Substituted aryl ketones

Abstract

The invention relates to novel substituted aryl ketones of the general formula (I) in which n represents the number 0, 1 or 2, A represents alkanediyl (alkylene), R 1 represents one of the groupings below where m, R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 each have one of the meanings given in the description, R 2 represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphenyl, R 3 represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkyl-sulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and R 4 represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic heterocyclic grouping, and to processes for their preparation, to intermediates and to the use of these compounds as herbicides.

1 - 12 . (Cancelled).  
     
     
         12 . A substituted aryl ketone of the formula (I)  
       
         
           
           
               
               
           
         
       
       wherein 
 n represents the number 0, 1 or 2,  
 A represents alkanediyl (alkylene),  
 R 1  represents one of the groupings below  
                     
 where  
 m represents the numbers 0 to 6,  
 R 5  represents halogen or represents in each case optionally substituted alkyl, alkylthio or aryl or—if m represents 2—optionally also together with a second radical R 5  represents alkanediyl (alkylene),  
 R 6  represents hydroxyl, formyloxy, halogen, or represents in each case optionally substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy, aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl or arylalkylsulphonyl,  
 R 10  represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,  
 R 11  represents hydrogen or represents in each case optionally substituted alkyl or cycloalkyl,  
 R 12  represents hydrogen or represents in each case optionally substituted alkyl or cycloalkyl, and  
 R 13  represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,  
 R 2  represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl,  
 R 3  represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl, and  
 R 4  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 or two oxygen atoms or one or two sulphur atoms, or one or two SO groupings or one or two SO 2  groupings), and which additionally contains one to three oxo groups (C═O) and/or thioxo groups (C═S) as components of the heterocycle, including all possible tautomeric forms of the compounds of the formula (I) and the possible salts and acid or base adducts of the compounds of the formula (I).  
 
     
     
         13 . A compound of the formula (I) according to  claim 12 , wherein 
 n represents the number 0 or 1,    m represents the number 0, 1, 2, 3 or 4,    A represents alkanediyl (alkylene) having 1 to 6 carbon atoms,    R 1  represents one of the groupings below                          R 2  represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl- or C 1 -C 4 -alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,    R 3  represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl- or C 1 -C 4 -alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino or dialkylaminosulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,    R 4  represents one of the heterocyclic groupings below                                            where in each case the broken bond is a single bond or a double bond,    Q represents oxygen or sulphur,    R 14  represents hydrogen, hydroxyl, mercapto, cyano, halogen, represents in each case optionally cyano-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl- or C 1 -C 4 -alkylsulphonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkylamino or dialkylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl, alkenyloxy, alkenylthio or alkenylamino having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 4 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R 14  and R 14  are located at a double bond—also together with the adjacent radical R 14  represents a benzo grouping, and    R 15  represents hydrogen, hydroxyl, amino, alkylideneamino having up to 4 carbon atoms, represents in each case optionally halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkylamino, dialkylamino or alkaneoylamino having in each case up to 6 carbon atoms in the alkyl groups, represents in each case optionally halogen-substituted alkenyl, alkinyl or alkenyloxy having in each case up to 6 carbon atoms in the alkenyl or alkinyl groups, represents in each case optionally halogen-substituted cycloalkyl, cycloalkylalkyl or cycloalkylamino having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 carbon atoms in the alkyl moiety, or represents in each case optionally halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenyl or benzyl, or together with an adjacent radical R 14  or R 15  represents optionally halogen- or C 1 -C 4 -alkyl-substituted alkanediyl having 3 to 5 carbon atoms,    where the individual radicals R 14  and R 15 —if more than one of them are attached to the same heterocyclic groupings—can have identical or different meanings within the scope of the above definition,    R 5  represents halogen, represents in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl or alkylthio having in each case 1 to 6 carbon atoms, represents optionally halogen-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted phenyl, or optionally also—if m represents 2—together with a second radical R 5  represents alkanediyl having 2 to 6 carbon atoms,    R 6  represents hydroxyl, formyloxy, or represents in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano- or halogen-substituted alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms, or represents in each case optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -halogenoalkoxy-substituted aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl or arylalkylsulphonyl having in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety,    R 10  represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups,    R 11  represents hydrogen, represents optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms,    R 12  represents hydrogen, represents optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms or represents optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, and    R 13  represents hydrogen, cyano, carbamoyl, halogen, or represents in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups.    
     
     
         14 . A compound of the formula (I) according to  claim 12  wherein 
 m represents the numbers 0, 1, 2 or 3,    A represents methylene, ethane-1,2-diyl(dimethylene), ethane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl(trimethylene), butane-1,2-diyl, butane-1,3-diyl or butane-1,4-diyl(tetramethylene),    R 2  represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy- ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl,    R 3  represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, represents in each case optionally fluorine- and/or chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, represents in each case optionally fluorine- and/or chlorine-substituted methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, or represents methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, dimethylaminosulphonyl or diethylaminosulphonyl,    R 4  represents one of the heterocyclic groupings below,                          R 5  represents fluorine, chlorine, bromine, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, represents optionally fluorine-, chlorine-, methyl- or methoxy-substituted phenyl, or optionally also—if m represents 2—together with a second radical R 5  represents ethane-1,2-diyl(dimethylene), propane-1,3-diyl(trimethylene) or butane-1,4-diyl(tetramethylene),    R 6  represents hydroxyl, formyloxy, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted 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, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy, represents in each case optionally cyano-, fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy, or represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, benzoyloxy, benzoylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl or phenylmethylsulphonyl,    R 10  represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, 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, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,    R 11  represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,    R 12  represents hydrogen, represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,    R 13  represents hydrogen, cyano, carbamoyl, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy- or ethoxy-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, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,    R 14  represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, butenyl, ethinyl, propinyl, butinyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, represents pyrrolidino, piperidino or morpholino, or—if two adjacent radicals R 14  and R 14  are located at a double bond—together with the adjacent radical R 14  also represents a benzo grouping, and    R 15  represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl or propenyloxy, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, 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 R 14  or R 15  represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl(trimethylene) or butane-1,4-diyl(tetramethylene).    
     
     
         15 . A compound of the formula (I) according to  claim 12  wherein 
 m represents the number 0, 1 or 2,    A represents methylene or dimethylene,    R 2  represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl,    R 3  represents nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl or dimethylaminosulphonyl,    R 5  represents in each case optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, represents phenyl, or optionally also—if m represents 2—together with a second radical R 5  represents ethane-1,2-diyl(dimethylene), propane-1,3-diyl(trimethylene) or butane-1,4-diyl(tetramethylene),    R 6  represents hydroxyl, formyloxy, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy, represents propenyloxy or propinyloxy, or represents in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenoxy, phenylthio, phenylsulphinyl, phenylsulphonyl, benzoyloxy, benzoylmethoxy, phenylsulphonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulphinyl or phenylmethylsulphonyl,    R 10  represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl,    R 11  represents hydrogen, represents in each case optionally fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl,    R 12  represents hydrogen, represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl,    R 13  represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine-, chlorine-, bromine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl,    R 14  represents hydrogen, hydroxyl, mercapto, cyano, fluorine, chlorine, bromine, iodine, represents in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, represents methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, represents in each case optionally fluorine- and/or chlorine-substituted ethenyl, propenyl, ethinyl, propinyl, propenyloxy, propenylthio or propenylamino, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclopropyloxy, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy or cyclopropylmethylamino, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or—if two adjacent radicals R 14  and R 14  are located at a double bond—together with the adjacent radical R 14  also represents a benzo grouping, and    R 15  represents hydrogen, hydroxyl, amino, represents in each case optionally fluorine- and/or chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethylamino, represents propenyl or propinyl, represents in each case optionally fluorine- and/or chlorine-substituted cyclopropyl, cyclobutyl or cyclopropylmethyl, or represents in each case optionally fluorine-, chlorine-, methyl-, ethyl-, n- or i-propyl-, methoxy-, ethoxy-, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R 14  or R 15  represents in each case optionally methyl- and/or ethyl-substituted propane-1,3-diyl(trimethylene) or butane-1,4-diyl(tetramethylene).    
     
     
         16 . A process for preparing a compound of the formula (I) according to  claim 12  comprising the step of: 
 (a) reacting a substituted benzoic acid of the formula (II)                          wherein    n, A, R 2 , R 3  and R 4  are each as defined in  claim 12 ,    or reactive derivatives of said substituted benzoic acid, said reactive deriviatives optionally being selected from the group consisting of corresponding acid halides, acid cyanides and esters    with a compound of the formula (III)      R 1 —H   (III)    wherein    R 1  is as defined in  claim 12 ,    optionally in the presence of a dehydrating agent, optionally in the presence of one or more reaction auxiliaries and optionally in the presence of a diluent, or    (b) reacting a substituted benzoyl ketone of the formula (Ia)                          wherein    n, A, R 2 , R 3 , R 4  and R 11  are each as defined in  claim 12 ,    with an orthoformic ester or a N,N-dimethyl-formamide acetal or with a cyanoformic ester or with carbon disulphide and an alkylating agent, and then with hydroxylamine or an acid adduct thereof,    optionally in the presence of one or more reaction auxiliaries and optionally in the presence of one or more diluents,    and, optionally, following the the step of said process (a) or said process (b) according to the invention, subjecting the resulting compound of the formula (I) to one or more substitution, oxidation or reduction reactions within the scope of the definition of the substituents and/or converting the compounds of the formula (I) into salt-like compounds.    
     
     
         17 . A compound of the formula (II)  
       
         
           
           
               
               
           
         
       
       wherein 
 n, A, R 2 , R 3  and R 4  are each as defined in  claim 12 ,  
 and reactive derivatives thereof.  
 
     
     
         18 . A process for preparing a compound of the formula (II) according to  claim 17  comprising the step of: 
 (α) reacting a compound of the formula (IV)                          wherein    n, A, R 2  and R 3  are each as defined in  claim 12  and    X 1  represents halogen or represents alkylsulphonyloxy    or derivatives thereof    with a heterocyclic compound of the formula (V)      H—R 4    (V)    wherein    R 4  is as defined in  claim 12 ,    optionally in the presence of an acid acceptor and optionally in the presence of a diluent, at temperatures between 10° C. and 150° C., optionally followed by one or more additional conversion reactions within the scope of the definition of the substituents, or    (β) reacting a compound of the formula (VI)                          wherein    n, R 2  and R 3  are each as defined in  claim 12 ,    or derivatives thereof    with a hydroxyalkylheterocycle of the formula (VII)                          wherein    A and R 4  are each as defined in  claim 12 ,    in the presence of one or more condensing agents and, optionally, in the presence of a diluent, at temperatures between −20° C. and +50° C., optionally followed by one or more additional conversion reactions within the scope of the definition of the substituents, or    (γ) reacting a compound of the formula (VI)                          wherein    n, R 2  and R 3  are each as defined in  claim 12 ,    or derivatives thereof    with a halogenoalkylheterocycle of the formula (VIII)                          wherein    A and R 4  are each as defined in  claim 12  and    X 2  represents halogen, represents alkylsulphonyloxy or represents arylsulphonyloxy,    optionally in the presence of an acid acceptor and optionally in the presence of a diluent, at temperatures between 0° C. and 150° C., optionally followed by one or more additional conversion reactions within the scope of the definition of the substituents.    
     
     
         19 . A compound of the formula (Ia)  
       
         
           
           
               
               
           
         
       
       wherein 
 n, A, R 2 , R 3 , R 4  and R 11  are each as defined in  claim 12 .  
 
     
     
         20 . A method for controlling one or more undesirable plants, comprising the step of allowing at least one compound of the formula (I) according to  claim 12  to act on said one or more undesirable plants and/or their habitats.