Benzenesulphonamide derivatives as herbicides or desiccant/defoliant compounds

This application is a 35 USC §371 National Phase Entry Application from PCT/EP2004/003624, filed Apr. 6, 2004, and designating the United States

The present invention relates to benzenesulfonamide derivatives of the formula I

in which the variables are as defined below:

X 1 is hydrogen or halogen; X 2 is hydrogen, cyano, CS—NH 2 , halogen, C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl; X 3 is hydrogen, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or phenyl-C 1 -C 4 -alkyl, where the phenyl radical for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; Y is a group —C(A)B, SO 2 or SO 2 NR 2 ; A is oxygen or sulfur; B is oxygen, sulfur, NR 2 or a bond; R 1 is hydrogen, halogen, hydroxyl, C 1 -C 8 -alkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cyclo-alkyl-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 5 -C 7 -cycloalkenyl, C 3 -C 8 -alkynyl, C 1 -C 8 -alkoxy, C 3 -C 7 -cycloalkyloxy, C 2 -C 8 -alkenyloxy, C 3 -C 8 -alkynyloxy, aryl, aryloxy, aryl-C 1 -C 4 -alkyl;

where the 13 last mentioned radicals for their part may be partially or fully halogenated and/or may be substituted by one to three substituents from the group consisting of cyano, NO 2 , hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 7 -cycloalkyloxy, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, amino, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -alkoxysulfonyl, formyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -haloalkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 3 -C 6 -alkynylcarbonyl, carboxy, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -haloalkoxycarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 3 -C 6 -alkynyloxycarbonyl, mercaptocarbonyl, C 1 -C 6 -alkylthiocarbonyl, C 1 -C 6 -haloalkylthiocarbonyl, C 2 -C 6 -alkenylthiocarbonyl, C 3 -C 6 -alkynylthiocarbonyl, aminocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di(C 1 -C 6 -alkylamino)carbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di(C 1 -C 6 -haloalkylamino)carbonyl, C 2 -C 6 -alkenyl-aminocarbonyl, di(C 2 -C 6 -alkenylamino)carbonyl, C 3 -C 6 -alkynylamino-carbonyl, di(C 3 -C 6 -alkynylamino)carbonyl, phenyl, phenoxy, phenyl-C 1 -C 4 -alkyl and phenyl-C 1 -C 4 -alkoxy; four- to six-membered heterocyclyl which may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; or four- to six-membered heterocyclyl-C 1 -C 4 -alkyl which may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; or five- or six-membered heteroaryl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, which radical may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino and di(C 1 -C 6 -alkyl)amino; or five- or six-membered heteroaryl-C 1 -C 4 -alkyl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, which radical may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino and di(C 1 -C 6 -alkyl)amino;

R 2 is hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 7 -cycloalkyl, where the four last mentioned radicals may be partially or fully halogenated; or R 1 and R 2 together with the nitrogen atom to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy; Q is a radical from the group consisting of Q 1 to Q 39

A 1 to A 17 are oxygen or sulfur;

R 3 , R 4 , R 7 , R 8 , R 11 , R 12 , R 18 , R 19 , R 27 , R 29 , R 32 , R 33 , R 38 , R 39 , R 44 , R 45 , R 46 and R 47 are hydrogen, cyano, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -cyanoalkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, phenyl-C 1 -C 6 -alkyl, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino; or

R 3 and R 4 , R 11 and R 12 , R 18 and R 19 , or R 46 and R 47 together with the atoms to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy;

R 5 , R 6 , R 9 , R 10 , R 15 , R 16 , R 20 , R 21 , R 30 , R 31 , R 35 , R 36 , R 41 , R 42 and R 43 are hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkoxysulfonyl, C 1 -C 6 -alkylsulfonyloxy, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino; or

R 5 and R 6 , R 9 and R 10 , R 15 and R 16 , R 20 and R 21 , or R 30 and R 31 together with the atoms to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or substituted by one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy;

R 13 , R 14 , R 22 , R 23 , R 25 and R 26

are hydrogen, halogen or C 1 -C 6 -alkyl;

R 17 , R 28 , R 34 , R 37 and R 40

are hydrogen, halogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyloxy, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 -alkenyloxy, C 3 -C 6 -alkynyl or C 3 -C 6 -alkynyloxy;

R 24 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -haloalkoxy, amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino;

and their agriculturally useful salts.

Moreover, the invention relates to processes and intermediates for preparing compounds of formula I, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling unwanted plants.

Furthermore, the invention relates to the use of the compounds of the formula I or of compositions comprising them for the desiccation and/or defoliation of plants.

Further, the invention relates to the preparation of herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I, and to methods for controlling unwanted vegetation or for the desiccation/defoliation of plants using the compounds I.

Substituted phenyluracils are disclosed in the literature, for example in WO 96/07323, WO 96/08151, WO 97/42176 and DE 44 37 197. Phenylpyrazoles are described in WO 95/32188. Bicyclic triazolones are described in WO 02/38562. Furthermore, phenyl-substituted pyrimidin(ethi)ones (WO 96/07647), phenylpyridazones (WO 99/52878) and triazole derivatives (WO 96/18618) are known from the literature. WO 93/03019 discloses phenyl-substituted sulfonamides.

However, the herbicidal or desiccant/defoliant properties of the prior-art compounds and/or their compatibilities with crop plants are not always entirely satisfactory. Accordingly, it was an object of the present invention to provide novel, in particular herbicidally active, compounds having improved properties.

The object also extends to providing novel compounds with desiccant/defoliant action.

We have found that this object is achieved by the benzenesulfonamide derivatives of the formula I and their herbicidal action.

Furthermore, we have found herbicidal compositions which comprise the compounds I and have very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling unwanted vegetation using the compounds I.

Furthermore, it has been found that the compounds I are also suitable for desiccating and defoliating plant parts, suitable plants being crop plants, such as cotton, potatoes, oilseed rape, sunflowers, soybeans or broad beans, in particular cotton. In this respect, the invention provides compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.

Depending on the substitution pattern, the compounds of the formula I may comprise one or more centers of chirality, in which case they are present as enantiomers or mixtures of diastereomers. The invention provides both the pure enantiomers or diastereomers and their mixtures.

The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally being immaterial. Suitable salts are, in general, the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the herbicidal action of the compounds I.

Suitable cations are in particular ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium, where, if desired, one to four hydrogen atoms may be replaced by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2-(2-hydroxyeth-1-oxy)eth-1-yl-ammonium, di-(2-hydroxyeth-1-yl)ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C 1 -C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(C 1 -C 4 -alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties mentioned for the substituents X 2 , X 3 , R 1 -R 47 or as radicals on phenyl, heterocyclyl or heteroaryl radicals are collective terms for individual enumerations of the individual group members. All hydrocarbon chains, i.e. all alkyl, alkylene, haloalkyl, cyanoalkyl, phenylalkyl, alkenyl, haloalkenyl, alkynyl, alkoxy, alkylenoxy, haloalkoxy, alkylamino, dialkylamino and alkoxyalkyl moieties can be straight-chain or branched. Unless indicated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. The term “halogen” denotes in each case fluorine, chlorine, bromine or iodine.

Examples of Other Meanings are:

C 1 -C 4 -alkyl and the alkyl moieties of C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 2 -C 6 -alkynyloxycarbonyl-C 1 -C 4 -alkyl, aryl-C 1 -C 4 -alkyl, cycloalkyl-C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 4 -alkyl and heteroaryl-C 1 -C 4 -alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl; C 1 -C 6 -alkyl and the C 1 -C 6 -alkyl moieties of C 1 -C 6 -cyanoalkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino, di(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkylthiocarbonyl, C 1 -C 6 -alkylaminocarbonyl, di(C 1 -C 6 -alkyl)aminocarbonyl: C 1 -C 4 -alkyl as mentioned above, and also, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-3-methylpropyl; C 1 -C 8 -alkyl: C 1 -C 6 -alkyl as mentioned above, and also, for example, heptyl, 2-methylhexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 2,2-dimethyl-3-methylbutyl, octyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 2,2-dimethylhexyl, 2,3-dimethylhexyl, 2,4-dimethylhexyl, 3,3-dimethylhexyl, 2,2,3-trimethylpentyl, 2,3,3-trimethylpentyl, 2,3,4-trimethylpentyl and 2,2,3,3-tetramethylbutyl; C 3 -C 7 -cycloalkyl and the C 3 -C 7 -cycloalkyl moieties of C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl and C 3 -C 7 -cycloalkyloxy: a monocyclic saturated hydrocarbon having 3 to 7 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl; C 5 -C 7 -cycloalkenyl: a monocyclic unsaturated hydrocarbon having 5 to 7 ring members, for example 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 2,4-cyclopentadienyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl, 2,5-cyclohexadienyl, 1-cycloheptenyl, 2-cycloheptenyl, 3-cycloheptenyl, 4-cycloheptenyl, 2,6-cycloheptadienyl, 3,5-cycloheptadienyl; four- to six-membered heterocyclyl: a monocyclic saturated or partially unsaturated hydrocarbon having four to six ring members as mentioned above which, in addition to carbon atoms, may comprise one to four nitrogen atoms, one or two oxygen atoms, one sulfur atom, one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen and one sulfur atom and which may be attached via a carbon atom or a nitrogen atom,

for example 2-oxetanyl, 3-oxetanyl, 3-thiethanyl, 1-azetidinyl, 2-azetidinyl, 1-azetinyl, 2-azetinyl; for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 1,2,3,4-tetrazolidin-5-yl; for example 1-pyrrolidinyl, 2-isothiazolidinyl, 2-isothiazolidinyl, 1-pyrazolidinyl, 3-oxazolidinyl, 3-thiazolidinyl, 1-imidazolidinyl, 1,2,4-triazolidin-1-yl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,3,4-tetrazolidin-5-yl; for example 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydropyrrol-3-yl, 4,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-4-yl, 2,3-dihydroisoxazolyl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-4-yl, 2,3-dihydroisothiazol-4-yl, 4,5-dihydroisothiazol-5-yl, 2,5-dihydroisothiazol-5-yl, 2,3-dihydroisothiazol-5-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-3-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazolyl, 2,3-dihydrothiazol-5-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazolyl, 3,4-dihydrothiazol-5-yl, 3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazolyl; for example 4,5-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, 4,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-1-yl, 4,5-dihydroisothiazol-1-yl, 2,3-dihydroisothiazol-1-yl, 2,3-dihydropyrazol-1-yl, 4,5-dihydropyrazol-1-yl, 3,4-dihydropyrazol-1-yl, 2,3-dihydroimidazol-1-yl, 4,5-dihydroimidazol-1-yl, 2,5-dihydroimidazol-1-yl, 2,3-dihydrooxazol-2-yl, 3,4-dihydrooxazol-2-yl, 2,3-dihydrothiazol-2-yl, 3,4-dihydrothiazol-2-yl; for example 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 1,3-dithian-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 4-tetrahydrothiopyranyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl, 1,2,4-hexahydrotriazin-3-yl, tetrahydro-1,3-oxazin-2-yl, tetrahydro-1,3-oxazin-6-yl, 2-morpholinyl, 3-morpholinyl; for example 1-piperidinyl, 1-hexahydropyridazinyl, 1-hexahydropyrimidinyl, 1-piperazinyl, 1,3,5-hexahydrotriazin-1-yl, 1,2,4-hexahydrotriazin-1-yl, tetrahydro-1,3-oxazin-1-yl, 1-morpholinyl; for example 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 5,6-dihydro-4H-1,3-oxazin-2-yl;

three- to seven-membered heterocyclyl: four- to six-membered heterocyclyl as mentioned above, and also

for example 2-oxiranyl, 1-aziridinyl, 2-aziridinyl, 2-thiiranyl; for example azepan-2-yl, azepan-3-yl, azepan-4-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 1,2-diazepan-3-yl, 1,2-diazepan-4-yl, 1,2-diazepan-5-yl; for example azepan-1-yl, 1,2-diazepan-1-yl, 1,4-oxazepan-4-yl, 1,4-thiazepan-4-yl; for example 2,3,6,7-tetrahydro-1H-azepin-2-yl, 2,3,6,7-tetrahydro-1H-azepin-3-yl, 2,3,6,7-tetrahydro-1H-azepin-4-yl, 2,3,4,5-tetrahydro-1H-azepin-2-yl, 2,3,4,5-tetrahydro-1H-azepin-3-yl, 2,3,4,5-tetrahydro-1H-azepin-4-yl, 1H-azepin-2-yl, 1H-azepin-3-yl, 1H-azepin-4-yl, oxepin-2-yl, oxepin-3-yl, oxepin-4-yl, thiepin-2-yl, thiepin-3-yl, thiepin-4-yl, 1,4-oxazepin-2-yl, 1,4-oxazepin-3-yl, 1,4-oxazepin-5-yl, 1,4-oxazepin-6-yl, 1,4-oxazepin-7-yl, 1,4-thiazepin-2-yl, 1,4-thiazepin-3-yl, 1,4-thiazepin-5-yl, 1,4-thiazepin-6-yl, 1,4-thiazepin-7-yl, 4,5,6,7-tetrahydro-1H-[1,3]-diazepin-2-yl, 4,5,6,7-tetrahydro-1H-[1,3]-diazepin-4-yl, 4,5,6,7-tetrahydro-1H-[1,3]-diazepin-5-yl, 4,5,6,7-tetrahydro-1H-[1,3]-diazepin-6-yl, 4,5,6,7-tetrahydro-1H-[1,3]-diazepin-7-yl, 2,3,4,5-tetrahydro-1H-[1,4]-diazepin-2-yl, 2,3,4,5-tetrahydro-1H-[1,4]-diazepin-3-yl, 2,3,4,5-tetrahydro-1H-[1,4]-diazepin-5-yl, 2,3,4,5-tetrahydro-1H-[1,4]-diazepin-6-yl, 2,3,4,5-tetrahydro-1H-[1,4]-diazepin-7-yl, 2,3-dihydro-1H-[1,2]diazepin-3-yl, 2,3-dihydro-1H-[1,2]diazepin-4-yl, 2,3-dihydro-1H-[1,2]diazepin-5-yl, 2,3-dihydro-1H-[1,2]diazepin-6-yl, 2,3-dihydro-1H-[1,2]diazepin-7-yl, 4,7-dihydro-[1,4]-oxazepin-2-yl, 4,7-dihydro-[1,4]-oxazepin-3-yl, 4,7-dihydro-[1,4]-oxazepin-5-yl, 4,7-dihydro-[1,4]-oxazepin-6-yl, 4,7-dihydro-[1,4]-oxazepin-7-yl, 2,3-dihydro-[1,3]-thiazepin-2-yl, 2,3-dihydro-[1,3]-thiazepin-4-yl, 2,3-dihydro-[1,3]-thiazepin-5-yl, 2,3-dihydro-[1,3]-thiazepin-6-yl, 2,3-dihydro-[1,3]-thiazepin-7-yl; for example azepin-1-yl, 2,3,6,7-tetrahydroazepin-1-yl, 2,3,4,5-tetrahydroazepin-1-yl, 4,5,6,7-tetrahydro-[1,3]-diazepin-1-yl, 2,3,4,5-tetrahydro-[1,4]-diazepin-1-yl, 2,3-dihydro-[1,2]diazepin-1-yl, 4,7-dihydro-[1,4]-oxazepin-4-yl, 2,3-dihydro-[1,3]-thiazepin-3-yl;

C 2 -C 4 -alkenyl and the alkenyl moieties of C 1 -C 6 -alkoxycarbonyl-C 2 -C 4 -alkenyl: ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl; C 3 -C 6 -alkenyl: for example 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl; C 2 -C 6 -alkenyl and the C 2 -C 6 -alkenyl moieties of C 2 -C 6 -alkenyloxy, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkenyloxycarbonyl, C 2 -C 6 -alkenyloxycarbonyl-C 1 -C 4 -alkyl, C 2 -C 6 -alkenylthiocarbonyl, C 2 -C 6 -alkenylaminocarbonyl, di(C 2 -C 6 -alkenyl)aminocarbonyl: C 3 -C 6 -alkenyl as mentioned above, and also ethenyl; C 2 -C 8 -alkenyl and the C 2 -C 8 -alkenyl moieties of C 2 -C 8 -alkenyloxy: C 2 -C 6 -alkenyl as mentioned above, and also, for example, 1-heptenyl, 2-heptenyl, 3-heptenyl, 2-methyl-1-hexenyl, 2-methyl-2-hexenyl, 2-methyl-3-hexenyl, 2-methyl-4-hexenyl, 2-methyl-5-hexenyl, 3-methyl-1-hexenyl, 3-methyl-2-hexenyl, 3-methyl-3-hexenyl, 3-methyl-4-hexenyl, 3-methyl-5-hexenyl, 2,2-dimethyl-3-pentenyl, 2,2-dimethyl-4-pentenyl, 2,3-dimethyl-1-pentenyl, 2,3-dimethyl-2-pentenyl, 2,3-dimethyl-3-pentenyl, 2,3-dimethyl-4-pentenyl, 2,4-dimethyl-1-pentenyl, 2,4-dimethyl-2-pentenyl, 3,3-dimethyl-1-pentenyl, 2,2-dimethyl-3-methyl-3-butentyl, 1-octenyl, 2-octenyl, 3-octenyl, 4-octenyl, 2-methyl-1-heptenyl, 2-methyl-2-heptenyl, 2-methyl-3-heptenyl, 2-methyl-4-heptenyl, 2-methyl-5-heptenyl, 2-methyl-6-heptenyl, 3-methyl-1-heptenyl, 3-methyl-2-heptenyl, 3-methyl-3-heptenyl, 3-methyl-4-heptenyl, 3-methyl-5-heptenyl, 3-methyl-6-heptenyl, 4-methyl-1-heptenyl, 4-methyl-2-heptenyl, 4-methyl-3-heptenyl, 2,2-dimethyl-3-hexenyl, 2,2-dimethyl-4-hexenyl, 2,2-dimethyl-5-hexenyl, 2,3-dimethyl-1-hexenyl, 2,3-dimethyl-2-hexenyl, 2,3-dimethyl-3-hexenyl, 2,3-dimethyl-4-hexenyl, 2,3-dimethyl-5-hexenyl, 2,4-dimethyl-1-hexenyl, 2,4-dimethyl-2-hexenyl, 2,4-dimethyl-3-hexenyl, 2,4-dimethyl-4-hexenyl, 2,4-dimethyl-5-hexenyl, 3,3-dimethyl-1-hexenyl, 3,3-dimethyl-4-hexenyl, 3,3-dimethyl-5-hexenyl, 2,2,3-trimethyl-3-pentenyl, 2,2,3-trimethyl-4-pentenyl, 2,3,3-trimethyl-1-pentenyl, 2,3,3-trimethyl-4-pentenyl, 2,3,4-trimethyl-1-pentenyl and 2,3,4-trimethyl-2-pentenyl; C 3 -C 6 -alkynyl and the C 3 -C 6 -alkynyl moieties of C 3 -C 6 -alkynyloxy, C 3 -C 6 -alkynyl-carbonyl, C 3 -C 6 -alkynyloxycarbonyl, C 3 -C 6 -alkynylthiocarbonyl, C 3 -C 6 -alkynyl-aminocarbonyl, di(C 3 -C 6 -alkynyl)aminocarbonyl: for example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl; C 3 -C 8 -alkynyl and the C 3 -C 8 -alkynyl moieties of C 3 -C 8 -alkynyloxy: C 3 -C 6 -alkynyl as mentioned above, and also, for example, 1-heptynyl, 2-heptynyl, 3-heptynyl, 2-methyl-3-hexynyl, 2-methyl-4-hexynyl, 2-methyl-5-hexynyl, 3-methyl-1-hexynyl, 3-methyl-4-hexynyl, 3-methyl-5-hexynyl, 2,2-dimethyl-3-pentynyl, 2,2-dimethyl-4-pentynyl, 2,3-dimethyl-4-pentynyl, 3,3-dimethyl-1-pentynyl, 1-octynyl, 2-octynyl, 3-octynyl, 4-octynyl, 2-methyl-3-heptynyl, 2-methyl-4-heptynyl, 2-methyl-5-heptynyl, 2-methyl-6-heptynyl, 3-methyl-1-heptynyl, 3-methyl-4-heptynyl, 3-methyl-5-heptynyl, 3-methyl-6-heptynyl, 4-methyl-1-heptynyl, 4-methyl-2-heptynyl, 2,2-dimethyl-3-hexynyl, 2,2-dimethyl-4-hexynyl, 2,2-dimethyl-5-hexynyl, 2,3-dimethyl-4-hexynyl, 2,3-dimethyl-5-hexynyl, 2,4-dimethyl-5-hexynyl, 3,3-dimethyl-1-hexynyl, 3,3-dimethyl-4-hexynyl, 3,3-dimethyl-5-hexynyl, 2,2,3-trimethyl-3-pentynyl, 2,2,3-trimethyl-4-pentynyl and 2,3,3-trimethyl-4-pentynyl; C 1 -C 4 -haloalkyl: a C 1 -C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and nonafluorobutyl; C 1 -C 6 -haloalkyl and the C 1 -C 6 -haloalkyl moieties of C 1 -C 6 -haloalkylthio, C 1 -C 6 -haloalkylsulfinyl, C 1 -C 6 -haloalkylsulfonyl, C 1 -C 6 -haloalkylcarbonyl, C 1 -C 6 -haloalkylthiocarbonyl, C 1 -C 6 -haloalkylaminocarbonyl, di(C 1 -C 6 -haloalkyl)aminocarbonyl: C 1 -C 4 -haloalkyl as mentioned above, and also, for example, 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl; C 1 -C 8 -haloalkyl: C 1 -C 6 -haloalkyl as mentioned above, and also, for example, 7-fluoroheptyl, 7-chloroheptyl, 7-bromoheptyl, 7-iodoheptyl, perfluoroheptyl, 8-fluorooctyl, 8-chlorooctyl, 8-bromooctyl, 8-iodooctyl and perfluorooctyl; C 2 -C 6 -haloalkenyl: a C 2 -C 6 -alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chlorovinyl, 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromovinyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl and 2,3-dibromobut-2-enyl; C 2 -C 8 -haloalkenyl: a C 2 -C 6 -haloalkenyl radical as mentioned above, and also, for example, 2-chloro-1-heptenyl, 3-chloro-1-heptenyl, 2,3-dichloro-1-heptenyl, 3,3-dichloro-1-heptenyl, 2,3,3-trichloro-1-heptenyl, 2-bromo-1-heptenyl, 3-bromo-1-heptenyl, 2,3-dibromo-1-heptenyl, 3,3-dibromo-1-heptenyl, 2,3,3-tribromo-1-heptenyl, 2-chloro-1-octenyl, 3-chloro-1-octenyl, 2,3-dichloro-1-octenyl, 3,3-dichloro-1-octenyl, 2,3,3-trichloro-1-octenyl, 2-bromo-1-octenyl, 3-bromo-1-octenyl, 2,3-dibromo-1-octenyl, 3,3-dibromo-1-octenyl and 2,3,3-tribromo-1-octenyl; C 3 -C 6 -haloalkynyl: a C 3 -C 6 -alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1,1-difluoroprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4-chlorobut-2-yn-1-yl, 1,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl and 6-iodohex-5-yn-1-yl; C 1 -C 4 -alkoxy and the C 1 -C 4 -alkoxy moieties of C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl and phenyl-C 1 -C 4 -alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy; C 1 -C 6 -alkoxy and the C 1 -C 6 -alkoxy moieties of C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 2 -C 4 -alkenyl, C 1 -C 6 -alkoxysulfonyl: C 1 -C 4 -alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy; C 1 -C 8 -alkoxy: C 1 -C 6 -alkoxy as mentioned above, and also, for example, heptoxy, 2-methylhexoxy, 3-methylhexoxy, 2,2-dimethylpentoxy, 2,3-dimethylpentoxy, 2,4-dimethylpentoxy, 3,3-dimethylpentoxy, 2,2-dimethyl-3-methylbutoxy, octoxy, 2-methylheptoxy, 3-methylheptoxy, 4-methylheptoxy, 2,2-dimethylhexoxy, 2,3-dimethylhexoxy, 2,4-dimethylhexoxy, 3,3-dimethylhexoxy, 2,2,3-trimethylpentoxy, 2,3,3-trimethylpentoxy, 2,3,4-trimethylpentoxy and 2,2,3,3-tetramethylbutoxy; C 1 -C 4 -haloalkoxy: a C 1 -C 4 -alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy; C 1 -C 6 -haloalkoxy and the C 1 -C 6 -haloalkoxy moieties of C 1 -C 6 -haloalkoxycarbonyl: C 1 -C 4 -haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy; C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl and the alkyl radicals of C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl: a C 1 -C 4 -alkyl which is substituted by C 1 -C 6 -alkoxy as mentioned above, i.e., for example, methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy)methyl, butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, (1,1-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)propyl, 3-(propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)butyl, 2-(ethoxy)butyl, 2-(propoxy)butyl, 2-(1-methylethoxy)-butyl, 2-(butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(propoxy)butyl, 3-(1-methylethoxy)butyl, 3-(butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl and 4-(1,1-dimethylethoxy)butyl; C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl: C 1 -C 4 -alkyl which is substituted by C 1 -C 6 -alkoxycarbonyl as mentioned above, i.e., for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, (1-methylethoxycarbonyl)methyl, butoxycarbonylmethyl, (1-methylpropoxycarbonyl)methyl, (2-methylpropoxycarbonyl)methyl, (1,1-dimethylethoxycarbonyl)methyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 2-(propoxycarbonyl)ethyl, 2-(1-methylethoxycarbonyl)ethyl, 2-(butoxycarbonyl)ethyl, 2-(1-methylpropoxycarbonyl)ethyl, 2-(2-methylpropoxycarbonyl)ethyl, 2-(1,1-dimethylethoxycarbonyl)ethyl, 2-(methoxycarbonyl)propyl, 2-(ethoxycarbonyl)propyl, 2-(propoxycarbonyl)propyl, 2-(1-methylethoxycarbonyl)propyl, 2-(butoxycarbonyl)propyl, 2-(1-methylpropoxycarbonyl)propyl, 2-(2-methylpropoxycarbonyl)propyl, 2-(1,1-dimethylethoxycarbonyl)propyl, 3-(methoxycarbonyl)propyl, 3-(ethoxycarbonyl)propyl, 3-(propoxycarbonyl)propyl, 3-(1-methylethoxycarbonyl)propyl, 3-(butoxycarbonyl)propyl, 3-(1-methylpropoxycarbonyl)propyl, 3-(2-methylpropoxycarbonyl)propyl, 3-(1,1-dimethylethoxycarbonyl)propyl, 2-(methoxycarbonyl)butyl, 2-(ethoxycarbonyl)butyl, 2-(propoxycarbonyl)butyl, 2-(1-methylethoxycarbonyl)butyl, 2-(butoxycarbonyl)butyl, 2-(1-methylpropoxycarbonyl)butyl, 2-(2-methylpropoxycarbonyl)butyl, 2-(1,1-dimethylethoxycarbonyl)butyl, 3-(methoxycarbonyl)butyl, 3-(ethoxycarbonyl)butyl, 3-(propoxycarbonyl)butyl, 3-(1-methylethoxycarbonyl)butyl, 3-(butoxycarbonyl)butyl, 3-(1-methylpropoxycarbonyl)butyl, 3-(2-methylpropoxycarbonyl)butyl, 3-(1,1-dimethylethoxycarbonyl)butyl, 4-(methoxycarbonyl)butyl, 4-(ethoxycarbonyl)butyl, 4-(propoxycarbonyl)butyl, 4-(1-methylethoxycarbonyl)butyl, 4-(butoxycarbonyl)butyl, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy and 4-(1,1-dimethylethoxycarbonyl)butyl; C 1 -C 4 -alkylthio: for example methylthio, ethylthio, n-propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio; C 1 -C 6 -alkylthio: C 1 -C 4 -alkylthio as mentioned above, and also, for example, pentylthio, methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio; C 1 -C 8 -alkylthio: C 1 -C 6 -alkylthio as mentioned above and the alkylthio moieties of C 1 -C 8 -alkylthio-C 1 -C 8 -alkyl, and also, for example, heptylthio, 2-methylhexylthio, 3-methylhexylthio, 2,2-dimethylpentylthio, 2,3-dimethylpentylthio, 2,4-dimethylpentylthio, 3,3-dimethylpentylthio, 2,2-dimethyl-3-methylbutylthio, octylthio, 2-methylheptylthio, 3-methylheptylthio, 4-methylheptylthio, 2,2-dimethylhexylthio, 2,3-dimethylhexylthio, 2,4-dimethylhexylthio, 3,3-dimethylhexylthio, 2,2,3-trimethylpentylthio, 2,3,3-trimethylpentylthio, 2,3,4-trimethylpentylthio and 2,2,3,3-tetramethylbutylthio; C 1 -C 6 -alkylamino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1,1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1,1-dimethylpropylamino, 1,2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1,1-dimethylbutylamino, 1,2-dimethylbutylamino, 1,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutylamino, 3,3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-1-methylpropylamino and 1-ethyl-2-methylpropylamino; di(C 1 -C 4 -alkyl)amino: for example N,N-dimethylamino, N,N-diethylamino, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N,N-di(1,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)-amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino and N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino; di(C 1 -C 6 -alkyl)amino and the dialkylamino moieties of di(C 1 -C 6 -alkyl)amino-C 1 -C 6 -alkyl, di(C 1 -C 6 -alkyl)aminocarbonyl and di(C 1 -C 6 -alkyl)aminocarbonyl-C 1 -C 6 -alkyl: di(C 1 -C 4 -alkyl)amino as mentioned above, for example, N,N-dipentylamino, N,N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino, N-methyl-N-hexylamino and N-ethyl-N-hexylamino; aryl and the aryl moieties of aryloxy and aryl-C 1 -C 4 -alkyl: a monocyclic to tricyclic aromatic carbocycle having 6 to 14 ring members, such as, for example, phenyl, naphthyl and anthracenyl; 5- or 6-membered heteroaryl and the 5- or 6-membered heteroaryl moieties of 5- or 6-membered heteroaryl-C 1 -C 6 -alkyl: aromatic 5- or 6-membered heterocycles which, in addition to carbon atoms, may comprise one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or sulfur atom as ring members, for example

2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl and tetrazol-2-yl; 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, 1,2,4-triazin-5-yl, 1,2,4-triazin-6-yl and 1,2,4,5-tetrazinyl.

In a particular embodiment, the variables of the compounds of the formula I are as defined below, these definitions being, both on their own and in combination with one another, particular embodiments of the compounds of the formula I:

Preference is given to the benzenesulfonamides of the formula I in which

X 1 is hydrogen, fluorine or chlorine;

particularly preferably hydrogen or fluorine; especially preferably fluorine.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which X 2 is hydrogen, cyano, CS—NH 2 or halogen;

particularly preferably hydrogen, cyano or halogen such as fluorine and chlorine; especially preferably chlorine.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which X 1 is hydrogen, fluorine or chlorine;

particularly preferably hydrogen or fluorine; especially preferably fluorine; and

X 2 is hydrogen, cyano, CS—NH 2 or halogen;

particularly preferably hydrogen, cyano, halogen such as fluorine and chlorine; especially preferably chlorine.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which X 3 is hydrogen, cyano, C 1 -C 6 -alkyl or phenyl-C 1 -C 4 -alkyl;

particularly preferably hydrogen, cyano, C 1 -C 4 -alkyl, such as CH 3 , and C 2 H 5 , or benzyl; especially preferably hydrogen or cyano; with extraordinary preference hydrogen.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is a group C(A)B;

particularly preferably C(A)B, where A is oxygen; especially preferably C(A)B, where A is oxygen and B is oxygen or sulfur; with extraordinary preference C(A)B, where A and B are oxygen.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is a group C(A)B;

particularly preferably C(A)B, where A is oxygen; especially preferably C(A)B, where A is oxygen and B is NR 2 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is a group C(A)B;

particularly preferably C(A)B, where A is oxygen; especially preferably C(A)B, where A is oxygen and B is a bond.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which R 1 is hydrogen, hydroxyl, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl, C 3 -C 7 -cycloalkyl, C 3 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -haloalkenyl, C 3 -C 8 -alkynyl, C 1 -C 8 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkoxycarbonyl-C 2 -C 4 -alkenyl, C 2 -C 6 -alkenyloxycarbonyl-C 1 -C 4 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl, aryl, aryl-C 1 -C 4 -alkyl;

four- to six-membered heterocyclyl which may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; four- to six-membered heterocyclyl-C 1 -C 4 -alkyl which may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; five- or six-membered heteroaryl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, which radicals may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, C 1 -C 4 -alkylamino and di(C 1 -C 4 -alkyl)amino; five- or six-membered heteroaryl-C 1 -C 4 -alkyl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, which radicals may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy;

particularly preferably

hydrogen, hydroxyl, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 7 -cycloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl-C 2 -C 4 -alkenyl, C 2 -C 4 -alkenyloxycarbonyl-C 1 -C 4 -alkyl, C 3 -C 6 -alkynyloxycarbonyl-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, phenyl, benzyl; five- or six-membered heterocyclyl which may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; five- or six-membered heteroaryl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, which radicals may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, amino, C 1 -C 4 -alkylamino and di(C 1 -C 4 -alkyl)amino;

especially preferably

C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 5 -C 6 -cycloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, phenyl, benzyl; five- or six-membered heterocyclyl which may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; five- or six-membered heteroaryl having one to four nitrogen atoms or having one to three nitrogen atoms and one oxygen or one sulfur atom or having one oxygen or sulfur atom, where the two last mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy;

with extraordinary preference

C 1 -C 4 -alkyl, such as C 3 , C 2 H 5 , CH(CH 3 ) 2 , —CH 2 —CH 2 —CH 3 , C 1 -C 4 -haloalkyl, such as CF 3 , C 5 -C 6 -cycloalkyl, C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, phenyl, benzyl, five- or six-membered heterocyclyl or five- or six-membered heteroaryl having one to four nitrogen atoms, where the two last mentioned radicals may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which R 2 is hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl,

particularly preferably hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially preferably hydrogen or C 1 -C 4 -alkyl, with extraordinary preference hydrogen, CH 3 , C 2 H 5 or CH(CH 3 ) 2 , with most extraordinary preference hydrogen or CH 3 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which R 1 and R 2 together with the nitrogen atom to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

particularly preferably a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; especially preferably a five- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; with extraordinary preference a five- or six-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; with most extraordinary preference a heterocycle from the group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,3,6-tetrahydropyridin-1-yl, piperazin-1-yl, morpholin-4-yl, which heterocycle may for its part be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is C(A)B, where A and B are oxygen; and R 1 has the preferred meanings mentioned above.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which

Y is C(A)B, where A is oxygen and B is NR 2 ; and R 2 is hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl, particularly preferably hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially preferably hydrogen or C 1 -C 4 -alkyl, with extraordinary preference hydrogen, CH 3 , C 2 H 5 or CH(CH 3 ) 2 ; with most extraordinary preference hydrogen or CH 3 ; with particular preference Y is C(=A)B, where A is oxygen and B is NR 2 ; R 2 is hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl,

particularly preferably hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially preferably hydrogen or C 1 -C 4 -alkyl, with extraordinary preference hydrogen, CH 3 , C 2 H 5 or CH(CH 3 ) 2 ; with most extraordinary preference hydrogen or CH 3 ; and

R 1 has the preferred meanings mentioned above. Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is C(A)B where A is oxygen and B is NR 2 ; and R 1 and R 2 together with the nitrogen atom to which they are attached, form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy;

particularly preferably a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; especially preferably a five- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; with extraordinary preference a five- or six-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy; with most extraordinary preference a heterocycle from the group consisting of pyrrolidin-1-yl, 2,3-dihydropyrrol-1-yl, 2,5-dihydropyrrol-1-yl, piperidin-1-yl, 1,2,3,4-tetrahydropyridin-1-yl, 1,2,3,6-tetrahydropyridin-1-yl, piperazin-1-yl, morpholin-4-yl, which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 4 -alkyl and C 1 -C 4 -alkoxy.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is C(A)B, where A is oxygen and B is a bond; and R 1 has the preferred meanings mentioned above. Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is a group SO 2 ; particularly preferably Y is SO 2 ; and R 1 has the preferred meanings mentioned above. Preference is also given to the benzenesulfonamide derivatives of the formula I in which Y is a group SO 2 NR 2 ; particularly preferably Y is SO 2 NR 2 ; and R 2 is hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl,

particularly preferably hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially preferably hydrogen or C 1 -C 4 -alkyl, with extraordinary preference hydrogen, CH 3 , C 2 H 5 or CH(CH 3 ) 2 ; with most extraordinary preference hydrogen or CH 3 ;

especially preferably Y is SO 2 NR 2 ; R 2 is hydrogen, C 1 -C 8 -alkyl or C 2 -C 8 -alkenyl,

particularly preferably hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkenyl, especially preferably hydrogen or C 1 -C 4 -alkyl, with extraordinary preference hydrogen, CH 3 , C 2 H 5 or CH(CH 3 ) 2 ; with most extraordinary preference hydrogen or CH 3 ; and

R 1 has the preferred meanings mentioned above. Preference is also given to the benzenesulfonamide derivatives of the formula I in which Q is Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 27 , Q 31 , Q 34 , Q 38 or Q 39 ;

particularly preferably Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 24 , Q 27 , Q 31 , Q 32 , Q 38 or Q 39 ; especially preferably Q 5 , Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 ; with extraordinary preference Q 21 , Q 32 or Q 38 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Q is Q 1 , Q 2 , Q 3 , Q 4 , Q 6 , Q 7 , Q 8 , Q 9 , Q 10 , Q 11 , Q 12 , Q 13 , Q 14 , Q 15 , Q 16 , Q 17 , Q 18 , Q 19 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 25 , Q 26 , Q 27 , Q 28 , Q 29 , Q 30 , Q 31 , Q 32 , Q 33 , Q 34 , Q 35 , Q 36 , Q 37 , Q 38 or Q 39 ,

particularly preferably Q 1 , Q 2 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 27 , Q 31 , Q 32 , Q 34 , Q 38 or Q 39 , especially preferably Q 1 , Q 2 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 24 , Q 27 , Q 31 , Q 32 , Q 38 or Q 39 , with extraordinary preference Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 , with most extraordinary preference Q 21 , Q 32 or Q 38 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which

Q is Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 ; particularly preferably

Q 7 , where Y is SO 2 , SO 2 NR 2 or C(A)B where B=oxygen or NR 2 ; Q 21 , where Y is SO 2 , SO 2 NR 2 or C(A)B where B=oxygen, sulfur or NR 2 , preferably Y is SO 2 NR 2 or C(A)B where B=oxygen or NR 2 , more preferably Y is SO 2 NR 2 or C(A)B where B=oxygen or NR 2 , and X 2 is hydrogen, cyano or halogen, such as fluorine or chlorine; Q 22 ; Q 27 ; Q 32 , where Y is SO 2 , SO 2 NR 2 or C(A)B where B=oxygen, sulfur or NR 2 ; Q 38 or Q 39 ;

especially preferably

Q 21 , where Y is SO 2 , SO 2 NR 2 or C(A)B where B=oxygen, sulfur or NR 2 , preferably Y is SO 2 NR 2 or C(A)B where B=oxygen or NR 2 , more preferably Y is SO 2 NR 2 or C(A)B where B=oxygen or NR 2 , and X 2 is hydrogen, cyano or halogen, such as fluorine or chlorine; Q 32 , where Y is SO 2 , SO 2 NR 2 or C(A)B where B=oxygen, sulfur or NR 2 ; or Q 38 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which X 1 is hydrogen, fluorine or chlorine;

particularly preferably hydrogen or fluorine; especially preferably fluorine;

X 2 is hydrogen, cyano, CS—NH 2 or halogen;

particularly preferably hydrogen, halogen, such as fluorine or chlorine; especially preferably chlorine; and

Q is Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 27 , Q 31 , Q 32 , Q 34 , Q 38 or Q 39 ,

particularly preferably Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 24 , Q 27 , Q 31 , Q 32 , Q 38 or Q 39 , especially preferably Q 5 , Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 , with extraordinary preference Q 21 , Q 32 or Q 38 .

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Q is Q 1 to Q 39 ; and R 3 , R 4 , R 7 , R 8 , R 11 , R 12 , R 18 , R 19 , R 27 , R 29 , R 32 , R 33 , R 38 , R 39 , R 44 , R 45 , R 46 and R 47 are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfonyl or amino;

preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylsulfonyl or amino; especially-preferably hydrogen, CH 3 , C 2 H 5 , CF 3 , CHF 2 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 2 CHF 2 , SO 2 CH 3 or amino;

R 5 , R 6 , R 9 , R 10 , R 15 , R 16 , R 20 , R 21 , R 30 , R 31 , R 35 , R 36 , R 41 , R 42 and R 43

are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfonyl or amino; preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylsulfonyl or amino; especially preferably hydrogen, CH 3 , C 2 H 5 , CF 3 , CHF 2 , OCH 3 , OCHF 2 , SO 2 CH 3 or amino;

R 13 , R 14 , R 22 , R 23 , R 25 and R 26

are hydrogen, halogen or C 1 -C 4 -alkyl; particularly preferably hydrogen, halogen or CH 3 ; especially preferably hydrogen, chlorine or bromine;

R 17 , R 28 , R 34 , R 37 or R 40

are hydrogen, halogen or C 1 -C 4 -alkyl; particularly preferably hydrogen, halogen or CH 3 ; especially preferably hydrogen, chlorine or bromine.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Q is Q 5 , Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 ,

particularly preferably Q 21 , Q 32 or Q 38 ;

A 1 , A 8 , A 9 , A 10 , A 11 , A 12 , A 13 , A 15 , A 16 and A 17 are oxygen; R 7 , R 8 , R 29 , R 32 , R 33 , R 38 , R 39 , R 44 , R 45 , R 46 , R 47

are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfonyl or amino; preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylsulfonyl or amino; especially preferably hydrogen, CH 3 , C 2 H 5 , CF 3 , CHF 2 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 2 CHF 2 , SO 2 CH 3 or amino;

R 30 , R 31 , R 35 , R 36 , R 41 , R 42 , R 43

are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylsulfonyl or amino; preferably hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylsulfonyl or amino; especially preferably hydrogen, CH 3 , C 2 H 5 , CF 3 , CHF 2 , OCH 3 , OCHF 2 , SO 2 CH 3 or amino; and

R 34 , R 37 , R 40

are hydrogen, halogen or C 1 -C 4 -alkyl; particularly preferably hydrogen, halogen or CH 3 ; especially preferably hydrogen, chlorine or bromine.

Preference is also given to the benzenesulfonamide derivatives of the formula I in which Q is Q 1 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 21 , Q 23 , Q 24 , Q 31 or Q 34 ; A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 , A 9 , A 14 , A 16 and A 17 are oxygen; and R 3 and R 4 , R 5 and R 6 , R 9 and R 10 , R 15 and R 16 , R 18 and R 19 , R 20 and R 21 , R 30 and R 31 or R 46 and R 47 together with the atoms to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; particularly preferably Q is Q 1 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 21 , Q 24 or Q 31 ; A 1 , A 2 , A 3 , A 4 , A 6 , A 8 , A 9 , A 16 and A 17 are oxygen; and R 3 and R 4 , R 5 and R 6 , R 9 and R 10 , R 15 and R 16 , R 18 and R 19 , R 20 and R 21 , R 30 and R 31 or R 46 and R 47 together with the atoms to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy; especially preferably Q is Q 7 or Q 21 , A 8 , A 9 , A 16 and A 17 are oxygen; R 29 is hydrogen, C 1 -C 6 -alkyl or amino; and R 30 and R 31 or R 46 and R 47 together with the atoms to which they are attached form a three- to seven-membered heterocycle which for its part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of C 1 -C 6 -alkyl and C 1 -C 6 -alkoxy.

Extraordinary preference is given to the compounds of the formula I.1 [corresponds to formula I where X 1 =fluorine; X 2 =chlorine; X 3 =hydrogen; Y=—C(A)B (where A=oxygen, B=NR 2 ); Q=Q 21 (where A 8 , A 9 =oxygen, R 29 =methyl, R 30 =trifluoromethyl and R 31 =hydrogen)], in particular to the compounds of the formulae I.1.1 to I.1.689 of Table 1, where the definitions of the variables X 1 , X 2 , X 3 , Y, A, B, R 1 , R 2 and Q are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own.

Extraordinary preference is also given to the compounds of the formula I.2, in particular to the compounds of the formulae I.2.1 to I.2.689 which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen.

Extraordinary preference is also given to the compounds of the formula I.3, in particular to the compounds of the formulae I.3.1 to I.3.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur.

Extraordinary preference is also given to the compounds of the formula I.4, in particular to the compounds of the formulae I.4.1 to I.4.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond.

Extraordinary preference is also given to the compounds of the formula I.5, in particular to the compounds of the formulae I.5.1 to I.5.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 .

Extraordinary preference is also given to the compounds of the formula I.6, in particular to the compounds of the formulae I.6.1 to I.6.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 .

Extraordinary preference is also given to the compounds of the formula I.7, in particular to the compounds of the formulae I.7.1 to I.7.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.8, in particular to the compounds of the formulae I.8.1 to I.8.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.9, in particular to the compounds of the formulae I.9.1 to I.9.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.10, in particular to the compounds of the formulae I.10.1 to I.10.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.11, in particular to the compounds of the formulae I.11.1 to I.11.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.12, in particular to the compounds of the formulae I.12.1 to I.12.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.13, in particular to the compounds of the formulae I.13.1 to I.13.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen.

Extraordinary preference is also given to the compounds of the formula I.14, in particular to the compounds of the formulae I.14.1 to I.14.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and B is oxygen.

Extraordinary preference is also given to the compounds of the formula I.15, in particular to the compounds of the formulae I.15.1 to I.15.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and B is sulfur.

Extraordinary preference is also given to the compounds of the formula I.16, in particular to the compounds of the formulae I.16.1 to I.16.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and B is a bond.

Extraordinary preference is also given to the compounds of the formula I.17, in particular to the compounds of the formulae I.17.1 to I.17.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and Y is SO 2 .

Extraordinary preference is also given to the compounds of the formula I.18, in particular to the compounds of the formulae I.18.1 to I.18.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and Y is SO 2 NR 2 .

Extraordinary preference is also given to the compounds of the formula I.19, in particular to the compounds of the formulae I.19.1 to I.19.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.20, in particular to the compounds of the formulae I.20.1 to I.20.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen, B is oxygen and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.21, in particular to the compounds of the formulae I.21.1 to I.21.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen, B is sulfur and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.22, in particular to the compounds of the formulae I.22.1 to I.22.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen, B is a bond and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.23, in particular to the compounds of the formulae I.23.1 to I.23.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen, Y is SO 2 and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.24, in particular to the compounds of the formulae I.24.1 to I.24.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is hydrogen, Y is SO 2 NR 2 and R 29 is amino.

Extraordinary preference is also given to the compounds of the formula I.25, in particular to the compounds of the formulae I.25.1 to I.25.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.26, in particular to the compounds of the formulae I.26.1 to I.26.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.27, in particular to the compounds of the formulae I.27.1 to I.27.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.28, in particular to the compounds of the formulae I.28.1 to I.28.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.29, in particular to the compounds of the formulae I.29.1 to I.29.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.30, in particular to the compounds of the formulae I.30.1 to I.30.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.31, in particular to the compounds of the formulae I.31.1 to I.31.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.32, in particular to the compounds of the formulae I.32.1 to I.32.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is oxygen and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.33, in particular to the compounds of the formulae I.33.1 to I.33.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is sulfur and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.34, in particular to the compounds of the formulae I.34.1 to I.34.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is a bond and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.35, in particular to the compounds of the formulae I.35.1 to I.35.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.36, in particular to the compounds of the formulae I.36.1 to I.36.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 NR 2 and Q is Q 5 (where A 1 =oxygen, R 7 =difluoromethyl and R 8 =methyl).

Extraordinary preference is also given to the compounds of the formula I.37, in particular to the compounds of the formulae I.37.1 to I.37.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.38, in particular to the compounds of the formulae I.38.1 to I.38.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.39, in particular to the compounds of the formulae I.39.1 to I.39.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.40, in particular to the compounds of the formulae I.40.1 to I.40.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.41, in particular to the compounds of the formulae I.41.1 to I.41.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.42, in particular to the compounds of the formulae I.42.1 to I.42.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 22 (where A 10 and A 11 =oxygen, A 12 =sulfur and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.43, in particular to the compounds of the formulae I.43.1 to I.43.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.44, in particular to the compounds of the formulae I.44.1 to I.44.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.45, in particular to the compounds of the formulae I.45.1 to I.45.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.46, in particular to the compounds of the formulae I.46.1 to I.46.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.47, in particular to the compounds of the formulae I.47.1 to I.47.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.48, in particular to the compounds of the formulae I.48.1 to I.48.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 22 (where A 10 , A 11 , A 12 =oxygen and R 32 , R 33 =methyl).

Extraordinary preference is also given to the compounds of the formula I.49, in particular to the compounds of the formulae I.49.1 to I.49.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 27 (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.50, in particular to the compounds of the formulae I.50.1 to I.50.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 27 (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.51, in particular to the compounds of the formulae I.51.1 to I.51.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 27 (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.52, in particular to the compounds of the formulae I.52.1 to I.52.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.53, in particular to the compounds of the formulae I.53.1 to I.53.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 27 (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.54, in particular to the compounds of the formulae I.54.1 to I.54.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 27 (where A 13 =oxygen, R 34 , R 36 =hydrogen, R 35 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.55, in particular to the compounds of the formulae I.55.1 to I.55.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.56, in particular to the compounds of the formulae I.56.1 to I.56.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.57, in particular to the compounds of the formulae I.57.1 to I.57.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.58, in particular to the compounds of the formulae I.58.1 to I.58.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.59, in particular to the compounds of the formulae I.59.1 to I.59.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.60, in particular to the compounds of the formulae I.60.1 to I.60.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =trifluoromethyl, R 36 =methyl).

Extraordinary preference is also given to the compounds of the formula I.61, in particular to the compounds of the formulae I.61.1 to I.61.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.62, in particular to the compounds of the formulae I.62.1 to I.62.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.63, in particular to the compounds of the formulae I.63.1 to I.63.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.64, in particular to the compounds of the formulae I.64.1 to I.64.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.65, in particular to the compounds of the formulae I.65.1 to I.65.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.66, in particular to the compounds of the formulae I.66.1 to I.66.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 27 (where A 13 =oxygen, R 34 =hydrogen, R 35 =methylsulfonyl, R 36 =amino).

Extraordinary preference is also given to the compounds of the formula I.67, in particular to the compounds of the formulae I.67.1 to I.67.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.68, in particular to the compounds of the formulae I.68.1 to I.68.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.69, in particular to the compounds of the formulae I.69.1 to I.69.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 methyl).

Extraordinary preference is also given to the compounds of the formula I.70, in particular to the compounds of the formulae I.70.1 to I.70.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.71, in particular to the compounds of the formulae I.71.1 to I.71.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.72, in particular to the compounds of the formulae I.72.1 to I.72.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =chlorine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.73, in particular to the compounds of the formulae I.73.1 to I.73.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.74, in particular to the compounds of the formulae I.74.1 to I.74.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.75, in particular to the compounds of the formulae I.75.1 to I.75.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.76, in particular to the compounds of the formulae I.76.1 to I.76.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.77, in particular to the compounds of the formulae I.77.1 to I.77.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.78, in particular to the compounds of the formulae I.78.1 to I.78.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.79, in particular to the compounds of the formulae I.79.1 to I.79.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.80, in particular to the compounds of the formulae I.80.1 to I.80.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.81, in particular to the compounds of the formulae I.81.1 to I.81.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.82, in particular to the compounds of the formulae I.82.1 to I.82.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is a bond and Q is Q 32 (where R 3 1=bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.83, in particular to the compounds of the formulae I.83.1 to I.83.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.84, in particular to the compounds of the formulae I.84.1 to I.84.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =difluoromethoxy, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.85, in particular to the compounds of the formulae I.85.1 to I.85.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.86, in particular to the compounds of the formulae I.86.1 to I.86.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.87, in particular to the compounds of the formulae I.87.1 to I.87.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.88, in particular to the compounds of the formulae I.88.1 to I.88.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.89, in particular to the compounds of the formulae I.89.1 to I.89.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.90, in particular to the compounds of the formulae I.90.1 to I.90.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =chlorine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.91, in particular to the compounds of the formulae I.91.1 to I.91.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.92, in particular to the compounds of the formulae I.92.1 to I.92.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.93, in particular to the compounds of the formulae I.93.1 to I.93.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.94, in particular to the compounds of the formulae I.94.1 to I.94.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.95, in particular to the compounds of the formulae I.95.1 to I.95.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.96, in particular to the compounds of the formulae I.96.1 to I.96.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.97, in particular to the compounds of the formulae I.97.1 to I.97.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.98, in particular to the compounds of the formulae I.98.1 to I.98.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.99, in particular to the compounds of the formulae I.99.1 to I.99.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.100, in particular to the compounds of the formulae I.100.1 to I.100.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is a bond and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.101, in particular to the compounds of the formulae I.101.1 to I.101.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.102, in particular to the compounds of the formulae I.102.1 to I.102.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =trifluoromethyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.103, in particular to the compounds of the formulae I.103.1 to I.103.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.104, in particular to the compounds of the formulae I.104.1 to I.104.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.105, in particular to the compounds of the formulae I.105.1 to I.105.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.106, in particular to the compounds of the formulae I.106.1 to I.106.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.107, in particular to the compounds of the formulae I.107.1 to I.107.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.108, in particular to the compounds of the formulae I.108.1 to I.108.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =chlorine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.109, in particular to the compounds of the formulae I.109.1 to I.109.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.110, in particular to the compounds of the formulae I.110.1 to I.110.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.111, in particular to the compounds of the formulae I.111.1 to I.111.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.112, in particular to the compounds of the formulae I.112.1 to I.112.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.113, in particular to the compounds of the formulae I.113.1 to I.113.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.114, in particular to the compounds of the formulae I.114.1 to I.114.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I. 115, in particular to the compounds of the formulae I.115.1 to I.115.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.116, in particular to the compounds of the formulae I.116.1 to I.116.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is oxygen and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.117, in particular to the compounds of the formulae I.117.1 to I.117.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is sulfur and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.118, in particular to the compounds of the formulae I.118.1 to I.118.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, B is a bond and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.119, in particular to the compounds of the formulae I.119.1 to I.119.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.120, in particular to the compounds of the formulae I.120.1 to I.120.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that X 1 is chlorine, Y is SO 2 NR 2 and Q is Q 32 (where R 37 =bromine, R 38 =methylsulfonyl, R 39 =methyl).

Extraordinary preference is also given to the compounds of the formula I.121, in particular to the compounds of the formulae I.121.1 to I.121.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.122, in particular to the compounds of the formulae I.122.1 to I.122.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.123, in particular to the compounds of the formulae I.123.1 to I.123.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.124, in particular to the compounds of the formulae I.124.1 to I.124.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.125, in particular to the compounds of the formulae I.125.1 to I.125.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.126, in particular to the compounds of the formulae I.126.1 to I.126.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 38 (where R 40 =chlorine, R 41 , R 43 =hydrogen, R 42 =trifluoromethyl).

Extraordinary preference is also given to the compounds of the formula I.127, in particular to the compounds of the formulae I.127.1 to I.127.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 39 (where A 1 =oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.128, in particular to the compounds of the formulae I.128.1 to I.128.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 39 (where A 1 oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.129, in particular to the compounds of the formulae I.129.1 to I.129.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 39 (where A 1 =oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.130, in particular to the compounds of the formulae I.130.1 to I.130.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 39 (where A 1 =oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.131, in particular to the compounds of the formulae I.131.1 to I.131.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 39 (where A 1 =oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.132, in particular to the compounds of the formulae I.132.1 to I.132.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 39 (where A 1 =oxygen, A 15 =sulfur, R 44 , R 45 =methyl).

Extraordinary preference is also given to the compounds of the formula I.133, in particular to the compounds of the formulae I.133.1 to I.133.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.134, in particular to the compounds of the formulae I.134.1 to I.134.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.135, in particular to the compounds of the formulae I.135.1 to I.135.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.136, in particular to the compounds of the formulae I.136.1 to I.136.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.137, in particular to the compounds of the formulae I.137.1 to I.137.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.138, in particular to the compounds of the formulae I.138.1 to I.138.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 7 (where A 16 , A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.139, in particular to the compounds of the formulae I. 139.1 to I.139.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —H 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.140, in particular to the compounds of the formulae I.140.1 to I.140.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.141, in particular to the compounds of the formulae I.141.1 to I.141.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.142, in particular to the compounds of the formulae I.142.1 to I.142.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.143, in particular to the compounds of the formulae I.143.1 to I.143.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.144, in particular to the compounds of the formulae I.144.1 to I.144.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 7 (where A 16 =sulfur, A 17 =oxygen and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.145, in particular to the compounds of the formulae I.145.1 to I.145.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.146, in particular to the compounds of the formulae I.146.1 to I.146.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.147, in particular to the compounds of the formulae I.147.1 to I.147.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.148, in particular to the compounds of the formulae I.148.1 to I.148.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.149, in particular to the compounds of the formulae I.149.1 to I.149.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.150, in particular to the compounds of the formulae I.150.1 to I.150.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 7 (where A 16 , A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.151, in particular to the compounds of the formulae I.151.1 to I.151.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.152, in particular to the compounds of the formulae I.152.1 to I.152.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is oxygen and Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.153, in particular to the compounds of the formulae I.153.1 to I.153.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is sulfur and Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.154, in particular to the compounds of the formulae I.154.1 to I.154.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that B is a bond and Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.155, in particular to the compounds of the formulae I.155.1 to I.155.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 and Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

Extraordinary preference is also given to the compounds of the formula I.156, in particular to the compounds of the formulae I.156.1 to I.156.689, which differ from the corresponding compounds of the formulae I.1.1 to I.1.689 in that Y is SO 2 NR 2 and Q is Q 7 (where A 16 =oxygen, A 17 =sulfur and R 46 , R 47 form a chain —CH 2 —CH 2 —O—CH 2 —).

The benzenesulfonamide derivatives of the formula I can be obtained by different routes, for example by one of the processes below:

Process A

Appropriately substituted aromatic compounds of the formula VIII are, by chlorosulfonylation, converted into the corresponding benzenesulfonyl chlorides of the formula VII which are then reacted with ammonia to give the corresponding sulfonamides of the formula V. The sulfonamides of the formula V are then reacted with (thio)phosgene of the formula VI to give the benzenesulfonyl iso(thio)cyanates of the formula II which are then reacted with amines of the formula III or alcohols or thiols of the formula IV to give the desired benzenesulfonamide derivatives of the formula I, where X 3 is hydrogen, Y is —C(A)B and B is NR 2 , oxygen or sulfur and the other radicals are as defined under claim 1 :

Q in formula VIII denotes the radicals Q 1 to Q 39 mentioned above or a substituent which is a precursor suitable for the synthesis of Q 1 to Q 39 , for example a nitro or carboxyl group.

The chlorosulfonylation of the aromatic compounds of the formula VIII to give the corresponding benzenesulfonyl chlorides of the formula VII is usually carried out at temperatures of from 0° C. to 150° C., preferably from 20° C. to 130° C., particularly preferably from 30° C. to 110° C., using, for example, chlorosulfonic acid, sulfonyl chloride (SO 2 Cl 2 ) or using sulfonyl chloride in the presence of chlorosulfonic acid in an inert organic solvent [cf. Houben-Weyl, Methoden der organischen Chemie (Methods of organic chemistry), Vol. 9, 1955, pp. 572-579].

Suitable solvents are halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, nitriles, such as acetonitrile and propionitrile, and also chlorosulfonic acid, particularly preferably chlorosulfonic acid.

It is also possible to use mixtures of the solvents mentioned.

If appropriate, this reaction can also be carried out in the presence of a metal catalyst, for example aluminum chloride, analogously to a Friedel-Crafts reaction [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 578-579].

Suitable acids and acid catalysts include inorganic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids, such as boron trifluoride, aluminum trichloride, iron(III) chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II) chloride.

The acid catalysts are generally employed in catalytic amounts; however, they can also be used in equimolar amounts, in excess, or, if appropriate, as solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of chlorosulfonic acid or sulfonyl chloride, based on VIII, or to work directly in chlorosulfonic acid, as solvent.

The reaction mixtures are worked up in a customary manner, for example by mixing with water, phase separation and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of viscous oils which can be freed from volatile components or purified under reduced pressure and at moderately elevated temperatures. If the intermediates and end products are obtained as solids, purification can also be carried out by recrystallization or digestion.

Furthermore, it is also possible to cleave dialkyl sulfides with chlorine in the presence of water, followed by conversion into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 580-582].

Analogously, it is also possible to convert thiophenols into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, p. 582].

Benzenesulfonyl chlorides of the formula VII can also be prepared by reacting benzenesulfonic acids with chlorinating agents such as thionyl chloride, phosgene, phosphorus trichloride or phosphorus pentachloride [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 564-568].

It is also possible to convert anilides via their diazonium salts with sulfur dioxide in the presence of copper(II) chloride (Meerwein reaction) into the corresponding benzenesulfonyl chlorides of the formula VII [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, p. 579-580].

The starting materials required for preparing the compounds I are known from the literature [for example CAS 112, 157842; JP 01/168662] or can be prepared in accordance with the literature cited.

Benzenesulfonyl chlorides of the formula VII in which Q is Q 7 are known, for example, from WO 02/38562.

The preparation of benzenesulfonyl chlorides of the formula VII in which Q is Q 21 is described, for example, in U.S. Pat. No. 5,169,430.

Benzenesulfonyl chlorides of the formula VII in which Q is Q 32 are known, for example, from WO 96/15115.

The preparation of benzenesulfonyl chlorides of the formula VII in which Q is Q 38 is described, for example, in WO 95/02580.

Benzenesulfonyl chlorides of the formula VII having other radicals Q can be prepared analogously to the methods mentioned above (cf. for example JP 05/164386). Further precursors are described in Böger, Wakabayashi, Peroxidizing Herbicides, Springer Verlag 1999.

The subsequent reaction of the benzenesulfonyl chlorides of the formula VII with gaseous or aqueous ammonia to give the corresponding sulfonamides of the formula V where

X 3 =hydrogen is usually carried out at temperatures of from −10° C. to 50° C., preferably from 0° C. to 30° C., particularly preferably from 5° C. to 15° C., in an inert organic solvent, if appropriate in the presence of a base [cf. U.S. Pat. No. 5,169,430; WO 95102580; Houben-Weyl, Methoden der organischen Chemie, Vol. 9, 1955, pp. 398-400 and 605].

Ammonia is preferably used in an excess of from 200 to 230%; however, it is also possible to use an auxiliary base.

Suitable auxiliary bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides, such as lithium amide, sodium amide, and potassium amide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C 5 -C 8 -alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butylmethyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methylethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethylformamide and dimethylacetamide, particularly preferably dioxane, tetrahydrofuran, 1,2-dichloroethane, toluene or cyclohexane.

It is also possible to use mixtures of the solvents mentioned.

Work-up and isolation of the products can be carried out in a manner known per se.

Further sulfonamides of formula V can be prepared by analogous reaction of benzenesulfonyl chlorides of the formula VII with an amine H 2 NX 3 .

Sulfonamides of the formula V, in which Q is Q 7 are described, for example, in WO 02/38562.

U.S. Pat. No. 5,169,430 and WO 95/02580 describe sulfonamides of the formula V in which Q is Q 21 and Q 28 , respectively.

The reaction of the sulfonamides of the formula V where X 3 =hydrogen with (thio)phosgene of the formula VI to give benzenesulfonyl iso(thio)cyanates of the formula II is usually carried out at temperatures of from 50° C. to 110° C., preferably from 60° C. to 90° C., in an inert organic solvent, if appropriate in the presence of a catalyst [cf. Houben-Weyl, Methoden der organischen Chemie, Vol. 11, 2, 1985, p. 1106; U.S. Pat. No. 4,379,769; DD 238 522].

Suitable catalysts are, for example, aliphatic isocyanates, such as, for example, n-propyl isocyanate, isopropyl isocyanate or n-butyl isocyanate.

The catalyst is generally employed in a substoichiometric amount of from 5% to 15% per mole of sulfonamide of the formula V.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C 5 -C 8 -alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, particularly preferably toluene, 1,2-dichloroethane or chlorobenzene.

It is also possible to use mixtures of the solvents mentioned.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of VI, based on V.

Work-up and isolation of the products can be carried out in a manner known per se.

The conversion of the sulfonamides of the formula V where X 3 =hydrogen into benzenesulfonyl iso(thio)cyanates of the formula II can also be carried out using diphosgene [ClC(O)OCCl 3 ] or using carbon disulfide in phosgene.

Expediently, the sulfonamides of the formula V where X 3 =hydrogen can also be initially pre-treated with thionyl chloride under reflux and then be reacted with phosgene to give benzenesulfonyl iso(thio)cyanates of the formula II (cf. DE 43 22 726).

Benzenesulfonyl iso(thio)cyanates of the formula II can also be prepared by reacting sulfonamides of the formula V where X 3 =hydrogen with chlorosulfonyl isocyanate (cf. DE 31 32 944).

Benzenesulfonyl iso(thio)cyanates of the II can furthermore be prepared in a manner known per se by reacting benzenesulfonyl chlorides of the formula VII with alkali metal isocyanates (cf. U.S. Pat. No. 4,546,179).

The reaction of benzenesulfonyl iso(thio)cyanates of the II with a primary amine of the formula III or an alcohol or thiol of the formula IV to give the desired benzenesulfonamide derivatives of the formula I where X 3 =hydrogen, Y=—C(A)B and B=NR 2 , oxygen or sulfur is usually carried out at temperatures of from 0° C. to 120° C., preferably from 10° C. to 100° C., particularly preferably from 20° C. to 70° C., in an inert organic solvent [cf. EP 162 723].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably from 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C 5 -C 8 -alkanes; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene; halogenated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran and also nitriles, such as acetonitrile and propionitrile, particularly preferably tetrahydrofuran, dioxane and 1,2-dichloroethane.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, it is possible to add, before or during the reaction, a base, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The benzenesulfonyl iso(thio)cyanates of the II are generally reacted in equimolar amounts with the primary amine of the formula III or the alcohol or thiol of the formula IV. It may be advantageous to employ an excess of III or IV, based on II.

Work-up and isolation of the products can be carried out in a manner known per se.

Process B

Sulfonamides of the formula V are reacted with (thio)carbamates of the formula IX to give the desired benzenesulfonamide derivatives of the formula I, where Y is —C(A)B and B is NR 2 and the other radicals are as defined under claim 1 :

Z in formula IX denotes a C 1 -C 6 -alkyl or phenyl radical, where both radicals for their part may be partially or fully halogenated and/or may carry one to three radicals from the group consisting of nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 20° C. to 100° C., in an inert organic solvent [cf. EP 141 777 and EP 101 670].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C 5 -C 8 -alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, tert-butyl methyl ether and toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine and 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with the (thio)carbamate of the formula IX. It may be advantageous to employ an excess of IX, based on V.

The work-up and isolation of the products can be carried out in a manner known per se.

By analogous reaction with carboxylic acid derivatives ZO(A)R 1 , it is possible to prepare benzenesulfonamide derivatives of the formula I where Y=—C(A)B and B=a bond.

Process C

Sulfonamides of the formula V can be reacted with iso(thio)cyanates of the formula X to give the desired benzenesulfonamide derivatives of the formula I where Y is —C(A)B and B is NH and the other radicals are as defined under claim 1 :

This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. EP 234 352].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C 5 -C 8 -alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, ethyl acetate, tert-butyl methyl ether, acetone and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with an iso(thio)cyanate of the formula X. It may be advantageous to employ an excess of X, based on V.

To bring the reaction to completion, the reaction mixture may, after addition of the components, be stirred at from 0 to 120° C., preferably from 10 to 100° C., in particular from 20 to 80° C., for another 20 min. to 24 h.

Work-up and isolation of the products can be carried out in a manner known per se.

Process D

Sulfonamides of the formula V can be reacted with halides of the formula XI to give the desired benzenesulfonamide derivatives of the formula I:

Hal in formula XI denotes halogen, such as fluorine, chlorine, bromine, particularly preferably chlorine.

This reaction is usually carried out at temperatures of from 0° C. to 150° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. JP 05/194386, CAS 120, 134277].

The reaction can be carried out under atmospheric pressure or under elevated pressure (up to 50 bar), preferably at 1 to 5 bar, continuously or batchwise.

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C 5 -C 8 -alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably 1,2-dichloroethane, tetrahydrofuran, ethyl acetate, acetonitrile and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine or 2,4,6-collidine.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonamides of the formula V are generally reacted in equimolar amounts with the isocyanate or isothiocyanate of the formula X. It may be advantageous to employ an excess of XI, based on V.

To bring the reaction to completion, the reaction mixture may, after addition of the components, be stirred at from 0 to 120° C., preferably from 10 to 100° C., in particular from 20 to 80° C., for another 20 min to 24 h.

Work-up and isolation of the products can be carried out in a manner known per se.

Analogously to process D described above, it is also possible to react sulfonamides of the formula V with anhydrides of the formula XII

A[C(=A)-R 1 ] 2   XII

to give the desired benzenesulfonamide derivatives of the formula I in which Y is —C(A)B where B is a bond and the other radicals are as defined under claim 1 .

Process E

Sulfonyl(thio)carbamates of the formula XIII are reacted with amines of the formula XIV to give the desired benzenesulfonamide derivatives of the formula I where Y is —C(A)B and B is NR 2 and the other radicals are as defined under claim 1 :

Z in formula XIII is C 1 -C 6 -alkyl or phenyl, where both radicals may for their part be partially or fully halogenated and/or may carry one to three radicals from the group consisting of nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -alkoxycarbonyl.

This reaction is usually carried out at temperatures of from 0° C. to 120° C., preferably from 10° C. to 100° C., in an inert organic solvent [cf. EP 120 814; EP 101 407].

Suitable solvents are aliphatic or cycloaliphatic hydrocarbons, such as pentane, 1,2,4-trimethylpentane, 2,2,3-trimethylpentane, 2,3,3-trimethylpentane, hexane, heptane, octane, nonane, mixtures of C 5 -C 8 -alkanes, pinane, cyclohexane, methylcyclohexane, o-, m-, p-cymene, petroleum fractions within a boiling point range of from 70° C. to 190° C., decalin, petroleum ether, ligroin; nitrated hydrocarbons, such as nitromethane, nitroethane, nitrobenzene, o-, m-, p-chloronitrobenzene and o-nitrotoluene; aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as 1,2-dichloroethane, 1,1-dichloroethane, 1,2-cis-dichloroethylene, 1,1,1- or 1,1,2-trichloroethane, trichloroethylene, tetrachloroethylene, 1,1,2,2- or 1,1,1,2-tetrachloroethane, pentachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, fluorobenzene, chlorobenzene, bromobenzene, iodobenzene, o-, m-, p-difluorobenzene, o-, m-, p-dichlorobenzene, o-, m-, p-dibromobenzene, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene, chloronaphthalene, dichloronaphthalene; ethers, such as diethyl ether, ethyl propyl ether, diisopropyl ether, tert-butyl methyl ether, n-butyl ethyl ether, di-n-butyl ether, diisobutyl ether, diisoamyl ether, dioxane, cyclohexyl methyl ether, ethylene glycol dimethyl ether, β,β′-dichlorodiethyl ether, tetrahydrofuran, anisole, thioanisole, phenetol; nitriles, such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone; esters, such as ethyl acetate, isobutyl acetate; amides, such as formamide, methylformamide, dimethylformamide; particularly preferably tetrahydrofuran, dioxane, dimethylformamide and also toluene.

It is also possible to use mixtures of the solvents mentioned.

As catalyst, a base can be added before or during the reaction, which accelerates the reaction and improves the quality of the product.

Suitable bases are, in general, organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tri(n-propyl)amine, N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine and 1,4-diazabicyclo[2.2.2]octane.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts.

The sulfonylcarbamates of the formula XII are generally reacted in equimolar amounts with an amine of the formula XIV. It may be advantageous to employ an excess of XIV, based on XII.

Work-up and isolation of the products can be carried out in a manner known per se.

The starting materials required for preparing the compounds I are known from the literature [cf. for example, CAS 112, 157842; JP 01/168662], or they can be prepared in accordance with the literature cited.

Process F

Compounds of the formula I in which the radicals Q carry the substituents R 3 , R 4 , R 7 , R 11 , R 18 , R 19 , R 24 , R 27 , R 29 , R 32 , R 39 , R 44 -R 47 on their nitrogen atoms [these radicals denoting, inter alia, C 1 -C 6 -alkyl or amino, C 1 -C 6 -alkylamino or di(C 1 -C 6 -alkyl)amino] can be prepared by reacting, either prior to the synthesis of the sulfonamide side chain (i.e. at the stage of the aromatic compounds of the formula VIII) or after synthesis of the sulfonamide side chain, with an alkyl halide, alkyl sulfate, alkyl tosylate or an electrophilic aminating agent of the formula XVII, analogously to the methods described in the literature.

Examples of electrophilic aminating agents of the formula XVII are 2,4-dinitrophenylhydroxylamine and o-mesitylenesulfonyl hydroxylamine.

The benzenesulfonyl chlorides of the formula VII mentioned above can be converted, for example, by action of alcohols, expediently in the presence of a base, into the corresponding benzenesulfonyl esters [Houben-Weyl, Methoden der organischen Synthese, Vol. 9, 1955, p. 663]. The benzenesulfonyl esters can then be alkylated or aminated on the free nitrogen atoms of the corresponding radicals Q. Subsequently, the benzenesulfonyl esters can be hydrolyzed again [cf. Kocienski, Protecting groups, Thieme-Verlag 1994; Greene, Wuts, Protecting groups in organic synthesis, Wiley 1999; Houben-Weyl, Methoden der organischen Chemie, Vol. E5 part 1, 1985, p. 223f.).

By way of example, an amination at the radical Q=Q 21 is shown here. The aminations of the other radicals Q and alkylations at the radicals Q can be carried out analogously. This route affords, for example, sulfonic acids of the formula XVI. These can then be converted using methods known from the literature into the desired benzenesulfonamide derivatives of the formula I.

This reaction is usually carried out at temperatures of from 10° C. to 80° C., preferably from 20° C. to 40° C., in an inert organic solvent in the presence of a base [cf. DE 19 652 431; WO 01/83459].

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of C 5 -C 8 -alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethyl formamide and dimethylacetamide, particularly preferably tetrahydrofuran, dioxane, acetonitrile and also dimethylformamide.

It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, inorganic compounds, for example alkali metal and alkaline earth metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides, such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal and alkaline earth metal carbonates, such as lithium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarbonate, alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to potassium carbonate and also calcium carbonate.

The bases are generally employed in catalytic amounts; however, they can also be employed in equimolar amounts, in excess or, if appropriate, as solvent.

The starting materials are generally reacted with one another in equimolar amounts. However, it may also be advantageous to employ an excess of XVII, based on XV.

Work-up and isolation of the products can be carried out in a manner known per se.

The starting materials required for preparing the compounds I are known from the literature [for example CAS 112, 157842; JP 01168662], or they can be prepared in accordance with the literature cited.

The present invention also provides benzenesulfonyl iso(thio)cyanates of the formula II

where X 1 , X 2 , A and Q are as defined under claim 1 .

The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the radicals X 1 , X 2 , A and Q of formula I.

Particular preference is given to intermediates of the formula IV in which

X 1 is hydrogen, fluorine or chlorine;

particularly preferably hydrogen or fluorine; especially preferably fluorine;

X 2 is hydrogen, cyano, CS—NH 2 or halogen;

particularly preferably hydrogen, halogen such as fluorine and chlorine; especially preferably chlorine; and

Q is Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 23 , Q 24 , Q 27 , Q 31 , Q 32 , Q 34 , Q 38 or Q 39 ,

particularly preferably Q 1 , Q 2 , Q 5 , Q 7 , Q 8 , Q 10 , Q 12 , Q 13 , Q 17 , Q 20 , Q 21 , Q 22 , Q 24 , Q 27 , Q 31 , Q 32 , Q 38 or Q 39 , especially preferably Q 5 , Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 , with extraordinary preference Q 7 , Q 21 , Q 22 , Q 27 , Q 32 , Q 38 or Q 39 , with most extraordinary preference Q 21 , Q 32 or Q 38 .

Herbicidal Efficacy

The herbicidal activity of the benzenesulfonamide derivatives of the formula I was demonstrated by the following greenhouse experiments:

The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

For the pre-emergence treatment, the active compounds, emulsified or suspended in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compounds.

For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant form, and only then treated with the active compounds, emulsified or suspended in water. The test plants were for this purpose either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

The application rate for the pre- and post-emergence treatment was from 62.5 to 3.1 g of a.s./ha.

Depending on the species, the plants were kept at 10-25° C. or 20-35° C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.

Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage, or normal course of growth.

The plants used in the greenhouse experiments were composed of the following species:

Scientific Name

Common Name

Abutilon theophrasti

Velvet leaf

Amaranthus retroflexus

Pigweed

Chenopodium album

Common lambsquarters

Commelina benghalensis

Bengal commelina

Galium aparine

Cleavers harrif

Ipomoea hederacea

Morning glory

Pharbitis purpurea

Common morning glory

Polygonum convolvulus

Wild buckwheat

Polygonum persicaria

Ladysthumb

Solanum nigrum

Common nightshade

At application rates of 12.5 and 6.2 g/ha, the compounds 3.1 and 3.18 (Table 3) showed very good pre-emergence activity against the unwanted plants pigweed, common lambsquarters, common morning glory and wild buckwheat.

Furthermore, compounds 3.24 (Table 3) and 4.16 (Table 4), when applied by the pre-emergence method at application rates of 6.2 and 3.1 g/ha, effected very good control of the unwanted plants velvet leaf, pigweed, common lambsquarters and morning glory.

The effectiveness of compound 3.32 (Table 3), when applied by the pre-emergence method at application rates of 62.5 and 31.2 g/ha, was very good against the unwanted plants velvet leaf, pigweed, common lambsquarters and common nightshade.

At application rates of 15.6 and 7.8 g/ha, the compounds 3.27, 3.19, 3.20 and 3.22 (Table 3) showed very good post-emergence activity against the unwanted plants pigweed, common lambsquarters, common morning glory and ladysthumb.

Furthermore, compounds 2.29 (Table 2) and 3.26 (Table 3), when applied by the post-emergence method at application rates of 15.6 and 7.8 g/ha, effected very good control of the unwanted plants pigweed, common lambsquarters and common morning glory.

The effectiveness of compound 3.42 (Table 3), when applied by the post-emergence method at application rates of 15.63 g/ha, was very good against the unwanted plants velvet leaf, common morning glory and ladiesthumb.

At application rates of 15.63 g/ha, the compounds 3.41 (Table 3) and 4.14 (Table 4) showed very good post-emergence activity against the unwanted plants pigweed, cleavers harrif and ladiesthumb.

Furthermore, compound 2.17 (Table 2), when applied by the post-emergence method at application rates of 15.63 g/ha, effected very good control of the unwanted plants velvet leaf, common lambsquarters and Bengal commelina.

The effectiveness of compound 2.28 (Table 2), when applied by the post-emergence method at application rates of 15.63 g/ha, was very good against the unwanted plants pigweed, common lambsquarters and common morning glory.

At application rates of 15.63 g/ha, the compound 2.27 (Table 2) showed very good post-emergence activity against the unwanted plants pigweed and common morning glory.

Desiccant/Defoliant Efficacy

The test plants used were young 4-leaf cotton plants (without cotyledons) which were grown under greenhouse conditions (rel. atmospheric humidity 50 to 70%; day/night temperature 27/20° C.).

The leaves of the young cotton plants were sprayed to runoff point with aqueous preparations of the active compounds (with addition of 0.15% by weight of the fatty alcohol alkoxylate Plurafac® LF 700 1) , based on the spray liquor). The amount of water applied was 1000 l/ha (converted). After 13 days, the number of leaves that had been shed and the degree of defoliation in % were determined. 1) A low-foam nonionic surfactant from BASF AG

The untreated control plants did not lose any leaves.