Title of Invention	SUBSTITUTED BENZOYLCYCLOHEXENONES
Abstract	Substituted benzoylcyclohexenones of the formula (I), 0) in which n represents the number 0, 1 or 2, A represents a single bond or represents alkanediyl(alkylene) having 1 to 6 carbon atoms, R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4- alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, 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 R^ -- in this case attached to the sam carbon atom to which R1and R2 are attached in this case represents a (C=0) grouping, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or Ci-C4-alkoxy-substitueted 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 6 carbon atoms in the alkyl groups, and Y represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxjr-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 ease 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-halogeno-alkylthio-, C1-C4-alk ylsulphinyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- aikyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl- carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino- substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aiyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, and Z represents an optionally substituted 4- to 12-menibered 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 0x0 groups (C=0) and/or thioxo groups (C=S) as components of the heterocycle including all possible tautomeric and, if appropriate, possible stereoisomeric forms of the compounds of the general formula (I),

Title of Invention

SUBSTITUTED BENZOYLCYCLOHEXENONES

Abstract

Substituted benzoylcyclohexenones of the formula (I), 0) in which n represents the number 0, 1 or 2, A represents a single bond or represents alkanediyl(alkylene) having 1 to 6 carbon atoms, R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4- alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, 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 R^ -- in this case attached to the sam carbon atom to which R1and R2 are attached in this case represents a (C=0) grouping, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or Ci-C4-alkoxy-substitueted 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 6 carbon atoms in the alkyl groups, and Y represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxjr-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 ease 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-halogeno-alkylthio-, C1-C4-alk ylsulphinyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- aikyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl- carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino- substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aiyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, and Z represents an optionally substituted 4- to 12-menibered 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 0x0 groups (C=0) and/or thioxo groups (C=S) as components of the heterocycle including all possible tautomeric and, if appropriate, possible stereoisomeric forms of the compounds of the general formula (I),

Full Text	FORM 2 THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003 COMPLETE SPECIFICATION [See Section 10; rule 13] "SUBSTITUTED BENZOYLCYCLOHEXENONES" BAYER AKTIENGESELLSCHAFT, a body corporate organized under the laws of Germany, of D-51368 Leverkusen, Germany and NIHON BAYER AGROCHEM K.K., of 10-8, Takanawa 4-chome, Minato-ku, Tokyo 108, Japan, >- T", '^"^- The following specification particularly describes the invention and the manner in which it is to be performed: The invention relates to novel substituted benzoylcyclohexenones, to processes for 5 their preparation and to their use as herbicides. ' .. It is already known that certain substituted benzoylcyclohexanediones have herbi- cidal 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. This invention, accordingly, provides the novel substituted benzoylcyclohexenones of the formula (I), ,-—' 15 (I) in which 20 n represents the number 0,1 or 2, A represents a single bond or represents alkanediyl (alkylene) having 1 to 6 carbon atoms, R' represents hydrogen, phenyl or optionally cyano-, halogen-, Ci-C4-alkoxy- or 2\| Ci-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, R1 represents hydrogen or optionally cyano-, halogen-, Ci-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, or together with R1 Le A 34 324-Foreign Counries represents alkanediyl (alkylene) having 1 to 6 carbon atoms, or together with R - 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=0) grouping, R represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halo¬gen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkyisulphinyl, alkylsulphonyl, alkyl-amino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, 10 R represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C1-C4- alkoxy-substituted alkyl, alkoxy, alkylthio, alkyisulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, and 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- 2p 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-alkyI-, C1-C44-haIogenoaIkyl-, C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio-, C1-C4-halogenoalkylthio-, C1-C4alkylsulphinyl-, C1-C4-halogeno- 2]5 alkyisulphinyl-, 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-C4alkyl-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 30 Le A 34 324-Foreign Coumies 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 0x0 groups (C=0) and/or thioxo groups (C=S) as components of the heterocycle, - 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). 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. 1) 20 Preferred meanings of the radicals or groupings present in the formulae shown above and below are defined below. n preferably represents the number 0 or 2. A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms. R1 preferably represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4- 2\|5 alkoxy- or Ci-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms. R2 preferably represents hydrogen or optionally cyano-, halogen-, Ci-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. Le A 34 324-Foreign Coimries R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups. R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio- carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl- 0 sulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups. Y preferably represents hydrogen, represents optionally cyano-, halogen- or Ci-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-halogeno- alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- alkyl-carbonyl-,C1-C4C4-alkoxy-carbonyl-, alkyl-carbonyl-amino-, Ci-C4-alkoxy-Garbonyl-amino-, Ci-C4-alkyl-sulphonyl-amino-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and 25j optionally 1 to 4 carbon atoms in the alkyl moiety. preferably represents one of the heterocyclic groupings below Le A 34 324-Foreign Counries >^ 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. Q represents oxygen or sulphur, 20 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-substi-tuted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkyl-sulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substi¬tuted 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-substi¬tuted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkyl-alkylamino 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 Le A 34 324-Foreign Counries 5 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 R represents a benzo grouping, and R6represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4 10 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 aUcenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen- 15 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 Ci-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical 5 or R6 represents 20l optionally halogen- or Ci-C4-alkyl-substituted alkanediyl having 3 to 5 carbon atoms, where the individual radicals R5 and R6 - if two or more of them are attached to the same heterocycHc groupings - may have identical or different meanings 25! in the context ofthe above definition. n particularly preferably represents the number 0. A particularly preferably represents a single bond or represents methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl). Le A 34 324-Foreign Counries R 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. 5R 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), propyhdene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl). R 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, ethyl-sulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i- ip propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or di-ethylaminosulphonyl. R4 particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamo¬ yl, 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- 30 or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propyl- sulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl- Le A 34 324-Foreign Counries amino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethyl-aminosulphonyl. 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-, methyl- thio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethyl- thio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethyl-sulphinyl-, methylsulphonyl-, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n-or i-propoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonyl- amino-, ethoxycarbonylamino-, methylsulphonylamino-, ethylsulphonyl- amino-, n- or i-propylsulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl. particularly preferably represents one of the heterocyclic groupings below A 34 324-Foreign Counries preferably represents oxygen, 1( R 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-, methyl-sulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted meth¬yl, 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-propyl¬sulphinyl, 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, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentyl-amino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyhnethoxy, cyclo-butylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropyl- Le A 34 324-Foreign Counries 11 methylthio, cyclobutylmethylthio, cyclopentyhnethylthio, cyclohexyl-methylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclo-pentylmethylamino 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. R preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substi-tuted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, repre- sents 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, cyclobutyl-methyl, 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 R5or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-l,5-diyl (pentamethylene). A very particularly preferably represents a single bond or represents methylene. R1 very particularly preferably represents hydrogen, phenyl or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl. Le A 34 324-Foreign Counries 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. R 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, meth- oxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methyl- sulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulphonyl. 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, meth- oxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methyl- sulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or di¬methylaminosulphonyl . 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-, ethoxy- carbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxy- Le A 34 324-Foreign Counries carbonylamino-, methylsulphonylamino- or ethylsulphonylamino-substituted phenyl or benzyl. Z very particularly preferably represents the heterocyclic groupings below R5 particularly preferably represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, meth-oxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methyl- sulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-sub- stituted 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-propyl- sulphonyl, 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, butenyl-oxy, propenylthio or represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropyl- thio, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropyktiethylthio or cyclopropylmethylamino. R6 particularly preferably represents hydrogen, represents amino, repre- sents 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, cyclo- Le A 34 324-Foreign Counries propyhnethyl, 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 (tetra-methylene) orpentane-l,5-diyl (pentamethylene). A most preferably represents methylene. Rl most preferably represents hydrogen. 1(\| R2 most preferably represents hydrogen. R3 most preferably represents chlorine, trifluoromethyl or methoxy. R4 most preferably represents chlorine, trifluoromethyl or methyl- 15\| sulphonyl. 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. 5 very particularly preferably represents hydrogen, methyl or ethyl. R6 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclo-pentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl. R5 most preferably represents hydrogen. Le A 34 324-Foreign Counries R6 most preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl. The invention preferably also provides the sodium, potassiimi, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4 alkyl)-animonium, tetra-(C1-C4-alkyl)-ammonium, tri-(Ci-C4-alkyl)-sulphonium, C5- or C5-cycloalkyl-ammonium and di-C1-C2alkyl)-benzyl-ammonium salts of compoxmds of the formula (I), in which A, n, R1 R'2, R3, R4, Y and Z are each as defined above, or else complex compounds (coordination compounds) of these compoxmds with metals such as copper, iron, cobalt, nickel. Preference according to the invention is given to compoimds of the formula (I) which contain a combination of the meanings mentioned above as being preferred. 15 20 25 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. 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. 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. 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. Le A 34 324-Foreign Counries The position of the radicals R1, R2, R3, R4 and A-Z can vary according to formula (I). ) The radical R3 is preferably in position (4) on the phenyl ring, particularly preferably in position (2). The radical R4 is preferably in position (4) on the phenyl ring, if the radical R^ is in position (2). 1) 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. 151 The present invention provides in particular the compounds of the general formulae (lA), (IB) and (IC) below. 20 Le A 34 324-Foreign Counries f In the general formulae (lA), (IB) and (IC), n. A, R1 R2 R3R4Y and Z have in each case the meanings given in the definitions above. Very particular emphasis is given to the compounds of the general formulae (lA), (IB) and (IC) in which A represents methylene. Examples of compounds of the general formula (I) according to the invention are 1 j) Usted in the groups below. Group 1 5 Here, R3 R4, R5 and R6 each have, for example, the meanings given in the table below: Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Couimes Le A 34 324-Foreign Counries Here, R^, R'*, R^ and R^ each have, for example, the meanings given above in Group 1. Group 3 1(' Le A 34 324-Foreign Coimries ! Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1. Group 5 (IA-5) 10 Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1. Le A 34 324-Foreign Counries Here, R3, R4, R5 and R6each have, for example, the meanings given above in the table below. Le A 34 324-Foreign Coimries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Coimries -^ Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreigi Coumies Le A 34 324-Foreign Counries Le A 34 324-Foreign Coimries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Coimries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries y- Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Covmrles Le A 34 324-Foreign Coimries Le A 34 324-Foreign Counries Le A 34 324-Foreign Coumies Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324-Foreign Conmies Le A 34 324-Foreign Counries Le A 34 324-Foreign Counries Le A 34 324'Foreign Counries Le A 34 324-Foreign Coumies Le A 34 324-Foreign Coiuiries Le A 34 324-Foreign Coiinries / Here, R3, R4, R5 and R6each have, for example, the meanings given above in Group 6. Group 8 Le A 34 324-Foreign Counries ■^ >3 r>4 T>5 „„j r)6 Here R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6. Group 9 (IB-4) 10 Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6. Group 10 (IB-5) Here, R3, R4, R5 and R6each have, for example, the meanings given above in 15 Group 6. The novel substituted benzoylcyclohexenones of the formula (I) have strong and selective herbicidal activity. The novel substituted benzoylcyclohexenones of the formula (I) are obtained when substituted cyclohexanediones of the formula (II) Le A 34 324-Foreign Counries in which are reacted with a halogenating agent, if appropriate in the presence of a reaction auxihary and if appropriate in the presence of a diluent, and the halogenocyclo-hexenones obtained in this way (in the first reaction step), of the formula (III) 0 in which A,R1R2R3R4andZ are as defined above, 15 X represents halogen, preferably represents fluorine or chlorine, particularly preferably represents chlorine, - after intermediate isolation or without intermediate isolation ("in situ") - 20 are reacted in a second reaction step with mercapto compounds of the formula (IV) HS-Y (IV) in which 25 Y is as defined above, Le A 34 324-Foreign Counries if appropriate in the presence of a reaction auxiUary and if appropriate in the presence of a diluent, 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 electrophiUc or nucleophilic substitution reactions or oxidation or reduction reactions, or the compounds of the formula (I) are converted in a customary manner into salts. Using, for example 2-[4-chloro-2-[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)-methyl]-benzoyl]-cyclohexane-l,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 Le A 34 324-Foreign Countries The formula (II) provides a general definition of the substituted benzoylcyclo-hexanediones to be used as starting materials in the process according to the in¬vention for preparing compounds of the general formula (I). In the general formula (II), A, R1R2R3R4and Z each preferably have those meanings which have akeady 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. 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). 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 l\|5 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. 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-dimethyl- formamide, N,N-diethyl-formamide, N,N-dipropyl-formamide and N,N-dibutyl- formamide, and also N-methyl-pyrrolidone. The formula (IV) provides a general definition of the mercapto compounds fiirther 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 Le A 34 324-Foreign Countries 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. The starting materials of the general formula (FV) are known organic chemicals for synthesis. 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 aUcoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithixrai 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-diisopropyl-amine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl-amine, 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-dimethyl- pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piper- idine, l,4-diazabicyclo[2.2.2]-octane (DABCO), l,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8 diazabicyclo[5.4.0]-undec-7-ene (DBU). 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, Le A 34 324-Foreign Countries aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for ex¬ample, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petro¬leum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofiiran 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-pyrrohdone 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. 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. 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 2(\| according to the invention under elevated or reduced pressure - in general between 0.1 bar and 10 bar. 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). Le A 34 324-Foreign Countries 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. The active compounds according to the invention can be used, for example, in connection with the following plants: Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, BelUs, Bidens, Capsella, Carduus, Cassia, Centaurea,~ Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidiimi, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotls, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, ^soncnus, ^phenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, HeUanthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia. 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, Sorghmn. Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea. Le A 34 324-Foreign Countries 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. 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 pahn plantations, cocoa plantations, soft Suit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops. 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 dicotyle¬donous crops, both by the pre-emergence and by the post-emergence method. 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. \| 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 Le A 34 324-Foreign Coimtries 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. 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, brashing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi¬layer coating. The active compoimds 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. 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. 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, Le A 34 324-Foreign Coimtries and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and water. Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diato-maceous 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 poly-oxyethylene 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. Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and poly- vinyl 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. 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. The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%. Le A 34 324-Foreign Countries 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 sub¬stances 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. Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfliresate, bensulfuron (-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap, benzoyl-prop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfiiron, 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, dimefiiron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxy-sulfuron, 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), glypho-sate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), Le A 34 324-Foreign Countries 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, metoxiuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, nebiiron, nicosulfiiron, nor-flurazon, 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 (-sodiimi), 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-tefliryl), 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. 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. The active compoimds can be used as such, in the form of their formulations or in the use forms prepared therefirom 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. Le A 34 324-Foreign Countries 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. 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 amoimts 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. The preparation and the use of the active compounds according to the invention is illustrated by the examples below. Le A 34 324-Foreign Countries Preparation examples: Example 1 A mixture of 1.3 g (3 mmol) of 2-[2,4-dichloro-3-[(3-methyl-2-oxo-tetrahydro-l(2H)-pyrimidinyl)-methyl]-benzoyl]-cyclohexane-l,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 IN 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. This gives 0.91 g (61% of theory) of l-[2,6-dichloro-3-[(6-oxo-2-phenylthio-l- cyclohexen-1 -yl)-carbonyl]-benzyl]-3-methyl-tetrahydro-2( 1 H)-pyrimidinone of melting point 140°C. 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 ex¬ample, the compoimds of the general formula (I) - or those of the general formula (ID) - listed in Table 1 below. 324-Foreign Countries Table 1; Examples of compounds of the formula (ID) Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreiga Coimtries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Coimtries Le A 34 324-Foreign Countries A94-^ Le A 34 324-Foreign Countries Le A 34 324-Foreign Coimtnes Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries 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. (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. (b) Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; hnear gradient from 10% acetonitrile to 90% acetonitrile - corresponding data are labelled b) in Table 1. Le A 34 324-Foreign Countries 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). The lambda max values were determined in the maxima of the chromatographic signals, using the UV spectra from 200 nm to 400 nm. Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreign Countries Le A 34 324-Foreiga Countries Le A 34 324-Foreign Countries Use examples Example A Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl poly glycol ether 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 concen¬tration. 15 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 hquor is chosen such that the particular amount of active compound desired is apphed in 1000 litres of water per hectare. 20 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: 0% = no effect (like untreated control) 100% == total destruction 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. Le A 34 324-Foreign Countries Example B Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether 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. 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 imit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are appUed in 10001 of water/ha. 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: 0% = no effect (like untreated control) 100% = total destruction 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. WE CLAIM: 1. Substituted benzoylcyclohexenones of the formula (I), 0) in which n represents the number 0, 1 or 2, A represents a single bond or represents alkanediyl(alkylene) having 1 to 6 carbon atoms, R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4- alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, 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 R^ -- in this case attached to the sam carbon atom to which R1and R2 are attached in this case represents a (C=0) grouping, R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or Ci-C4-alkoxy-substitueted 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 6 carbon atoms in the alkyl groups, and Y represents hydrogen, represents optionally cyano-, halogen- or C1-C4-alkoxjr-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 ease 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-halogeno-alkylthio-, C1-C4-alk ylsulphinyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4- aikyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl- carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino- substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aiyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, and Z represents an optionally substituted 4- to 12-menibered 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 0x0 groups (C=0) and/or thioxo groups (C=S) as components of the heterocycle including all possible tautomeric and, if appropriate, possible stereoisomeric forms of the compounds of the general formula (I), 2. Compounds as claimed in claim 1, wherein 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 Ci-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms, or together with Ri 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-7halogen- or C1-C4-aiko 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-substitueted alkyl, alkoxy, alkyLlthio, alkylsulphinyl, alkylsulphonyl, alkylatnino, dialkylamino or dialkylamino sulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups, represents hydrogen, represents optionally cyano-, halogen- or 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-halogeno-alkylthio-, C1-C4 alkylsulphinyl-, C1-C4-halogenoalkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alk7l-carbonyl-amino-, C1-C4-alkoxy^-carbonyl-amino-, C1-C4-alkyl-sulphonyl-aminosubsuituted aryl or aiylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, represents one of the heterocyclic groupings below 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, Q represents oxygen or sulphur, R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-aIkylthio-, C1-C4-alkylsulphinyl- or C1-C4--alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, allklthio, alkylsulphinyl or alkylsulphonyl having in each ease up to 6 carbon atoms in the alkyl groups, represents in each ease 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, alkcnylthio, alkinylthio or alkenyl- amino having in each ease 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 cycloalkylalkyl-amino 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, benxylthio 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 ease up to 6 carbon a:toms 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, where the individual radicals R5 or 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. Compound as claimed in claim 1 or 2, wherein 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-, i- or s-butyl, R2 represent hydrogen or represent 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-bulyl, or together with Rl represents methylene, ethylidene (ethane-1,1 -diyl), dimethylen (ethane-1,2-diyl), propylidene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl), -WC 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 diethylamino sulphonyl, R4 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each ease 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, methyl-thio, ethylthio, n- or i-propylthio, n-, i-, s-or t-butylthio, methyl-sulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylaminb, 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-, nor i-propoxycarbonyl-substituted ethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl or butinyl, or represents in each case optionally nitro-, amino-, cyano-, carbomoyl-, 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-, trilluoromethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propyl-sulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl, Q 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-, methylsuiphonyl -, ethylsulphonyl-, n- or i-propylsuiphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-bulyl, 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, methylsuiphonyl, 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, propertylthio, butenylthio, propenylarnino or butenylamino, represents in each case optionally fluorineand/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl^ cyclohexyl, cyclopropyloxy, cyclohexyl, cyclohexyl, cyclopentylthio cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamiho, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentyl- methoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylamino, cyclopentylmethylamino, cyclohexylmethylamino, 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, benayl, benzyloxy benzylthio or benzylainino, or - in the case that two adjacent radicals R^ 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 shlorine-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- ort-butyl-mmethoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R^ ^orR^ represents in each case optionally methyl- and/ or ethyl-substituted propane-l,3-diyl(trimethylene), butane- 1,4-diyl (tetramethylene) • or pentane-l,5-diyl (pentamethylene). 4. Com^pounds as claimed in any of claims 1 to 3, wherein 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, n-, or together with Ri 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, methyl-sulphonyl, 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, methyl-sulphonyl, 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-propcxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i- propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethyl- sulphinyl-, methylsulphonyl, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, methoxycarbonyl-, ethoxycarbonyl-, aceiylamino-, propionylamino-, methoxycarbonylamino-, ethoxy- carbonylamino-, methylsulphonylamino- or ethylsulphonylamino substituted phenyl or ben2yl, R5 represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, methoxyn -, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio- , methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n- , i- or s-butyl, methoxy, ehtoxy, n- or i-propoxy, n-, i- or s- butoxy, methylthio, ethylthio, n- or i-propylthio, n-, or i- or s-butylthio, methylsulphinyl, ethylsulphinyl, n- or i- propylsulphinyl, methylsulphonyl, ethylsulphonyl, n-ori- 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 ethyenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio or represents in each case optionally fljorine- and/or chlorine-subsituted cyclopropyl, cyclopropyloxy, cyclopropylthio, cycloprpylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethylthior or cyclopropylmethylamino, and R6 represents hydrogen, represents amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, methoxy, ethox^, methylamino or ethylamino, represents dimethylamino, or represents in each case optionally fljorine- and/or chlorine-substituted cyclopropyl, cyclopropylmethyl, phenyl or benzyl, or together with an adjacent radical RS or R^ represent in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane- 1,4-diyl (tetramethylene) or pentane-l,5-diyl (pentamethylene). 5. Compounds as claimed in any of claims 1 to 4, wherein 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 ben2yl. 6. Compounds as claimed in any of claims 1 to 5, wherein R5 represents hydrogen, and R6 represents methyl, ethyl,n- or i-propyl, n-, i-,s- or t-butyl, cyclopropyl, cyclopropylmethyl, or phenyl. 7. Compounds as claimed in any of claims 1 to 6, wherein n represents the num.ber 0, 8. Compounds as claimed in any of claims 1 to 7, wherein Z represents one of the groupings below 9. Compounds as claimed in any of claims 1 to 8, wherein Q represents oxygen. 10. Compounds as claimed in any of claims 1 to 9, wherein 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 amiono-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trifluoromethyl-, methoxy or ethoxy-substitued phenyl. 11. Compound of the formula (lA) in which n, A, Ri, R2, R3, R4, y and Z are as defined in any of claims 1 to 9. 12. Compounds of the formula (IB) in which n, A, R1, R2, R3, R4 y and Z are as defined in any of claims 1 to 9. 13. Compounds of the formula (IC) in which n, A, R1, R2, R3, R4, y and Z are as defined in any of claims 1 to 9. ^ 14. Sodium, potassium, magnesium, calcium, ammonium, C1-C4-aIkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1 C4-aIkyl)-ammonium-, tetra-( Ci-C4-alkyl)-ammoniu, tri-( C1-C4-alkyl)-sulphonium, Cs- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-ben2yl-ammonium salts of compounds of the formula (I) as claimed in any of claims 1 to 13, and their complex compounds with metals such as copper, iron, cobalt, nickel. 15. Process for preparing compounds as claimed in any of claims 1 to 12, wherein the compounds of the formula (II) OD in which A, R1, R2, R3, R4 and Z are as defined in any of claims 1 to 9. 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) (m) in which A, R1, R2, R3, R4, and Z are as defined in any of claims 1 to 9 and X represents halogen - after intermediate isolation or without intermediate isolation ("in situ")- are reacted in a second reaction step with mercapto compounds of the formula (IV) HS-Y (IV) in which Y is as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, 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. 16. Substituted bezoylcyclohexenones of the formula (1) substantially as hereinbefore described with reference to the foregoing examples. 17. Process for preparing the compounds substantially as hereinbefore described with reference to the foregoing examples. [DR. DEEPA K.JTIKU] OF REMFRY & SAGAR ATTORNEY FOR THE APPLICANTS Dated this 23rd day of February, 2001. 127

Full Text

FORM 2
THE PATENTS ACT 1970 [39 OF 1970] & THE PATENTS RULES, 2003
COMPLETE SPECIFICATION
[See Section 10; rule 13]
"SUBSTITUTED BENZOYLCYCLOHEXENONES"
BAYER AKTIENGESELLSCHAFT, a body corporate organized under the laws of Germany, of D-51368 Leverkusen, Germany and NIHON BAYER AGROCHEM K.K., of 10-8, Takanawa 4-chome, Minato-ku, Tokyo 108, Japan,
>- T", '^"^-
The following specification particularly describes the invention and the manner in which it is to be performed:

The invention relates to novel substituted benzoylcyclohexenones, to processes for
5 their preparation and to their use as herbicides. ' ..
It is already known that certain substituted benzoylcyclohexanediones have herbi-
cidal 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.
This invention, accordingly, provides the novel substituted benzoylcyclohexenones
of the formula (I), ,-—'
15

(I)

in which

20

n represents the number 0,1 or 2,
A represents a single bond or represents alkanediyl (alkylene) having 1 to 6 carbon atoms,

R' represents hydrogen, phenyl or optionally cyano-, halogen-, Ci-C4-alkoxy- or
2| Ci-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms,
R1 represents hydrogen or optionally cyano-, halogen-, Ci-C4-alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms, or together with R1

Le A 34 324-Foreign Counries

represents alkanediyl (alkylene) having 1 to 6 carbon atoms, or together with R - 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=0) grouping,
R represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halo¬gen, or represents in each case optionally cyano-, halogen- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkyisulphinyl, alkylsulphonyl, alkyl-amino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,
10
R represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,
halogen, or represents in each case optionally cyano-, halogen- or C1-C4-
alkoxy-substituted alkyl, alkoxy, alkylthio, alkyisulphinyl, alkylsulphonyl,
alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to
6 carbon atoms in the alkyl groups, and
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-
2p 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-alkyI-, C1-C44-haIogenoaIkyl-, C1-C4-alkoxy-C1-C4-alkyl-, C1-C4-alkoxy-, C1-C4-halogenoalkoxy-, C1-C4-alkylthio-, C1-C4-halogenoalkylthio-, C1-C4alkylsulphinyl-, C1-C4-halogeno-
2]5 alkyisulphinyl-, 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-C4alkyl-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
30

Le A 34 324-Foreign Coumies
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 0x0 groups (C=0) and/or thioxo groups (C=S) as components of the heterocycle,
- 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).
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.
1)

20

Preferred meanings of the radicals or groupings present in the formulae shown above and below are defined below.
n preferably represents the number 0 or 2.
A preferably represents a single bond or represents alkanediyl (alkylene) having 1 to 4 carbon atoms.

R1 preferably represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4-
2|5 alkoxy- or Ci-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms.
R2 preferably represents hydrogen or optionally cyano-, halogen-, Ci-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.

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R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or Ci-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups.
R preferably represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thio-
carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or
Ci-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-
0 sulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in
each case 1 to 5 carbon atoms in the alkyl groups.
Y preferably represents hydrogen, represents optionally cyano-, halogen- or Ci-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-halogeno-
alkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-
alkyl-carbonyl-,C1-C4C4-alkoxy-carbonyl-, alkyl-carbonyl-amino-, Ci-C4-alkoxy-Garbonyl-amino-, Ci-C4-alkyl-sulphonyl-amino-substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and
25j optionally 1 to 4 carbon atoms in the alkyl moiety.
preferably represents one of the heterocyclic groupings below

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>^

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.
Q represents oxygen or sulphur,

20

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-substi-tuted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkyl-sulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substi¬tuted 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-substi¬tuted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkyl-alkylamino 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

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5
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 R
represents a benzo grouping, and
R6represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C1-C4
10 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 aUcenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-
15 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 Ci-C4-alkoxy-substituted phenyl or benzyl, or together with an adjacent radical 5 or R6 represents
20l optionally halogen- or Ci-C4-alkyl-substituted alkanediyl having 3 to
5 carbon atoms,
where the individual radicals R5 and R6 - if two or more of them are attached
to the same heterocycHc groupings - may have identical or different meanings
25! in the context ofthe above definition.
n particularly preferably represents the number 0.
A particularly preferably represents a single bond or represents methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).

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R 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.
5R 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), propyhdene
(propane-1,1-diyl) or trimethylene (propane-1,3-diyl).
R 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, ethyl-sulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-
ip propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or
t-butylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or di-ethylaminosulphonyl.
R4 particularly preferably represents hydrogen, nitro, cyano, carboxyl, carbamo¬
yl, 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-
30 or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propyl-
sulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butyl-

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amino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethyl-aminosulphonyl.
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-, methyl-
thio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethyl-
thio-, trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, trifluoromethyl-sulphinyl-, methylsulphonyl-, ethylsulphonyl-, trifluoromethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n-or i-propoxycarbonyl-, acetylamino-, propionylamino-, methoxycarbonyl-
amino-, ethoxycarbonylamino-, methylsulphonylamino-, ethylsulphonyl-
amino-, n- or i-propylsulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl.
particularly preferably represents one of the heterocyclic groupings below

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preferably represents oxygen,

1(

R 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-, methyl-sulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted meth¬yl, 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-propyl¬sulphinyl, 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, cyclo-pentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentyl-amino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyhnethoxy, cyclo-butylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropyl-

Le A 34 324-Foreign Counries
11
methylthio, cyclobutylmethylthio, cyclopentyhnethylthio, cyclohexyl-methylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclo-pentylmethylamino 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.
R preferably represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substi-tuted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, repre-
sents 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, cyclobutyl-methyl, 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 R5or R6 represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) or pentane-l,5-diyl
(pentamethylene).
A very particularly preferably represents a single bond or represents methylene.
R1 very particularly preferably represents hydrogen, phenyl or in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl.

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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.
R 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, meth-
oxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methyl-
sulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or
dimethylaminosulphonyl.
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, meth-
oxy, ethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methyl-
sulphonyl, ethylsulphonyl, methylamino, ethylamino, dimethylamino or di¬methylaminosulphonyl .
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-, ethoxy-
carbonyl-, acetylamino-, propionylamino-, methoxycarbonylamino-, ethoxy-

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carbonylamino-, methylsulphonylamino- or ethylsulphonylamino-substituted phenyl or benzyl.
Z very particularly preferably represents the heterocyclic groupings below

R5 particularly preferably represents hydrogen, fluorine, chlorine, bromine, represents in each case optionally fluorine-, chlorine-, meth-oxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, methyl-
sulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-sub-
stituted 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-propyl-
sulphonyl, 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, butenyl-oxy, propenylthio or represents in each case optionally fluorine-
and/or chlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropyl-
thio, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropyktiethylthio or cyclopropylmethylamino.
R6 particularly preferably represents hydrogen, represents amino, repre-
sents 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, cyclo-

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propyhnethyl, 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 (tetra-methylene) orpentane-l,5-diyl (pentamethylene).
A most preferably represents methylene.
Rl most preferably represents hydrogen.
1(| R2 most preferably represents hydrogen.
R3 most preferably represents chlorine, trifluoromethyl or methoxy.
R4 most preferably represents chlorine, trifluoromethyl or methyl-
15| sulphonyl.
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.
5 very particularly preferably represents hydrogen, methyl or ethyl.
R6 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclo-pentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl.
R5 most preferably represents hydrogen.

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R6 most preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl.
The invention preferably also provides the sodium, potassiimi, magnesium, calcium,
ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1-C4
alkyl)-animonium, tetra-(C1-C4-alkyl)-ammonium, tri-(Ci-C4-alkyl)-sulphonium,
C5- or C5-cycloalkyl-ammonium and di-C1-C2alkyl)-benzyl-ammonium salts of
compoxmds of the formula (I), in which A, n, R1 R'2, R3, R4, Y and Z are each as
defined above, or else complex compounds (coordination compounds) of these
compoxmds with metals such as copper, iron, cobalt, nickel.
Preference according to the invention is given to compoimds of the formula (I) which contain a combination of the meanings mentioned above as being preferred.
15

20
25

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.
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.
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.
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.

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The position of the radicals R1, R2, R3, R4 and A-Z can vary according to formula (I).
) The radical R3 is preferably in position (4) on the phenyl ring, particularly preferably
in position (2).
The radical R4 is preferably in position (4) on the phenyl ring, if the radical R^ is in position (2).
1)
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.
151 The present invention provides in particular the compounds of the general formulae
(lA), (IB) and (IC) below.

20

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f

In the general formulae (lA), (IB) and (IC), n. A, R1 R2 R3R4Y and Z have in each case the meanings given in the definitions above.
Very particular emphasis is given to the compounds of the general formulae (lA), (IB) and (IC) in which A represents methylene.

Examples of compounds of the general formula (I) according to the invention are
1 j) Usted in the groups below.
Group 1

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

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Here, R^, R'*, R^ and R^ each have, for example, the meanings given above in Group 1.
Group 3

1('

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!

Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 1.
Group 5

(IA-5)

10

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

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Here, R3, R4, R5 and R6each have, for example, the meanings given above in the table below.

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-^

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y-

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/

Here, R3, R4, R5 and R6each have, for example, the meanings given above in Group 6.

Group 8

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■^
>3 r>4 T>5 „„j r)6
Here R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6.
Group 9

(IB-4)

10

Here, R3, R4, R5 and R6 each have, for example, the meanings given above in Group 6.
Group 10

(IB-5)

Here, R3, R4, R5 and R6each have, for example, the meanings given above in
15 Group 6.
The novel substituted benzoylcyclohexenones of the formula (I) have strong and selective herbicidal activity.
The novel substituted benzoylcyclohexenones of the formula (I) are obtained when
substituted cyclohexanediones of the formula (II)

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in which

are reacted with a halogenating agent, if appropriate in the presence of a reaction auxihary and if appropriate in the presence of a diluent, and the halogenocyclo-hexenones obtained in this way (in the first reaction step), of the formula (III)

0

in which
A,R1R2R3R4andZ are as defined above,
15 X represents halogen, preferably represents fluorine or chlorine, particularly
preferably represents chlorine,
- after intermediate isolation or without intermediate isolation ("in situ") -
20 are reacted in a second reaction step with mercapto compounds of the formula (IV)
HS-Y (IV)
in which
25 Y is as defined above,

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if appropriate in the presence of a reaction auxiUary and if appropriate in the presence of a diluent,
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 electrophiUc or nucleophilic substitution reactions or oxidation or reduction reactions, or the compounds of the formula (I) are converted in a customary manner into salts.
Using, for example 2-[4-chloro-2-[(3,4-dimethyl-5-oxo-4,5-dihydro-lH-l,2,4-triazol-l-yl)-methyl]-benzoyl]-cyclohexane-l,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

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The formula (II) provides a general definition of the substituted benzoylcyclo-hexanediones to be used as starting materials in the process according to the in¬vention for preparing compounds of the general formula (I). In the general formula (II), A, R1R2R3R4and Z each preferably have those meanings which have akeady 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.
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).
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
l|5 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.

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-dimethyl-
formamide, N,N-diethyl-formamide, N,N-dipropyl-formamide and N,N-dibutyl-
formamide, and also N-methyl-pyrrolidone.
The formula (IV) provides a general definition of the mercapto compounds fiirther 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

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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.
The starting materials of the general formula (FV) are known organic chemicals for synthesis.
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 aUcoxides, such as, for example, sodium acetate, potassium acetate or calcium acetate, lithixrai 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-diisopropyl-amine, N,N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexyl-amine, 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-dimethyl-
pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piper-
idine, l,4-diazabicyclo[2.2.2]-octane (DABCO), l,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or 1,8 diazabicyclo[5.4.0]-undec-7-ene (DBU).
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,

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aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for ex¬ample, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petro¬leum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofiiran 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-pyrrohdone 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.
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.
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
2(| according to the invention under elevated or reduced pressure - in general between
0.1 bar and 10 bar.
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).

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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.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda,
Anthemis, Aphanes, Atriplex, BelUs, Bidens, Capsella, Carduus, Cassia, Centaurea,~
Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,
Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium,
Lepidiimi, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotls, Papaver,
Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala,
Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, ^soncnus, ^phenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Dicotyledonous crops of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita,
HeUanthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon,
Nicotiana, Phaseolus, Pisum, Solanum, Vicia.
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, Sorghmn.
Monocotyledonous crops of the genera: Allium, Ananas, Asparagus, Avena,
Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

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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.
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 pahn plantations, cocoa plantations, soft Suit plantings and
hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
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 dicotyle¬donous crops, both by the pre-emergence and by the post-emergence method.
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.
| 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

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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.
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, brashing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi¬layer coating.
The active compoimds 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.
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.
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,

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and also their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethyl-formamide and dimethyl sulphoxide, and water.
Suitable solid carriers are: for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diato-maceous 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 poly-oxyethylene 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.
Tackifiers, such as carboxymethylcellulose, natural and synthetic polymers in the
form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and poly-
vinyl 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.
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.
The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

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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 sub¬stances 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.
Possible components for the mixtures are known herbicides, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine,
azafenidin, azimsulfuron, beflubutamid, benazolin (-ethyl), benfliresate, bensulfuron
(-methyl), bentazon, benzfendizone, benzobicyclon, benzofenap, benzoyl-prop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl), chlomethoxyfen, chloramben,
chloridazon, chlorimuron (-ethyl), chlomitrofen, chlorsulfiiron, 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,
dimefiiron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxy-sulfuron, 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), glypho-sate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl),

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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, metoxiuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, nebiiron, nicosulfiiron, nor-flurazon, 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 (-sodiimi), 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-tefliryl), 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.
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.
The active compoimds can be used as such, in the form of their formulations or in the use forms prepared therefirom 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.

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

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Preparation examples: Example 1
A mixture of 1.3 g (3 mmol) of 2-[2,4-dichloro-3-[(3-methyl-2-oxo-tetrahydro-l(2H)-pyrimidinyl)-methyl]-benzoyl]-cyclohexane-l,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 IN 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.
This gives 0.91 g (61% of theory) of l-[2,6-dichloro-3-[(6-oxo-2-phenylthio-l-
cyclohexen-1 -yl)-carbonyl]-benzyl]-3-methyl-tetrahydro-2( 1 H)-pyrimidinone of
melting point 140°C.
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 ex¬ample, the compoimds of the general formula (I) - or those of the general formula (ID) - listed in Table 1 below.

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Table 1; Examples of compounds of the formula (ID)

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A94-^

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

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

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Use examples Example A
Pre-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl poly glycol ether
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 concen¬tration.
15 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 hquor is chosen such that the particular amount of active compound desired is apphed in 1000 litres of water per hectare.
20
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:
0% = no effect (like untreated control) 100% == total destruction
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.

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Example B
Post-emergence test
Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether
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.
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 imit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are appUed in 10001 of water/ha.
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:
0% = no effect (like untreated control) 100% = total destruction
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.

WE CLAIM:
1. Substituted benzoylcyclohexenones of the formula (I),

0)

in which
n represents the number 0, 1 or 2,
A represents a single bond or represents alkanediyl(alkylene) having 1 to 6 carbon atoms,
R1 represents hydrogen, phenyl or optionally cyano-, halogen-, C1-C4- alkoxy- or C1-C4-alkylthio-substituted alkyl having 1 to 6 carbon atoms,
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 R^ -- in this case attached to the sam
carbon atom to which R1and R2 are attached in this case represents a (C=0) grouping,
R3 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or Ci-C4-alkoxy-substitueted 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 6 carbon atoms in the alkyl groups, and
Y represents hydrogen, represents optionally cyano-,
halogen- or C1-C4-alkoxjr-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 ease 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-halogeno-alkylthio-, C1-C4-alk
ylsulphinyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-
alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-
aikyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alkyl-
carbonyl-amino-, C1-C4-alkoxy-carbonyl-amino-
substituted aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aiyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, and
Z represents an optionally substituted 4- to 12-menibered 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 0x0 groups (C=0)

and/or thioxo groups (C=S) as components of the heterocycle including all possible tautomeric and, if appropriate, possible stereoisomeric forms of the compounds of the general formula (I),
2. Compounds as claimed in claim 1, wherein
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 Ci-C4-alkylthio-substituted alkyl having 1 to 5 carbon atoms, or together with Ri 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-7halogen- or C1-C4-aiko 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-substitueted alkyl, alkoxy, alkyLlthio, alkylsulphinyl, alkylsulphonyl,

alkylatnino, dialkylamino or dialkylamino sulphonyl having in each case 1 to 5 carbon atoms in the alkyl groups,
represents hydrogen, represents optionally cyano-,
halogen- or 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-halogeno-alkylthio-, C1-C4
alkylsulphinyl-, C1-C4-halogenoalkylsulphinyl-, C1-C4-alkylsulphonyl-, C1-C4-halogenoalkylsulphonyl-, C1-C4-alkyl-carbonyl-, C1-C4-alkoxy-carbonyl-, C1-C4-alk7l-carbonyl-amino-, C1-C4-alkoxy^-carbonyl-amino-, C1-C4-alkyl-sulphonyl-aminosubsuituted aryl or aiylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety,
represents one of the heterocyclic groupings below

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,
Q represents oxygen or sulphur,
R5 represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C1-C4-alkoxy-, C1-C4-aIkylthio-, C1-C4-alkylsulphinyl- or C1-C4--alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy,

alkoxycarbonyl, allklthio, alkylsulphinyl or alkylsulphonyl
having in each ease up to 6 carbon atoms in the alkyl
groups, represents in each ease 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, alkcnylthio, alkinylthio or alkenyl-
amino having in each ease 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 cycloalkylalkyl-amino 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, benxylthio 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 ease up to 6 carbon a:toms 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,
where the individual radicals R5 or 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. Compound as claimed in claim 1 or 2, wherein
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-, i- or s-butyl,
R2 represent hydrogen or represent 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-bulyl, or together with Rl represents methylene, ethylidene (ethane-1,1 -diyl), dimethylen (ethane-1,2-diyl), propylidene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl),
-WC

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
diethylamino sulphonyl,
R4 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each ease 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, methyl-thio, ethylthio, n- or i-propylthio, n-, i-, s-or t-butylthio, methyl-sulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylaminb, 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-, nor
i-propoxycarbonyl-substituted ethenyl, propenyl, butenyl,
pentenyl, ethinyl, propinyl or butinyl, or represents in
each case optionally nitro-, amino-, cyano-, carbomoyl-,
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-, trilluoromethylsulphonyl-, acetyl-,
propionyl-, n- or i-butyroyl-, methoxycarbonyl-,
ethoxycarbonyl-, n- or i-propoxycarbonyl-, acetylamino-,
propionylamino-, methoxycarbonylamino-,
ethoxycarbonylamino-, methylsulphonylamino-,
ethylsulphonylamino-, n- or i-propyl-sulphonylamino-substituted phenyl, naphthyl, benzyl or phenylethyl,

Q 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-, methylsuiphonyl
-, ethylsulphonyl-, n- or i-propylsuiphonyl-substituted
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-bulyl, 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,
methylsuiphonyl, 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, propertylthio, butenylthio,
propenylarnino or butenylamino, represents in each case
optionally fluorineand/or chlorine-substituted cyclopropyl,
cyclobutyl, cyclopentyl^ cyclohexyl, cyclopropyloxy,
cyclohexyl, cyclohexyl, cyclopentylthio
cyclopropylthio, cyclobutylthio, cyclopentylthio,
cyclohexylthio, cyclopropylamino, cyclobutylamino,
cyclopentylamiho, cyclohexylamino, cyclopropylmethyl,
cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,
cyclopropylmethoxy, cyclobutylmethoxy, cyclopentyl-
methoxy, cyclohexylmethoxy, cyclopropylmethylthio,
cyclobutylmethylamino, cyclopentylmethylamino,
cyclohexylmethylamino, 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, benayl, benzyloxy benzylthio or benzylainino, or - in the case that two adjacent radicals R^ 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 shlorine-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-
ort-butyl-mmethoxy-, ethoxy-, n- or i-propoxy-substituted
phenyl or benzyl, or together with an adjacent radical R^
^orR^ represents in each case optionally methyl- and/ or
ethyl-substituted propane-l,3-diyl(trimethylene), butane-
1,4-diyl (tetramethylene) • or pentane-l,5-diyl
(pentamethylene).
4. Com^pounds as claimed in any of claims 1 to 3, wherein
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, n-, or together with Ri 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, methyl-sulphonyl, 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, methyl-sulphonyl, 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-propcxy-, difluoromethoxy-,
trifluoromethoxy-, methylthio-, ethylthio-, n- or i-
propylthio-, difluoromethylthio-, trifluoromethylthio-,
methylsulphinyl-, ethylsulphinyl-, trifluoromethyl-
sulphinyl-, methylsulphonyl, ethylsulphonyl-,
trifluoromethylsulphonyl-, acetyl-, propionyl-,
methoxycarbonyl-, ethoxycarbonyl-, aceiylamino-,
propionylamino-, methoxycarbonylamino-, ethoxy-
carbonylamino-, methylsulphonylamino- or
ethylsulphonylamino substituted phenyl or ben2yl,
R5 represents hydrogen, fluorine, chlorine, bromine,
represents in each case optionally fluorine-, chlorine-,
methoxyn -, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-
, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-,
ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-
, i- or s-butyl, methoxy, ehtoxy, n- or i-propoxy, n-, i- or s-
butoxy, methylthio, ethylthio, n- or i-propylthio, n-, or i- or
s-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-
propylsulphinyl, methylsulphonyl, ethylsulphonyl, n-ori-
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 ethyenyl, propenyl, butenyl,
ethinyl, propinyl, butinyl, propenyloxy, butenyloxy,
propenylthio or represents in each case optionally fljorine-
and/or chlorine-subsituted cyclopropyl, cyclopropyloxy,
cyclopropylthio, cycloprpylamino, cyclopropylmethyl,
cyclopropylmethoxy, cyclopropylmethylthior or
cyclopropylmethylamino, and

R6 represents hydrogen, represents amino, represents in each
case optionally fluorine- and/or chlorine-, methoxy- or
ethoxy-substituted methyl, ethyl, methoxy, ethox^,
methylamino or ethylamino, represents dimethylamino, or
represents in each case optionally fljorine- and/or
chlorine-substituted cyclopropyl, cyclopropylmethyl,
phenyl or benzyl, or together with an adjacent radical RS
or R^ represent in each case optionally methyl- and/or
ethyl-substituted propane-1,3-diyl (trimethylene), butane-
1,4-diyl (tetramethylene) or pentane-l,5-diyl
(pentamethylene).
5. Compounds as claimed in any of claims 1 to 4, wherein
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
ben2yl.
6. Compounds as claimed in any of claims 1 to 5, wherein
R5 represents hydrogen, and

R6 represents methyl, ethyl,n- or i-propyl, n-, i-,s- or t-butyl, cyclopropyl, cyclopropylmethyl, or phenyl.
7. Compounds as claimed in any of claims 1 to 6, wherein n represents the num.ber 0,
8. Compounds as claimed in any of claims 1 to 7, wherein Z represents one of the groupings below

9. Compounds as claimed in any of claims 1 to 8, wherein Q represents oxygen.
10. Compounds as claimed in any of claims 1 to 9, wherein
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 amiono-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trifluoromethyl-, methoxy or ethoxy-substitued phenyl.

11. Compound of the formula (lA)

in which n, A, Ri, R2, R3, R4, y and Z are as defined in any of claims 1 to 9.
12. Compounds of the formula (IB)

in which n, A, R1, R2, R3, R4 y and Z are as defined in any of claims 1 to 9.
13. Compounds of the formula (IC)

in which n, A, R1, R2, R3, R4, y and Z are as defined in any of
claims 1 to 9. ^
14. Sodium, potassium, magnesium, calcium, ammonium, C1-C4-aIkyl-ammonium, di-(C1-C4-alkyl)-ammonium, tri-(C1 C4-aIkyl)-ammonium-, tetra-( Ci-C4-alkyl)-ammoniu, tri-( C1-C4-alkyl)-sulphonium, Cs- or C6-cycloalkyl-ammonium

and di-(C1-C2-alkyl)-ben2yl-ammonium salts of compounds of the formula (I) as claimed in any of claims 1 to 13, and their complex compounds with metals such as copper, iron, cobalt, nickel.
15. Process for preparing compounds as claimed in any of claims 1 to 12, wherein the compounds of the formula (II)

OD

in which
A, R1, R2, R3, R4 and Z are as defined in any of claims 1 to 9.
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)

(m)

in which
A, R1, R2, R3, R4, and Z are as defined in any of claims 1 to 9 and
X represents halogen
- after intermediate isolation or without intermediate isolation ("in situ")- are reacted in a second reaction step with mercapto compounds of the formula (IV)
HS-Y (IV)

in which
Y is as defined above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
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.

16. Substituted bezoylcyclohexenones of the formula (1) substantially as hereinbefore described with reference to the foregoing examples.
17. Process for preparing the compounds substantially as hereinbefore described with reference to the foregoing examples.

[DR. DEEPA K.JTIKU]
OF REMFRY & SAGAR
ATTORNEY FOR THE APPLICANTS
Dated this 23rd day of February, 2001.
127

Documents:

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194-mum-2001-correspondence(21-02-2007).pdf

194-mum-2001-correspondence(ipo)-(26-07-2007).pdf

194-mum-2001-form 1(23-02-2001).pdf

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194-mum-2001-form 3(31-05-2001).pdf

194-mum-2001-form 5(23-02-2001).pdf

194-mum-2001-petition under rule 138(28-07-2006).pdf

194-mum-2001-power of athority(08-06-2001).pdf

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Patent Number

208422

Indian Patent Application Number

194/MUM/2001

PG Journal Number

40/2008

Publication Date

03-Oct-2008

Grant Date

26-Jul-2007

Date of Filing

23-Feb-2001

Name of Patentee

BAYER AKTIENGESELLSCHAFT

Applicant Address

D-51368 LEVERKUSEN,

Inventors:

#	Inventor's Name	Inventor's Address
1	STEFAN HERRMANN	VIRNEBURGSTR. 4A, 40764 LANGENFELD,
2	DOROTHEE HOISCHEN	HORTENSIENSTR.31, 40474 DUSSELDORF
3	STEFAN LEHR	RICARDAHUCH-STR.38, 40764 LANGENFELD
4	OTTO SCHALLNER	NOLDEWEG 22, 40789 MONHEIM
5	MARK-WILHELM DREWES	GOETHESTR. 38, 40764 LANGENFELD
6	DIETER FEUCHT	ACKERWEG 9, 40789 MONHEIM,
7	ROLF PONTZEN	AM KLOSTER 69, 42799 LEICHLINGEN,
8	AKIHIKO YANAGI	2-40-11-303, HIGASHIJONAN, OYAMA-SHI, TOCHIGI 323-0829,
9	TOSHIO GOTO	214-18, KOGANEI, KOKUBUNJI-MACHI, SHIMOTSUGA-GUN, TOCHIGI 329-041
10	SEISHI ITO	1-41-10, EKIHIGASHITOURI, OYAMA-SHI, TOCHIGI 323-0022
11	CHIEKO UENO	7-2-1-606, JOTO, OYAMA-SHI, TOCHIGI 3230807
12	KLAUS-HELMUT MULLER	SOLFSTR.19,40593 DUSSELDORF,
13	HANSGEORG SCHWARZ	HEINENBUSCH 19E, 40764 LANGENFELD,
14	PETER DAHMEN	ALTERBRUCKER STR. 61, 41470 NEUSS,
15	SHINICHI NARABU	13850, YUKI, OAZA, YUKI-SHI, IBARAKI 307-0001

PCT International Classification Number

C07D 239/10

PCT International Application Number

N/A

PCT International Filing date

PCT Conventions:

#	PCT Application Number	Date of Convention	Priority Country
1	100 10937.3	2000-03-06	Germany