WO 2002/070483 discloses several 5- and 6-membered heteroaromatic diamide compounds activity. Furthermore, in WO 2007/020050 is heterobicylic diamide compounds described and their use of for controlling harmful pests in agriculture.

›DISCLOSURE OF THE INVENTION · 1 of 5

The present invention is intended to provide a compound having excellent efficacy of controlling pests.

The present inventors have intensively studied in order to find out a compound having excellent efficacy of controlling pests and, as a result, found out that a hydrazide compound represented by the following formula (1) has excellent controlling efficacy. Thus, the present invention has been completed.

According to the present invention, there is provided:

A hydrazide compound represented by the formula (1) (hereinafter referred to as the present compound), an N-oxide thereof or suitable salt thereof:

wherein

A 1 and A 2 independently represent an oxygen atom or a sulfur atom;

E represents, together with the two contiguous linking carbon atoms, a 5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-membered fused heterobicyclic ring system;

R 1 represents a hydrogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6 trialkylsilyl;

or represents phenyl, C7-C9 phenylalkyl or phenylcarbonyl: each said phenyl ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

R 2 and R 3 independently represent a hydrogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6 trialkylsilyl;

R 2 and R 3 are taken together with the two nitrogen atoms to which they are attached to form a 5- to 8-membered ring containing two nitrogen atoms, one or more CH 2 or C(═O), and optionally one or two ring members selected from the group consisting of (1) an oxygen atom, (2) a sulfur atom, (3) S(═O), (4) S(═O) 2 and (4) NR a (wherein R a represents C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, or a phenyl optionally substituted with one or more independent substituents from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms);

›DISCLOSURE OF THE INVENTION · 2 of 5

and wherein the ring at the carbon atoms is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) C1-C6 alkyl optionally substituted with one or more halogen atoms, and (3) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms;

R 4 represents a halogen atom, cyano, nitro, hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6 alkoxy optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, or C3-C6 trialkylsilyl;

or represents a phenyl, benzyl, phenoxy, or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

n represents an integer of 0 to 3 (provided that, when n is an integer of 2 or more, R 4 's may be the same or different);

Q represents Q1, Q2, Q3, Q4, Q5 or Q6:

A 31 , A 32 , A 33 and A 34 represent an oxygen atom, or a sulfur atom;

m represents an integer of 0 to 2;

R 6 represents a hydrogen atom; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C1-C6 alkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (3) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (6) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; naphthyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; 3- to 8-membered non-aromatic heterocyclic ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

›DISCLOSURE OF THE INVENTION · 3 of 5

R 7 and R 8 represent C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; or C7-C9 phenylalkyl whose phenyl ring moiety optionally is substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

R 9 and R 10 independently represent a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; or C7-C9 phenylalkyl whose phenyl ring moiety optionally is substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; R 11 represents C1-C6 alkyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; or a phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; or 3- to 8-membered non-aromatic heterocyclic ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 12 and R 13 independently represent C1-C6 alkyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; or phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

›DISCLOSURE OF THE INVENTION · 4 of 5

J represents J1 or J2:

X a r Y a r Z a r X b , Y b and Z b independently represent CH or a nitrogen atom;

R 19a and R 19b represent a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; C7-C9 phenylalkyl whose phenyl ring is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; or C7-C9 pyridinylalkyl whose pyridine ring is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

R 20a and R 20b represent a halogen atom; cyano; nitro; thiocyanato; C1-C6 alkyl optionally substituted with one or more halogen atoms; C1-C6 alkoxy optionally substituted with one or more halogen atoms; C2-C6 cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substituted with one or more halogen atoms; C2-C6 alkenyloxy optionally substituted with one or more halogen atoms; C2-C6 alkynyloxy optionally substituted with one or more halogen atoms; C1-C6 alkylthio optionally substituted with one or more halogen atoms; C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms; C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms; or phenoxy optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

›DISCLOSURE OF THE INVENTION · 5 of 5

p represents an integer of 0 to 3 (provided that, when p is an integer of 2 or 3, two or more R 20a s may be the same or different); and

q represents an integer of 0 to 3 (provided that, when q is an integer of 2 or 3, two or more R 20b s may be the same or different).

Furthermore this invention also contains a method of controlling an invertebrate pest applying the present compound, an N-oxide thereof or an agricultural suitable salt thereof by contacting directly to a pest, or to a place where a pest inhabits. With includes the use of the present compound, an N-oxide thereof or an agricultural suitable salt thereof as active ingredient in a pesticidal composition.

A composition comprising of the present compound, an N-oxide thereof or an agricultural suitable salt thereof and at least one additional component selected from the group of surfactants, solid diluents and liquid diluents. This invention also includes a method for controlling an invertebrate pest by using the present compound, an N-oxide thereof or an agricultural suitable salt thereof as active ingredient in a pesticidal composition and a biological active amount of at least one additional compound or agent. The invention also pertains to the use of the present compound, an N-oxide thereof or an agricultural suitable salt thereof for manufacturing a pesticidal preparation.

›BEST MODE FOR CARRYING OUT THE INVENTION · 1 of 15

The compounds of this invention include every possible sterioisomer in terms of enantiomers and diastereomers that can be formed from different configuration at centers of asymmetry and different double bond configuration according to well-accepted definition of configuration isomers (Eliel, Ernest L., Wilien, Samuel H., Stereochemistry of Organic Compounds , John Wiley & Son, 1994). The compounds of the invention can be present as a mixture of the above-mentioned isomers, as a single diastereomer or in an optically enriched form as active ingredients. Furthermore, the compounds of formula I of this invention can be present as an N-oxide thereof or an agricultural suitable salt thereof. All available nitrogen atoms whose lone pairs are not part of an aromatic molecular H-orbital according to Hückel's rule can be oxidized at their lone pairs to form N-oxides by using commonly known methods. Agricultural suitable salts of the compounds of this invention can be formed by addition of an inorganic or organic acid to the compound like for example hydrochloric, hydrobromic, sulfuric, nitric and phosphoric acid as well as acetic, propionic, butyric, oxalic, malonic, tartaric, lactic, maleic, fumaric, citric, p-toluenesulfonic and salicylic acid. In case where compounds contain acidic moieties like carboxyl, sulfonyl or phenol, salts can be formed by addition of an inorganic or organic base like e.g. the hydroxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium or amines like ammonia, pyridine or triethylamine. The term ‘aromatic’ and ‘heteroaromatic’ indicates that the carbocyclic or heterocyclic ring system is fully unsaturated with a planar ring system allowing the ring systems p-orbitals and optionally lone pair orbitals of heteroatoms, which are perpendicular to the ring plane to overlap to form a Π-molecular orbital with (4n+2) H-electrons according to Hückel's rule (n is 0 or a positive integer). The term ‘non-aromatic’ or ‘non-aromatic heterocyclic ring system’ refers to a ring system, which is fully or partial saturated or which is fully unsaturated but does not fulfill the requirements of Hückel's rule as mentioned above. The term ‘hetero’ in ‘heteroaromatic’, ‘heterobicyclic’ and ‘non-aromatic heterocyclic ring’ denotes a ring system that contains at least one or more atom different from carbon, selected from the group of oxygen, nitrogen and sulfur. The heterocyclic ring system can be attached at any available carbon or nitrogen atom by replacement of hydrogen.

Hereinafter, the examples of the “substituents” are illustrated.

Examples of the 5- or 6-membered heteroaromatic ring system substituted with (R 4 ), include E-1 to E-39 shown below. The heteroaromatic ring systems E-1 to E-39 are attached with their upper right bond of an available carbon atom to the nitrogen atom of the —NR 1 (C=A 1 )J moiety. The hydrazide moiety —(C=A 2 ) N R 2 NR 3 Q is attached with the —(C=A 2 ) carbon atom to an available carbon atom at the lower right bond of the exemplified ring systems E-1 to E-39.

Examples of the 8-, 9- or 10-membered fused heterobicyclic ring system substituted with (R 4 ), include E-40 to E-109 shown below. Substitution of said heterobicyclic ring systems with substituents R 4 is possible by substitution of carbon and nitrogen H-atoms on the aromatic ring systems as well as on non-aromatic linking moieties (E-97-101, E-103, E-105, E-107-109). The heteroaromatic ring systems E-40 to E-109 are attached with their upper right bond of an available carbon atom to the nitrogen atom of the —NR 1 (C=A 1 )J moiety. The hydrazide moiety —(C=A 2 ) N R 2 NR 3 Q is attached with the —(C=A 2 ) carbon atom to an available carbon atom at the lower right bond of the exemplified ring systems E-40 to E-109.

Preferred ring systems include E-2, E-4, E-7, E-12, E-13, E-22, E-40 and E47; most preferred E-2 and E-4.

Examples of a halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of C1-C6 alkyl optionally substituted with one or more halogen atoms include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl as well as fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl and pentafluoroethyl.

Examples of C1-C6 alkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (3) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (6) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms include methyl, trifluoromethyl, trichloromethyl, chloromethyl, dichloromethyl, fluoromethyl, difluoromethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, ethylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, dimethylaminomethyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, ethyl, pentafluoroethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.

Examples of C2-C6 cyanoalkyl include cyanomethyl and 2-cyanoethyl.

Examples of C2-C6 cyanoalkoxy include cyanomethoxy and 2-cyanoethoxy.

Examples of C1-C6 hydroxyalky include hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1-hydroxypropyl, 2-hydroxypropyl, 3-hydroxypropyl and 2-hydroxy-isopropyl.

Examples of C1-C6 alkoxy optionally substituted with one or more halogen atoms include methoxy, trifluoromethoxy, ethoxy, 2,2,2-trifluoroethoxy, propyloxy, isopropyloxy, butoxy, isobutyloxy, sec-butoxy, tert-butoxy, pentyloxy and hexyloxy.

Examples of C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms include methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl and 2-isopropyloxyethyl.

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Examples of C2-C6 alkoxyalkyloxy optionally substituted with one or more halogen atoms include 2-(methoxy)ethoxy.

Examples of C2-C6 alkenyl optionally substituted with one or more halogen atoms include 2-propenyl, 3-chloro-2-propenyl, 2-chloro-2-propenyl, 3,3-dichloro-2-propenyl, 2-butenyl, 3-butenyl, 2-methyl-2-propenyl, 3-methyl-2-butenyl, 2-pentenyl and 2-hexenyl as well as polyenes like 1,3-pentadienyl and 2,4-hexadienyl and all possible diastereomers.

Examples of C2-C6 alkenyloxy optionally substituted with one or more halogen atoms include 2-propenyloxy, 3,3-dichloro-2-propenoxy and 2-methyl-2-propenyloxy.

Examples of C2-C6 alkynyl optionally substituted with one or more halogen atoms include 2-propynyl, 3-chloro-2-propynyl, 3-bromo-2-propynyl, 2-butynyl and 3-butynyl as well as polyynes like 2,5-hexadiynyl.

Examples of C2-C6 alkynyloxy optionally substituted with one or more halogen atoms include 2-propynyloxy, 3-chloro-2-propynyloxy and 2-butynyloxy.

Examples of C1-C6 alkylthio optionally substituted with one or more halogen atoms include methylthio, trifluoromethylthio, ethylthio, propylthio, isopropylthio, butylthio, isobutylthio, sec-butylthio, tert-butylthio, pentylthio and hexylthio.

Examples of C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms include methylsulfinyl, trifluoromethylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, butylsulfinyl, isobutylsulfinyl, sec-butylsulfinyl, tert-butylsulfinyl, pentylsulfinyl and hexylsulfinyl. The definition includes both sulfoxide enantiomers.

Examples of C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms include methylsulfonyl, trifluoromethylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, pentylsulfonyl and hexylsulfonyl.

Examples of C1-C6 alkylamino include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino and tert-butylamino.

Examples of C1-C6 alkylamino optionally substituted with one or more halogen atoms alkylamino include methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, sec-butylamino, isobutylamino, tert-butylamino, 2-fluoroethyl amino, 2,2,2-trifluoroethyl amino, 2,2,3,3,3-pentafluoropropyl amino and 2,2,3,3,4,4,4-heptafluoroamino.

Examples of C2-C8 dialkylamino include dimethylamino, diethylamino, ethylmethylamino, di-n-propylamino, diisopropylamino and di-n-butylamino.

Examples of C2-C8 dialkylamino optionally substituted with one or more halogen atoms include dimethylamino, diethylamino, ethylmethylamino, bis(2,2,2-trifluoroethyl)amino, di-n-propylamino, diisopropylamino and di-n-butylamino.

Examples of C3-C6 cycloalkylamino include cyclopropyl amino, cyclobutylamino, cyclopentylamino and cyclohexylamino.

Examples of C2-C6 alkylcarbonyl include acetyl, propionyl, isobutyryl and trimethylacetyl.

Examples of C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms include acetyl, trifluoroacetyl, trichloroacetyl, propionyl, pentafluoropropionyl, isobutyryl and trimethylacetyl.

Examples of C2-C6 alkoxycarbonyl include methoxycarbonyl, ethoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl.

Examples of C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms include methoxycarbonyl, ethoxycarbonyl, 2-fluoroethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, isopropoxycarbonyl and tert-butoxycarbonyl.

Examples of C2-C6 alkylaminocarbonyl include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonylcarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl and tert-butylaminocarbonyl.

Examples of C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms include methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, n-butylaminocarbonyl, sec-butylaminocarbonyl, isobutylaminocarbonyl, tert-butylaminocarbonyl, 2-fluoroethylaminocarbonyl, 2,2,2-trifluoroethylaminocarbonyl, 2,2,3,3,3-pentafluoropropylcarbonylaminocarbonyl and 2,2,3,3,4,4,4-heptafluorobutylaminocarbonyl.

Examples of C3-C8 dialkylaminocarbonyl include dimethylaminocarbonyl and diethylaminocarbonyl.

Examples of C4-C6 cycloalkylaminocarbonyl include cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl and cyclohexylaminocarbonyl.

Examples of C3-C6 trialkylsilyl include trimthylsilyl, triethylsilyl and tertbutyldimethylsilyl.

Examples of C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms include cyclopropyl, 2-methylcyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Examples of phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 2-iodophenyl, 2,6-difluorophenyl, 2,6-dichlorophenyl, 2-chloro-6-fluorophenyl, 2-chloro-4-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl, 2-(trifluoromethyl)phenyl, 3-(trifluoromethyl)phenyl, 4-(trifluoromethyl)phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 2-(trifluoromethoxy)phenyl, 2-(methylthio)phenyl, 2-(methylsulfinyl)phenyl and 2-(methylsulfonyl)phenyl.

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Examples of benzyl optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include benzyl, 2-fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl, 2-iodobenzyl, 2,6-difluorobenzyl, 2,6-dichlorobenzyl, 2-chloro-6-fluorobenzyl, 2-chloro-4-fluorobenzyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl, 2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-ethylbenzyl, 2-isopropylbenzyl, 2-tert-butylbenzyl, 2-(trifluoromethyl)benzyl, 3-(trifluoromethyl)benzyl, 4-(trifluoromethyl)benzyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 2-ethoxybenzyl, 2-(trifluoromethoxy)benzyl, 2-(methylthio)benzyl, 2-(methylsulfinyl)benzyl and 2-(methylsulfonyl)benzyl.

Examples of C7-C9 phenylalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include benzyl, 1-phenylethyl, 2-phenylethyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-cyanobenzyl, 3-cyanobenzyl, 4-cyanobenzyl, 2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-(trifluoromethyl)benzyl, 3-(trifluoromethyl)benzyl, 4-(trifluoromethyl)benzyl, 2-methoxybenzyl, 3-methoxybenzyl and 4-methoxybenzyl.

Examples of phenoxy optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include phenoxy, 2-chlorophenoxy, 3-chlorophenoxy, 4-chlorophenoxy, 2-cyanophenoxy, 3-cyanophenoxy, 4-cyanophenoxy, 2-nitrophenoxy, 3-nitrophenoxy, 4-nitrophenoxy, 2-methylphenoxy, 3-methylphenoxy, 4-methylphenoxy, 2-(trifluoromethyl)phenoxy, 3-(trifluoromethyl)phenoxy, 4-(trifluoromethyl)phenoxy, 2-methoxyphenoxy, 3-methoxyphenoxy, 4-methoxyphenoxy and 4-(trifluoromethoxy)phenoxy.

Examples of C7-C9 phenoxyalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms include phenoxymethyl, phenoxyethyl, 2-chlorophenoxymethyl, 2-chlorophenoxyethyl, 3-chlorophenoxymethyl, 3-chlorophenoxyethyl, 4-chlorophenoxymethyl, 4-chlorophenoxyethyl, 2-cyanophenoxymethyl, 2-cyanophenoxyethyl, 3-cyanophenoxymethyl, 3-cyanophenoxyethyl, 4-cyanophenoxymethyl, 4-cyanophenoxyethyl, 2-nitrophenoxymethyl, 2-nitrophenoxyethyl, 3-nitrophenoxymethyl, 3-nitrophenoxyethyl, 4-nitrophenoxymethyl, 4-nitrophenoxyethyl, 2-methylphenoxymethyl, 2-methylphenoxyethyl, 3-methylphenoxymethyl, 3-methylphenoxyethyl, 4-methylphenoxymethyl, 4-methylphenoxyethyl, 2-(trifluoromethyl)phenoxymethyl, 2-(trifluoromethyl)phenoxyethyl, 3-(trifluoromethyl)phenoxymethyl, 3-(trifluoromethyl)phenoxyethyl, 4-(trifluoromethyl)phenoxymethyl, 4-(trifluoromethyl)phenoxyethyl, 2-methoxyphenoxymethyl, 2-methoxyphenoxyethyl, 3-methoxyphenoxymethyl, 3-methoxyphenoxyethyl, 4-methoxyphenoxymethyl, 4-methoxyphenoxyethyl, 4-(trifluoromethoxy)phenoxymethyl and 4-(trifluoromethoxy)phenoxyethyl.

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Examples of phenylcarbonyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include benzoyl, 2-fluorobenzoyl, 3-fluorobenzoyl, 4-fluorobenzoyl, 2-chlorobenzoyl, 3-chlorobenzoyl, 4-chlorobenzoyl, 2-bromobenzoyl, 2-iodobenzoyl, 2,6-difluorobenzoyl, 2,6-dichlorobenzoyl, 2-chloro-6-fluorobenzoyl, 2-chloro-4-fluorobenzoyl, 2-cyanobenzoyl, 3-cyanobenzoyl, 4-cyanobenzoyl, 2-nitrobenzoyl, 3-nitrobenzoyl, 4-nitrobenzoyl, 2-methylbenzoyl, 3-methylbenzoyl, 4-methylbenzoyl, 2-ethylbenzoyl, 2-isopropylbenzoyl, 2-tert-butylbenzoyl, 2-(trifluoromethyl)benzoyl, 3-(trifluoromethyl)benzoyl, 4-(trifluoromethyl)benzoyl, 2-methoxybenzoyl, 3-methoxybenzoyl, 4-methoxybenzoyl, 2-ethoxybenzoyl, 2-(trifluoromethoxy)benzoyl, 2-(methylthio)benzoyl, 2-(methylsulfinyl)benzoyl and 2-(methylsulfonyl)benzoyl.

Examples of naphthyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms include 1-naphthyl and 2-naphthyl.

Examples of 5- or 6-membered heteroaromatic ring optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl optionally substituted with one or more halogen atoms, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl include 2-pyridinyl, 3-fluoro-2-pyridinyl, 3-chloro-2-pyridinyl, 3-bromo-2-pyridinyl, 3-iodo-2-pyridinyl, 3-methyl-2-pyridinyl, 3-trifluoromethyl-2-pyridinyl, 3-methoxy-2-pyridinyl, 3-cyano-2-pyridinyl, 3-nitro-2-pyridinyl, 3-pyridinyl, 2-chloro-3-pyridinyl, 4-chloro-3-pyridinyl, 4-pyridinyl, 3-chloro-4-pyridinyl, 3,5-dichloro-4-pyridinyl, 2-pyrimidinyl, 4-methyl-2-pyrimidinyl, 4,6-dimethyl-2-pyrimidinyl, 4-pyrimidinyl, 5-chloro-4-pyrimidinyl, pyrazinyl, 3-methyl-2-pyrazinyl, 2-thiazolyl, 1-methyl-5-pyrazolyl, 4-chloro-1-methyl-5-pyrazolyl, 4-chloro-1,3-dimethyl-5-pyrazolyl and 4-chloro-5-methyl-3-isooxazolyl.

Examples of 3- to 8-membered non-aromatic heterocyclic ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms include pyrrolidin-1-yl, piperidino, 3,5-dimethylpiperidino, hexamethyleneimin-1-yl, heptamethyleneimin-1-yl, morpholino, 2,6-dimethylmorpholino, thiomorpholin-4-yl, 4-methylpiperazin-1-yl, 4-(ethoxycarbonyl)piperazin-1-yl and 4-phenylpiperazin-1-yl.

Examples of C7-C9 pyridinylalkyl whose pyridine ring is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms include 2-pyridinylmethyl, 3-pyridinylmethyl, 4-pyridinylmethyl, 3-chloro-2-pyridinylmethyl and 2-chloro-3-pyridinylmethyl.

Examples of R 2 and R 3 are taken together with the two nitrogen atoms to which they are attached to form a 5- to 8-membered ring containing two nitrogen atoms, one or more CH 2 or C(═O), and optionally one or two ring members selected from the group consisting of (1) an oxygen atom, (2) a sulfur atom, (3) S(═O), (4) S(═O) 2 and (4) NR a are shown below as ring T. Said ring at the carbon atoms is substituted by one or more independent G 6 , which represents a halogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms, and C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms. Further ring members from nitrogen —NR a — (not included the two contiguous linking nitrogen atoms) with free valences can be substituted by R a which is selected from the group consisting of C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, or a phenyl optionally substituted with one or more independent substituents selected from the group consisting of a halogen atom, cyano, nitro, C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6 alkoxy optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C1-C6 alkylamino optionally substituted with one or more halogen atoms, C2-C6 dialkylamino optionally substituted with one or more halogen atoms, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms.

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Said ring systems T are connected with the left upper nitrogen atom from the two contiguous linking nitrogen atoms via —(C=A 2 )- moiety with the ring system E, which represents, a 5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-membered fused heterobicyclic ring system.

The substituent Q represents Q1, Q2, Q3, Q4, Q5 or Q6:

A 31 , A 32 , A 33 and A 34 represent an oxygen atom, or a sulfur atom; m represents an integer of 0 to 2. Substituents R 6 to R 13 are selected as explained above in the summary of the invention.

J represents J1 or J2. Examples for said ring J1 and J2 are shown below as J-1.1 to J-1.8 and J-2.1 to J-2.8. The ring systems J-1.1 to J-1.8 and J-2.1 to J-2.8 are connected with their very left carbon atom via the —(C=A 1 )- group of the —NR 1 (C=A 1 )J moiety with the ring system E, which represents, a 5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-membered fused heterobicyclic ring system. One nitrogen atom is substituted by R 19a (J1) or R 19b (J2) Ring carbon atoms are optionally substituted by 1 to 3 substituents R 20a (J1) or R 20b (J2) provided that, when 2 or 3 substituents R 20a (J1) or R 20b (J2) are present, two or more R 20a 's and R 20b 's may be the same or different. Substituents R 19a (J1), R 19b (J2), R 20a (J1) and R 20b (J2) are selected as explained above in the summary of the invention.

Preferred ring systems include J-1.1, J-1.2, J-2.1 and J-2.2; most preferred J-1.1 and J-1.2.

Detailed examples of the group represented by J1 include 1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)pyrazol-5-yl, 1-(2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)pyrazol-5-yl, a 3-fluoro-1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)-3-fluoropyrazol-5-yl, 3-fluoro-1-(2-pyridinyl)pyrazol-5-yl, 3-fluoro-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-phenylpyrazol-5-yl, 3-chloro-1-(2-chlorophenyl)pyrazol-5-yl, 3-chloro-1-(2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-phenylpyrazol-5-yl, 3-bromo-1-(2-chlorophenyl)pyrazol-5-yl, 3-bromo-1-(2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 3-iodo-1-phenylpyrazol-5-yl, 3-iodo-1-(2-chlorophenyl)pyrazol-5-yl, 3-iodo-1-(2-pyridinyl)pyrazol-5-yl, 3-iodo-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 3-methyl-1-phenylpyrazol-5-yl, 1-(2-chlorophenyl)-3-methylpyrazol-5-yl, 3-methyl-1-(2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-methylpyrazol-5-yl, 1-phenyl-3-(trifluoromethyl)pyrazol-5-yl, 1-(2-chlorophenyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 3-chloro-1-methylpyrazol-5-yl, 3-chloro-1-ethylpyrazol-5-yl, 3-chloro-1-isopropylpyrazol-5-yl, 1-tert-butyl-3-chloropyrazol-5-yl, 3-chloro-1-(3-fluoro-2-pyridinyl)pyrazol-5-yl, 1-(3-bromo-2-pyridinyl)-3-chloropyrazol-5-yl, 3-chloro-1-(3-iodo-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-methyl-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-trifluoromethyl-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-methoxy-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-cyano-2-pyridinyl)pyrazol-5-yl, 3-chloro-1-(3-nitro-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-methylpyrazol-5-yl, 3-bromo-1-ethylpyrazol-5-yl, 3-bromo-1-isopropylpyrazol-5-yl, 3-bromo-1-tert-butylpyrazol-5-yl, 3-bromo-1-(3-fluoro-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-bromo-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-iodo-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-methyl-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-trifluoromethyl-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-methoxy-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-cyano-2-pyridinyl)pyrazol-5-yl, 3-bromo-1-(3-nitro-2-pyridinyl)pyrazol-5-yl, 1-methyl-3-(trifluoromethyl)pyrazol-5-yl, 1-ethyl-3-(trifluoromethyl)pyrazol-5-yl, 1-isopropyl-3-(trifluoromethyl)pyrazol-5-yl, 1-tert-butyl-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-fluoro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-bromo-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-iodo-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-methyl-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-trifluoromethyl-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-methoxy-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-cyano-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-nitro-2-pyridinyl)-3-(trifluoromethyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-ethylpyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-isopropylpyrazol-5-yl, 3-tert-butyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(methylthio)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(ethylthio)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(isopropylthio)pyrazol-5-yl, 3-tert-butylthio-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(methylsulfinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(ethylsulfinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(isopropylsulfinyl)pyrazol-5-yl, 3-tert-butylsulfinyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(methylsulfonyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(ethylsulfonyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(isopropylsulfonyl)pyrazol-5-yl, 3-tert-butylsulfonyl-1-(3-chloro-2-pyridinyl)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-(2,2,2-trifluoroethoxy)pyrazol-5-yl, 1-(3-chloro-2-pyridinyl)-3-cyanopyrazol-5-yl, 1-(2-chlorophenyl)pyrrol-2-yl, 1-(3-chloro-2-pyridinyl)pyrrol-2-yl, 4-chloro-1-(2-chlorophenyl)pyrrol-2-yl, 4-chloro-1-(3-chloro-2-pyridinyl)pyrrol-2-yl, 5-chloro-1-(2-chlorophenyl)pyrrol-2-yl, 5-chloro-1-(3-chloro-2-pyridinyl)pyrrol-2-yl, 1-(2-chlorophenyl)-4,5-dichloropyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-4,5-dichloropyrrol-2-yl, 4-bromo-1-(2-chlorophenyl)pyrrol-2-yl, 4-bromo-1-(3-chloro-2-pyridinyl)pyrrol-2-yl, 5-bromo-1-(2-chlorophenyl)pyrrol-2-yl, 5-bromo-1-(3-chloro-2-pyridinyl)pyrrol-2-yl, 1-(2-chlorophenyl)-4,5-dibromopyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-4,5-dibromopyrrol-2-yl, 1-(2-chlorophenyl)-4-iodopyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-4-iodopyrrol-2-yl, 1-(2-chlorophenyl)-5-iodopyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-5-iodopyrrol-2-yl, 1-(2-chlorophenyl)-4,5-diiodopyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-4,5-diiodopyrrol-2-yl, 1-(2-chlorophenyl)-4-(trifluoromethyl)pyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-4-(trifluoromethyl)pyrrol-2-yl, 1-(2-chlorophenyl)-5-(trifluoromethyl)pyrrol-2-yl, 1-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrrol-2-yl, 1-(2-chlorophenyl)imidazol-2-yl, 1-(3-chloro-2-pyridinyl)imidazol-2-yl, 4-chloro-1-(2-chlorophenyl)imidazol-2-yl, 4-chloro-1-(3-chloro-2-pyridinyl)imidazol-2-yl, 4-bromo-1-(2-chlorophenyl)imidazol-2-yl, 4-bromo-1-(3-chloro-2-pyridinyl)imidazol-2-yl, 1-(2-chlorophenyl)-4-(trifluoromethyl)imdazol-2-yl, 1-(3-chloro-2-pyridinyl)-4-(trifluoromethyl)imidazol-2-yl, 1-(2-chlorophenyl)-1,2,4-triazol-5-yl, 1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl, 3-chloro-1-(2-chlorophenyl)-1,2,4-triazol-5-yl, 3-chloro-1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl, 3-bromo-1-(2-chlorophenyl)-1,2,4-triazol-5-yl, 3-bromo-1-(3-chloro-2-pyridinyl)-1,2,4-triazol-5-yl, 1-(2-chlorophenyl)-3-(trifluoromethyl)-1,2,4-triazol-5-yl and 1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1,2,4-triazol-5-yl.

›BEST MODE FOR CARRYING OUT THE INVENTION · 6 of 15

Examples of the group represented by J2 include 1-methyl-3-phenylpyrazol-4-yl, 3-(2-chlorophenyl)-1-methylpyrazol-4-yl, 1-methyl-3-(2-pyridinyl)pyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-methylpyrazol-4-yl, 1-methyl-5-phenylpyrazol-4-yl, 5-(2-chlorophenyl)-1-methylpyrazol-4-yl, 1-methyl-5-(2-pyridinyl)pyrazol-4-yl, 5-(3-chloro-2-pyridinyl)-1-methylpyrazol-4-yl, 3-phenyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 3-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 3-(2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 5-phenyl-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 5-(2-chlorophenyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 5-(2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 5-(3-chloro-2-pyridinyl)-1-(2,2,2-trifluoroethyl)pyrazol-4-yl, 1-(difluoromethyl)-3-phenylpyrazol-4-yl, 3-(2-chlorophenyl)-1-(difluoromethyl)pyrazol-4-yl, 1-(difluoromethyl)-3-(2-pyridinyl)pyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-(difluoromethyl)pyrazol-4-yl, 1-(difluoromethyl)-5-phenylpyrazol-4-yl, 5-(2-chlorophenyl)-1-(difluoromethyl)pyrazol-4-yl, 1-(difluoromethyl)-5-(2-pyridinyl)pyrazol-4-yl, 5-(3-chloro-2-pyridinyl)-1-(difluoromethyl)pyrazol-4-yl, 3-(2-chlorophenyl)-1-ethylpyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-ethylpyrazol-4-yl, 5-(2-chlorophenyl)-1-ethylpyrazol-4-yl, 5-(3-chloro-2-pyridinyl)-1-ethylpyrazol-4-yl, 3-(2-chlorophenyl)-1-isopropylpyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-isopropylpyrazol-4-yl, 5-(2-chlorophenyl)-1-isopropylpyrazol-4-yl, 5-(3-chloro-2-pyridinyl)-1-isopropylpyrazol-4-yl, 3-(2-chlorophenyl)-1-tert-butylpyrazol-4-yl, 3-(3-chloro-2-pyridinyl)-1-tert-butylpyrazol-4-yl, 5-(2-chlorophenyl)-1-tert-butylpyrazol-4-yl and 5-(3-chloro-2-pyridinyl)-1-tert-butylpyrazol-4-yl.

Hereinafter, preferred embodiments of the present invention are illustrated.

Preferred compounds are:

Preferred Compound 1: The compound according to the present compound, an N-oxide thereof or suitable salt thereof, wherein E is a 5- or 6-membered heteroaromatic ring.

Preferred Compound 2: The compound according to the Preferred Compound 1, wherein

A 1 and A 2 are oxygen atoms; and

R 1 is a hydrogen atom or alkyl optionally substituted with one or more halogen atoms.

Preferred Compound 3: The compound according to the Preferred Compound 2, wherein J is J-1.1, J-1.2, J-2.1, J-2.2 or J-2.3:

wherein

R 19a and R 19b represent a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

R 20a and R 20b represent a halogen atom, cyano, C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6 alkoxy optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyloxy, C2-C6 alkoxyalkyloxy optionally substituted with one or more halogen atoms, C2-C6 alkenyloxy optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms;

or phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

or phenoxy optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

p represents an integer of 0 to 3; and

q represents an integer of 0 to 3 (provided that, when p is an integer of 2 or 3, two or more R 20a 's may be the same or different and, when q is an integer of 2 or 3, two or more R 20b 's may be the same or different).

Preferred Compound 4: The compound according to the present compound, an N-oxide thereof or suitable salt thereof, wherein

Q is Q1;

A 31 is oxygen; and

R 6 represents a hydrogen atom; C1-C6 alkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (3) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (6) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms;

›BEST MODE FOR CARRYING OUT THE INVENTION · 7 of 15

C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

3- to 8-membered non-aromatic heterocyclic optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

or C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms.

Preferred Compound 5: The compound according to the Preferred Compound 4, wherein A 1 and A 2 are oxygen atoms.

Preferred Compound 6: The compound according to the present compound, an N-oxide thereof or suitable salt thereof, wherein

Q is Q2;

A 32 is oxygen; and

R 7 is C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

or C7-C9 phenylalkyl whose ring moiety is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms.

Preferred Compound 7: The compound according to the Preferred Compound 6, wherein A 1 and A 2 are oxygen atoms.

Preferred Compound 8: The compound according to the present compound, an N-oxide thereof or suitable salt thereof, wherein

Q is Q4;

A 34 is oxygen; and

R 9 and R 10 independently represent a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

›BEST MODE FOR CARRYING OUT THE INVENTION · 8 of 15

Preferred Compound 9: The compound according to the Preferred Compound 8, wherein A 1 and A 2 are oxygen atoms.

Preferred Compound 10: A hydrazide compound represented by the formula (II-1) or (II-2),

wherein

X a represents a nitrogen atom or CR 20aax ;

Y and Z represent independently a nitrogen atom or CR 4b , but not Y and Z are CR 4b at the same time;

R 1 represets a hydrogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 2 and R 3 are taken together with the two nitrogen atoms to which they are attached to form a 5- to 8-membered ring containing two nitrogen atoms, one or more CH 2 or C(═O), and optionally one or two ring members selected from the group consisting of (1) an oxygen atom, (2) a sulfur atom, (3) S(═O), (4) S(═O) 2 and (4) NR a (wherein R a represents C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, or a phenyl optionally substituted with one or more independent substituents from (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

R 4a , R 4b and R 4c independently represent a halogen atom, cyano, nitro, hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 alkoxy optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl;

or represents independently phenyl, benzyl, phenoxy, or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

›BEST MODE FOR CARRYING OUT THE INVENTION · 9 of 15

M is a hydrogen atom; C1-C6 alkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (3) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (4) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (6) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, and (7) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms; C1-C6 alkoxy optionally substituted with one or more halogen atoms; C1-C6 alkylthio optionally substituted with one or more halogen atoms; C1-C6 alkylamino; C2-C8 dialkylamino;

phenyl, C7-C9 phenylalkyl or C7-C9 phenoxyalkyl: each said phenyl ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

or 3- to 8-membered non-aromatic heterocyclic ring optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 19ax represents a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 cyanoalkyl; C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

C7-C9 phenylalkyl whose phenyl ring is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms;

or C7-C9 pyridinylalkyl whose pyridine ring is optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms, (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (6) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (7) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (8) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (9) C1-C6 alkylamino optionally substituted with one or more halogen atoms, (10) C2-C6 dialkylamino optionally substituted with one or more halogen atoms, (11) C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atoms, (13) C2-C6 alkylaminocarbonyl optionally substituted with one or more halogen atoms and (14) C3-C6 dialkylaminocarbonyl optionally substituted with one or more halogen atoms; and

›BEST MODE FOR CARRYING OUT THE INVENTION · 10 of 15

R 20ax , R 20ay and R 20az represent a halogen atom; cyano; nitro; thiocyanato; C1-C6 alkyl optionally substituted with one or more halogen atoms; C1-C6 alkoxy optionally substituted with one or more halogen atoms; C2-C6 cyanoalkyloxy; C2-C6 alkoxyalkyloxy optionally substituted with one or more halogen atoms; C2-C6 alkenyloxy optionally substituted with one or more halogen atoms; C2-C6 alkynyloxy optionally substituted with one or more halogen atoms; C1-C6 alkylthio optionally substituted with one or more halogen atoms; C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms; C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms; phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) C1-C6 alkyl optionally substituted with one or more halogen atoms and (5) C1-C6 alkoxy optionally substituted with one or more halogen atoms;

Preferred Compound 11: The compound according to the Preferred Compound 10, wherein

R 1 is a hydrogen atom;

R 2 is a hydrogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 3 is a hydrogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms or C2-C6 alkoxycarbonyl;

R 4a is a halogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 4c is a hydrogen atom, a halogen atom, cyano or C1-C6 alkyl optionally substituted with one or more halogen atoms; R 19a is

wherein

X b is a nitrogen atom or CR 21a ;

R 20ax and R 23ay are independently a hydrogen atom, a halogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6 alkoxy optionally substituted with one or more halogen atoms or C1-C6 alkylthio optionally substituted with one or more halogen atoms;

R 20az is a hydrogen atom; and

R 21a , R 21b and R 21c are independently selected from the group consisting of a hydrogen atom, a halogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms.

Preferred Compound 12: The compound according to the Preferred Compound 11, wherein

X a and X b are nitrogen atoms;

Y is CH; and

Z is a nitrogen atom.

Preferred Compound 13: The compound according to the Preferred Compound 11, wherein

X a and X b are nitrogen atoms;

Y is a nitrogen atom; and

Z is CH.

Preferred Compound 14: The compound according to the Preferred Compound 11, wherein R 4b is a hydrogen atom.

Preferred Compound 15: The compound according to the Preferred Compound 14, wherein M is a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino or C2-C8 dialkylamino.

Preferred Compound 16: The compound according to the Preferred Compound 15, wherein

R 2 is a hydrogen atom, methyl or ethyl;

R 3 is a hydrogen atom, methyl, ethyl or methoxycarbonyl;

R 4a is methyl, chloro, bromo or iodo;

R 4c is hydrogen, fluoro, chloro, bromo, iodo or cyano;

R 20ay is chloro, bromo, iodo, trifluoromethyl or pentafluoroethoxy;

R 22b is a hydrogen atom;

R 22c is chloro or bromo; and

M is hydrogen, methoxy, ethoxy, methylamino or dimethylamino.

Preferred Compound 17: The compound of the Preferred Compound 16, wherein

R 2 is a hydrogen atom;

R 3 is methyl or ethyl; and

M is a hydrogen atom.

Preferred Compound 18: The compound of the Preferred Compound 17, wherein

R 2 and R 3 are independently hydrogen, methyl or ethyl; and

M is methoxy or ethoxy.

Preferred Compound 19: A hydrazide compound represented by the formula (II-1),

X a , Y, Z, R 1 , R 2 , R 3 , R 4a , R 4b , R 4c , M, R 19ax , R 20ax , R 20ay , and R 20az are described above.

Preferred Compound 20: The compound according to the Preferred Compound 19, wherein

R 1 is a hydrogen atom;

R 2 is a hydrogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 3 is a hydrogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms or C2-C6 alkoxycarbonyl;

R 4a is a halogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 4c is a hydrogen atom, a halogen atom, cyano or 1-C6 alkyl optionally substituted with one or more halogen atoms;

R 19a is

wherein

X b is a nitrogen atom or CR 21a ;

R 20 az is a hydrogen atom; and

R 21a , R 21b and R 21c are independently selected from the group consisting of a hydrogen atom, a halogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms.

Preferred Compound 21: The compound according to the Preferred Compound 20, wherein

X a and X b are nitrogen atoms;

Y is CH; and

Z is a nitrogen atom.

Preferred Compound 22: The compound according to the Preferred Compound 20, wherein

X a and X b are nitrogen atoms;

Y is a nitrogen atom; and

Z is CH.

Preferred Compound 23: The compound according to the Preferred Compound 20, wherein R 4b is a hydrogen atom.

Preferred Compound 24: The compound according to the Preferred Compound 23, wherein M is a hydrogen atom, C1-C6 alkyl, C1-C6 alkoxy, amino, C1-C6 alkylamino or C2-C8 dialkylamino.

Preferred Compound 25: The compound according to the Preferred Compound 24, wherein

R 2 is a hydrogen atom, methyl or ethyl;

R 3 is a hydrogen atom, methyl, ethyl or methoxycarbonyl;

R 4a is methyl, chloro, bromo or iodo;

›BEST MODE FOR CARRYING OUT THE INVENTION · 11 of 15

R 4c is hydrogen, fluoro, chloro, bromo, iodo or cyano;

R 20ay is chloro, bromo, iodo, trifluoromethyl or pentafluoroethoxy;

R 22b is a hydrogen atom;

R 22c is chloro or bromo; and

M is hydrogen, methoxy, ethoxy, methylamino or dimethylamino.

Preferred Compound 26: The compound of the Preferred Compound 25, wherein

R 2 is a hydrogen atom;

R 3 is methyl or ethyl; and

M is a hydrogen atom.

Preferred Compound 27: The compound of the Preferred Compound 26, wherein

R 2 and R 3 are independently hydrogen, methyl or ethyl; and

M is methoxy or ethoxy.

This invention further pertains to:

A pesticide comprising the present compound or an N-oxide thereof or suitable salt thereof as an active ingredient.

A method of controlling a pest which comprises applying the present compound, an N-oxide thereof or suitable salt thereof directly to a pest, or to a place where a pest inhabits.

Use of the present compound, an N-oxide thereof or suitable salt thereof for controlling a pest.

Use of the present compound, an N-oxide thereof or suitable salt thereof for manufacturing a pesticidal preparation.

Hereinafter, a process for producing the present compound will be explained.

The present compound can be produced, for example, by the following Process A-1 to Process C-1.

Process A-1

Among the present compounds, a compound represented by the formula (1):

wherein R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , J and n are as defined above;

E represents, together with the two contiguous linking carbon atoms, a 5- or 6-membered heteroaromatic ring system or a 8-, 9- or 10-membered fused heterobicyclic ring system;

Q′ represents a group selected from the group consisting of Q1 to Q6 (provided that the compound wherein Q′ is Q4, and R 8 and R 9 are a hydrogen atom is excluded) (hereinafter, referred to as the compound (I)) can be produced by reacting a compound represented by the formula (2):

wherein R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , J and n are as defined above (hereinafter, referred to as the compound (2)), and a compound represented by the formula (3):

L 1 -Q′ (3)

wherein Q′ is as defined above; and

L 1 represents a halogen atom or a Q′-O— (provided that the case where Q′ is Q4, and R 8 and R 9 are a hydrogen atom is excluded) (hereinafter, referred to as the compound (3)).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methlpyrrolidone, 1,3-dimethyl-2-imidadzolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (3) to be used in the reaction is usually 1 to 2 mols per 1 mol of the compound (2).

The reaction is performed in the presence of a base, if necessary. Examples of the base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, and inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base when the reaction is performed in the presence of the base is usually 1 to 2 mols per 1 mol of the compound (2), while the base may be used in an excess amount in case that the base used is liquid under the reaction conditions such as pyridine, and the like.

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-i) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-i) may be further purified by recrystallization, chromatography, or the like.

Process A-2

Among the present compounds, a compound represented by the formula (I-ii):

wherein R 1 , R 2 , R 3 , R 4 , A 1 , A 2 , A 34 , J and n are as defined above, and R 9a represents C1-C6 alkyl optionally substituted with at least one halogen atom; C2-C6 alkoxyalkyl optionally substituted with at least one halogen atom; C2-C6 alkenyl optionally substituted with at least one halogen atom; 3-C6 alkynyl optionally substituted with at least one halogen atom; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom and (2) C1-C6 alkyl group; a phenyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom (2) cyano group, (3) nitro group, (4) C1-C6 alkyl optionally substituted with at least one halogen atom, (5) C1-C6 alkoxy optionally substituted with at least one halogen atom, (6) C1-C6 alkylthio optionally substituted with at least one halogen atom, (7) C1-C6 alkylsulfinyl optionally substituted with at least one halogen atom, (8) C1-C6 alkylsulfonyl optionally substituted with at least one halogen atom, (9) C2-C6 dialkylamino optionally substituted with at least one halogen atom and (10) C2-C6 alkoxycarbonyl optionally substituted with at least one halogen atom; 5- to 6-membered heteroaryl optionally substituted with one or more independent substituents selected from the group consisting of (1) halogen atom, (2) cyano group, (3) nitro group, (4) C1-C6 alkyl optionally substituted with at least one halogen atom and (5) C1-C6 alkoxy optionally substituted with at least one halogen atom; or C7-C9 phenylaklyl whose benzene ring moiety may be substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano group, (3) nitro group, (4) C1-C6 alkyl optionally substituted with at least one halogen atom and (5) C1-C6 alkoxy optionally substituted with at least one halogen atom (hereinafter, referred to as the compound (1-ii)) can be produced by reacting the compound (2) with a compound represented by the formula (4):

›BEST MODE FOR CARRYING OUT THE INVENTION · 12 of 15

A34=C═N—R 9a (4)

wherein A 34 and R 9a are as defined above (hereinafter, referred to as the compound (4)).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (4) used in the reaction is usually 1 to 2 mols per 1 mol of the compound (2).

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is a usually a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-ii) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-ii) may be further purified by recrystallization, chromatography, or the like.

Process A-3

Among the present compounds, a compound represented by the formula (1-iii):

wherein R 1 , R 2 , R 3 , R 4 , A″ A 2 , A 34 , J and n are as defined above (hereinafter, referred to as the compound (I-iii)) can be produced by reacting the compound (2) and a cyanate or a thiocyanate.

The reaction is performed in the presence of a solvent. Examples of the solvent used in the reaction include acids such as organic acids such as acetic acids, and the like and mineral acids such as hydrochloric acid, and the like, as well as a mixture of these acids and water, chloroform, or the like.

The amount of the cyanate or the thiocyanate used in the reaction is usually 1 to 2 mols per 1 mol of the compound (2).

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

Examples of the cyanate or the thiocyanate include potassium cyanate, sodium cyanate, ammonium cyanate, potassium thiocyanate, sodium thiocyanate and ammonium thiocyanate.

After completion of the reaction, the compound (I-iii) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated Compound (I-iii) may be further purified by recrystallization, chromatography, or the like.

Process B-1

The present compound can be produced by reacting a compound represented by the formula (6):

wherein R 1 , R 2 , R 3 , R 4 , A 2 , Q and n are as defined above (hereinafter, referred to as Compound (6)) and a compound represented by the formula (7):

wherein A 1 and J are as define above, and L 2 represents a halogen atom (hereinafter, referred to as the compound (7)).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (7) used in the reaction is usually 1 to 2 mols per 1 mol of the compound (6).

The reaction is performed in the presence of a base, if necessary. Examples of the base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazadicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, and inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base when the reaction is performed in the presence of the base is usually 1 to 2 mole per 1 mol of the compound (6), while the base may be used in an excess amount in case that the base used is liquid under the reaction conditions such as pyridine, and the like.

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the present compound can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitation by filtration. The isolated present compound may be further purified by recrystallization, chromatography, or the like.

Process B-2

Among the present compounds, a compound represented by the formula (I-iv):

wherein R 1 , R 2 , R 3 , R 4 , A 2 , J, Q and n are as defined above (hereinafter referred to as the compound (I-iv)) can be produced by reacting the compound (6) and a compound represented by the formula (8):

wherein J is as defined above (hereinafter, referred to as the compound (8)) in the presence of a dehydrating agent.

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (8) used in the reaction is usually 1 to 2 mols per 1 mol of the compound (6).

›BEST MODE FOR CARRYING OUT THE INVENTION · 13 of 15

Examples of the dehydrating agent to be used in the reaction include carbodiimides such as dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), and the like. The amount of the dehydrating agent to be used is usually 1 to 2 mols per 1 mol of the compound (6).

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (I-iv) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-iv) may be further purified by recrystallization, chromatography, or the like.

Process C-1

Among the present compounds, a compound represented by the formula (I-v):

wherein R 2 , R 3 , R 4 , J, Q and n are as defined above (hereinafter, referred to as the compound (1-v)) can be produced by reacting a compound represented by the formula (9):

wherein R 4 , J and n are as defined above (hereinafter, referred to as the compound (9)) and a compound represented by the formula (10):

wherein R 2 , R 3 and Q are as defined above (hereinafter, referred to as the compound (10)).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidaozolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (10) to be used in the reaction is usually 1 to 20 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 48 hours.

After completion of the reaction, the compound (1-v) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-v) may be further purified by recrystallization, chromatography, or the like.

Process C-2

Among the present compounds, a compound represented by the formula (I-yl):

wherein R 2 , R 3 , R 4 , A 1 , J, Q and n are as defined above, R 1-a represents C1-C6 alkyl optionally substituted with at least one halogen atom; C2-C6 cyanoalkyl group; C2-C6 alkoxyalkyl optionally substituted with at least one halogen atom; C2-C6 alkenyl optionally substituted with at least one halogen atom; C3-C6 alkynyl optionally substituted with at least one halogen atom; or C7-C9 phenylalkyl in which a benzene ring part may be substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, (2) cyano group, (3) nitro group, (4) C1-C6 alkyl optionally substituted with at least one halogen atom and (5) C1-C6 alkoxy optionally substituted with at least one halogen atom (hereinafter, referred to as the compound (1-yl)) can be produced by reacting a compound represented by the formula (11):

wherein R 1-a , R 4 , A 1 , J and n are as defined above, and L 3 represents a halogen atom (hereinafter, referred to as the compound (11)) and the compound (10).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichlorethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-diethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The amount of the compound (10) to be used in the reaction is usually 1 to 2 mols per 1 mol of the compound (11).

The reaction is performed in the presence of a base, if necessary. Examples of the base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, and inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base to be used when the reaction is performed in the presence of the base is usually 1 to 2 mols per 1 mol of the compound (11), while the base may be used in an excess amount in the case that the base used is liquid under the reaction conditions such as pyridine and the like.

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-yl) can be isolated after pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-yl) may be further purified by recrystallization, chromatography or the like.

Process C-3

The compound (1-yl) can also be produced by reacting a compound represented by the formula (12):

wherein R 4 , R 1-a , A 1 , J and n are as defined above (hereinafter, referred to as Compound (12)) and the compound (10) in the presence of a dehydrating agent.

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichlroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

›BEST MODE FOR CARRYING OUT THE INVENTION · 14 of 15

The amount of the compound (10) used in the reaction is usually 1 to 2 mols per 1 mol of the compound (12).

Examples of the dehydrating agent used in the reaction include carbodiimides such as dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC), and the like. The amount of the dehydrating agent to be used is usually 1 to 2 mols per 1 mol of the compound (12).

The reaction temperature is usually in a range of 0 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (1-yl) can be isolated by pouring the reaction mixture into water and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (1-yl) may be further purified by recrystallization, chromatography, or the like.

Then, a process for producing intermediates for producing the present compound will be explained.

Reference Process 1

Among the compound (2), a compound represented by the formula (2-i):

wherein R 2 , R 3 , R 4 , J and n are as defined above (hereinafter, referred to as the compound (2-i)) can be produced by reacting the compound (9) and a compound represented by the formula (13):

wherein R 2 and R 3 are as defined above (hereinafter, referred to as the compound (13)).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like, hydrocarbons such as toluene, benzene, xylene and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, alcohols such as methanol, ethanol, 2-propanol, and the like, and a mixture thereof.

The amount of the compound (13) to be used in the reaction is usually 1 to 5 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of −50 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-i) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (2-i) may be further purified by recrystallization, chromatography, or the like.

Reference Process 2

Among the compound (2), a compound represented by the formula (2-ii):

wherein R 2 , R 3 , R 4 , J and n are as defined above (hereinafter, referred to as Compound (2-ii)) can be produced by reacting a compound represented by the formula (14):

wherein R 4 , J and n are as defined above (hereinafter, referred to as the compound (14)) and the compound (13).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, alcohols such as methanol, ethanol, 2-propanol, and the like, and a mixture thereof.

The amount of the compound (13) to be used in the reaction is usually 1 to 5 mols per 1 mol of the compound (14).

The reaction temperature is usually in a range of −50 to 100° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-ii) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (2-ii) may be further purified by recrystallization, chromatography, or the like.

Reference Process 3

Among the compound (2), a compound represented by the formula (2-iii):

wherein R 1-n , R 2 , R 3 , R 4 , A 1 , J and n are as defined above (hereinafter, referred to as the compound (2-iii)) can be produced by reacting the compound (11) and the compound (13).

The amount of Compound (13) used in the reaction is usually 2 to 10 mols per 1 mol of the compound (11).

The reaction temperature is usually in a range of −50 to 100° C., and the reaction time is in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (2-iii) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (2-iii) may be further purified by recrystallization, chromatography, or the like.

Reference Process 4

The compound (9) can be produced by reacting a compound represented by the formula (16).

wherein R 4 and n are as defined above (hereinafter, referred to as the compound (16)) and a compound represented by the formula (7′):

wherein J and L 2 are as defined above (hereinafter, referred to as Compound (7′)).

The reaction is performed in the presence or the absence of a solvent in the presence of a base. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

›BEST MODE FOR CARRYING OUT THE INVENTION · 15 of 15

The amount of the compound (7′) used in the reaction is usually 0.5 to 2 mols per 1 mol of the compound (16).

Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, and inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base to be used is usually 1 to 2 mols per 1 mol of the compound (16), while the base may be used in an excess amount in case that the base is liquid under the reaction conditions such as pyridine, and the like.

The reaction temperature is usually in a range of 50 to 150° C., and the reaction time is usually in a range of 1 to 24 hours.

After completion of the reaction, the compound (9) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitates by filtration. The isolated compound (9) may be further purified by recrystallization, chromatography, or the like.

Reference Process 5

The compound (9) can be produced by reacting a compound represented by the formula (17):

wherein R 4 and n are as defined above (hereinafter, referred to as Compound (17)) and the compound (7′).

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

The process comprises the following step 5-1 and step 5-2.

›Step 5-1

This step is performed by reacting the compound (17) and the compound (7′) in the presence of a base.

The amount of the compound (7′) to be used in this step is usually 1 to 2 mols per 1 mol of the compound (17). Examples of the base include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, and inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base to be used is usually 1 to 2 mols per 1 mol of the compound (17).

The reaction temperature of this step is usually in a range of 0 to 50° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of this step, usually, the reaction mixture is used as it is in the next step 5-2.

›Step 5-2 · 1 of 16

This step is performed by reacting the reaction mixture in the step 5-1 and a sulfonyl halide in the presence of a base.

Examples of the sulfonyl halide used in this step include methanesulfonyl chloride, p-toluenesulfonyl chloride, and trifluoromethanesulfonyl chloride. The amount of the sulfonyl halide to be used in this step is usually 1 to 2 mols per 1 mol of the compound (17) used in the step 5-1.

Examples of the base include the same bases as those described with respect to the step 5-1. The amount of the base is usually 2 to 4 mols per 1 mol of the compound (17) used in the step 5-1.

The reaction temperature of this step is usually in a range of 0 to 50° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of this step, the compound (9) can be isolated by pouring the reaction mixture into water, followed by conventional extraction with an organic solvent. The isolated compound (9) may be further purified by recrystallization, chromatography, or the like.

Reference Process 6

The compound (14) can be produced by reacting the compound (9) with a thiocarbonylation agent.

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, diglyme, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, pyridines such as pyridine, picoline, lutidine, and the like, and a mixture thereof.

Examples of the thiocarbonylation agent to be used in the reaction include diphosphorus pentasulfide, a Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide), and the like.

The amount of the thiocarbonylation agent to be used in the reaction is usually 1 to 3 mols per 1 mol of the compound (9).

The reaction temperature is usually in a range of 0° C. to 200° C., and the reaction time is usually in a range of 1 to 24 hours.

After completion of the reaction, the compound (14) can be isolated by collecting a precipitate deposited in the reaction mixture by filtration, or extracting the reaction mixture with an organic solvent. The isolated compound (14) may be further purified by recrystallization, chromatography, or the like.

Reference Process 7

The compound (11) can be produced by reacting the compound (12) with a halogenating agent.

The reaction is performed in the presence or the absence of a solvent. Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, methyl tert-butyl ether, and the like, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, chlorobenzene, and the like, hydrocarbons such as toluene, benzene, xylene, and the like, nitriles such as acetonitrile, and the like, aprotic polar solvents such as N,N-dimethylformamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, dimethyl sulfoxide, and the like, and a mixture thereof.

Examples of the halogenating agent to be used in the reaction include thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide, phosphorus pentachloride, oxalyl chloride, and phosgene.

The amount of the halogenating agent to be used in the reaction is usually 1 to 2 mols per 1 mol of the compound (12) and, in some cases, the halogenating agent may be used in an excess amount.

The reaction temperature is usually in a range of 0° C. to 150° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (11) can be isolated by collecting a precipitate deposited in the reaction mixture, or concentrating the reaction mixture. The isolated compound (11) is usually used as it is in the next step and, if necessary, may be further purified by recrystallization, or the like.

Reference Process 8

The compound (12) can be produced by reacting a compound represented by the formula (18′):

wherein R 1-a , R 4 and n are as defined above (hereinafter, referred to as the compound (18′)) and the compound (7).

The amount of the compound (7) to be used in the reaction is usually 1 to 2 mols per 1 mol of the compound (18′).

The reaction is performed in the presence of a base. Examples of the base to be used include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo[5,4,0]7-undecene (DBU), 1,5-diazabicyclo[4,3,0]5-nonene (DBN), and the like, tertiary amines such as triethylamine, N,N-diisopropylethylamine, and the like, inorganic bases such as potassium carbonate, sodium hydride, and the like. The amount of the base to be used is usually 1 to 2 mols per 1 mol of the compound (18′).

The reaction temperature is usually in a range of 0 to 50° C., and the reaction time is usually in range of 0.1 to 24 hours.

After completion of the reaction, the compound (12) can be isolated by pouring the reaction mixture into water, followed by conventional extraction with an organic solvent, or collecting a deposited precipitate by filtration. The isolated compound (12) may be further purified by recrystallization, chromatography, or the like.

Reference Process 9

The compound (6) can be produced by reacting a compound represented by the formula (20):

›Step 5-2 · 2 of 16

wherein R′, R 4 and n are as defined above (hereinafter, referred to as the compound 20)) and the compound (10).

The amount of the compound (10) to be used in the reaction is usually 1 to 2 mols per 1 mol of the compound (20).

The reaction temperature is usually in a range of −20 to 150° C., and the reaction time is usually in a range of 0.1 to 24 hours.

After completion of the reaction, the compound (20) can be isolated by pouring the reaction mixture into water, and extracting the mixture with an organic solvent, or collecting a deposited precipitate by filtration. The isolated Compound (20) may be further purified by recrystallization, chromatography, or the like.

The compounds (3), (4) and (13) are known compounds, or can be produced from known compounds according to known processes (e.g. see Organic Functional Group Preparations, 2nd edition, Vol. 1, chapter 12, pp. 359-376 (Stanley R. Sandler, Wolf Karo.) or Organic Functional Group Preparations, 2nd edition, Vol. 1, chapter 14, pp. 434-465 (Stanley R. Sandler, Wolf Karo.)).

As an aspect of the compound (2), the following compound is mentioned:

A hydrazide compound of the formula (II):

wherein

X a represents a nitrogen atom or CR 20ax ;

Y and Z represent independently a nitrogen atom or CR 4b , but not Y and Z are CR 4b at the same time;

R 1 is a hydrogen atom or C1-C6 alkyl optionally substituted with one or more halogen atoms;

R 2 represent a hydrogen atom, C1-C6 alkyl optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C1-C6 hydroxyalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C4-C6 cycloalkylaminocarbonyl, or C3-C6 trialkylsilyl;

R 4a , R 4b and R 4c are independently a halogen atom, cyano, nitro, hydroxyl, carboxyl, C1-C6 alkyl optionally substituted with one or more halogen atoms, C1-C6 alkoxy optionally substituted with one or more halogen atoms, C2-C6 cyanoalkyl, C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, C2-C6 alkenyl optionally substituted with one or more halogen atoms, C2-C6 alkynyl optionally substituted with one or more halogen atoms, C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, C1-C6 alkylthio optionally substituted with one or more halogen atoms, C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, C1-C6 alkylamino, C2-C8 dialkylamino, C3-C6 cycloalkylamino, C2-C6 alkylcarbonyl optionally substituted with one or more halogen atoms, C2-C6 alkoxycarbonyl, C2-C6 alkylaminocarbonyl, C3-C8 dialkylaminocarbonyl, C3-C6 trialkylsilyl;

or represents independently phenyl, benzyl or phenoxy, each ring optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

›Step 5-2 · 3 of 16

or 5- or 6-membered heteroaromatic optionally substituted with one or more substituents selected from the group consisting of (1) a halogen atom, (2) cyano, (3) nitro, (4) hydroxyl, (5) carboxyl, (6) C1-C6 alkyl optionally substituted with one or more halogen atoms, (7) C1-C6 hydroxyalkyl, (8) C1-C6 alkoxy optionally substituted with one or more halogen atoms, (9) C2-C6 cyanoalkyl, (10) C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms, (11) C2-C6 alkenyl optionally substituted with one or more halogen atoms, (12) C2-C6 alkynyl optionally substituted with one or more halogen atoms, (13) C3-C6 cycloalkyl optionally substituted with one or more halogen atoms, (14) C1-C6 alkylthio optionally substituted with one or more halogen atoms, (15) C1-C6 alkylsulfinyl optionally substituted with one or more halogen atoms, (16) C1-C6 alkylsulfonyl optionally substituted with one or more halogen atoms, (17) C1-C6 alkylamino, (18) C2-C8 dialkylamino, (19) C3-C6 cycloalkylamino, (20) C2-C6 alkylcarbonyl, (21) C2-C6 alkoxycarbonyl, (22) C2-C6 alkylaminocarbonyl, (23) C3-C8 dialkylaminocarbonyl, (24) C4-C6 cycloalkylaminocarbonyl and (25) C3-C6 trialkylsilyl;

R 19ax represent a hydrogen atom; C1-C6 alkyl optionally substituted with one or more halogen atoms; C2-C6 cyanoalkyl; C2-C6 alkoxyalkyl optionally substituted with one or more halogen atoms; C2-C6 alkenyl optionally substituted with one or more halogen atoms; C2-C6 alkynyl optionally substituted with one or more halogen atoms; C3-C6 cycloalkyl optionally substituted with one or more independent substituents selected from the group consisting of (1) a halogen atom, and (2) C1-C6 alkyl optionally substituted with one or more halogen atoms;

›Step 5-2 · 4 of 16

The compound (10) can be produced, for example, according to the following scheme (1).

In Scheme (I), A 34 , L 1 , Q′, R 2 , R 3 and R 9a are as defined above.

Among the compound (10), a compound represented by the formula (10-i):

wherein R 2 , R 3 and R 7 are as defined above, can be produced, for example, according to the following scheme (2).

In Scheme (2), R 2 , R 3 and R 7 are as defined above.

The compound (17) can be produced, for example, according to the following Scheme (3).

In Scheme (3), R 4 and n are as defined above.

The compounds (16), (18′) and (20) can be produced, for example, according to the following Scheme (4).

In Scheme (4), R 1-a , R 4 and n are as defined above, and L 4 represents a leaving group (e.g. a halogen atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy etc.).

The compound (8) can be produced, for example, according to the process shown in the following Scheme (7).

In Scheme (7), J is as defined above, R′ 7 represents a methyl or an ethyl group, LDA represents lithium diisopropylamide, n-BuLi represents normal butyl lithium, and t-BuLi represents tertiary butyl lithium.

Among the compound (8), a compound represented by the

wherein R 13a , R 14a , X a , Y a , Z a and p are as defined above, can be produced, for example, according to the process shown in the following Scheme (8).

In Scheme (8), R 13a , R 14a , X a , Y a , Z a , p, LDA and n-BuLi are as defined above, and L 5 represents a leaving group (e.g. a halogen atom, a methanesulfonyloxy group, a p-toluenesulfonyloxy group, a methylsulfonyl etc.).

Among the compound (8), a compound represented by the formula (8-ii):

wherein R 14a and p are as defined above, R 18a , R 18b , R 18c and R 18d each, independently, represent a hydrogen atom, a halogen atom, cyano group, nitro group, C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6 alkoxy optionally substituted with at least one halogen atom, C1-C6 alkylthio optionally substituted with at least one halogen atom, C1-C6 alkylsulfinyl optionally substituted with at least one halogen atom, or C1-C6 alkylsulfonyl optionally substituted with at least one halogen atom, can be produced, for example, according to the process shown in the following Scheme (9).

In Scheme (9), R 14a , R 18a , R 18b , R 18c , R 18d , LDA and p are as defined above, and L 6 represents a leaving group (e.g. a halogen atom, a methylsulfonyl etc.).

Among the compound (8), a compound represented by the formula (8-iii):

wherein R 18a , R 18b , R 18c , R 18d and R 18e independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6 alkoxy optionally substituted with at least one halogen atom, C1-C6 alkylthio optionally substituted with at least one halogen atom, C1-C6 alkylsulfinyl optionally substituted with at least one halogen atom, or C1-C6 alkylsulfonyl optionally substituted with at least one halogen atom, can be produced, for example, according to the process shown in the following Scheme (10).

In Scheme (10), R 18a , R 18b , R 18c , R 18d and R 18e are as defined above.

Among the compound (8), a compound represented by the formula (8-iv):

wherein X 18 represents —N═, or —CR 18e ═; R 18a , R 18b , R 18c , R 18d and R 18e are as defined above, and R 14a-1 represents C1-C6 alkyl optionally substituted with at least one halogen atom, can be produced, for example, according to the process shown in the following Scheme (11).

In Scheme (11), R 14a-1 , R 17 , R 18a , R 18b , R 18c , R 18d and X 18 are as defined above, and R 20 represents a methyl or an ethyl group.

Among the compound (8), a compound represented by the formula (8-vii):

wherein R 13b , R 14b , X b , Y b , Z b and q are as defined above, can be produced, for example, according to the process shown in the following Scheme (14).

In Scheme (14), R 13b , R 14b , R 17 , X b , Y b , Z b , L 5 and q are as defined above.

Among the compound (8), a compound represented by the formula (8-viii) and the formula (8-ix):

[wherein

R 13b , is as defined above;

X 19 represents —N═, or —CR 19e ═; and

R 19a , R 19b , R 19c , R 19d and R 19e , each, independently, represent a hydrogen atom, a halogen atom, cyano group, a nitro group, C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6 alkoxy optionally substituted with at least one halogen atom, C1-C6 alkylthio optionally substituted with at least one halogen atom, C1-C6 alkylsulfinyl optionally substituted with at least one halogen atom, or C1-C6 alkylsulfonyl optionally substituted with at least one halogen atom]

can be produced, for example, according to the process shown in the following Scheme (15).

In Scheme (15), R 13b , R 17 , R 19a , R 19b , R 19c , R 19d , L 5 and X 19 are as defined above.

Among the compound (7), a compound represented by the

wherein L 2 and J are as defined above, can be produced, for example, according to the process shown in the following Scheme (16).

In Scheme (16), L 2 and J are as defined above.

Among the compound (7), a compound represented by the formula (7-ii):

wherein L 2 and J are as defined above, can be produced, for example, according to the process shown in the following scheme (17).

In Scheme (17), L 2 and J are as defined above, LDA represents lithium diisopropylamide, n-BuLi represents normal butyl lithium, and t-BuLi represents tertiary butyl lithium.

›Step 5-2 · 5 of 16

Among the compound (8), a compound represented by the formula (8-v):

wherein R 18a , R 18b , R 18c , R 18d and X 18 are as defined above, and R 14ax , R 14ay , X 14az and X independently represent a hydrogen atom, a halogen atom, cyano group, C1-C6 alkyl optionally substituted with at least one halogen atom, C1-C6 alkoxy optionally substituted with at least one halogen atom, C1-C6 alkylthio optionally substituted with at least one halogen atom, C1-C6 alkylsulfinyl optionally substituted with at least one halogen atom, or C1-C6 alkylsulfonyl optionally substituted with at least one halogen atom, can be produced, for example, according to the process shown in the following Scheme (18).

In Scheme (18) R 18a , R 18b , R 18c , R 18d , X 18 , R 14ax , R 14ay , and X 14az are as defined above.

The compounds (21) in scheme (18) can be produced, for example, according to the process shown in the following Scheme (19).

In Scheme (19), R 18a , R 18b , R 18c , R 18d , R 18e , X 18 , R 14ax , R 14ay , X 14az and L 6 are as defined above

Among the compounds (21) in scheme (18), a compound represented by the formula (21-i), the formula (21-ii), and the formula (21-iii):

wherein R 18a , R 18b , R 18c , R 18d and X 18 are as defined above, and halo(x) and halo(y) independently represent a halogen atom, can be produced, for example, according to the process shown in the following Scheme (20).

In Scheme (20), R 18a , R 18b , R 18c , R 18d , X 18 , halo(x) and halo(y) are as defined above.

Among the compound (8), a compound represented by the formula (8-yl):

wherein R 18a , R 18b , R 18c , R 18d and X 18 are as defined above, R 14ay-1 represents a hydrogen atom or a halogen atom, R 30 represents C1-C6 alkyl optionally substituted with at least one halogen atom, and r represents an integer of 0 to 2, can be produced, for example, according to the process shown in the following Scheme (21).

In Scheme (21), R 18a , R 18b , R 18c , R 18d , X 18 , R 14ay-1 , R 30 , r and L 4 are as defined above.

The specific examples of the present compound are summarized in the following compounds 1 to 277.

Compound 1:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 2:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 3:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 4:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 5:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 6:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 7:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 8:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 9:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 10:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 11:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 12:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 13:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 14:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 15:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 16:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 17:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 18:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 19:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 20:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 21:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 22:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 23:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 24:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 25:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 26:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 27:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

›Step 5-2 · 6 of 16

Compound 28:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 29:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 30:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 31:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 32:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 33:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 34:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 35:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 36:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 37:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 38:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 39:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 40:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 41:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 42:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 43:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 44:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 45:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 46:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 47:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 48:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 49:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 50:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 51:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 52:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 53:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 54:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 55:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 56:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 57:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 58:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 59:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 60:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 61:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 62:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 63:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 64:

Compounds of formula 1A wherein R 2 , R 3 , M, R 19a , R 20ay and X corresponds to a row in Table A, and E substituted with (R 4 ) n is:

Compound 65:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 66:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 67:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 68:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

›Step 5-2 · 7 of 16

Compound 69:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 70:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 71:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 72:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 73:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 74:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 75:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 76:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 77:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 78:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 79:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 80:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 81:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 82:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 83:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 84:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 85:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 86:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 87:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 88:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 89:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 90:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 91:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 92:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 93:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 94:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 95:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 96:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 97:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 98:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 99:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 100:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 101:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 102:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 103:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 104:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 105:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 106:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 107:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 108:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 109:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 110:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 111:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 112:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

›Step 5-2 · 8 of 16

Compound 113:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 114:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 115:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 116:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 117:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 118:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 119:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 120:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 121:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 122:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 123:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 124:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 125:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 126:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 127:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 128:

Compounds of formula 2A wherein R 2 , R 3 , M and R 20ay corresponds to a row in Table B, and E substituted with (R 4 ) n is:

Compound 129:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 130:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 131:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 132:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 133:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 134:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 135:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 136:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 137:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 138:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 139:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 140:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 141:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 142:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 143:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 144:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 145:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 146:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 147:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 148:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 149:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 150:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 151:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 152:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 153:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 154:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 155:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 156:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

›Step 5-2 · 9 of 16

Compound 157:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 158:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 159:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 160:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 161:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 162:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 163:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 164:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 165:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 166:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 167:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 168:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 169:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 170:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 171:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 172:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 173:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 174:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 175:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 176:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 177:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 178:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 179:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 180:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 181:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 182:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 183:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 184:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 185:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 186:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 187:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 188:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 189:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 190:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 191:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 192:

Compounds of formula 3A wherein R 2 , R 3 , M and R 20ax corresponds to a row in Table C, and E substituted with (R 4 ) n is:

Compound 193: