ||||
| (trifluoromethyl)isonicotinic acid | |||||
| ethyl 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2- | 2267343-59-7 | ||||
| (trifluoromethyl)isonicotinate | |||||
| 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy]- | 2267342-98-1 | ||||
| 2-(trifluoromethyl)isonicotinic acid | |||||
| ethyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy) | 2267342-97-0 | ||||
| phenoxy]-2-(trifluoromethyl)isonicotinate | |||||
| 2-nitro-5-(pyridin-3-yloxy)isonicotinic acid | 1984094-45-2 | ||||
| 2-chloro-5-(4-methoxyphenoxy)isonicotinic acid | 1215868-10-2 | ||||
| 2-methyl-5-(4-nitrophenoxy)isonicotinic acid | 52736-42-2 | ||||
| ethyl 2-methyl-5-(4-nitrophenoxy)isonicotinate | 52685-78-6 | ||||
| 3-methoxy-5-[2-methoxy-4-(trifluoromethoxy)phenoxy] | 2267345-11-7 | ||||
| pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy] | 2267344-46-5 | ||||
| pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[2-methyl-4-(trifluoromethoxy)phenoxy]-2- | 2597220-53-4 | ||||
| (trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[2-chloro-4-(trifluoromethoxy)phenoxy]-3-fluoro-2- | 2600737-76-4 | ||||
| (trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl- | 2451904-00-8 | ||||
| 2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[3-fluoro-2-methoxy-4-(trifluoromethoxy) | 2451905-95-4 | ||||
| phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]- | 2451906-03-7 | ||||
| 3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]- | 2451905-97-6 | ||||
| 3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 7 -C 12 -carbocyclyl 6- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| provided that the compound of formula (1) is not: | |||||
| 2-cyclopropyl-3-fluoro-5-[2-methoxy-4-(trifluoro- | 2267344-96-5 | ||||
| methoxy)phenoxy]isonicotinic acid | |||||
| ethyl 2-cyclopropyl-3-fluoro-5-[2-methoxy-4- | 2267344-95-4 | ||||
| (trifluoromethoxy)phenoxy]isonicotinate | |||||
| 5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-2- | 2267344-69-2 | ||||
| (trifluoromethyl)isonicotinic acid | |||||
| 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]-2- | 2267343-60-0 | ||||
| (trifluoromethyl)isonicotinic acid | |||||
| ethyl 3-fluoro-5-[4-(trifluoromethoxy)phenoxy]- | 2267343-59-7 | ||||
| 2-(trifluoromethyl)isonicotinate | |||||
| 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy) | 2267342-98-1 | ||||
| phenoxy]-2-(trifluoromethyl)isonicotinic acid | |||||
| ethyl 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy) | 2267342-97-0 | ||||
| phenoxy]-2-(trifluoromethyl)isonicotinate | |||||
| 2-nitro-5-(pyridin-3-yloxy)isonicotinic acid | 1984094-45-2 | ||||
| 2-chloro-5-(4-methoxyphenoxy)isonicotinic acid | 1215868-10-2 | ||||
| 2-methyl-5-(4-nitrophenoxy)isonicotinic acid | 52736-42-2 | ||||
| ethyl 2-methyl-5-(4-nitrophenoxy)isonicotinate | 52685-78-6 | ||||
| 3-methoxy-5-[2-methoxy-4-(trifluoromethoxy) | 2267345-11-7 | ||||
| phenoxy]pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[2-methoxy-4-(trifluoromethoxy)phenoxy] | 2267344-46-5 | ||||
| pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[2-methyl-4-(trifluoromethoxy)phenoxy]- | 2597220-53-4 | ||||
| 2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[2-chloro-4-(trifluoromethoxy)phenoxy]-3-fluoro- | 2600737-76-4 | ||||
| 2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[2-methoxy-4-(trifluoromethoxy)phenoxy]-3-methyl- | 2451904-00-8 | ||||
| 2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 3-fluoro-5-[3-fluoro-2-methoxy-4-(trifluoromethoxy) | 2451905-95-4 | ||||
| phenoxy]-2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]- | 2451906-03-7 | ||||
| 3-methyl-2-(trifluoromethyl)pyridine-4-carboxylic acid | |||||
| 5-[3-fluoro-2-methoxy-4-(trifluoromethoxy)phenoxy]- | 2451905-97-6 | ||||
| 3-methoxy-2-(trifluoromethyl)pyridine-4-carboxylic |
| or | R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 )—, —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxycarbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L SC is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L SC substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to four R 6S substituents, | wherein C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl and 3- to 14-membered heterocyclylsulfonyl are optionally substituted with one to four R 6S substituents, wherein R 6S is selected from the group consisting of halogen, cyano, isocyano, nitro, hydroxyl, mercapto, pentafluorosulfanyl, oxo, methylidene, halomethylidene, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 3 -C 8 -cycloalkyl sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 3 -C 8 -cycloalkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl, 3- to 7-membered heterocyclyl, —N(R 15 ) 2 , —O(C═O)R 16 , —C(═O)R 16 , —C(═O)(OR 17 ), —C(═O)N(R 18 ) 2 , —S(═O) 2 N(R 19 ) 2 , —O—Si(C 1 -C 6 -alkyl) 3 or —Si(C 1 -C 6 -alkyl) 3 , | wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, | and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, | R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, | wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, |
| W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, | provided that the compound of formula (2) is not: | |||||
| 2-(2-amino-2-phenylethoxy)-1H-isoindole-1,3(2H)- | 1640226-54-5 | |||||
| dione | ||||||
| 2-{[rac-(1R,2R)-1-amino-1-(4-chlorophenyl)propan- | 2085782-61-0 | |||||
| 2-yl]oxy}-1H-isoindole-1,3(2H)-dione | ||||||
| 2-{[rac-(1S,2S)-1-amino-1-(4-chlorophenyl)propan-2- | 2085782-62-1 | |||||
| yl]oxy}-1H-isoindole-1,3(2H)-dione hydrochloride | ||||||
| (1:1) | ||||||
| 2-{[1-amino-1-(4-fluorophenyl)-2-methylpropan-2- | 1227082-96-3 | |||||
| yl]oxy}-1H-isoindole-1,3(2H)-dione | ||||||
| tert-butyl {(1RS)-2-[(1,3-dioxo-1,3-dihydro-2H- | 2102206-02-8 | |||||
| isoindol-2-yl)oxy]-1-phenyl-ethyl}carbamate | ||||||
| tert-butyl {1-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2- | 937641-57-1 | |||||
| yl)oxy]-3-phenylpropan-2-yl}carbamate | ||||||
| tert-butyl {rac-(1R,2R)-1-(4-chlorophenyl)-2-[(1,3- | 2085782-59-6 | |||||
| dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy] | ||||||
| propyl}carbamate | ||||||
| tert-butyl {2-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2- | 1227082-95-2. | |||||
| yl)oxy]-1-(4-fluorophenyl)-2-methylpropyl}carbamate | ||||||
| tert-butyl {1-(2-chloro-4-methylphenyl)-3-[(1,3- | 2446131-06-0 | |||||
| dioxo-1,3-dihydro-2H-isoindol-2-yl)oxy]propan-2- | ||||||
| yl}carbamate | ||||||
| 2-[2-amino-3-(2-chloro-4-methylphenyl)propoxy]-1H- | 2446131-05-9 | |||||
| isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2-[2-amino-3-(2-chloro-4-methylphenyl)propoxy]-1H- | 2446131-04-8 | |||||
| isoindole-1,3(2H)-dione | ||||||
| 2-[2-amino-3-(4-bromo-2-methylphenyl)propoxy]-1H- | 2446130-92-1 | |||||
| isoindole-1,3(2H)-dione trifluoroacetate | ||||||
| 2-[2-amino-3-(4-bromo-2-methylphenyl)propoxy]-1H- | 2446130-91-0 | |||||
| isoindole-1,3(2H)-dione | ||||||
| 2-[rac-2-amino-3-(4-bromo-2-chlorophenyl)propoxy] | 2446130-90-9 | |||||
| isoindoline-1,3-dione 2,2,2-trifluoroacetic acid | ||||||
| 2-[rac-2-amino-3-(4-bromo-2-chlorophenyl)propoxy] | 2446130-89-6 | |||||
| isoindoline-1,3-dione | ||||||
| 2-[2-amino-3-(3,4-dimethylphenyl)propoxy]-1H- | 2446130-88-5 | |||||
| isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2-[2-amino-3-(3,4-dimethylphenyl)propoxy]-1H- | 2446130-87-4 | |||||
| isoindole-1,3(2H)-dione | ||||||
| 2-[2-amino-3-(4-isopropyl-2-methylphenyl)propoxy]- | 2446130-86-3 | |||||
| 1H-isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2-[2-amino-3-(4-isopropyl-2-methylphenyl)propoxy]- | 2446130-85-2 | |||||
| 1H-isoindole-1,3(2H)-dione | ||||||
| 2-[2-amino-3-(2-chloro-4-isopropylphenyl)propoxy]- | 2446130-84-1 | |||||
| 1H-isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2-[2-amino-3-(2-chloro-4-isopropylphenyl)propoxy]- | 2446130-83-0 | |||||
| 1H-isoindole-1,3(2H)-dione | ||||||
| 2-[rac-2-amino-3-(2,4-dichlorophenyl)propoxy] | 2446130-82-9 | |||||
| isoindoline-1,3-dione 2,2,2-trifluoroacetic acid | ||||||
| 2-[rac-2-amino-3-(2,4-dichlorophenyl)propoxy] | 2446130-81-8 | |||||
| isoindoline-1,3-dione | ||||||
| 2-[2-amino-3-(4-cyclopropyl-2-methylphenyl)propoxy]- | 2446130-80-7 | |||||
| 1H-isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2446130-79-4 2-[2-amino-3-(4-cyclopropyl-2- | 2446130-79-4 | |||||
| methylphenyl)propoxy]-1H-isoindole-1,3(2H)-dione | ||||||
| 2-[2-amino-3-(2-chloro-4-cyclopropylphenyl)propoxy]- | 2446130-78-3 | |||||
| 1H-isoindole-1,3(2H)-dione trifluoroacetate (1:1) | ||||||
| 2-[rac-2-amino-3-(2,4-dimethylphenyl)propoxy] | 2446130-65-8 | |||||
| isoindoline-1,3-dione 2,2,2-trifluoroacetic acid | ||||||
| 2-[rac-2-amino-3-(2,4-dimethylphenyl)propoxy] | 2446130-64-7 | |||||
| isoindoline-1,3-dione | ||||||
| tert-butyl {(1S)-2-[(1,3-dioxo-1,3-dihydro-2H- | 2102206-02-8 | |||||
| isoindol-2-yl)oxy]-1-phenylethyl} carbamate |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| or | R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 )—, —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| or | R 3 or R 4 , together with R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, | X 1 is halogen. |
| or | R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, | X 1 is halogen. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | W is hydrogen, tert-butoxycarbonyl, benzyl, allyl or (4-methoxyphenyl)methyl, | X 1 is halogen. |
| or | R 3 and R 5 or R 4 and R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl, | X 1 is halogen. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| 2-bromo-5-phenoxyisonicotinonitrile | 1802894-72-9 |
| 5-(3,4-dichlorophenoxy)-2-(ethylsulfanyl)isonicotinonitrile | 99908-98-2 |
| 5-(3,4-dichlorophenoxy)-2-(methylsulfanyl)isonicotinonitrile | 99908-97-1 |
| 3-fluoro-5-phenoxy-pyridine-4-carbonitrile | 2584885-70-9 |
| 3-(4-fluorophenoxy)-5-methyl-pyridine-4-carbonitrile | 1873324-58-3 |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | provided that the compound of formula (9) is not: | ||||||
| 2-bromo-5-phenoxyisonicotinonitrile | 1802894-72-9 | ||||||
| 5-(3,4-dichlorophenoxy)-2-(ethylsulfanyl)isonicotinonitrile | 99908-98-2 | ||||||
| 5-(3,4-dichlorophenoxy)-2-(methylsulfanyl)isonicotinonitrile | 99908-97-1 | ||||||
| 3-fluoro-5-phenoxy-pyridine-4-carbonitrile | 2584885-70-9 | ||||||
| 3-(4-fluorophenoxy)-5-methyl-pyridine-4-carbonitrile | 1873324-58-3 |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | provided that at least one of R 7 and R 8 is different from hydrogen. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyl-oxy, C 2 -C 6 -haloalkenyloxy, C 2 -C 6 -alkylnyloxy, C 2 -C 6 -haloalkylnyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkyl-sulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, or two substituents C 1 -C 6 -alkyl attached to the same carbon atom form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, and wherein C 3 -C 8 -cycloalkylsulfanyl, C 3 -C 8 -cycloalkylsulfinyl, C 3 -C 8 -cycloalkyl-sulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyloxy, C 3 -C 8 -cycloalkenyl, C 6 -C 14 -aryl, 5- or 6-membered heteroaryl and 3- to 7-membered heterocyclyl are furthermore optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, | and wherein R 15 is hydrogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl is optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, and wherein said C 3 -C 8 -cycloalkyl is optionally substituted with one to four substituents independently selected from the group consisting of halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 3 -C 8 -cycloalkyl and C 3 -C 8 -halocycloalkyl, | R 16 , R 17 , R 18 and R 19 are independently hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl, | wherein said C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl are furthermore optionally substituted with one to three substituents independently selected from the group consisting of cyano, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl, |
| E 1 is chlorine, bromine or iodine, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl | and salts, solvates or salts of the solvates thereof, | provided that the compound of formula (13) is not: | |
| (2RS)-1-chloro-3-phenylpropan-2-amine | 749167-08-6 | |||
| (2RS)-1-chloro-3-phenylpropan-2-amine | 776253-38-4 | |||
| 1-chloro-3-phenylpropan-2-amine | 748709-78-6 | |||
| (2RS)-1-chloro-3-phenylpropan-2-amine | 100431-28-5 | |||
| hydrochloride (1:1) | ||||
| 1-chloro-3-phenylpropan-2-amine hydro- | 49557-36-0 | |||
| chloride (1:1) | ||||
| (2RS)-1-chloro-3-phenylpropan-2-amine | 100431-27-4 | |||
| hydrochloride (1:1) | ||||
| 3-(2-amino-3-chloropropyl)phenol | 790605-82-2 | |||
| 3-(2-amino-3-chloropropyl)phenol hydro- | 66033-01-0 | |||
| chloride (1:1) | ||||
| (2RS)-1-chloro-3-(2,4,5-trifluorophenyl) | 2101321-88-2 | |||
| propan-2-amine | ||||
| (2RS)-1-chloro-3-(2,4,5-trifluorophenyl) | 2101321-89-3 | |||
| propan-2-amine hydrochloride (1:1) | ||||
| 1-chloro-3-(3,4,5-trimethoxyphenyl)propan- | 690946-87-3 | |||
| 2-amine | ||||
| 1-chloro-3-(3,4,5-trimethoxyphenyl)propan- | 49557-34-8 | |||
| 2-amine hydrochloride (1:1) | ||||
| 5-[(2RS)-2-amino-3-chloropropyl]-2- | 855594-92-2 | |||
| methoxybenzenesulfonamide | ||||
| (2S)-1-bromo-3-phenylpropan-2-amine | 2446130-69-2 | |||
| trifluoroacetate (1:1) | ||||
| 1-chloro-3-(3,4-dichlorophenyl)propan-2-amine | 2446132-79-0 | |||
| 1-chloro-3-(2-chloro-4-methyl-phenyl)propan- | 2446132-78-9 | |||
| 2-amine hydrochloride (1:1) | ||||
| 1-chloro-3-(2-chloro-4-methyl-phenyl)propan- | 2446132-77-8 | |||
| 2-amine | ||||
| 1-(2-bromo-4-methylphenyl)-3-chloropropan- | 2446132-73-4 | |||
| 2-amine | ||||
| 1-chloro-3-[4-(difluoromethyl)phenyl]propan- | 2446132-71-2 | |||
| 2-amine | ||||
| 1-chloro-3-(2,4-dimethylphenyl)propan-2- | 2446130-67-0 | |||
| amine hydrochloride (1:1) | ||||
| 1-chloro-3-(2,4-dimethylphenyl)propan-2-amine | 2446130-66-9 | |||
| 1-chloro-3-(2-cyclopropyl-4-methylphenyl) | 2446132-98-3 | |||
| propan-2-amine hydrochloride (1:1) | ||||
| 1-chloro-3-(2-cyclopropyl-4-methylphenyl) | 2446132-97-2 | |||
| propan-2-amine | ||||
| 1-chloro-3-(3,4-dichlorophenyl)propan-2-amine | 2446132-80-3 | |||
| hydrochloride (1:1) | ||||
| 1-chloro-3-(3,4-dichlorophenyl)propan-2-amine | 2446132-79-0 | |||
| 1-(2-bromo-4-methylphenyl)-3-chloropropan-2- | 2446132-74-5 | |||
| amine hydrochloride (1:1) | ||||
| 1-(2-bromo-4-methylphenyl)-3-chloropropan-2- | 2446132-73-4 | |||
| amine | ||||
| 1-chloro-3-[4-(difluoromethyl)phenyl]propan-2- | 2446132-72-3 | |||
| amine hydrochloride (1:1) | ||||
| 1-chloro-3-[4-(difluoromethyl)phenyl]propan-2-amine | 2446132-71-2 | |||
| 1-chloro-3-[4-(trifluoromethoxy)phenyl]propan-2- | 2446132-68-7 | |||
| amine hydrochloride (1:1) | ||||
| 1-chloro-3-[4-(trifluoromethoxy)phenyl]propan- | 2446132-67-6 | |||
| 2-amine |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| E 1 is hydroxyl or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| E 1 is hydroxyl or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| E 1 is hydroxyl or halogen, | E 2 is hydroxyl, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. |
| or | R 3 or R 4 , together with R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, wherein | said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 2 -C 6 -alkenyloxy, C 2 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -haloalkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 and —Si(C 1 -C 6 -alkyl) 3 in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkoxy, C 3 -C 6 -cycloalkenyl, 3- to 7-membered heterocyclyl and 5- to 14-membered heteroaryl in turn are optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, | and wherein R 33 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, R 34 , R 35 , R 36 R 37 R 38 R 39 R 40 R 41 and R 42 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl or C 1 -C 6 -alkoxy, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | and wherein R 43 is hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 3 -C 8 -cycloalkyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl and C 2 -C 6 -haloalkenyl in turn are optionally substituted with one to three substituents independently selected from the group consisting of cyano, amino, nitro, hydroxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-carbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl in turn is optionally substituted with one to three substituents independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -halo-alkoxycarbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl and 3- to 7-membered heterocyclyl, wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl and 3- to 7-membered heterocyclyl furthermore are optionally substituted with two substituents forming together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl, |
| E 1 is hydroxyl or halogen, | E 2 is hydroxyl, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | E 1 is hydroxyl or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. | X 1 is halogen, | provided that the compound of formula (17) is not: | |||
| 3-fluoro-N-[1-hydroxy-3-(1,3-thiazol-5-yl)propan-2- | 2401565-47-5 | ||||||
| yl]isonicotinamide | |||||||
| 3,5-difluoro-N-[1-hydroxy-3-(3-methylphenyl)propan- | 2320368-11-2 | ||||||
| 2-yl]isonicotinamide | |||||||
| 2,3,6-trifluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 2244743-83-5 | ||||||
| 3-fluoro-N-[1-(2-furyl)-2-hydroxyethyl]isonicotinamide | 2059459-53-7 | ||||||
| 3-fluoro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1989396-90-8 | ||||||
| 2,3-difluoro-N-(1-hydroxy-3-phenylpropan-2-yl) | 1981173-05-0 | ||||||
| isonicotinamide | |||||||
| 2,5-dichloro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1980405-63-7 | ||||||
| isonicotinamide | |||||||
| 2,5-dichloro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1980302-09-7 | ||||||
| isonicotinamide | |||||||
| 2,3-difluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1974533-81-7 | ||||||
| 3-chloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1973629-86-5 | ||||||
| yl]isonicotinamide | |||||||
| 3-fluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1973629-30-9 | ||||||
| yl]isonicotinamide | |||||||
| 2,5-dichloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1967438-29-4 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1959278-64-8 | ||||||
| yl]isonicotinamide | |||||||
| 2,5-dichloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1959236-26-0 | ||||||
| yl]isonicotinamide | |||||||
| 3-fluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1931533-43-5 | ||||||
| yl]isonicotinamide | |||||||
| 3-chloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1931497-04-9 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1930826-16-6 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1927015-76-6 | ||||||
| isonicotinamide | |||||||
| 2,3-difluoro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1925455-07-7 | ||||||
| isonicotinamide | |||||||
| 3-chloro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1917081-29-8 | ||||||
| 3-chloro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1915936-28-5 | ||||||
| 3-fluoro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1912922-24-7 | ||||||
| 2,5-dichloro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1777469-26-7 | ||||||
| N-[1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl]-3- | 1645524-54-4 | ||||||
| fluoroisonicotinamide | |||||||
| 3-bromo-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1645411-96-6 | ||||||
| 3-chloro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1536213-85-0 | ||||||
| 3-chloro-N-(1-hydroxy-3-phenylpropan-2-yl)isonicotinamide | 1502570-09-3 | ||||||
| 3-fluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1484007-71-7 | ||||||
| 3-fluoro-N-(1-hydroxy-3-phenylpropan-2-yl)isonicotinamide | 1480368-34-0 | ||||||
| N-[1-(4-bromo-2-methylphenyl)-2-hydroxyethyl]-3,5- | 383363-40-4 | ||||||
| dichloroisonicotinamide | |||||||
| 3,5-dichloro-N-[2-hydroxy-1-(4-iodophenyl)ethyl] | 383363-39-1 | ||||||
| isonicotinamide | |||||||
| N-[1-(4-bromophenyl)-2-hydroxyethyl]-3,5- | 383363-38-0 | ||||||
| dichloroisonicotinamide | |||||||
| 3-fluoro-N-(3-hydroxy-1-phenylpropyl)isonicotinamide | 2061624-70-0 | ||||||
| 3-chloro-N-(3-hydroxy-1-phenylpropyl)isonicotinamide | 2060122-00-9 | ||||||
| 3-chloro-N-[3-hydroxy-1-(2-thienyl)propyl]isonicotinamide | 1445717-69-0 | ||||||
| 3-fluoro-N-[3-hydroxy-1-(2-thienyl)propyl]isonicotinamide | 1445585-43-2 | ||||||
| N-(1-chloro-3-phenylpropan-2-yl)-3-fluoroisonicotinamide | 1541746-51-3 | ||||||
| 3-chloro-N-(2-chloro-1-phenylethyl)isonicotinamide | 1533735-18-0 | ||||||
| 3-chloro-N-(1-chloro-3-phenylpropan-2-yl)isonicotinamide | 1526301-69-8 | ||||||
| N-(2-bromo-1-phenylethyl)-3-fluoroisonicotinamide | 1523082-29-2 | ||||||
| N-(1-bromo-3-phenylpropan-2-yl)-3-chloroisonicotinamide | 1520840-25-8 | ||||||
| N-(1-bromo-3-phenylpropan-2-yl)-3-fluoroisonicotinamide | 1514112-13-0 | ||||||
| N-(2-bromo-1-phenylethyl)-3-chloroisonicotinamide | 1500301-56-3 | ||||||
| N-(2-chloro-1-phenylethyl)-3-fluoroisonicotinamide | 1499905-22-4 | ||||||
| 2,5-dichloro-N-(1-hydroxy-3-phenylpropan-2-yl) | 1715804-10-6 | ||||||
| isonicotinamide |
| wherein | m is 1 or 2, | R 3 and R 4 are hydrogen, | R 5 is hydrogen, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 7 -C 12 -carbocyclyl, C 6 -C 14 -aryl or 7- to 14-membered heterocyclyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | X 1 is halogen, | E 1 is hydroxyl or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl, | provided that the compound of formula (17) is not: | |||
| 3-fluoro-N-[1-hydroxy-3-(1,3-thiazol-5-yl)propan-2-yl] | 2401565-47-5 | ||||||
| isonicotinamide | |||||||
| 3,5-difluoro-N-[1-hydroxy-3-(3-methylphenyl)propan-2-yl] | 2320368-11-2 | ||||||
| isonicotinamide | |||||||
| 2,3,6-trifluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 2244743-83-5 | ||||||
| 3-fluoro-N-[1-(2-furyl)-2-hydroxyethyl]isonicotinamide | 2059459-53-7 | ||||||
| 3-fluoro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1989396-90-8 | ||||||
| 2,3-difluoro-N-(1-hydroxy-3-phenylpropan-2-yl) | 1981173-05-0 | ||||||
| isonicotinamide | |||||||
| 2,5-dichloro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1980405-63-7 | ||||||
| isonicotinamide | |||||||
| 2,5-dichloro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1980302-09-7 | ||||||
| isonicotinamide | |||||||
| 2,3-difluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1974533-81-7 | ||||||
| 3-chloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1973629-86-5 | ||||||
| yl]isonicotinamide | |||||||
| 3-fluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1973629-30-9 | ||||||
| yl]isonicotinamide | |||||||
| 2,5-dichloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1967438-29-4 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1959278-64-8 | ||||||
| yl]isonicotinamide | |||||||
| 2,5-dichloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1959236-26-0 | ||||||
| yl]isonicotinamide | |||||||
| 3-fluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1931533-43-5 | ||||||
| yl]isonicotinamide | |||||||
| 3-chloro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1931497-04-9 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(2RS)-1-hydroxy-3-phenylpropan-2- | 1930826-16-6 | ||||||
| yl]isonicotinamide | |||||||
| 2,3-difluoro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1927015-76-6 | ||||||
| isonicotinamide | |||||||
| 2,3-difluoro-N-[(1RS)-2-hydroxy-1-phenylethyl] | 1925455-07-7 | ||||||
| isonicotinamide | |||||||
| 3-chloro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1917081-29-8 | ||||||
| 3-chloro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1915936-28-5 | ||||||
| 3-fluoro-N-[(1RS)-2-hydroxy-1-phenylethyl]isonicotinamide | 1912922-24-7 | ||||||
| 2,5-dichloro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1777469-26-7 | ||||||
| N-[1-(4-chloro-3-fluorophenyl)-2-hydroxyethyl]-3- | 1645524-54-4 | ||||||
| fluoroisonicotinamide | |||||||
| 3-bromo-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1645411-96-6 | ||||||
| 3-chloro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1536213-85-0 | ||||||
| 3-chloro-N-(1-hydroxy-3-phenylpropan-2-yl)isonicotinamide | 1502570-09-3 | ||||||
| 3-fluoro-N-(2-hydroxy-1-phenylethyl)isonicotinamide | 1484007-71-7 | ||||||
| 3-fluoro-N-(1-hydroxy-3-phenylpropan-2-yl)isonicotinamide | 1480368-34-0 | ||||||
| N-[1-(4-bromo-2-methylphenyl)-2-hydroxyethyl]-3,5- | 383363-40-4 | ||||||
| dichloroisonicotinamide | |||||||
| 3,5-dichloro-N-[2-hydroxy-1-(4-iodophenyl)ethyl] | 383363-39-1 | ||||||
| isonicotinamide | |||||||
| N-[1-(4-bromophenyl)-2-hydroxyethyl]-3,5- | 383363-38-0 | ||||||
| dichloroisonicotinamide | |||||||
| 3-fluoro-N-(3-hydroxy-1-phenylpropyl)isonicotinamide | 2061624-70-0 | ||||||
| 3-chloro-N-(3-hydroxy-1-phenylpropyl)isonicotinamide | 2060122-00-9 | ||||||
| 3-chloro-N-[3-hydroxy-1-(2-thienyl)propyl]isonicotinamide | 1445717-69-0 | ||||||
| 3-fluoro-N-[3-hydroxy-1-(2-thienyl)propyl]isonicotinamide | 1445585-43-2 | ||||||
| N-(1-chloro-3-phenylpropan-2-yl)-3-fluoroisonicotinamide | 1541746-51-3 | ||||||
| 3-chloro-N-(2-chloro-1-phenylethyl)isonicotinamide | 1533735-18-0 | ||||||
| 3-chloro-N-(1-chloro-3-phenylpropan-2-yl)isonicotinamide | 1526301-69-8 | ||||||
| N-(2-bromo-1-phenylethyl)-3-fluoroisonicotinamide | 1523082-29-2 | ||||||
| N-(1-bromo-3-phenylpropan-2-yl)-3-chloroisonicotinamide | 1520840-25-8 | ||||||
| N-(1-bromo-3-phenylpropan-2-yl)-3-fluoroisonicotinamide | 1514112-13-0 | ||||||
| N-(2-bromo-1-phenylethyl)-3-chloroisonicotinamide | 1500301-56-3 | ||||||
| N-(2-chloro-1-phenylethyl)-3-fluoroisonicotinamide | 1499905-22-4 | ||||||
| 2,5-dichloro-N-(1-hydroxy-3-phenylpropan-2-yl) | 1715804-10-6 | ||||||
| isonicotinamide |
| or | R 3 or R 4 , together with R 5 form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, | L is a direct bond, carbonyl, C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene-, —C 1 -C 6 -alkylene-C(═O)—, —NR L1 —, —NR L2 (C═O)—, —C(═O)NR L3 —, —NR L4 S(═O) 2 —, —S(═O) 2 NR L5 —, —C(═NOR L6 )—, —C(═N—N(R L7 ) 2 ), —C(═NR L8 )— or a group of formula | |||||
| wherein | said C 1 -C 6 -alkylene, C 2 -C 6 -alkenylene, C 2 -C 6 -alkynylene, —C(═O)—C 1 -C 6 -alkylene- and —C 1 -C 6 -alkylene-C(═O)— are optionally substituted with one to three substituents L SA , | # is the point of attachment to the heterocyclyl-moiety, | ## is the point of attachment to R 6 , | L 1 is a direct bond or C 1 -C 6 -alkylene, | L 2 is a direct bond or C 1 -C 6 -alkylene, | E is C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl or 3- to 7-membered heterocyclyl, | wherein said C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkenyl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three substituents L SC , |
| R L1 , R L2 , R L3 and R L4 are independently hydrogen or C 1 -C 6 -alkyl, | R L5 , R L6 , R L7 and R L8 are independently hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 2 -C 6 -alkenyl, | L SA is independently halogen, cyano, hydroxyl, carboxyl, methylidene, halomethylidene, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkoxy-carbonyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | or | two substituents L SA that are bound to the same carbon atom form together with the carbon atom which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | L Sc is independently halogen, cyano, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 alkenyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 or 3- to 7-membered heterocyclyl, | and/or | two L Sc substituents form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring, |
| R 6 is C 3 -C 12 -carbocyclyl, C 6 -C 14 -aryl, 3- to 14-membered heterocyclyl, 5- to 14-membered heteroaryl, C 3 -C 12 -carbocyclyloxy, C 6 -C 14 -aryloxy, 5- to 14-membered heteroaryloxy, 3- to 14-membered heterocyclyloxy, C 3 -C 12 -carbocyclylsulfanyl, C 6 -C 14 -arylsulfanyl, 5- to 14-membered heteroarylsulfanyl, 3- to 14-membered heterocyclylsulfanyl, C 3 -C 12 -carbocyclyl-sulfinyl, C 6 -C 14 -arylsulfinyl, 5- to 14-membered heteroarylsulfinyl, 3- to 14-membered heterocyclyl sulfinyl, C 3 -C 12 -carbocyclylsulfonyl, C 6 -C 14 -arylsulfonyl, 5- to 14-membered heteroaryl-sulfonyl, 3- to 14-membered heterocyclylsulfonyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylsulfanyl, C 1 -C 3 -alkylsulfinyl or C 1 -C 3 -alkylsulfonyl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | X 1 is halogen, | E 1 is hydroxyl or halogen, | W is hydrogen, tert-butoxycarbonyl, benzyl or (4-methoxyphenyl)methyl. |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl, 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen or halogen, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein said C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | R 31 is C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 -haloalkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl or 3- to 7-membered heterocyclyl, | wherein said C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkynyl and C 2 -C 6 -haloalkynyl in turn are optionally substituted with one to three R 8Sa substituents, said C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 6 -C 14 -aryl, 5- to 14-membered heteroaryl and 3- to 7-membered heterocyclyl in turn are optionally substituted with one to three R 8Sc substituents, | and wherein R 8Sa is independently selected from the group consisting of cyano, amino, nitro, hydroxyl, formyl, carboxyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkyl-carbonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -halo-alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, —O—Si(C 1 -C 6 -alkyl) 3 , —Si(C 1 -C 6 -alkyl) 3 , 3- to 7-membered heterocyclyl and —N(R 32 ) 2 , | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl substituents that may be identical or different, R 32 is hydrogen, formyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 8 -cycloalkyl or C 1 -C 6 -alkylcarbonyl, | R 8Sc is independently selected from the group consisting of halogen, cyano, amino, nitro, hydroxyl, formyl, carboxyl, oxo, methylidene, halomethylidene, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxy-carbonyl, C 2 -C 6 -alkenyl, C 1 -C 6 -alkylsulfanyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -halocycloalkyl, —O—Si(C 1 -C 6 -alkyl) 3 and 3- to 7-membered heterocyclyl, | wherein said 3- to 7-membered heterocyclyl in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, or two R 8Sc substituents optionally form together with the carbon atom to which they are attached to a C 3 -C 8 -cycloalkyl-ring or a 3- to 7-membered heterocyclyl-ring, | wherein said 3- to 7-membered heterocyclyl-ring in turn is optionally substituted with one to three substituents C 1 -C 6 -alkyl that may be identical or different, |
| R 9 is hydrogen, halogen, cyano or (C 1 -C 4 )-alkyl, | Q is C 6 -C 14 -aryl, C 3 -C 12 -carbocyclyl 3- to 14-membered heterocyclyl or 5- to 14-membered heteroaryl, |
| wherein | § 1 is the point of attachment to oxygen, | A 1 is CH or N, | Q S is C 3 -C 4 -cycloalkyl, C 3 -C 8 -halocycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl or C 2 -C 6 -alkynyl, provided that the compound of formula (8) does not represent: |
| 2-fluoro-3-(3,3,3-trifluoroprop-1-en-2-yl)phenol | 2168012-00-6 | ||
| 3-(1-ethoxyvinyl)-2-fluorophenol | 2137960-04-2 | ||
| 1-(2-fluoro-3-hydroxyphenyl)cyclopropanecarbonitrile | 1881320-49-5 | ||
| 3-(1-aminocyclopropyl)-2-fluorophenol | 1785193-75-0 | ||
| 1-(2-fluoro-3-hydroxyphenyl)cyclopropanecarboxylic acid | 1507131-96-5 | ||
| 2-fluoro-3-(prop-1-en-2-yl)phenol | 1375066-38-8 | ||
| 3-cyclopropyl-2-fluoro-phenol | 2290421-25-7 | ||
| 2-fluoro-3-(1-fluorocyclopropyl)phenol | 2385918-06-7 | ||
| 3-(2,2-difluorocyclopropyl)-2-fluoro-phenol | 2435608-24-3 | ||
| 2-fluoro-3-vinyl-phenol | 2290411-18-4 | ||
| 2-fluoro-3-[(E)-prop-1-enyl]phenol | 2435608-23-2 | ||
| 2-fluoro-3-isopropenyl-phenol | 1375066-38-8 | ||
| 3-ethyl-2-fluoro-phenol | 1243456-02-1 | ||
| 2-fluoro-3-propyl-phenol | 2284409-52-3 | ||
| 3-butyl-2-fluoro-phenol | 2284271-78-7 |
| Ex N o | R 7 | R 8 | R 9 | Q | |||
| L—R 6 | LogP | ||||||
| I-001 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.56 [a] |
| phenyl)methyl | |||||||
| I-002 1) | chloro | H | H | 3-chlorophenyl | Ring 1 | (2,4-dimethyl- | 4.51 [a] |
| phenyl)methyl | |||||||
| I-003 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.08 [a] |
| phenyl)methyl | |||||||
| I-004 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (4-bromo-2-chloro- | 4.32 [a] |
| phenyl)methyl | |||||||
| I-005 | chloro | H | H | 3-methoxyphenyl | Ring 1 | (2,4-dimethyl- | 4.18 [a] |
| phenyl)methyl | |||||||
| I-006 | chloro | H | H | 3-methoxyphenyl | Ring 1 | (4-bromo-2-chloro- | 4.37 [a] |
| phenyl)methyl | |||||||
| I-007 | chloro | H | H | 3-methylphenyl | Ring 1 | (2,4-dimethyl- | 4.55 [a] |
| phenyl)methyl | |||||||
| I-008 | methyl | H | H | 3-methylphenyl | Ring 1 | (2,4-dimethyl- | 3.61 [a] |
| phenyl)methyl | |||||||
| I-009 | methyl | H | H | 3-methoxyphenyl | Ring 1 | (2,4-dimethyl- | 3.29 [a] |
| phenyl)methyl | |||||||
| I-010 | methyl | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 3.41 [a] |
| phenyl)methyl | |||||||
| I-011 1) | chloro | H | H | 3-chlorophenyl | Ring 1 | (2,4-dimethyl- | 4.53 [a] |
| phenyl)methyl | |||||||
| I-012 1) | chloro | H | H | 3-chlorophenyl | Ring 1 | (2,4-dimethyl- | 4.53 [a] |
| phenyl)methyl | |||||||
| I-013 2) | chloro | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 4.89 [a] |
| phenyl)methyl | |||||||
| I-014 3) | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dimethyl- | 4.89 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-015 | methyl | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 3.94 [a] |
| phenyl)methyl | |||||||
| I-016 | cyclopropyl | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 4.87 [a] |
| phenyl)methyl | |||||||
| I-017 | methyl | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dimethyl- | 4.03 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-018 | methyl | H | H | 3-chlorophenyl | Ring 1 | (2,4-dimethyl- | 3.76 [a] |
| phenyl)methyl | |||||||
| I-019 2) | chloro | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 4.89 [a] |
| phenyl)methyl | |||||||
| I-020 2) | chloro | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 4.89 [a] |
| phenyl)methyl | |||||||
| I-021 3) | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dimethyl- | 4.93 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-022 3) | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dimethyl- | 4.93 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-023 | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (4-bromo-2-chloro- | 5.11 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-024 | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dichloro- | 4.98 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-025 | chloro | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dichloro- | 4.98 [a] |
| phenyl)methyl | |||||||
| I-026 | chloro | H | H | 3-cyclopropylphenyl | Ring 1 | (4-bromo-2-chloro- | 5.16 [a] |
| phenyl)methyl | |||||||
| I-027 | ethyl | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dimethyl- | 4.40 [a] |
| phenyl)methyl | |||||||
| I-028 | methyl | H | H | 3-cyclopropylphenyl | Ring 1 | (2,4-dichloro- | 4.08 [a] |
| phenyl)methyl | |||||||
| I-029 | methyl | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dichloro- | 4.23 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-030 | methyl | H | H | 3-cyclopropylphenyl | Ring 1 | (2-chloro-4- | 3.98 [a] |
| methylphenyl)methyl | |||||||
| I-031 | methyl | H | H | 3-cyclopropyl-2- | Ring 1 | (2-chloro-4-methyl- | 4.08 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-032 | chloro | H | H | 2-fluoro-3-methylphenyl | Ring 1 | (2,4-dimethyl- | 4.59 [a] |
| phenyl)methyl | |||||||
| I-033 | trifluoromethyl | H | H | 3-cyclopropyl-2- | Ring 1 | (2,4-dimethyl- | 5.20 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-034 | trifluoromethyl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.89 [a] |
| phenyl)methyl | |||||||
| I-035 | chloro | H | H | 3-(difluoromethoxy)-2- | Ring 1 | (2,4-dimethyl- | 4.23 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-036 | chloro | H | H | 3-bicyclo[4.2.0]octa-1,3,5- | Ring 1 | (2,4-dimethyl- | 4.88 [a] |
| trienyl | phenyl)methyl | ||||||
| I-037 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | [2-chloro-4-(1-methyl- | 3.37 [a] |
| 1H-pyrazol-4- | |||||||
| yl)phenyl]methyl | |||||||
| I-038 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (4-acetyl-2-chloro- | 3.47 [a] |
| phenyl)methyl | |||||||
| I-039 | H | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 3.47 [a] |
| phenyl)methyl | |||||||
| I-040 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (2-chloro-4-vinyl- | 4.29 [a] |
| phenyl)methyl | |||||||
| I-041 | chloro | H | H | 3-(difluoromethyl)phenyl | Ring 1 | [2-chloro-4-(oxolan-3- | 3.81 [a] |
| yl)phenyl]methyl | |||||||
| I-042 4) | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 2 | 4-chlorophenyl | 4.19 [a] |
| I-043 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 3 | 2,4-difluorophenyl | 4.30 [a] |
| I-044 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 2,3-dihydro-1- | 3.57 [a] |
| benzofuran-5-yl | |||||||
| I-045 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 4-methoxyphenyl | 3.60 [a] |
| I-046 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 1-phenylcyclopropyl | 4.21 [a] |
| I-047 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 4 | 4-methoxyphenyl | 4.14 [a] |
| I-048 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 4-methylphenyl | 3.96 [a] |
| I-049 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 3,4-dimethylphenyl | 4.24 [a] |
| I-050 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 4-chlorophenyl | 3.99 [a] |
| I-051 5) | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 5 | 4-chlorophenyl | 3.33 [a] |
| I-052 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 2,3-dihydro-1,4- | 3.48 [a] |
| benzodioxin-6-yl | |||||||
| I-053 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | naphthalen-2-yl | 4.20 [a] |
| I-054 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | indan-5-yl | 4.41 [a] |
| I-055 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 4-(trifluoro- | 4.26 [a] |
| methoxy)phenyl | |||||||
| I-056 | pyrrolidin-1-yl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 3.50 [a] |
| phenyl)methyl | |||||||
| I-057 | cyano | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 4.12 [a] |
| phenyl)methyl | |||||||
| I-058 6) | oxolan-3-yl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 3.78 [a] |
| phenyl)methyl | |||||||
| I-059 | vinyl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 4.19 [a] |
| phenyl)methyl | |||||||
| I-060 | 2-trimethyl- | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 5.53 [a] |
| silylethyn-1-yl | phenyl)methyl | ||||||
| I-061 | acetyl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 4.07 [a] |
| phenyl)methyl | |||||||
| I-062 | chloro | fluoro | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.66 [a] |
| phenyl)methyl | |||||||
| I-063 | chloro | H | H | phenyl | Ring 1 | (2,4-dimethyl- | 4.17 [a] |
| phenyl)methyl | |||||||
| I-064 | chloro | H | H | 3-methylsulfanylphenyl | Ring 1 | (2,4-dimethyl- | 4.66 [a] |
| phenyl)methyl | |||||||
| I-065 | chloro | H | H | 3-(difluoromethoxy)phenyl | Ring 1 | (2,4-dimethyl- | 4.38 [a] |
| phenyl)methyl | |||||||
| I-066 | chloro | H | H | 3-cyclopropyl-2- | Ring 1 | (2-chloro-4-methyl- | 5.04 [a] |
| fluorophenyl | phenyl)methyl | ||||||
| I-067 | methoxy | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-4-methyl- | 4.51 [a] |
| phenyl)methyl | |||||||
| I-068 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 5-(trifluoromethyl)-3- | 4.40 [a] |
| thienyl]methyl | |||||||
| I-069 | methyl | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-4-methyl- | 4.07 [a] |
| phenyl)methyl | |||||||
| I-070 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | phenyl | 3.64 [a] |
| I-071 | chloro | H | H | 2,3-difluorophenyl | Ring 1 | (2,4-dichloro- | 4.40 [a] |
| phenyl)methyl | |||||||
| I-072 | chloro | H | H | 5-(trifluoromethyl)-3- | Ring 1 | (2,4-dichloro- | 4.75 [a] |
| thienyl | phenyl)methyl | ||||||
| I-073 7) | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 6 | 4-chlorophenyl | 4.08 [a] |
| I-074 | ethynyl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-ethynyl-2-methyl- | 3.75 [a] |
| phenyl)methyl | |||||||
| I-075 | chloro | H | H | 3-ethynylphenyl | Ring 1 | (2,4-dimethyl- | 4.33 [a] |
| phenyl)methyl | |||||||
| I-076 | chloro | H | H | 3-chloro-4-methylphenyl | Ring 1 | (2,4-dimethyl- | 4.97 [a] |
| phenyl)methyl | |||||||
| I-077 | chloro | iodo | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.66 [a] |
| phenyl)methyl | |||||||
| I-078 | chloro | H | H | 3-(2-methoxy-2- | Ring 1 | (2,4-dimethyl- | 4.08 [a] |
| oxoethyl)phenyl | phenyl)methyl | ||||||
| I-079 | chloro | H | H | 3-bromo-2-fluorophenyl | Ring 1 | (2-chloro-4-methyl- | 4.70 [a] |
| phenyl)methyl | |||||||
| I-080 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 4-cyanophenyl | 3.30 [a] |
| I-081 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 14 | (2,4-dimethyl- | 2.64 [a] |
| phenyl)methyl | |||||||
| I-082 | chloro | H | fluoro | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.97 [a] |
| phenyl)methyl | |||||||
| I-083 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (4-chloro-2-methyl- | 4.59 [a] |
| phenyl)methyl | |||||||
| I-084 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 9 | (2,4-dimethyl- | 2.86 [a] |
| phenyl)methyl | |||||||
| I-085 | chloro | H | H | 3-formylphenyl | Ring 1 | (2,4-dimethyl- | 3.64 [a] |
| phenyl)methyl | |||||||
| I-086 | chloro | H | H | naphthalen-2-yl | Ring 1 | (2,4-dimethyl- | 4.77 [a] |
| phenyl)methyl | |||||||
| I-087 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-4-methyl- | 4.66 [a] |
| phenyl)methyl | |||||||
| I-088 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 11 | (2,4-dimethyl- | 2.62 [a] |
| phenyl)methyl | |||||||
| I-089 | chloro | H | H | 3-pyridin-2-ylphenyl | Ring 1 | (2,4-dimethyl- | 3.87 [a] |
| phenyl)methyl | |||||||
| I-090 | chloro | H | H | 3-(trifluoromethyl- | Ring 1 | (2,4-dichloro- | 5.16 [a] |
| thio)phenyl | phenyl)methyl | ||||||
| I-091 | ethynyl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-bromo-2-methyl- | 4.19 [a] |
| phenyl)methyl | |||||||
| I-092 | chloro | H | H | 3-ethylphenyl | Ring 1 | (2,4-dimethyl- | 5.04 [a] |
| phenyl)methyl | |||||||
| I-093 | chloro | H | H | quinolin-3-yl | Ring 1 | (2,4-dimethyl- | 3.65 [a] |
| phenyl)methyl | |||||||
| I-094 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 10 | (2,4-dimethyl- | 4.49 [a] |
| phenyl)methyl | |||||||
| I-095 | chloro | H | H | 3-methylsulfonylphenyl | Ring 1 | (2,4-dimethyl- | 3.25 [a] |
| phenyl)methyl | |||||||
| I-096 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 1-methyl-1H-indol-3- | 4.01 [a] |
| yl | |||||||
| I-097 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 5-methyl-2-thienyl | 3.87 [a] |
| I-098 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 12 | (2,4-dimethyl- | 4.62 [a] |
| phenyl)methyl | |||||||
| I-099 | chloro | H | H | 3-vinylphenyl | Ring 1 | (2,4-dichloro- | 4.85 [a] |
| phenyl)methyl | |||||||
| I-100 | chloro | H | H | indan-5-yl | Ring 1 | (2,4-dimethyl- | 5.16 [a] |
| phenyl)methyl | |||||||
| I-101 | chloro | H | H | 3-cyclobutylphenyl | Ring 1 | (2,4-dimethyl- | 5.50 [a] |
| phenyl)methyl | |||||||
| I-102 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2,4-dichloro- | 4.71 [a] |
| phenyl)methyl | |||||||
| I-103 | chloro | H | H | 3-chlorophenyl | Ring 1 | (2-chloro-4-methyl- | 4.66 [a] |
| phenyl)methyl | |||||||
| I-104 | chloro | H | H | 3-bromophenyl | Ring 1 | (2,4-dimethyl- | 4.74 [a] |
| phenyl)methyl | |||||||
| I-105 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | [2-chloro-4-(trifluoro- | 4.84 [a] |
| methyl)phenyl]methyl | |||||||
| I-106 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 14 | (4-chloro- | 2.45 [a] |
| phenyl)methyl | |||||||
| I-107 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-cyclopropyl-2- | 4.88 [a] |
| methylphenyl)methyl | |||||||
| I-108 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 15 | 4-chlorophenyl | 2.12 [a] |
| I-109 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 13 | 4-methylphenyl | 4.59 [a] |
| I-110 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-methyl- | 4.31 [a] |
| phenyl)methyl | |||||||
| I-111 | chloro | H | H | 2,3-dihydro-1-benzofuran- | Ring 1 | (2,4-dimethyl- | 4.23 [a] |
| 5-yl | phenyl)methyl | ||||||
| I-112 | ethyl(methyl)- | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-4- | 4.59 [a] |
| amino | methylphenyl)methyl | ||||||
| I-113 | chloro | H | H | 3-(oxetan-3-yl)phenyl | Ring 1 | (2,4-dimethyl- | 3.68 [a] |
| phenyl)methyl | |||||||
| I-114 | chloro | H | H | 2,2-difluoro-1,3- | Ring 1 | (2,4-dimethyl- | 4.65 [a] |
| benzodioxol-5-yl | phenyl)methyl | ||||||
| I-115 | chloro | H | H | 3-bromo-2-fluorophenyl | Ring 1 | (2,4-dichloro- | 4.69 [a] |
| phenyl)methyl | |||||||
| I-116 | chloro | H | H | indan-4-yl | Ring 1 | (2,4-dimethyl- | 5.14 [a] |
| phenyl)methyl | |||||||
| I-117 | chloro | H | H | 3-acetylphenyl | Ring 1 | (2,4-dimethyl- | 3.70 [a] |
| phenyl)methyl | |||||||
| I-118 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-5-methyl- | 4.52 [a] |
| phenyl)methyl | |||||||
| I-119 | chloro | H | H | 1-benzothiophen-6-yl | Ring 1 | (2,4-dimethyl- | 4.59 [a] |
| phenyl)methyl | |||||||
| I-120 | chloro | H | H | 4-(trifluoromethoxy)phenyl | Ring 1 | (2,4-dimethyl- | 4.76 [a] |
| phenyl)methyl | |||||||
| I-121 | chloro | methyl- | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.67 [a] |
| sulfanyl | phenyl)methyl | ||||||
| I-122 8) | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 7 | 4-methoxyphenyl | 4.07 [a] |
| I-123 | pyridin-4-yl | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethylphenyl) | 3.28 [a] |
| methyl | |||||||
| I-124 | chloro | methyl | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.55 [a] |
| phenyl)methyl | |||||||
| I-125 | chloro | H | H | 5-(trifluoromethyl)pyridin- | Ring 1 | (2,4-dichloro- | 3.71 [a] |
| 3-yl | phenyl)methyl | ||||||
| I-126 | chloro | H | H | 3-(2-methoxy- | Ring 1 | (2,4-dimethyl- | 4.15 [a] |
| ethoxy)phenyl | phenyl)methyl | ||||||
| I-127 | chloro | H | chloro | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 5.08 [a] |
| phenyl)methyl | |||||||
| I-128 | chloro | H | H | 6-(trifluoromethyl)pyridin- | Ring 1 | (2,4-dichloro- | 4.44 [a] |
| 2-yl | phenyl)methyl | ||||||
| I-129 | H | 3-(trifluoro- | chloro | 2-methoxyethyl | Ring 1 | (2,4-dimethyl- | 4.51 [a] |
| methyl) | phenyl)methyl | ||||||
| phenoxy | |||||||
| I-130 | chloro | H | H | 2,3-dihydro-1-benzofuran- | Ring 1 | (2,4-dichloro- | 4.30 [a] |
| 5-yl | phenyl)methyl | ||||||
| I-131 | chloro | but-3-en-2- | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 5.19 [a] |
| ylamino | phenyl)methyl | ||||||
| I-132 | chloro | H | H | 3-(dimethylamino)phenyl | Ring 1 | (2,4-dimethyl- | 4.47 [a] |
| phenyl)methyl | |||||||
| I-133 | chloro | phenyl | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 5.04 [a] |
| phenyl)methyl | |||||||
| I-134 | chloro | H | H | 3-acetyloxyphenyl | Ring 1 | (2,4-dimethyl- | 3.90 [a] |
| phenyl)methyl | |||||||
| I-135 | chloro | H | H | 2-fluoro-3-methylphenyl | Ring 1 | (2,4-dichloro- | 4.75 [a] |
| phenyl)methyl | |||||||
| I-136 | chloro | H | H | 2-fluoro-3-methylphenyl | Ring 1 | (2-chloro-4- | 4.66 [a] |
| methylphenyl)methyl | |||||||
| I-137 | hydroxy | H | H | 3-(difluoromethyl)phenyl | Ring 1 | (4-bromo-2-chloro- | 4.56 [a] |
| phenyl)methyl | |||||||
| I-138 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (5-chloro-3- | 4.38 [a] |
| thienyl)methyl | |||||||
| I-139 9) | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 8 | 4-chlorophenyl | 4.47 [a] |
| I-140 | chloro | H | H | 6,7-dihydro-5H- | Ring 1 | (2,4-dimethyl- | 3.17 [a] |
| cyclopenta[b]pyridin-3-yl | phenyl)methyl | ||||||
| I-141 | chloro | H | H | 3-ethyl-2-fluorophenyl | Ring 1 | (2,4-dichloro- | 5.16 [a] |
| phenyl)methyl | |||||||
| I-142 | chloro | H | H | 3-ethoxyphenyl | Ring 1 | (2,4-dimethyl- | 4.59 [a] |
| phenyl)methyl | |||||||
| I-143 10) | chloro | H | H | 3-[2- | Ring 1 | (2,4-dimethyl- | 4.38 [a] |
| fluorocyclopropyl]phenyl | phenyl)methyl | ||||||
| I-144 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2,4-dimethyl- | 4.59 [a] |
| phenyl)methyl | |||||||
| I-145 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,5-dichloro-3- | 4.83 [a] |
| thienyl)methyl | |||||||
| I-146 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 15 | 4-methylphenyl | 2.06 [a] |
| I-147 | chloro | H | H | 2-fluoro-3-methoxyphenyl | Ring 1 | (2,4-dimethyl- | 4.06 [a] |
| phenyl)methyl | |||||||
| I-148 | chloro | H | H | 3-(trifluoromethoxy)phenyl | Ring 1 | (2,4-dichloro- | 4.88 [a] |
| phenyl)methyl | |||||||
| I-149 | chloro | H | H | 2-fluoro-3- | Ring 1 | (2,4-dichloro- | 4.88 [a] |
| (trifluoromethoxy)phenyl | phenyl)methyl | ||||||
| I-150 | chloro | cyclopropyl | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.70 [a] |
| phenyl)methyl | |||||||
| I-151 | chloro | H | H | 3-chloro-2-fluorophenyl | Ring 1 | (2-chloro-3-methyl- | 4.62 [a] |
| phenyl)methyl | |||||||
| I-152 | methoxy | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.55 [a] |
| phenyl)methyl | |||||||
| I-153 | chloro | H | H | 3-(methoxymethyl)phenyl | Ring 1 | (2,4-dimethyl- | 4.10 [a] |
| phenyl)methyl | |||||||
| I-154 | chloro | H | H | 2-fluoro-3- | Ring 1 | (2,4-dimethyl- | 4.47 [a] |
| methylsulfanylphenyl | phenyl)methyl | ||||||
| I-155 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 15 | 4-methoxyphenyl | 1.90 [a] |
| I-156 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-ethynyl-2-methyl- | 4.08 [a] |
| phenyl)methyl | |||||||
| I-157 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | 2,3-dimethylphenyl | 4.23 [a] |
| I-158 | chloro | H | H | 3-(trifluoromethyl)phenyl | Ring 1 | (4-bromo-2-methyl- | 4.81 [a] |
| phenyl)methyl | |||||||
| 1) Ex I-011 and Ex I-012 are the 2 enantiomers of Ex I-002 | |||||||
| Ex I-011: Optical rotation: +68.3° (c = 1.20, CDCl 3 , 20° C.); concentration is expressed in g/100 mL. | |||||||
| Ex I-012: Optical rotation −65.0° (c = 1.20, CDCl 3 , 20° C.); concentration is expressed in g/100 mL. | |||||||
| 2) Ex I-019 and Ex I-020 are the 2 enantiomers of Ex I-013 | |||||||
| Ex I-019: Optical rotation: +74.1° (c = 0.81, CDCl 3 , 25° C.); concentration c is expressed in g/100 mL. | |||||||
| Ex I-020: Optical rotation: −66.7° (c = 1.02, CDCl 3 , 25° C.); concentration c is expressed in g/100 mL. | |||||||
| 3) Ex I-021 and Ex I-022 are the 2 enantiomers of Ex I-014 | |||||||
| Ex I-021: Optical rotation: −76° (c = 1, CDCl 3 , 25° C.); concentration c is expressed in g/100 mL. | |||||||
| Ex I-022: Optical rotation: +74° (c = 1, CDCl 3 , 25° C.); concentration c is expressed in g/100 mL. | |||||||
| 4) Ex I-042 is a mixture of stereoisomers | |||||||
| 5) Ex I-051 is a mixture of stereoisomers | |||||||
| 6) Ex I-058 is a mixture of stereoisomers | |||||||
| 7) Ex I-073 is a mixture of stereoisomers | |||||||
| 8) Ex I-122 is a mixture of stereoisomers | |||||||
| 9) Ex I-139 is a mixture of stereoisomers | |||||||
| 10) Ex I-143 is a mixture of stereoisomers |
| Ex N o | R 7 | R 8 | R 9 | Q | U 1 | LogP |
| 1-01 | chloro | fluoro | H | 3-(trifluoromethyl)phenyl | hydroxy | 2.28 [a] |
| 1-02 | acetyl | H | H | 3-(trifluoromethyl)phenyl | hydroxy | 2.54 [a] |
| 1-03 | 2-trimethylsilylethyn-1-yl | H | H | 3-(trifluoromethyl)phenyl | methoxy | 5.35 [a] |
| 1-04 | acetyl | H | H | 3-(trifluoromethyl)phenyl | methoxy | 3.59 [a] |
| 1-05 | 1-ethoxyethen-1-yl | H | H | 3-(trifluoromethyl)phenyl | methoxy | 4.70 [a] |
| 1-06 | chloro | H | H | 3-cyclopropyl-2-fluorophenyl | hydroxy | 2.97 [a] |
| 1-07 | chloro | H | H | 3-(trifluoromethyl)phenyl | methoxy | 3.84 [a] |
| 1-08 | chloro | H | H | 3-methylphenyl | hydroxy | 2.60 [a] |
| 1-09 | chloro | H | H | 3-methoxyphenyl | hydroxy | 2.34 [a] |
| 1-10 | chloro | H | H | 3-(difluoromethyl)phenyl | hydroxy | 2.48 [a] |
| 1-11 | chloro | H | H | 3-chlorophenyl | hydroxy | 2.76 [a] |
| 1-12 | chloro | H | H | 3-cyclopropylphenyl | hydroxy | 2.87 [a] |
| 1-13 | chloro | H | H | 3-(trifluoromethyl)phenyl | hydroxy | 2.84 [a] |
| 1-14 | chloro | H | fluoro | 3-(trifluoromethyl)phenyl | hydroxy | 2.95 [a] |
| 1-15 | methoxy | H | H | 3-(trifluoromethyl)phenyl | hydroxy | 2.86 [a] |
| 1-16 | chloro | H | chloro | 3-(trifluoromethyl)phenyl | hydroxy | |
| 1-17 | chloro | iodo | H | 3-(trifluoromethyl)phenyl | hydroxy | 2.49 [a] |
| Ex No | R 7 | R 8 | R 9 | Q |
| L—R 6 | LogP | |||
| 3-01 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.14 [a] | |||
| 3-02 | Cl | H | H | 3-cyclopropylphenyl |
| (4-bromo-2- chlorophenyl)methyl | 5.75 [a] | |||
| 3-03 | Cl | H | H | 3-cyclopropylphenyl |
| (2,4-dichlorophenyl)methyl | 5.62 [a] | |||
| 3-04 | Cl | H | H | 3-cyclopropyl-2-fluorophenyl |
| (2,4-dichlorophenyl)methyl | 5.54 [a] | |||
| 3-05 | Cl | H | H | 3-cyclopropyl-2-fluorophenyl |
| (4-bromo-2- chlorophenyl)methyl | 5.62 [a] | |||
| 3-06 | Cl | H | H | 3-cyclopropyl-2-fluorophenyl |
| (2,4-dimethylphenyl)methyl | 5.38 [a] | |||
| 3-07 | Cl | H | H | 3-methylphenyl |
| (2,4-dimethylphenyl)methyl | 5.16 [a] | |||
| 3-08 | Cl | H | H | 3-methoxyphenyl |
| (4-bromo-2- chlorophenyl)methyl | 5.05 [a] | |||
| 3-09 | Cl | H | H | 3-methoxyphenyl |
| (2,4-dimethylphenyl)methyl | 4.80 [a] | |||
| 3-10 | Cl | H | H | 3-(difluoromethyl)phenyl |
| (4-bromo-2- chlorophenyl)methyl | 5.00 [a] | |||
| 3-11 | Cl | H | H | 3-(difluoromethy)phenyl |
| (2,4-dimethylphenyl)methyl | 4.69 [a] | |||
| 3-12 | Cl | H | H | 3-chlorophenyl |
| (2,4-dimethylphenyl)methyl | 5.11 [a] | |||
| 3-13 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.20 [a] |
| Ex No | R 7 | R 8 | R 9 | X 1 |
| L—R 6 | LogP | |||
| 7-01 | Cl | H | H | Br |
| (2,4-dimethylphenyl)methyl | 3.31 [a] | |||
| 7-02 | H | H | H | Br |
| (4-methylphenyl)methyl | 2.31 [a] | |||
| 7-03 | CF 3 | H | H | Br |
| (2,4-dimethylphenyl)methyl | 2.43 [a] | |||
| 7-04 | Cl | H | H | Br |
| (2,4-dichlorophenyl)methyl | 3.45 [a] | |||
| 7-05 | Cl | H | H | Br |
| (2-chloro-4-methylphenyl)methyl | 3.38 [a] | |||
| 7-06 | Cl | H | H | Br |
| (4-chloro-2-methylphenyl)methyl | 3.44 [a] | |||
| 7-07 | Cl | H | H | Br |
| (2-chloro-3-methylphenyl)methyl | 3.44 [a] | |||
| 7-08 | methoxy | H | H | Br |
| (2-chloro-4-methylphenyl)methyl | ||||
| 7-09 | Cl | H | H | Br |
| (2-chloro-5-methylphenyl)methyl | 3.46 [a] |
| Ex No | R 7 | R 8 | R 9 | Q | LogP |
| 9-01 | Cl | H | H | 3-(trifluoromethyl)phenyl | 3.77 [a] |
| Ex No | R 7 | R 8 | R 9 | Q | LogP |
| 10-01 | Cl | H | H | 3-(trifluoromethyl) | 2.41 [a] |
| phenyl |
| Ex No | R 7 | R 8 | R 9 | Q |
| L—R 6 | LogP | |||
| 12-01 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-(trifluoromethoxy)phenyl | 3.90 + 4.56 [a] | |||
| 12-02 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| indan-5-yl | 3.87 + 4.65 [a] | |||
| 12-03 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| naphthalen-2-yl | 4.49 [a] | |||
| 12-04 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 2,3-dihydro-1,4- benzodioxin-6-yl | 3.72 [a] | |||
| 12-05 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-chlorophenyl | 3.73 + 4.38 [a] | |||
| 12-06 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-chlorophenyl | 3.61 + 4.32 [a] | |||
| 12-07 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 3,4-dimethylphenyl | 4.55 [a] | |||
| 12-08 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methylphenyl | 4.26 [a] | |||
| 12-09 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methoxyphenyl | 3.65 [a] | |||
| 12-10 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 1-phenylcyclopropyl | 4.50 [a] | |||
| 12-11 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methoxyphenyl | 3.81 [a] | |||
| 12-12 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 2,3-dihydro-1- benzofuran-5-yl | 3.87 [a] | |||
| 12-13 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 2,4-difluorophenyl | 4.81 [a] | |||
| 12-14 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-chlorophenyl | 3.83 + 4.01 + 4.66 [a] | |||
| 12-15 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methoxyphenyl | 4.47 [a] | |||
| 12-16 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-chlorophenyl | 5.00 [a] | |||
| 12-17 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| phenyl | 3.94 [a] | |||
| 12-18 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-cyanophenyl | 3.01 [a] |
| L—R 6 | LogP | Salt |
| 13-01 | ||
| (2,4-dimethylphenyl)methyl | 1.13 [a] | HCl |
| 13-02 | ||
| (2,4-dimethylphenyl)methyl | 1.16 [a] | HCl |
| 13-03 | ||
| (2,4-dimethylphenyl)methyl | 1.28 [a] | HCl |
| 13-04 | ||
| (2-chloro-4-methylpheny)methyl | 1.09 [a] | HCl |
| 13-05 | ||
| [5-(trifluoromethyl)-3-thienyl]methyl | 1.29 [a] | HCl |
| 13-06 | ||
| (5-chloro-3-thienyl)methyl | 1.04 [a] | HCl |
| 13-07 | ||
| (2-chloro-3-methylphenyl)methyl | 1.32 [a] | HCl |
| 13-08 | ||
| (2-chloro-5-methylphenyl)methyl | 1.27 [a] | HCl |
| 13-09 | ||
| (2,4-dimethylphenyl)methyl | 0.69 [a] | — |
| Ex No | R 7 | R 8 | R 9 | Q |
| L—R 6 | LogP | |||
| 14-01 | Cl | F | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.03 [a] | |||
| 14-02 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.32 [a] | |||
| 14-03 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (4-methylphenyl)methyl | 5.00 [a] | |||
| 14-04 | Cl | I | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.18 [a] | |||
| 14-05 | methoxy | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.26 [a] | |||
| 14-06 | Cl | H | F | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.45 [a] | |||
| 14-07 | Cl | H | Cl | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.45 [a] | |||
| 14-08 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (4-bromo-2- methylphenyl)methyl | 5.31 [a] | |||
| 14-09 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| [2-chloro-4-(trifluoromethyl) phenyl]methyl | 5.36 [a] | |||
| 14-10 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| [5-(trifluoromethyl)-3- thienyl]methyl | 4.96 [a] | |||
| 14-11 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (5-chloro-3-thienyl)methyl | 4.96 [a] | |||
| 14-12 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methylphenyl | 4.49 [a] |
| Ex No | R 7 | R 8 | R 9 | Q |
| L—R 6 | LogP | |||
| 16-01 | Cl | F | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.74 [a] | |||
| 16-02 | methoxy | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | ||||
| 16-03 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 4.80 [a] | |||
| 16-04 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (4-methylphenyl)methyl | 4.59 [a] | |||
| 16-05 | Cl | I | H | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.28 [a] | |||
| 16-06 | Cl | H | F | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.16 [a] | |||
| 16-07 | Cl | H | Cl | 3-(trifluoromethyl)phenyl |
| (2,4-dimethylphenyl)methyl | 5.35 [a] | |||
| 16-08 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (4-bromo-2- methylphenyl)methyl | ||||
| 16-09 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| [2-chloro-4- (trifluoromethyl)phenyl]methyl | 4.97 [a] | |||
| 16-10 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| [5-(trifluoromethyl)-3- thienyl]methyl | 4.59 [a] | |||
| 16-11 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| (5-chloro-3-thienyl)methyl | 4.48 [a] | |||
| 16-12 | Cl | H | H | 3-(trifluoromethyl)phenyl |
| 4-methylphenyl | 4.19 [a] |
| Ex No | R 7 | R 8 | R 9 | X 1 |
| L—R 6 | LogP | |||
| 17-01 | H | H | H | Br |
| (4-methylphenyl)methyl | 2.80 [a] | |||
| 17-02 | Cl | H | H | Br |
| (2-chloro-4- methylphenyl)methyl | 3.94 [a] | |||
| 17-03 | methoxy | H | H | Br |
| (2-chloro-4- methylphenyl)methyl | 3.94 [a] | |||
| 17-04 | Cl | H | H | Br |
| (4-chloro-2- methylphenyl)methyl | 3.98 [a] | |||
| 17-05 | Cl | H | H | Br |
| (2-chloro-3- methylphenyl)methyl | 3.97 [a] | |||
| 17-06 | Cl | H | H | Br |
| (2-chloro-5- methylphenyl)methyl |
| Ex No | R 7 | R 8 | R 9 | X 1 |
| L—R 6 | LogP | |||
| 18-01 | H | H | H | Br |
| (4-methylphenyl)methyl | 2.78 [a] | |||
| 18-02 | Cl | H | H | Br |
| (2-chloro-4- methylphenyl)methyl | 3.85 [a] | |||
| 18-03 | methoxy | H | H | Br |
| (2-chloro-4- methylphenyl)methyl | 4.12 [a] | |||
| 18-04 | Cl | H | H | Br |
| (2-chloro-5- methylphenyl)methyl | ||||
| 18-05 | Cl | H | H | Br |
| (4-chloro-2- methylphenyl)methyl | ||||
| 18-06 | Cl | H | H | Br |
| (2-chloro-3- methylphenyl)methyl |
| Ex No | R 7 | R 8 | R 9 | Q |
| LogP | ||||
| 32- 01 | Cl | H | H | 3- (trifluoro- methyl) phenyl |
| 2.11 [a] |
| Solvent: | 5% | by volume of Dimethyl sulfoxide |
| 10% | by volume of Acetone | |
| Emulsifier: | 1 μl | of Tween ® 80 per mg of active ingredient |
| Solvent: | 5% | by volume of Dimethyl sulfoxide |
| 10% | by volume of Acetone | |
| Emulsifier: | 1 μl | of Tween ® 80 per mg of active ingredient |
| Solvent: | 5% | by volume of Dimethyl sulfoxide |
| 10% | by volume of Acetone | |
| Emulsifier: | 1 μl | of Tween ® 80 per mg of active ingredient |
| Solvent: | 5% | by volume of Dimethyl sulfoxide |
| 10% | by volume of Acetone | |
| Emulsifier: | 1 μl | of Tween ® 80 per mg of active ingredient |
| Solvent: | 5% | by volume of Dimethyl sulfoxide |
| 10% | by volume of Acetone | |
| Emulsifier: | 1 μl | of Tween ® 80 per mg of active ingredient |
Claims as granted
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15 codes- A01P3/00
- A01N43/88
- A01N43/54
- A01N43/40
- C07F7/08
- C07D413/14
- C07D405/12
- C07D401/12
- C07D401/04
- C07D213/84
- C07D213/81
- C07D213/79
- C07D213/76
- C07D209/48
- C07D413/04
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