Substituted benzoycyclohexenones

Abstract

The invention relates to novel substituted benzoylcyclohexenones of the formula (I), 1

Description

[0001] The invention relates to novel substituted benzoylcyclohexenones, to processes for their preparation and to their use as herbicides.

[0002] It is already known that certain substituted benzoylcyclohexanediones have herbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, WO-A-96/26200, WO-A-97/46530, WO-A-99/07688, WO-A-00/05221). However, the activity of these compounds is not in all respects satisfactory.

[0003] This invention, accordingly, provides the novel substituted benzoylcyclohexenones of the formula (I), 2

[0004] in which

[0005] n represents the number 0, 1 or 2,

[0006] A represents a single bond or represents alkanediyl (alkylene) having 1 to 6 carbon atoms,

[0007] R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms,

[0008] R2 represents hydrogen or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, or together with R1 represents alkanediyl (alkylene) having 1 to 6 carbon atoms, or together with R1—in this case attached to the same carbon atom—and the carbon atom to which R1 and R2 are attached in this case represents a (C═O) grouping,

[0009] R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,

[0010] R4 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, and

[0011] Y represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 10 carbon atoms, represents in each case optionally cyano-, halogen-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkenyl or alkinyl having in each case 2 to 10 carbon atoms, or represents in each case optionally nitro-, amino-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio-, C1-C4-halogenoalkylthio-, C1-C4-alkylsulphinyl-, C1-C4-halogenoalkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl-carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino-, C1-C4-alkyl-sulphonyl-amino-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, and

[0012] Z represents an optionally substituted 4- to 12-membered saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which contains 1 to 4 hetero atoms (up to 4 nitrogen atoms and optionally—alternatively or additionally—one oxygen atom or one sulphur atom, or one SO grouping or one SO2 grouping), and which contains additionally one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle,

[0013] including all possible tautomeric and, if appropriate, possible stereoisomeric forms of the compounds of the general formula (I), and the possible salts or metal-coordinated derivatives of the compounds of the general formula (I).

[0014] In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl, are in each case straight-chain or branched—including in combination with heteroatoms, such as in alkoxy.

[0015] Preferred meanings of the radicals or groupings present in the formulae shown above and below are defined below.

[0016] n preferably represents the number 0 or 2.

[0017] A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms.

[0018] R1 preferably represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms.

[0019] R2 preferably represents hydrogen or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms, or together with R1 represents alkanediyl (alkylene) having 1 to 5 carbon atoms.

[0020] R3 preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups.

[0021] R4 preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups.

[0022] Y preferably represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano-, halogen-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case optionally nitro-, amino-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio, C1-C4-halogenoalkylthio-, C1-C4-alkylsulphinyl-, C1-C4-halogenoalkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl-carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino-, C1-C4-alkyl-sulphonyl-amino-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety.

[0023] Z preferably represents one of the heterocyclic groupings below 34

[0024] in which the bond drawn broken in each case denotes a single bond or a double bond, and in which each heterocycle preferably only carries two substituents of the definition R5 and/or R6 in any combination.

[0025] Q represents oxygen or sulphur,

[0026] R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio, alkinylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—also together with the adjacent radical R5 represents a benzo grouping, and

[0027] R6 represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents optionally halogen- or C1-C4-alkyl-substituted alkanediyl having 3 to 5 carbon atoms,

[0028] where the individual radicals R5 and R6—if two or more of them are attached to the same heterocyclic groupings—may have identical or different meanings in the context of the above definition.

[0029] n particularly preferably represents the number 0.

[0030] A particularly preferably represents a single bond or represents methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).

[0031] R1 particularly preferably represents hydrogen, phenyl or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl.

[0032] R2 particularly preferably represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or together with R1 represents methylene, ethylidene (ethane-1,1-diyl), dimethylene (ethane-1,2-diyl), propylidene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl).

[0033] R3 particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.

[0034] R4 particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl.

[0035] Y particularly preferably represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted ethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl or butinyl, or represents in each case optionally nitro-, amino-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxymethyl-, ethoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl.

[0036] Z particularly preferably represents one of the heterocyclic groupings below 5

[0037] Q preferably represents oxygen,

[0038] R5 preferably represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or—in the case that two adjacent radicals R5 and R5 are located at a double bond—together with the adjacent radical R5 also represents a benzo grouping.

[0039] R6 preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl or propenyloxy, represented in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).

[0040] A very particularly preferably represents a single bond or represents methylene.

[0041] R1 very particularly preferably represents hydrogen, phenyl or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl.

[0042] R2 very particularly preferably represents hydrogen or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, or together with R1 represents methylene or dimethylene.

[0043] R3 very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulphonyl.

[0044] R4 very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulphonyl.

[0045] Y very particularly preferably represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propinyl or butinyl, or represents in each case optionally nitro-, amino-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxymethyl-, ethoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, methylsulphonylamino- or ethylsulphonylamino-substituted phenyl or benzyl.

[0046] Z very particularly preferably represents the heterocyclic groupings below 6

[0047] R5 particularly preferably represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, 1- or s-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i- or s-butylamino, dimethylamino or diethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio or represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropylthio, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethylthio or cyclopropylmethylamino.

[0048] R6 particularly preferably represents hydrogen, represents amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylamino or ethylamino, represents dimethylamino, or represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropylmethyl, phenyl or benzyl, or together with an adjacent radical R5 or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).

[0049] A most preferably represents methylene.

[0050] R1 most preferably represents hydrogen.

[0051] R2 most preferably represents hydrogen.

[0052] R3 most preferably represents chlorine, trifluoromethyl or methoxy.

[0053] R4 most preferably represents chlorine, trifluoromethyl or methylsulphonyl.

[0054] Y most preferably represents hydrogen, represents in each case optionally fluorine-, chlorine- or methoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, pentenyl or represents optionally amino-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trifluoromethyl-, methoxy- or ethoxy-substituted phenyl.

[0055] R5 very particularly preferably represents hydrogen, methyl or ethyl.

[0056] R6 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl.

[0057] R5 most preferably represents hydrogen.

[0058] R6 most preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl.

[0059] The invention preferably also provides the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I), in which A, n, R1, R2, R1, R4, Y and Z are each as defined above, or else complex compounds (coordination compounds) of these compounds with metals such as copper, iron, cobalt, nickel.

[0060] Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings mentioned above as being preferred.

[0061] Particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred.

[0062] Very particular preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred.

[0063] Most preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being most preferred.

[0064] The general or preferred radical definitions listed above apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

[0065] The position of the radicals R1, R2, R3, R4 and A-Z can vary according to formula (I).

[0066] The radical R3 is preferably in position (4) on the phenyl ring, particularly preferably in position (2).

[0067] The radical R4 is preferably in position (4) on the phenyl ring, if the radical R3 is in position (2).

[0068] The radical A-Z is preferably in position (2) on the phenyl ring, particularly preferably in position (3), and particular preference is given to the substitution pattern (2)-R3, (4)-R4 and (3)-A-Z.

[0069] The present invention provides in particular the compounds of the general formulae (IA), (IB) and (IC) below. 7

[0070] In the general formulae (IA), (IB) and (IC), n, A, R1, R2, R1, R4, Y and Z have in each case the meanings given in the definitions above.

[0071] Very particular emphasis is given to the compounds of the general formulae (IA), (IB) and (IC) in which A represents methylene.

[0072] Examples of compounds of the general formula (I) according to the invention are listed in the groups below.

[0073] Group 1 8

[0074] Here, R3, R4, R5 and R6 each have, for example, the meanings given in the table below:

		(position)
	R3	R4	R5	R6
	H	—	CF3	CH3
	F	—	CF3	CH3
	Cl	—	CF3	CH3
	Br	—	CF3	CH3
	I	—	CF3	CH3
	NO2	—	CF3	CH3
	CN	—	CF3	CH3
	CH3	—	CF3	CH3
	OCH3	—	CF3	CH3
	CF3	—	CF3	CH3
	OCHF2	—	CF3	CH3
	OCF3	—	CF3	CH3
	SO2CH3	—	CF3	CH3
	H	—	OCH3	CH3
	F	—	OCH3	CH3
	Cl	—	OCH3	CH3
	Br	—	OCH3	CH3
	I	—	OCH3	CH3
	NO2	—	OCH3	CH3
	CN	—	OCH3	CH3
	CH3	—	OCH3	CH3
	OCH3	—	OCH3	CH3
	CF3	—	OCH3	CH3
	OCHF2	—	OCH3	CH3
	OCF3	—	OCH3	CH3
	SO2CH3	—	OCH3	CH3
	H	—	SCH3	CH3
	F	—	SCH3	CH3
	Cl	—	SCH3	CH3
	Br	—	SCH3	CH3
	I	—	SCH3	CH3
	NO2	—	SCH3	CH3
	CN	—	SCH3	CH3
	CH3	—	SCH3	CH3
	OCH3	—	SCH3	CH3
	CF3	—	SCH3	CH3
	OCHF2	—	SCH3	CH3
	OCF3	—	SCH3	CH3
	SO2CH3	—	SCH3	CH3
	H	—	OC2H5	CH3
	F	—	OC2H5	CH3
	Cl	—	OC2H5	CH3
	Br	—	OC2H5	CH3
	I	—	OC2H5	CH3
	NO2	—	OC2H5	CH3
	CN	—	OC2H5	CH3
	CH3	—	OC2H5	CH3
	OCH3	—	OC2H5	CH3
	CF3	—	OC2H5	CH3
	OCHF2	—	OC2H5	CH3
	OCF3	—	OC2H5	CH3
	SO2CH3	—	OC2H5	CH3
	H	—	N(CH3)2	CH3
	F	—	N(CH3)2	CH3
	Cl	—	N(CH3)2	CH3
	Br	—	N(CH3)2	CH3
	I	—	N(CH3)2	CH3
	NO2	—	N(CH3)2	CH3
	CN	—	N(CH3)2	CH3
	CH3	—	N(CH3)2	CH3
	OCH3	—	N(CH3)2	CH3
	CF3	—	N(CH3)2	CH3
	OCHF2	—	N(CH3)2	CH3
	OCF3	—	N(CH3)2	CH3
	SO2CH3	—	N(CH3)2	CH3
	H	—	OCH3	9
	F	—	OCH3	10
	Cl	—	OCH3	11
	Br	—	OCH3	12
	I	—	OCH3	13
	NO2	—	OCH3	14
	CN	—	OCH3	15
	CH3	—	OCH3	16
	OCH3	—	OCH3	17
	CF3	—	OCH3	18
	OCHF2	—	OCH3	19
	OCF3	—	OCH3	20
	SO2CH3	—	OCH3	21
	H	(3-) Cl	CF3	CH3
	F	(3-) Cl	CH3	CH3
	Cl	(3-) Cl	OCH3	CH3
	Br	(3-) Cl	Br	22
	Cl	(3-) Cl	CF3	CH3
	NO2	(3-) Cl	CH3	CH3
	Cl	(3-) Cl	SCH3	CH3
	CH3	(3-) Cl	Cl	CH3
	OCH3	(3-) Cl	OCH3	CH3
	CF3	(3-) Cl	CF3	CH3
	OCHF2	(3-) Cl	CH3	CH3
	OCF3	(3-) Cl	CH3	CH3
	SO2CH3	(3-) Cl	OCH3	CH3
	F	—	C2H5	OCH3
	Cl	—	C2H5	OCH3
	Br	—	C2H5	OCH3
	CF3	—	C2H5	OCH3
	SO2CH3	—	C2H5	OCH3
	F	—	C2H5	C2H5
	Cl	—	C2H5	C2H5
	Br	—	C2H5	C2H5
	CF3	—	C2H5	C2H5
	SO2CH3	—	C2H5	C2H5

[0075] Group 2 23

[0076] Here, R3, R4, R5 and R each have, for example, the meanings given above in Group 1.

[0077] Group 3 24

[0078] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1.

[0079] Group 4 25

[0080] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1.

[0081] Group 5 26

[0082] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1.

[0083] Group 6 27

[0084] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in the table below.

		(position)
	R3	R4	R5	R6
	Cl	(2-) Cl	CF3	CH3
	Cl	(2-) Cl	SCH3	CH3
	Cl	(2-) Cl	SC2H5	CH3
	Cl	(2-) Cl	SC3H7	CH3
	Cl	(2-) Cl	SC3H7-i	CH3
	Cl	(2-) Cl	28	CH3
	Cl	(2-) Cl	29	CH3
	Cl	(2-) Cl	30	CH3
	Cl	(2-) Cl	31	CH3
	Cl	(2-) Cl	32	CH3
	Cl	(2-) Cl	SCH═C═CH2	CH3
	Cl	(2-) Cl	SCH2CN	CH3
	Cl	(2-) Cl	SCH2CH2CN	CH3
	Cl	(2-) Cl	OCH3	CH3
	Cl	(2-) Cl	OC2H5	CH3
	Cl	(2-) Cl	OC3H7	CH3
	Cl	(2-) Cl	OC3H7-i	CH3
	Cl	(2-) Cl	OC4H9	CH3
	Cl	(2-) Cl	OCH2CF3	CH3
	Cl	(2-) Cl	33	CH3
	Cl	(2-) Cl	OC6H5	CH3
	Cl	(2-) Cl	H	CH3
	Cl	(2-) Cl	CH3	CH3
	Cl	(2-) Cl	C2H5	CH3
	Cl	(2-) Cl	C3H7	CH3
	Cl	(2-) Cl	C3H7-i	CH3
	Cl	(2-) Cl	C4H9	CH3
	Cl	(2-) Cl	C4H9-i	CH3
	Cl	(2-) Cl	C4H9-s	CH3
	Cl	(2-) Cl	C4H9-t	CH3
	Cl	(2-) Cl	34	CH3
	Cl	(2-) Cl	35	CH3
	Cl	(2-) Cl	CH═CHCH3	CH3
	Cl	(2-) Cl	36	CH3
	Cl	(2-) Cl	37	CH3
	Cl	(2-) Cl	38	CH3
	Cl	(2-) Cl	N(CH3)2	CH3
	Cl	(2-) Cl	39	CH3
	Cl	(2-) Cl	Cl	CH3
	Cl	(2-) Cl	Br	CH3
	SO2CH3	(2-) Cl	CF3	CH3
	SO2CH3	(2-) Cl	SCH3	CH3
	SO2CH3	(2-) Cl	SC2H5	CH3
	SO2CH3	(2-) Cl	SC3H7	CH3
	SO2CH3	(2-) Cl	SC3H7-i	CH3
	SO2CH3	(2-) Cl	40	CH3
	SO2CH3	(2-) Cl	41	CH3
	SO2CH3	(2-) Cl	42	CH3
	SO2CH3	(2-) Cl	43	CH3
	SO2CH3	(2-) Cl	44	CH3
	SO2CH3	(2-) Cl	SCH═C═CH2	CH3
	SO2CH3	(2-) Cl	SCH2CN	CH3
	SO2CH3	(2-) Cl	SCH2CH2CN	CH3
	SO2CH3	(2-) Cl	OCH3	CH3
	SO2CH3	(2-) Cl	OC2H5	CH3
	SO2CH3	(2-) Cl	OC3H7	CH3
	SO2CH3	(2-) Cl	OC3H7-i	CH3
	SO2CH3	(2-) Cl	OC4H9	CH3
	SO2CH3	(2-) Cl	OCH2CF3	CH3
	SO2CH3	(2-) Cl	45	CH3
	SO2CH3	(2-) Cl	OC6H5	CH3
	SO2CH3	(2-) Cl	H	CH3
	SO2CH3	(2-) Cl	CH3	CH3
	SO2CH3	(2-) Cl	C2H5	CH3
	SO2CH3	(2-) Cl	C3H7	CH3
	SO2CH3	(2-) Cl	C3H7-i	CH3
	SO2CH3	(2-) Cl	C4H9	CH3
	SO2CH3	(2-) Cl	C4H9-i	CH3
	SO2CH3	(2-) Cl	C4H9-s	CH3
	SO2CH3	(2-) Cl	C4H9-t	CH3
	SO2CH3	(2-) Cl	46	CH3
	SO2CH3	(2-) Cl	47	CH3
	SO2CH3	(2-) Cl	CH═CHCH3	CH3
	SO2CH3	(2-) Cl	48	CH3
	SO2CH3	(2-) Cl	49	CH3
	SO2CH3	(2-) Cl	50	CH3
	SO2CH3	(2-) Cl	N(CH3)2	CH3
	SO2CH3	(2-) Cl	51	CH3
	SO2CH3	(2-) Cl	Cl	CH3
	SO2CH3	(2-) Cl	Br	CH3
	Cl	(2-) SO2CH3	CF3	CH3
	Cl	(2-) SO2CH3	SCH3	CH3
	Cl	(2-) SO2CH3	SC2H5	CH3
	Cl	(2-) SO2CH3	SC3H7	CH3
	Cl	(2-) SO2CH3	SC3H7-i	CH3
	Cl	(2-) SO2CH3	52	CH3
	Cl	(2-) SO2CH3	53	CH3
	Cl	(2-) SO2CH3	54	CH3
	Cl	(2-) SO2CH3	55	CH3
	Cl	(2-) SO2CH3	56	CH3
	Cl	(2-) SO2CH3	SCH═C═CH2	CH3
	Cl	(2-) SO2CH3	SCH2CN	CH3
	Cl	(2-) SO2CH3	SCH2CH2CN	CH3
	Cl	(2-) SO2CH3	OCH3	CH3
	Cl	(2-) SO2CH3	OC2H5	CH3
	Cl	(2-) SO2CH3	OC3H7	CH3
	Cl	(2-) SO2CH3	OC3H7-i	CH3
	Cl	(2-) SO2CH3	OC4H9	CH3
	Cl	(2-) SO2CH3	OCH2CF3	CH3
	Cl	(2-) SO2CH3	57	CH3
	Cl	(2-) SO2CH3	OC6H5	CH3
	Cl	(2-) SO2CH3	H	CH3
	Cl	(2-) SO2CH3	CH3	CH3
	Cl	(2-) SO2CH3	C2H5	CH3
	Cl	(2-) SO2CH3	C3H7	CH3
	Cl	(2-) SO2CH3	C3H7-i	CH3
	Cl	(2-) SO2CH3	C4H9	CH3
	Cl	(2-) SO2CH3	C4H9-i	CH3
	Cl	(2-) SO2CH3	C4H9-s	CH3
	Cl	(2-) SO2CH3	C4H9-t	CH3
	Cl	(2-) SO2CH3	58	CH3
	Cl	(2-) SO2CH3	59	CH3
	Cl	(2-) SO2CH3	CH═CHCH3	CH3
	Cl	(2-) SO2CH3	60	CH3
	Cl	(2-) SO2CH3	61	CH3
	Cl	(2-) SO2CH3	62	CH3
	Cl	(2-) SO2CH3	N(CH3)2	CH3
	Cl	(2-) SO2CH3	63	CH3
	Cl	(2-) SO2CH3	Cl	CH3
	Cl	(2-) SO2CH3	Br	CH3
	Cl	(2-) Cl	CF3	64
	Cl	(2-) Cl	SCH3	65
	Cl	(2-) Cl	SC2H5	66
	Cl	(2-) Cl	SC3H7	67
	Cl	(2-) Cl	SC3H7-i	68
	Cl	(2-) Cl	69	70
	Cl	(2-) Cl	71	72
	Cl	(2-) Cl	73	74
	Cl	(2-) Cl	75	76
	Cl	(2-) Cl	77	78
	Cl	(2-) Cl	SCH═C═CH2	79
	Cl	(2-) Cl	SCH2CN	80
	Cl	(2-) Cl	SCH2CH2CN	81
	Cl	(2-) Cl	OCH3	82
	Cl	(2-) Cl	OC2H5	83
	Cl	(2-) Cl	OC3H7	84
	Cl	(2-) Cl	OC3H7-i	85
	Cl	(2-) Cl	OC4H9	86
	Cl	(2-) Cl	OCH2CF3	87
	Cl	(2-) Cl	88	89
	Cl	(2-) Cl	OC6H5	90
	Cl	(2-) Cl	H	91
	Cl	(2-) Cl	CH3	92
	Cl	(2-) Cl	C2H5	93
	Cl	(2-) Cl	C3H7	94
	Cl	(2-) Cl	C3H7-i	95
	Cl	(2-) Cl	C4H9	96
	Cl	(2-) Cl	C4H9-i	97
	Cl	(2-) Cl	C4H9-s	98
	Cl	(2-) Cl	C4H9-t	99
	Cl	(2-) Cl	100	101
	Cl	(2-) Cl	102	103
	Cl	(2-) Cl	CH═CHCH3	104
	Cl	(2-) Cl	105	106
	Cl	(2-) Cl	107	108
	Cl	(2-) Cl	109	110
	Cl	(2-) Cl	N(CH3)2	111
	Cl	(2-) Cl	112	113
	Cl	(2-) Cl	Cl	114
	Cl	(2-) Cl	Br	115
	SO2CH3	(2-) Cl	CF3	116
	SO2CH3	(2-) Cl	SCH3	117
	SO2CH3	(2-) Cl	SC2H5	118
	SO2CH3	(2-) Cl	SC3H7	119
	SO2CH3	(2-) Cl	SC3H7-i	120
	SO2CH3	(2-) Cl	121	122
	SO2CH3	(2-) Cl	123	124
	SO2CH3	(2-) Cl	125	126
	SO2CH3	(2-) Cl	127	128
	SO2CH3	(2-) Cl	129	130
	SO2CH3	(2-) Cl	SCH═C═CH2	131
	SO2CH3	(2-) Cl	SCH2CN	132
	SO2CH3	(2-) Cl	SCH2CH2CN	133
	SO2CH3	(2-) Cl	OCH3	134
	SO2CH3	(2-) Cl	OC2H5	135
	SO2CH3	(2-) Cl	OC3H7	136
	SO2CH3	(2-) Cl	OC3H7-i	137
	SO2CH3	(2-) Cl	OC4H9	138
	SO2CH3	(2-) Cl	OCH2CF3	139
	SO2CH3	(2-) Cl	140	141
	SO2CH3	(2-) Cl	OC6H5	142
	SO2CH3	(2-) Cl	H	143
	SO2CH3	(2-) Cl	CH3	144
	SO2CH3	(2-) Cl	C2H5	145
	SO2CH3	(2-) Cl	C3H7	146
	SO2CH3	(2-) Cl	C3H7-i	147
	SO2CH3	(2-) Cl	C4H9	148
	SO2CH3	(2-) Cl	C4H9-i	149
	SO2CH3	(2-) Cl	C4H9-s	150
	SO2CH3	(2-) Cl	C4H9-t	151
	SO2CH3	(2-) Cl	152	153
	SO2CH3	(2-) Cl	154	155
	SO2CH3	(2-) Cl	CH═CHCH3	156
	SO2CH3	(2-) Cl	157	158
	SO2CH3	(2-) Cl	159	160
	SO2CH3	(2-) Cl	161	162
	SO2CH3	(2-) Cl	N(CH3)2	163
	SO2CH3	(2-) Cl	164	165
	SO2CH3	(2-) Cl	Cl	166
	SO2CH3	(2-) Cl	Br	167
	Cl	(2-) SO2CH3	CF3	168
	Cl	(2-) SO2CH3	SCH3	169
	Cl	(2-) SO2CH3	SC2H5	170
	Cl	(2-) SO2CH3	SC3H7	171
	Cl	(2-) SO2CH3	SC3H7-i	172
	Cl	(2-) SO2CH3	173	174
	Cl	(2-) SO2CH3	175	176
	Cl	(2-) SO2CH3	177	178
	Cl	(2-) SO2CH3	179	180
	Cl	(2-) SO2CH3	181	182
	Cl	(2-) SO2CH3	SCH═C═CH2	183
	Cl	(2-) SO2CH3	SCH2CN	184
	Cl	(2-) SO2CH3	SCH2CH2CN	185
	Cl	(2-) SO2CH3	OCH3	186
	Cl	(2-) SO2CH3	OC2H5	187
	Cl	(2-) SO2CH3	OC3H7	188
	Cl	(2-) SO2CH3	OC3H7-i	189
	Cl	(2-) SO2CH3	OC4H9	190
	Cl	(2-) SO2CH3	OCH2CF3	191
	Cl	(2-) SO2CH3	192	193
	Cl	(2-) SO2CH3	OC6H5	194
	Cl	(2-) SO2CH3	H	195
	Cl	(2-) SO2CH3	CH3	196
	Cl	(2-) SO2CH3	C2H5	197
	Cl	(2-) SO2CH3	C3H7	198
	Cl	(2-) SO2CH3	C3H7-i	199
	Cl	(2-) SO2CH3	C4H9	200
	Cl	(2-) SO2CH3	C4H9-i	201
	Cl	(2-) SO2CH3	C4H9-s	202
	Cl	(2-) SO2CH3	C4H9-t	203
	Cl	(2-) SO2CH3	204	205
	Cl	(2-) SO2CH3	206	207
	Cl	(2-) SO2CH3	CH═CHCH3	208
	Cl	(2-) SO2CH3	209	210
	Cl	(2-) SO2CH3	211	212
	Cl	(2-) SO2CH3	213	214
	Cl	(2-) SO2CH3	N(CH3)2	215
	Cl	(2-) SO2CH3	216	217
	Cl	(2-) SO2CH3	Cl	218
	Cl	(2-) SO2CH3	Br	219
	Cl	(2-) Cl	CF3	N(CH3)2
	Cl	(2-) Cl	SCH3	N(CH3)2
	Cl	(2-) Cl	SC2H5	N(CH3)2
	Cl	(2-) Cl	SC3H7	N(CH3)2
	Cl	(2-) Cl	SC3H7-i	N(CH3)2
	Cl	(2-) Cl	220	N(CH3)2
	Cl	(2-) Cl	221	N(CH3)2
	Cl	(2-) Cl	222	N(CH3)2
	Cl	(2-) Cl	223	N(CH3)2
	Cl	(2-) Cl	224	N(CH3)2
	Cl	(2-) Cl	SCH═C═CH2	N(CH3)2
	Cl	(2-) Cl	SCH2CN	N(CH3)2
	Cl	(2-) Cl	SCH2CH2CN	N(CH3)2
	Cl	(2-) Cl	OCH3	N(CH3)2
	Cl	(2-) Cl	OC2H5	N(CH3)2
	Cl	(2-) Cl	OC3H7	N(CH3)2
	Cl	(2-) Cl	OC3H7-i	N(CH3)2
	Cl	(2-) Cl	OC4H9	N(CH3)2
	Cl	(2-) Cl	OCH2CF3	N(CH3)2
	Cl	(2-) Cl	225	N(CH3)2
	Cl	(2-) Cl	OC6H5	N(CH3)2
	Cl	(2-) Cl	H	N(CH3)2
	Cl	(2-) Cl	CH3	N(CH3)2
	Cl	(2-) Cl	C2H5	N(CH3)2
	Cl	(2-) Cl	C3H7	N(CH3)2
	Cl	(2-) Cl	C3H7-i	N(CH3)2
	Cl	(2-) Cl	C4H9	N(CH3)2
	Cl	(2-) Cl	C4H9-i	N(CH3)2
	Cl	(2-) Cl	C4H9-s	N(CH3)2
	Cl	(2-) Cl	C4H9-t	N(CH3)2
	Cl	(2-) Cl	226	N(CH3)2
	Cl	(2-) Cl	227	N(CH3)2
	Cl	(2-) Cl	CH═CHCH3	N(CH3)2
	Cl	(2-) Cl	228	N(CH3)2
	Cl	(2-) Cl	229	N(CH3)2
	Cl	(2-) Cl	230	N(CH3)2
	Cl	(2-) Cl	N(CH3)2	N(CH3)2
	Cl	(2-) Cl	231	N(CH3)2
	Cl	(2-) Cl	Cl	N(CH3)2
	Cl	(2-) Cl	Br	N(CH3)2
	SO2CH3	(2-) Cl	CF3	N(CH3)2
	SO2CH3	(2-) Cl	SCH3	N(CH3)2
	SO2CH3	(2-) Cl	SC2H5	N(CH3)2
	SO2CH3	(2-) Cl	SC3H7	N(CH3)2
	SO2CH3	(2-) Cl	SC3H7-i	N(CH3)2
	SO2CH3	(2-) Cl	232	N(CH3)2
	SO2CH3	(2-) Cl	233	N(CH3)2
	SO2CH3	(2-) Cl	234	N(CH3)2
	SO2CH3	(2-) Cl	235	N(CH3)2
	SO2CH3	(2-) Cl	236	N(CH3)2
	SO2CH3	(2-) Cl	SCH═C═CH2	N(CH3)2
	SO2CH3	(2-) Cl	SCH2CN	N(CH3)2
	SO2CH3	(2-) Cl	SCH2CH2CN	N(CH3)2
	SO2CH3	(2-) Cl	OCH3	N(CH3)2
	SO2CH3	(2-) Cl	OC2H5	N(CH3)2
	SO2CH3	(2-) Cl	OC3H7	N(CH3)2
	SO2CH3	(2-) Cl	OC3H7-i	N(CH3)2
	SO2CH3	(2-) Cl	OC4H9	N(CH3)2
	SO2CH3	(2-) Cl	OCH2CF3	N(CH3)2
	SO2CH3	(2-) Cl	237	N(CH3)2
	SO2CH3	(2-) Cl	OC6H5	N(CH3)2
	SO2CH3	(2-) Cl	H	N(CH3)2
	SO2CH3	(2-) Cl	CH3	N(CH3)2
	SO2CH3	(2-) Cl	C2H5	N(CH3)2
	SO2CH3	(2-) Cl	C3H7	N(CH3)2
	SO2CH3	(2-) Cl	C3H7-i	N(CH3)2
	SO2CH3	(2-) Cl	C4H9	N(CH3)2
	SO2CH3	(2-) Cl	C4H9-i	N(CH3)2
	SO2CH3	(2-) Cl	C4H9-s	N(CH3)2
	SO2CH3	(2-) Cl	C4H9-t	N(CH3)2
	SO2CH3	(2-) Cl	238	N(CH3)2
	SO2CH3	(2-) Cl	239	N(CH3)2
	SO2CH3	(2-) Cl	CH═CHCH3	N(CH3)2
	SO2CH3	(2-) Cl	240	N(CH3)2
	SO2CH3	(2-) Cl	241	N(CH3)2
	SO2CH3	(2-) Cl	242	N(CH3)2
	SO2CH3	(2-) Cl	N(CH3)2	N(CH3)2
	SO2CH3	(2-) Cl	243	N(CH3)2
	SO2CH3	(2-) Cl	Cl	N(CH3)2
	SO2CH3	(2-) Cl	Br	N(CH3)2
	Cl	(2-) SO2CH3	CF3	N(CH3)2
	Cl	(2-) SO2CH3	SCH3	N(CH3)2
	Cl	(2-) SO2CH3	SC2H5	N(CH3)2
	Cl	(2-) SO2CH3	SC3H7	N(CH3)2
	Cl	(2-) SO2CH3	SC3H7-i	N(CH3)2
	Cl	(2-) SO2CH3	244	N(CH3)2
	Cl	(2-) SO2CH3	245	N(CH3)2
	Cl	(2-) SO2CH3	246	N(CH3)2
	Cl	(2-) SO2CH3	247	N(CH3)2
	Cl	(2-) SO2CH3	248	N(CH3)2
	Cl	(2-) SO2CH3	SCH═C═CH2	N(CH3)2
	Cl	(2-) SO2CH3	SCH2CN	N(CH3)2
	Cl	(2-) SO2CH3	SCH2CH2CN	N(CH3)2
	Cl	(2-) SO2CH3	OCH3	N(CH3)2
	Cl	(2-) SO2CH3	OC2H5	N(CH3)2
	Cl	(2-) SO2CH3	OC3H7	N(CH3)2
	Cl	(2-) SO2CH3	OC3H7-i	N(CH3)2
	Cl	(2-) SO2CH3	OC4H9	N(CH3)2
	Cl	(2-) SO2CH3	OCH2CF3	N(CH3)2
	Cl	(2-) SO2CH3	249	N(CH3)2
	Cl	(2-) SO2CH3	OC6H5	N(CH3)2
	Cl	(2-) SO2CH3	H	N(CH3)2
	Cl	(2-) SO2CH3	CH3	N(CH3)2
	Cl	(2-) SO2CH3	C2H5	N(CH3)2
	Cl	(2-) SO2CH3	C3H7	N(CH3)2
	Cl	(2-) SO2CH3	C3H7-i	N(CH3)2
	Cl	(2-) SO2CH3	C4H9	N(CH3)2
	Cl	(2-) SO2CH3	C4H9-i	N(CH3)2
	Cl	(2-) SO2CH3	C4H9-s	N(CH3)2
	Cl	(2-) SO2CH3	C4H9-t	N(CH3)2
	Cl	(2-) SO2CH3	250	N(CH3)2
	Cl	(2-) SO2CH3	251	N(CH3)2
	Cl	(2-) SO2CH3	CH═CHCH3	N(CH3)2
	Cl	(2-) SO2CH3	252	N(CH3)2
	Cl	(2-) SO2CH3	253	N(CH3)2
	Cl	(2-) SO2CH3	254	N(CH3)2
	Cl	(2-) SO2CH3	N(CH3)2	N(CH3)2
	Cl	(2-) SO2CH3	255	N(CH3)2
	Cl	(2-) SO2CH3	Cl	N(CH3)2
	Cl	(2-) SO2CH3	Br	N(CH3)2
	Cl	(2-) Cl	CH3	OCH3
	Cl	(2-) Cl	C2H5	OCH3
	Cl	(2-) Cl	C3H7	OCH3
	Cl	(2-) Cl	SCH3	OCH3
	Cl	(2-) Cl	SC2H5	OCH3
	Cl	(2-) Cl	OCH3	OCH3
	Cl	(2-) Cl	OC2H5	OCH3
	Cl	(2-) Cl	CH3	OC2H5
	Cl	(2-) Cl	C2H5	OC2H5
	Cl	(2-) Cl	C3H7	OC2H5
	Cl	(2-) Cl	SCH3	OC2H5
	Cl	(2-) Cl	SC2H5	OC2H5
	Cl	(2-) Cl	OCH3	OC2H5
	Cl	(2-) Cl	OC2H5	OC2H5
	Cl	(2-) SO2CH3	CH3	OCH3
	Cl	(2-) SO2CH3	C2H5	OCH3
	Cl	(2-) SO2CH3	C3H7	OCH3
	Cl	(2-) SO2CH3	SCH3	OCH3
	Cl	(2-) SO2CH3	SC2H5	OCH3
	Cl	(2-) SO2CH3	OCH3	OCH3
	Cl	(2-) SO2CH3	OC2H5	OCH3
	Cl	(2-) SO2CH3	CH3	OC2H5
	Cl	(2-) SO2CH3	C2H5	OC2H5
	Cl	(2-) SO2CH3	C3H7	OC2H5
	Cl	(2-) SO2CH3	SCH3	OC2H5
	Cl	(2-) SO2CH3	SC2H5	OC2H5
	Cl	(2-) SO2CH3	OCH3	OC2H5
	Cl	(2-) SO2CH3	OC2H5	OC2H5
	SO2CH3	(2-) Cl	Cl	OCH3
	SO2CH3	(2-) Cl	Br	OCH3
	SO2CH3	(2-) Cl	CH3	OCH3
	SO2CH3	(2-) Cl	C2H5	OCH3
	SO2CH3	(2-) Cl	C3H7	OCH3
	SO2CH3	(2-) Cl	SCH3	OCH3
	SO2CH3	(2-) Cl	SC2H5	OCH3
	SO2CH3	(2-) Cl	OCH3	OC2H5
	SO2CH3	(2-) Cl	OC2H5	OC2H5
	SO2CH3	(2-) Cl	CH3	OC2H5
	SO2CH3	(2-) Cl	C2H5	OC2H5
	SO2CH3	(2-) Cl	C3H7	OC2H5
	SO2CH3	(2-) Cl	SCH3	OC2H5
	SO2CH3	(2-) Cl	SC2H5	OC2H5
	SO2CH3	(2-) Cl	OCH3	OC2H5
	CF3	(2-) Cl	Br	CH3
	CF3	(2-) Cl	SCH3	CH3
	CF3	(2-) Cl	OCH3	CH3
	CF3	(2-) Cl	N(CH3)2	CH3
	CF3	(2-) Cl	CF3	CH3
	CF3	(2-) NO2	Br	CH3
	CF3	(2-) NO2	SCH3	CH3
	CF3	(2-) NO2	OCH3	CH3
	CF3	(2-) NO2	N(CH3)2	CH3
	CF3	(2-) NO2	CF3	CH3
	CF3	(2-) CH3	Br	CH3
	CF3	(2-) CH3	SCH3	CH3
	CF3	(2-) CH3	OCH3	CH3
	CF3	(2-) CH3	N(CH3)2	CH3
	CF3	(2-) CH3	CF3	CH3
	CF3	(2-) OCH3	Br	CH3
	CF3	(2-) OCH3	SCH3	CH3
	CF3	(2-) OCH3	OCH3	CH3
	CF3	(2-) OCH3	N(CH3)2	CH3
	CF3	(2-) OCH3	CF3	CH3
	SO2CH3	(2-) NO2	Br	CH3
	SO2CH3	(2-) NO2	SCH3	CH3
	SO2CH3	(2-) NO2	OCH3	CH3
	SO2CH3	(2-) NO2	N(CH3)2	CH3
	SO2CH3	(2-) NO2	CF3	CH3
	SO2CH3	(2-) CF3	Br	CH3
	SO2CH3	(2-) CF3	SCH3	CH3
	SO2CH3	(2-) CF3	OCH3	CH3
	SO2CH3	(2-) CF3	N(CH3)2	CH3
	SO2CH3	(2-) CF3	CF3	CH3
	SO2CH3	(2-) SO2CH3	Br	CH3
	SO2CH3	(2-) SO2CH3	SCH3	CH3
	SO2CH3	(2-) SO2CH3	OCH3	CH3
	SO2CH3	(2-) SO2CH3	N(CH3)2	CH3
	SO2CH3	(2-) SO2CH3	CF3	CH3
	CN	(2-) Cl	Br	CH3
	CN	(2-) Cl	SCH3	CH3
	CN	(2-) Cl	OCH3	CH3
	CN	(2-) Cl	N(CH3)2	CH3
	CN	(2-) Cl	CF3	CH3
	CN	(2-) NO2	Br	CH3
	CN	(2-) NO2	SCH3	CH3
	CN	(2-) NO2	OCH3	CH3
	CN	(2-) NO2	N(CH3)2	CH3
	CN	(2-) NO2	CF3	CH3
	CN	(2-) CF3	Br	CH3
	CN	(2-) CF3	SCH3	CH3
	CN	(2-) CF3	OCH3	CH3
	CN	(2-) CF3	N(CH3)2	CH3
	CN	(2-) CF3	CF3	CH3
	CN	(2-) SO2CH3	Br	CH3
	CN	(2-) SO2CH3	SCH3	CH3
	CN	(2-) SO2CH3	OCH3	CH3
	CN	(2-) SO2CH3	N(CH3)2	CH3
	CN	(2-) SO2CH3	CF3	CH3
	Br	(2-) NO2	Br	CH3
	Br	(2-) NO2	SCH3	CH3
	Br	(2-) NO2	OCH3	CH3
	Br	(2-) NO2	N(CH3)2	CH3
	Br	(2-) NO2	CF3	CH3
	Br	(2-) CF3	Br	CH3
	Br	(2-) CF3	SCH3	CH3
	Br	(2-) CF3	OCH3	CH3
	Br	(2-) CF3	N(CH3)2	CH3
	Br	(2-) CF3	CF3	CH3
	Br	(2-) SO2CH3	Br	CH3
	Br	(2-) SO2CH3	SCH3	CH3
	Br	(2-) SO2CH3	OCH3	CH3
	Br	(2-) SO2CH3	N(CH3)2	CH3
	Br	(2-) SO2CH3	CF3	CH3
	Br	(2-) CH3	Br	CH3
	Br	(2-) CH3	SCH3	CH3
	Br	(2-) CH3	OCH3	CH3
	Br	(2-) CH3	N(CH3)2	CH3
	Br	(2-) CH3	CF3	CH3
	Cl	(2-) OCH3	CF3	CH3
	Cl	(2-) OCH3	SCH3	CH3
	Cl	(2-) OCH3	SC2H5	CH3
	Cl	(2-) OCH3	SC3H7	CH3
	Cl	(2-) OCH3	SC3H7-i	CH3
	Cl	(2-) OCH3	256	CH3
	Cl	(2-) OCH3	257	CH3
	Cl	(2-) OCH3	258	CH3
	Cl	(2-) OCH3	259	CH3
	Cl	(2-) OCH3	260	CH3
	Cl	(2-) OCH3	SCH═C═CH2	CH3
	Cl	(2-) OCH3	SCH2CN	CH3
	Cl	(2-) OCH3	SCH2CH2CN	CH3
	Cl	(2-) OCH3	OCH3	CH3
	Cl	(2-) OCH3	OC2H5	CH3
	Cl	(2-) OCH3	OC3H7	CH3
	Cl	(2-) OCH3	OC3H7-i	CH3
	Cl	(2-) OCH3	OC4H9	CH3
	Cl	(2-) OCH3	OCH2CF3	CH3
	Cl	(2-) OCH3	261	CH3
	Cl	(2-) OCH3	OC6H5	CH3
	Cl	(2-) OCH3	H	CH3
	Cl	(2-) OCH3	CH3	CH3
	Cl	(2-) OCH3	C2H5	CH3
	Cl	(2-) OCH3	C3H7	CH3
	Cl	(2-) OCH3	C3H7-i	CH3
	Cl	(2-) OCH3	C4H9	CH3
	Cl	(2-) OCH3	C4H9-i	CH3
	Cl	(2-) OCH3	C4H9-s	CH3
	Cl	(2-) OCH3	C4H9-t	CH3
	Cl	(2-) OCH3	262	CH3
	Cl	(2-) OCH3	263	CH3
	Cl	(2-) OCH3	CH═CHCH3	CH3
	Cl	(2-) OCH3	264	CH3
	Cl	(2-) OCH3	265	CH3
	Cl	(2-) OCH3	266	CH3
	Cl	(2-) OCH3	N(CH3)2	CH3
	Cl	(2-) OCH3	267	CH3
	Cl	(2-) OCH3	Cl	CH3
	Cl	(2-) OCH3	Br	CH3
	SO2CH3	(2-) OCH3	CF3	CH3
	SO2CH3	(2-) OCH3	SCH3	CH3
	SO2CH3	(2-) OCH3	SC2H5	CH3
	SO2CH3	(2-) OCH3	SC3H7	CH3
	SO2CH3	(2-) OCH3	SC3H7-i	CH3
	SO2CH3	(2-) OCH3	268	CH3
	SO2CH3	(2-) OCH3	269	CH3
	SO2CH3	(2-) OCH3	270	CH3
	SO2CH3	(2-) OCH3	271	CH3
	SO2CH3	(2-) OCH3	272	CH3
	SO2CH3	(2-) OCH3	SCH═C═CH2	CH3
	SO2CH3	(2-) OCH3	SCH2CN	CH3
	SO2CH3	(2-) OCH3	SCH2CH2CN	CH3
	SO2CH3	(2-) OCH3	OCH3	CH3
	SO2CH3	(2-) OCH3	OC2H5	CH3
	SO2CH3	(2-) OCH3	OC3H7	CH3
	SO2CH3	(2-) OCH3	OC3H7-i	CH3
	SO2CH3	(2-) OCH3	OC4H9	CH3
	SO2CH3	(2-) OCH3	OCH2CF3	CH3
	SO2CH3	(2-) OCH3	273	CH3
	SO2CH3	(2-) OCH3	OC6H5	CH3
	SO2CH3	(2-) OCH3	H	CH3
	SO2CH3	(2-) OCH3	CH3	CH3
	SO2CH3	(2-) OCH3	C2H5	CH3
	SO2CH3	(2-) OCH3	C3H7	CH3
	SO2CH3	(2-) OCH3	C3H7-i	CH3
	SO2CH3	(2-) OCH3	C4H9	CH3
	SO2CH3	(2-) OCH3	C4H9-i	CH3
	SO2CH3	(2-) OCH3	C4H9-s	CH3
	SO2CH3	(2-) OCH3	C4H9-t	CH3
	SO2CH3	(2-) OCH3	274	CH3
	SO2CH3	(2-) OCH3	275	CH3
	SO2CH3	(2-) OCH3	CH═CHCH3	CH3
	SO2CH3	(2-) OCH3	276	CH3
	SO2CH3	(2-) OCH3	277	CH3
	SO2CH3	(2-) OCH3	278	CH3
	SO2CH3	(2-) OCH3	N(CH3)2	CH3
	SO2CH3	(2-) OCH3	279	CH3
	SO2CH3	(2-) OCH3	Cl	CH3
	SO2CH3	(2-) OCH3	Br	CH3
	Cl	(2-) OCH3	CF3	280
	Cl	(2-) OCH3	SCH3	281
	Cl	(2-) OCH3	SC2H5	282
	Cl	(2-) OCH3	SC3H7	283
	Cl	(2-) OCH3	SC3H7-i	284
	Cl	(2-) OCH3	285	286
	Cl	(2-) OCH3	287	288
	Cl	(2-) OCH3	289	290
	Cl	(2-) OCH3	291	292
	Cl	(2-) OCH3	293	294
	Cl	(2-) OCH3	SCH═C═CH2	295
	Cl	(2-) OCH3	SCH2CN	296
	Cl	(2-) OCH3	SCH2CH2CN	297
	Cl	(2-) OCH3	OCH3	298
	Cl	(2-) OCH3	OC2H5	299
	Cl	(2-) OCH3	OC3H7	300
	Cl	(2-) OCH3	OC3H7-i	301
	Cl	(2-) OCH3	OC4H9	302
	Cl	(2-) OCH3	OCH2CF3	303
	Cl	(2-) OCH3	304	305
	Cl	(2-) OCH3	OC6H5	306
	Cl	(2-) OCH3	H	307
	Cl	(2-) OCH3	CH3	308
	Cl	(2-) OCH3	C2H5	309
	Cl	(2-) OCH3	C3H7	310
	Cl	(2-) OCH3	C3H7-i	311
	Cl	(2-) OCH3	C4H9	312
	Cl	(2-) OCH3	C4H9-i	313
	Cl	(2-) OCH3	C4H9-s	314
	Cl	(2-) OCH3	C4H9-t	315
	Cl	(2-) OCH3	316	317
	Cl	(2-) OCH3	318	319
	Cl	(2-) OCH3	CH═CHCH3	320
	Cl	(2-) OCH3	321	322
	Cl	(2-) OCH3	323	324
	Cl	(2-) OCH3	325	326
	Cl	(2-) OCH3	N(CH3)2	327
	Cl	(2-) OCH3	328	329
	Cl	(2-) OCH3	Cl	330
	Cl	(2-) OCH3	Br	331
	SO2CH3	(2-) OCH3	CF3	332
	SO2CH3	(2-) OCH3	SCH3	333
	SO2CH3	(2-) OCH3	SC2H5	334
	SO2CH3	(2-) OCH3	SC3H7	335
	SO2CH3	(2-) OCH3	SC3H7-i	336
	SO2CH3	(2-) OCH3	337	338
	SO2CH3	(2-) OCH3	339	340
	SO2CH3	(2-) OCH3	341	342
	SO2CH3	(2-) OCH3	343	344
	SO2CH3	(2-) OCH3	345	346
	SO2CH3	(2-) OCH3	SCH═C═CH2	347
	SO2CH3	(2-) OCH3	SCH2CN	348
	SO2CH3	(2-) OCH3	SCH2CH2CN	349
	SO2CH3	(2-) OCH3	OCH3	350
	SO2CH3	(2-) OCH3	OC2H5	351
	SO2CH3	(2-) OCH3	OC3H7	352
	SO2CH3	(2-) OCH3	OC3H7-i	353
	SO2CH3	(2-) OCH3	OC4H9	354
	SO2CH3	(2-) OCH3	OCH2CF3	355
	SO2CH3	(2-) OCH3	356	357
	SO2CH3	(2-) OCH3	OC6H5	358
	SO2CH3	(2-) OCH3	H	359
	SO2CH3	(2-) OCH3	CH3	360
	SO2CH3	(2-) OCH3	C2H5	361
	SO2CH3	(2-) OCH3	C3H7	362
	SO2CH3	(2-) OCH3	C3H7-i	363
	SO2CH3	(2-) OCH3	C4H9	364
	SO2CH3	(2-) OCH3	C4H9-i	365
	SO2CH3	(2-) OCH3	C4H9-s	366
	SO2CH3	(2-) OCH3	C4H9-t	367
	SO2CH3	(2-) OCH3	368	369
	SO2CH3	(2-) OCH3	370	371
	SO2CH3	(2-) OCH3	CH═CHCH3	372
	SO2CH3	(2-) OCH3	373	374
	SO2CH3	(2-) OCH3	375	376
	SO2CH3	(2-) OCH3	377	378
	SO2CH3	(2-) OCH3	N(CH3)2	379
	SO2CH3	(2-) OCH3	380	381
	SO2CH3	(2-) OCH3	Cl	382
	SO2CH3	(2-) OCH3	Br	383
	Cl	(2-) OCH3	CF3	N(CH3)2
	Cl	(2-) OCH3	SCH3	N(CH3)2
	Cl	(2-) OCH3	SC2H5	N(CH3)2
	Cl	(2-) OCH3	SC3H7	N(CH3)2
	Cl	(2-) OCH3	SC3H7-i	N(CH3)2
	Cl	(2-) OCH3	384	N(CH3)2
	Cl	(2-) OCH3	385	N(CH3)2
	Cl	(2-) OCH3	386	N(CH3)2
	Cl	(2-) OCH3	387	N(CH3)2
	Cl	(2-) OCH3	388	N(CH3)2
	Cl	(2-) OCH3	SCH═C═CH2	N(CH3)2
	Cl	(2-) OCH3	SCH2CN	N(CH3)2
	Cl	(2-) OCH3	SCH2CH2CN	N(CH3)2
	Cl	(2-) OCH3	OCH3	N(CH3)2
	Cl	(2-) OCH3	OC2H5	N(CH3)2
	Cl	(2-) OCH3	OC3H7	N(CH3)2
	Cl	(2-) OCH3	OC3H7-i	N(CH3)2
	Cl	(2-) OCH3	OC4H9	N(CH3)2
	Cl	(2-) OCH3	OCH2CF3	N(CH3)2
	Cl	(2-) OCH3	389	N(CH3)2
	Cl	(2-) OCH3	OC6H5	N(CH3)2
	Cl	(2-) OCH3	H	N(CH3)2
	Cl	(2-) OCH3	CH3	N(CH3)2
	Cl	(2-) OCH3	C2H5	N(CH3)2
	Cl	(2-) OCH3	C3H7	N(CH3)2
	Cl	(2-) OCH3	C3H7-i	N(CH3)2
	Cl	(2-) OCH3	C4H9	N(CH3)2
	Cl	(2-) OCH3	C4H9-i	N(CH3)2
	Cl	(2-) OCH3	C4H9-s	N(CH3)2
	Cl	(2-) OCH3	C4H9-t	N(CH3)2
	Cl	(2-) OCH3	390	N(CH3)2
	Cl	(2-) OCH3	391	N(CH3)2
	Cl	(2-) OCH3	CH═CHCH3	N(CH3)2
	Cl	(2-) OCH3	392	N(CH3)2
	Cl	(2-) OCH3	393	N(CH3)2
	Cl	(2-) OCH3	394	N(CH3)2
	Cl	(2-) OCH3	N(CH3)2	N(CH3)2
	Cl	(2-) OCH3	395	N(CH3)2
	Cl	(2-) OCH3	Cl	N(CH3)2
	Cl	(2-) OCH3	Br	N(CH3)2
	SO2CH3	(2-) OCH3	CF3	N(CH3)2
	SO2CH3	(2-) OCH3	SCH3	N(CH3)2
	SO2CH3	(2-) OCH3	SC2H5	N(CH3)2
	SO2CH3	(2-) OCH3	SC3H7	N(CH3)2
	SO2CH3	(2-) OCH3	SC3H7-i	N(CH3)2
	SO2CH3	(2-) OCH3	396	N(CH3)2
	SO2CH3	(2-) OCH3	397	N(CH3)2
	SO2CH3	(2-) OCH3	398	N(CH3)2
	SO2CH3	(2-) OCH3	399	N(CH3)2
	SO2CH3	(2-) OCH3	400	N(CH3)2
	SO2CH3	(2-) OCH3	SCH═C═CH2	N(CH3)2
	SO2CH3	(2-) OCH3	SCH2CN	N(CH3)2
	SO2CH3	(2-) OCH3	SCH2CH2CN	N(CH3)2
	SO2CH3	(2-) OCH3	OCH3	N(CH3)2
	SO2CH3	(2-) OCH3	OC2H5	N(CH3)2
	SO2CH3	(2-) OCH3	OC3H7	N(CH3)2
	SO2CH3	(2-) OCH3	OC3H7-i	N(CH3)2
	SO2CH3	(2-) OCH3	OC4H9	N(CH3)2
	SO2CH3	(2-) OCH3	OCH2CF3	N(CH3)2
	SO2CH3	(2-) OCH3	401	N(CH3)2
	SO2CH3	(2-) OCH3	OC6H5	N(CH3)2
	SO2CH3	(2-) OCH3	H	N(CH3)2
	SO2CH3	(2-) OCH3	CH3	N(CH3)2
	SO2CH3	(2-) OCH3	C2H5	N(CH3)2
	SO2CH3	(2-) OCH3	C3H7	N(CH3)2
	SO2CH3	(2-) OCH3	C3H7-i	N(CH3)2
	SO2CH3	(2-) OCH3	C4H9	N(CH3)2
	SO2CH3	(2-) OCH3	C4H9-i	N(CH3)2
	SO2CH3	(2-) OCH3	C4H9-s	N(CH3)2
	SO2CH3	(2-) OCH3	C4H9-t	N(CH3)2
	SO2CH3	(2-) OCH3	402	N(CH3)2
	SO2CH3	(2-) OCH3	403	N(CH3)2
	SO2CH3	(2-) OCH3	CH═CHCH3	N(CH3)2
	SO2CH3	(2-) OCH3	404	N(CH3)2
	SO2CH3	(2-) OCH3	405	N(CH3)2
	SO2CH3	(2-) OCH3	406	N(CH3)2
	SO2CH3	(2-) OCH3	N(CH3)2	N(CH3)2
	SO2CH3	(2-) OCH3	407	N(CH3)2
	SO2CH3	(2-) OCH3	Cl	N(CH3)2
	SO2CH3	(2-) OCH3	Br	N(CH3)2
	Cl	(2-) OCH3	CH3	OCH3
	Cl	(2-) OCH3	C2H5	OCH3
	Cl	(2-) OCH3	C3H7	OCH3
	Cl	(2-) OCH3	SCH3	OCH3
	Cl	(2-) OCH3	SC2H5	OCH3
	Cl	(2-) OCH3	OCH3	OCH3
	Cl	(2-) OCH3	OC2H5	OCH3
	Cl	(2-) OCH3	CH3	OC2H5
	Cl	(2-) OCH3	C2H5	OC2H5
	Cl	(2-) OCH3	C3H7	OC2H5
	Cl	(2-) OCH3	SCH3	OC2H5
	Cl	(2-) OCH3	SC2H5	OC2H5
	Cl	(2-) OCH3	OCH3	OC2H5
	Cl	(2-) OCH3	OC2H5	OC2H5
	SO2CH3	(2-) OCH3	Cl	OCH3
	SO2CH3	(2-) OCH3	Br	OCH3
	SO2CH3	(2-) OCH3	CH3	OCH3
	SO2CH3	(2-) OCH3	C2H5	OCH3
	SO2CH3	(2-) OCH3	C3H7	OCH3
	SO2CH3	(2-) OCH3	SCH3	OCH3
	SO2CH3	(2-) OCH3	SC2H5	OCH3
	SO2CH3	(2-) OCH3	OCH3	OC2H5
	SO2CH3	(2-) OCH3	OC2H5	OC2H5
	SO2CH3	(2-) OCH3	CH3	OC2H5
	SO2CH3	(2-) OCH3	C2H5	OC2H5
	SO2CH3	(2-) OCH3	C3H7	OC2H5
	SO2CH3	(2-) OCH3	SCH3	OC2H5
	SO2CH3	(2-) OCH3	SC2H5	OC2H5
	SO2CH3	(2-) OCH3	OCH3	OC2H5
	Cl	(2-) F	OCH3	CH3
	Cl	(2-) F	OCH3	C2H5
	Cl	(2-) F	C2H5	OCH3
	Cl	(2-) F	C2H5	C2H5
	Cl	(2-) F	OC2H5	CH3
	Cl	(2-) F	OC2H5	C2H5
	Cl	(2-) F	OCH3	408
	Cl	(2-) F	OC2H5	409
	Cl	(2-) F	SCH3	CH3
	Cl	(2-) F	SCH3	410
	Cl	(2-) F	CH3	CH3
	Cl	(2-) F	CH3	411

[0085] Group 7 412

[0086] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6.

[0087] Group 8 413

[0088] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6.

[0089] Group 9 414

[0090] Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6.

[0091] Group 10 415

[0092] Here, R3, R4, R and R6 each have, for example, the meanings given above in Group 6.

[0093] The novel substituted benzoylcyclohexenones of the formula (I) have strong and selective herbicidal activity.

[0094] The novel substituted benzoylcyclohexenones of the formula (I) are obtained when substituted cyclohexanediones of the formula (II) 416

[0095] in which

[0096] A, R1, R2, R3, R4 and Z are as defined above,

[0097] are reacted with a halogenating agent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and the halogenocyclohexenones obtained in this way (in the first reaction step), of the formula (III) 417

[0098] in which

[0099] A, R1, R2, R3, R4 and Z are as defined above,

[0100] X represents halogen, preferably represents fluorine or chlorine, particularly preferably represents chlorine,

[0101] after intermediate isolation or without intermediate isolation (“in situ”)

[0102] are reacted in a second reaction step with mercapto compounds of the formula (IV)

HS—Y  (IV)

[0103] in which

[0104] Y is as defined above,

[0105] if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

[0106] and, if appropriate, the compounds of the formula (I) obtained in this manner are subsequently subjected in a customary manner, within the scope of the definition of the substituents, to electrophilic or nucleophilic substitution reactions or oxidation or reduction reactions, or the compounds of the formula (I) are converted in a customary manner into salts.

[0107] Using, for example 2-[4-chloro-2-[(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-methyl]-benzoyl]-cyclohexane-1,3-dione and phosgene and then thiophenol as starting materials, the course of the reaction in the process according to the invention can be illustrated by the following equation 418

[0108] The formula (II) provides a general definition of the substituted benzoylcyclohexanediones to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I). In the general formula (II), A, R1, R2, R3, R4 and Z each preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred, very particularly preferred or most preferred for A, R1, R2, R3, R4 and Z.

[0109] The starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. WO-A-00/05221).

[0110] The first reaction step of the process according to the invention for preparing the compounds of the general of the general formula (I) is carried out using a halogenating agent. The halogenating agent used can be a customary halogenating agent suitable for converting enols into the corresponding halogenoalkenes. Here, halogen preferably represents fluorine, chlorine or bromine, in particular chlorine, i.e. preference is given to using chlorinating agents or brominating agents. These include, preferably, phosgene, oxalyl chloride, oxalyl bromide, phosphorus(III) chloride, phosphorus(III) bromide, phosphoryl chloride, thionyl chloride and thionyl bromide.

[0111] The first reaction step of the process according to the invention for preparing the compounds of the general formula (I) is preferably carried out using a reaction auxiliary. Suitable reaction auxiliaries are the reaction auxiliaries customarily used for halogenating reactions. These preferably include acetonitrile, N,N-dimethylformamide, N,N-diethyl-formamide, N,N-dipropyl-formamide and N,N-dibutylformamide, and also N-methyl-pyrrolidone.

[0112] The formula (IV) provides a general definition of the mercapto compounds further to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I). In the general formula (IV), Y preferably has in particular that meaning which has already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for Y.

[0113] The starting materials of the general formula (IV) are known organic chemicals for synthesis.

[0114] The second reaction step of the process according to the invention for preparing compounds of the general formula (I) is preferably carried out using a reaction auxiliary. Suitable reaction auxiliaries are, in general, the customary inorganic or organic bases or acid acceptors. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo[2.2.2]-octane (DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8 diazabicyclo[5.4.0]-undec-7-ene (DBU).

[0115] The first and the second step of the process according to the invention for preparing the compounds of the general formula (I) are preferably carried out using diluents. Suitable diluents are especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate; sulphoxides, such as dimethyl sulphoxide; alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether or ethylene glycol monoethyl ether.

[0116] When carrying out the first and the second step of the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the steps are carried out at temperatures between −20° C. and +150° C., preferably between 0° C. and 120° C.

[0117] The two steps of the process according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure—in general between 0.1 bar and 10 bar.

[0118] For carrying out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components. The reaction is generally carried out in a suitable diluent in the presence of a suitable reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. Work-up is carried out by customary methods (cf. the Preparation Examples).

[0119] The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. Weeds in the broadest sense are understood to mean all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

[0120] The active compounds according to the invention can be used, for example, in connection with the following plants:

[0121] Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

[0122] Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

[0123] Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

[0124] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saecharum, Secale, Sorghum, Triticale, Triticum, Zea.

[0125] However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.

[0126] The active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and areas with and without tree plantings. Similarly, the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.

[0127] The compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil or on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.

[0128] At certain concentrations or application rates, the active compounds according to the invention can also be employed for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of other active compounds.

[0129] According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

[0130] The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating.

[0131] The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic substances impregnated with active compound, and microencapsulations in polymeric substances.

[0132] These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is to say liquid solvents and/or solid carriers, optionally with the use of surfactants, that is to say emulsifiers and/or dispersants and/or foam formers.

[0133] If the extender used is water, it is also possible to use, for example, organic solvents as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.

[0134] Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks, such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic meals, and granules of organic material, such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates and protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.

[0135] Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils.

[0136] It is possible to use colorants, such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0137] The formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

[0138] For controlling weeds, the active compounds according to the invention, as such or in their formulations, can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants (“safeners”), finished formulations or tank mixes being possible. Also possible are mixtures with weed-killers comprising one or more known herbicides and a safener.

[0139] Possible components for the mixtures are known herbicides, for example

[0140] acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfuron, chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phemnedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazol, prometryn, propachlor, propanil, propaquizafop, propisochlor, procarbazone (-sodium), propyzamide, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.

[0141] A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.

[0142] The active compounds can be used as such, in the form of their formulations or in the use forms, prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.

[0143] The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.

[0144] The amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

[0145] The preparation and the use of the active compounds according to the invention is illustrated by the examples below.

PREPARATION EXAMPLES

Example 1

[0146] 419

[0147] A mixture of 1.3 g (3 mmol) of 2-[2,4-dichloro-3-[(3-methyl-2-oxo-tetrahydro-1(2H)-pyrimidinyl)-methyl]-benzoyl]-cyclohexane-1,3-dione, 1.0 g (7.5 mmol) of oxalyl chloride, 2 drops of N,N-dimethyl-formamide and 30 ml of methylene chloride is heated under reflux for 30 minutes and then concentrated under water pump vacuum. The residue is taken up in 50 ml of tetrahydrofuran and admixed with 0.33 g (3 mmol) of thiophenol. With ice-cooling, 0.50 g (4.5 mmol) of triethylamine is then added dropwise. The ice-cooling is removed, and the mixture is then stirred at room temperature for 2 hours and subsequently concentrated under water pump vacuum. The residue is taken up in methylene chloride, washed once each with 1N hydrochloric acid, water and saturated aqueous sodium chloride solution, dried with sodium sulphate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with diethyl ether and the resulting crystalline product is isolated by filtration with suction.

[0148] This gives 0.91 g (61% of theory) of 1-[2,6-dichloro-3-[(6-oxo-2-phenylthio-1-cyclohexen-1-yl)-carbonyl]-benzyl]-3-methyl-tetrahydro-2(1H)-pyrimidinone of melting point 140° C.

[0149] Analogously to Example 1 and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula (I)—or those of the general formula (ID)—listed in Table 1 below.

TABLE 1
Examples of compounds of the formula (ID)
	(ID)
420
Ex.		(position)	(position)	(position)		Physical
No.	n	R3	R4	—A-Z	Y	data
2	0	(2)	(4)	(3)	C6H5	m.p.: 169° C.
		Cl	Cl	421		logP = 3.02a)
3	0	(2)	(4)	(3)	C6H5	m.p.: 149° C.
		Cl	Cl	422		logP = 3.30a)
4	0	(2)	(4)	(3)	C6H5	m.p.: 159° C.
		Cl	Cl	423		logP = 3.29a)
5	0	(2)	(4)	(3)	C6H5	m.p.: 163° C.
		Cl	Cl	424		logP = 3.50a)
6	0	(2)	(4)	(3)	C6H5	m.p.: 195° C.
		Cl	SO2CH3	425		logP = 2.84a)
7	0	(2)	(4)	(3)	C6H5	m.p.: 234° C.
		Cl	SO2CH3	426		logP = 2.67a)
8	0	(2)	(4)	(3)	C6H5	m.p.: 203° C.
		Cl	SO2CH3	427		logP = 2.56a)
9	0	(2)	(4)	(3)	C6H5	m.p.: 184° C.
		Cl	SO2CH3	428		logP = 2.79a)
10	0	(2)	(4)	(3)	C6H5	m.p.: 228° C.
		Cl	SO2CH3	429		logP = 3.13a)
11	0	(2)	(4)	(3)	C6H5	m.p.: 176° C.
		Cl	Cl	430		logP = 3.06a)
12	0	(2)	(4)	(3)	C6H5	m.p.: 145° C.
		Cl	Cl	431		logP = 3.69a)
13	0	(2)	(4)	(3)	C6H5	m.p.: 207° C.
		Cl	Cl	432		logP = 3.10a)
14	2	(2)	(4)	(3)	C6H5	m.p.: 180° C.
		Cl	Cl	433		logP = 2.62a)
15	1	(2)	(4)	(3)	C6H5
		Cl	Cl	434
16	0	(4)	—	(2)	C6H5	logP = 3.58a)
		CF3		435
17	0	(4)	—	(2)	CH3	logP = 2.63a)
		CF3		436
18	0	(4)	—	(2)	C6H5	logP = 3.30a)
		CF3		437
19	0	(4)	—	(2)	CH3	logP = 2.41a)
		CF3		438
20	0	(4)	—	(2)	C6H5	logP = 3.25a)
		CF3		439
21	0	(2)	(4)	(3)	C6H5
		Cl	Cl	440
22	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	441
23	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	442
24	0	(2)	(4)	(3)	C6H5
		Cl	Cl	443
25	0	(2)	(4)	(3)	C6H5
		Cl	Cl	444
26	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	445
27	0	(2)	(4)	(3)	C6H5
		Cl	Cl	446
28	0	(2)	(4)	(3)	C6H5
		Cl	Cl	447
29	0	(2)	(4)	(3)	C6H5
		Cl	Cl	448
30	0	(2)	(4)	(3)	C6H5
		Cl	Cl	449
31	0	(2)	(4)	(3)	C6H5
		Cl	Cl	450
32	0	(2)	(4)	(3)	C6H5
		Cl	Cl	451
33	0	(2)	(4)	(3)	C6H5
		Cl	Cl	452
34	0	(2)	(4)	(3)	C6H5
		Cl	Cl	453
35	0	(2)	(4)	(3)	C6H5
		Cl	Cl	454
36	0	(2)	(4)	(3)	C6H5
		Cl	Cl	455
37	0	(2)	(4)	(3)	C6H5
		Cl	Cl	456
38	0	(2)	(4)	(3)	C6H5
		Cl	Cl	457
39	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	458
40	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	459
41	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	460
42	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	461
43	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	462
44	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	463
45	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	464
46	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	465
47	0	(2)	(4)	(3)	C6H5
		Cl	CF3	466
48	0	(2)	(4)	(3)	C6H5
		Cl	CF3	467
49	0	(2)	(4)	(3)	C6H5
		Cl	CF3	468
50	0	(2)	(4)	(3)	C6H5
		Cl	CF3	469
51	0	(2)	(4)	(3)	C6H5
		Cl	CF3	470
52	0	(2)	—	(4)	C6H5
		Cl		471
53	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	472
54	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	473
55	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	474
56	0	(2)	(4)	(3)	C6H5	m.p.: 85° C.
		Cl	SO2CH3	475
57	0	(2)	(4)	(3)	C6H5	m.p.: 226° C.
		Cl	SO2CH3	476
58	0	(2)	—	(4)	C6H5	m.p.: 183° C.
		Cl		477
59	0	(2)	(4)	(3)	C6H5	m.p.: 159° C.
		Cl	SO2CH3	478
60	0	(2)	—	(4)	C6H5	m.p.: 77° C.
		NO2		479
61	0	(4)	—	(2)	C6H5	m.p.: 167° C.
		CF3		480
62	0	(2)	(4)	(3)	C2H5	nD20 = 1.6122
		Cl	Cl	481
63	0	(2)	(4)	(3)	CH3	nD20 = 1.6018
		Cl	Cl	482
64	0	(2)	(4)	(3)	C6H5	m.p.: 116° C.
		Cl	SO2CH3	483
65	0	(2)	—	(4)	C6H5	m.p.: 88° C.
		Cl		484
66	0	(2)	—	(4)	C6H5	m.p.: 59° C.
		Cl		485
67	0	(2)	(4)	(3)	CH3	m.p.: 82° C.
		Cl	SCH3	486
68	0	(2)	(4)	(3)	C2H5	m.p.: 64° C.
		Cl	SC2H5	487
69	0	(2)	(4)	(3)	CH3	m.p.: 100° C.
		Cl	SO2CH3	488
70	0	(2)	(4)	(3)	489	m.p.: 96° C.
		Cl	SO2CH3	490
71	0	(4)	—	(2)	C6H5
		F		491
72	0	(4)	—	(2)	C6H5
		Cl		492
73	0	(4)	—	(2)	C6H5
		Br		493
74	0	(4)	—	(2)	C6H5
		I		494
75	0	(4)	—	(2)	C6H5
		CN		495
76	0	(4)	—	(2)	C6H5
		CF3		496
77	0	(4)	—	(2)	C6H5
		CF3		497
78	0	(2)	(4)	(3)	C6H5
		Cl	Cl	498
79	0	(2)	(4)	(3)	C6H5
		Cl	Cl	499
80	0	(2)	(4)	(3)	C6H5
		Cl	Cl	500
81	0	(2)	(4)	(3)	CH3
		Cl	Cl	501
82	0	(2)	(4)	(3)	CH3
		Cl	Cl	502
83	0	(2)	(4)	(3)	CH3
		Cl	Cl	503
84	0	(2)	(4)	(3)	C2H5
		Cl	Cl	504
85	0	(2)	(4)	(3)	C2H5
		Cl	Cl	505
86	0	(2)	(4)	(3)	C2H5
		Cl	Cl	506
87	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	507
88	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	508
89	0	(2)	(4)	(3)	C6H5
		Cl	SO2CH3	509
90	0	(2)	(4)	(3)	CH3
		Cl	SO2CH3	510
91	0	(2)	(4)	(3)	CH3
		Cl	SO2CH3	511
92	0	(2)	(4)	(3)	CH3
		Cl	SO2CH3	512
93	0	(2)	(4)	(3)	C2H5
		Cl	SO2CH3	513
94	0	(2)	(4)	(3)	C2H5
		Cl	SO2CH3	514
95	0	(2)	(4)	(3)	C2H5
		Cl	SO2CH3	515
96	0	(2)	(4)	(3)	C6H5	m.p.: 94° C.
		Br	Br	516
97	0	(2)	(4)	(3)	C6H5
		Br	Br	517
98	0	(2)	(4)	(3)	C6H5	m.p.: 86° C.
		Br	Br	518
99	0	(2)	(4)	(3)	CH3
		Br	Br	519
100	0	(2)	(4)	(3)	C2H5
		Br	Br	520
101	0	(2)	(4)	(3)	C6H5
		CH3	SO2CH3	521
102	0	(2)	(4)	(3)	C6H5
		CH3	SO2CH3	522
103	0	(2)	(4)	(3)	C6H5
		CH3	SO2CH3	523
104	0	(2)	(4)	(3)	CH3
		CH3	SO2CH3	524
105	0	(2)	(4)	(3)	C2H5
		CH3	SO2CH3	525
106	0	(2)	(4)	(3)	C6H5
		CH3	SO2CH3	526
107	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	527
108	0	(2)	(4)	(3)	C6H5
		OCH3	Cl	528
109	0	(2)	(4)	(3)	CH3
		OCH3	Cl	529
110	0	(2)	(4)	(3)	C2H5
		OCH3	Cl	530
111	0	(2)	—	(4)	C6H5
		Br		531
112	0	(2)	—	(4)	C6H5
		I		532
113	0	(2)	—	(4)	C6H5
		CF3		533
114	0	(2)	—	(4)	C6H5
		CN		534
115	0	(2)	—	(4)	C6H5
		NO2		535
116	0	(2)	—	(4)	C6H5
		NO2		536
117	0	(2)	—	(4)	C6H5
		NO2		537
118	0	(2)	—	(4)	CH3
		NO2		538
119	0	(2)	—	(4)	C2H5
		NO2		539
120	0	(2)	(4)	(3)	C6H5	m.p.: 154° C.
		Cl	Cl	540		logP = 4.02a)
121	0	(2)	(4)	(3)	C6H5	m.p.: 156° C.
		Cl	Cl	541		logP = 3.98a)
122	0	(2)	(4)	(3)	C6H5	logP = 3.11a)
		Cl	SO2CH3	542

[0150] The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43° C.

[0151] (a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding data are labelled a) in Table 1.

[0152] (b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile—corresponding data are labelled b) in Table 1.

[0153] Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms), with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

[0154] The lambda max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm.

TABLE 2
Further examples of the compounds of the formula (I)
	(I)
543
Ex		(position)	(position)	(position)	(position)		Physical
No.	n	R1, R2	R3	R4	—A-Z	Y	data
123	0	(4) CH3,	(2)	(4)	(3)	C6H5	m.p.:
		(4) CH3	Cl	Cl	544		77° C.
124	0	(5) CH3,	(2)	(4)	(3)	C6H5	m.p.:
		(5) CH3	Cl	Cl	545		85° C.
125	0	(4) CH3,	(2)	(4)	(3)	C6H5	m.p.:
		(4) CH3	Cl	SO2CH3	546		99° C.
126	0	(5) CH3,	(2)	(4)	(3)	C6H5	m.p.:
		(5) CH3	Cl	SO2CH3	547		104° C.
127	0	(3)	(2)	(4)	(3)	C6H5	m.p.:
		—CH2CH2—(5)	Cl	Cl	548		84° C.
128	0	(3)	(4)	—	(2)	C6H5	m.p.:
		—CH2CH2—(5)	Br		549		186° C.
129	0	(3)	(4)	—	(2)	C6H5	m.p.:
		—CH2CH2—(5)	CF3		550		197° C.
130	0	(3)	(2)	—	(4)	C6H5	m.p.:
		—CH2CH2—(5)	NO2		551		84° C.
131	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	Cl	552
132	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	Cl	553
133	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	Cl	554
134	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	SO2CH3	555
135	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	SO2CH3	556
136	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Cl	SO2CH3	557
137	0	(3)	(2)	(4)	(3)	CH3
		—CH2CH2—(5)	Cl	SO2CH3	558
138	0	(3)	(2)	(4)	(3)	C2H5
		—CH2CH2—(5)	Cl	SO2CH3	559
139	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Br	Br	560
140	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	Br	Br	561
141	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	CH3	SO2CH3	562
142	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	CH3	SO2CH3	563
143	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	OCH3	Cl	564
144	0	(3)	(2)	(4)	(3)	C6H5
		—CH2CH2—(5)	OCH3	Cl	565

USE EXAMPLES

Example A

[0155] Pre-Emergence Test

Solvent    5 parts by weight of acetone
Emulsifier 1 part by weight of alkylaryl polyglycol ether

[0156] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

[0157] Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of active compound in the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 litres of water per hectare.

[0158] After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control. The figures denote:

[0159] 0%=no effect (like untreated control)

[0160] 100%=total destruction

[0161] In this test, for example, the compound of the Preparation Example 16 exhibits strong activity against weeds, and is tolerated well by some crop plants, such as, for example, maize.

Example B

[0162] Post-Emergence Test

Solvent    5 parts by weight of acetone
Emulsifier 1 part by weight of alkylaryl polyglycol ether

[0163] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

[0164] Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 l of water/ha.

[0165] After three weeks, the degree of damage to the plants is rated in % damage in comparison to the development of the untreated control.

[0166] The figures denote:

[0167] 0%=no effect (like untreated control)

[0168] 100%=total destruction

[0169] In this test, for example, the compounds of Preparation Examples 1, 2, 5, 16, 17, 18, 19 and 20 exhibit strong activity against weeds, and they are tolerated well by some crop plants, such as, for example, maize and wheat.

Claims

1. Substituted benzoylcyclohexenones of the formula (I),

2. Compounds according to claim 1, characterized in that n represents the number 0 or 2, A represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms, R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms, R2 represents hydrogen or optionally cyano-, halogen-, C1-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms, or together with R1 represents alkanediyl (alkylene) having 1 to 5 carbon atoms, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups, R4 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups, Y represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl having 1 to 6 carbon atoms, represents in each case optionally cyano-, halogen-, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, or represents in each case optionally nitro-, amino-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, halogen-, C1-C4-alkyl-, C1-C4-halogenoalkyl-, C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio, C1-C4-halogenoalkylthio-, C1-C4-alkylsulphinyl-, C1-C4-halogenoalkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl-carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino-, C1-C4-alkyl-sulphonyl-amino-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, Z represents one of the heterocyclic groupings below 567568in which the bond drawn broken in each case denotes a single bond or a double bond, and in which each heterocycle preferably only carries two substituents of the definition R5 and/or R6 in any combination, Q represents oxygen or sulphur, R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-alkylthio-, C1-C4-alkylsulphinyl- or C1-C4-alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio, aikinylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R5 and R5 are located at a double bond—also together with the adjacent radical R5 represents a benzo grouping, and R6 represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C1-C4-alkyl- or C1-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R or R6 represents optionally halogen- or C1-C4-alkyl-substituted alkanedjyl having 3 to 5 carbon atoms, where the individual radicals R5 and R6—if two or more of them are attached to the same heterocyclic groupings—may have identical or different meanings in the context of the above definition.

3. Compounds according to claim 1 or 2, characterized in that A represents a single bond or represents methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl), R1 represents hydrogen, phenyl or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-substituted methyl, ethyl, n- or i-propyl, n-, 1- or s-butyl, R2 represents hydrogen or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, or together with R1 represents methylene, ethylidene (ethane-1,1-diyl), dimethylene (ethane-1,2-diyl), propylidene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl), R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, R4 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each case optionally cyano-, fluonrne-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl, Y represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted ethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl or butinyl, or represents in each case optionally nitro-, amino-, cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, iodine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxymethyl-, ethoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl, Z represents one of the heterocyclic groupings below 569Q represents oxygen, R5 represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or—in the case that two adjacent radicals R5 and R5 are located at a double bond—together with the adjacent radical R5 also represents a benzo grouping, and R6 represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl or propenyloxy, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R5 or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).

4. Compounds according to any of claims 1 to 3, characterized in that A represents a single bond or represents methylene, R1 represents hydrogen, phenyl or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, R2 represents hydrogen or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, or together with R1 represents methylene or dimethylene, R3 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulphonyl, R4 represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulphonyl, Y represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, pentenyl, propinyl or butinyl, or represents in each case optionally nitro-, amino-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxymethyl-, ethoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, methylsulphonylamino- or ethylsulphonylamino-substituted phenyl or benzyl, R5 represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or 1-propoxy-, methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- or s-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i- or s-butylamino, dimethylamino or diethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio or represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropylthio, cyclopropylamino, cyclopropylmnethyl, cyclopropylmethoxy, cyclopropylmethylthio or cyclopropylmethylamino, and R6 represents hydrogen, represents amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethoxy, methylamino or ethylamino, represents dimethylamino, or represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropylmethyl, phenyl or benzyl, or together with an adjacent radical R or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-1,5-diyl (pentamethylene).

5. Compounds according to any of claims 1 to 4, characterized in that R1 represents hydrogen, R2 represents hydrogen, R3 represents chlorine, trifluoromethyl or methoxy, R4 represents chlorine, trifluoromethyl or methylsulphonyl, R5 represents hydrogen, methyl or ethyl, and R6 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl.

6. Compounds according to any of claims 1 to 5, characterized in that R5 represents hydrogen, and R6 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl.

7. Compounds according to any of claims 1 to 6, characterized in that n represents the number 0.

8. Compounds according to any of claims 1 to 7, characterized in that Z represents one of the groupings below 570

9. Compounds according to any of claims 1 to 8, characterized in that Q represents oxygen.

10. Compounds according to any of claims 1 to 9, characterized in that Y represents hydrogen, represents in each case optionally fluorine-, chlorine- or methoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- or chlorine-substituted propenyl, butenyl, pentenyl or represents optionally amino-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trifluoromethyl-, methoxy- or ethoxy-substituted phenyl.

11. Compounds of the formula (IA)

12. Compounds of the formula (IB)

13. Compounds of the formula (IC)

14. Sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-ammonium-, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I) according to any of claims 1 to 13, and their complex compounds with metals such as copper, iron, cobalt, nickel.

15. Process for preparing compounds according to any of claims 1 to 12, characterized in that compounds of the formula (II)

16. Herbicidal compositions, characterized in that they comprise at least one compound according to any of claims 1 to 12 and customary extenders.

17. Use of at least one compound according to any of claims 1 to 12 for controlling undesirable plants.

18. Method for controlling undesirable plants, characterized in that at least one compound according to any of claims 1 to 13 or a composition according to claim 16 is allowed to act on the undesirable plants and/or their habitat.