Phenyl-substituted cyclic enaminones

Abstract

The present invention relates to novel phenyl-substituted cyclic enaminones of the formula (I): in which Ar, X, Z, Y, K, n and m are each as defined in the description, to a plurality of processes and intermediates for their preparation and to their use as herbicides and pesticides.

1 . Compounds of the general formula (I)  
       
         
           
           
               
               
           
         
       
       in which 
 K represents oxygen or sulphur,  
 Ar represents in each case substituted phenyl, naphthyl or represents in each case optionally substituted mono- or bicyclic hetaryl having 5 to 10 ring atoms,  
 X represents CN,  
                     
 Y represents halogen or in each case optionally substituted alkyl, alkoxy, phenyl, phenylalkyl, hetaryl, hetarylalkyl or represents the groups  
                     
  two adjacent Y n  represent an in each case optionally substituted saturated or unsaturated cycle which may optionally be interrupted by heteroatoms, and  
 Z represents hydrogen, represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkyl-alkyl, alkoxyalkyl, phenoxyalkyl, phenylalkyl-oxyalkyl, phenylthioalkyl, phenylalkyl-thioalkyl, phenyl, phenylalkyl, hetaryl, hetaryl-alkyl or represents the groups  
                     
  or cyano,  
 l represents 0 to 3,  
 m represents 1 to 3,  
 n represents, depending on m, 0 to 4,  
 R 1  represents hydrogen, represents in each case optionally substituted, saturated or unsaturated alkyl or cycloalkyl, each of which is optionally interrupted by heteroatoms, represents in each case optionally substituted phenyl or hetaryl, represents in each case optionally substituted phenylalkyl or hetarylalkyl,  
 R 2  represents hydrogen, represents in each case optionally substituted, saturated or unsaturated alkyl or alkoxy, represents in each case optionally substituted phenyl, phenylalkyl or phenylalkyloxy, or  
 R 1 , R 2  together with the nitrogen atom to which they are attached represents an optionally substituted cycle which is optionally interrupted by heteroatoms,  
 R 3  represents hydrogen, represents in each case optionally substituted alkyl or alkoxy, represents in each case optionally substituted phenyl or phenylalkyl,  
 R 4  represents hydrogen or represents optionally substituted alkyl, and  
 R 5 ,R 6  independently of one another represent hydrogen or represent optionally substituted alkyl,  
  except for compounds of the following formula  
                     
 
     
     
         2 . Compounds according to  claim 1 , characterized in that 
 Ar represents Ar 1 , where Ar 1  represents phenyl, naphthyl or mono- or bicyclic hetaryl having five to ten ring atoms, each of which radicals is optionally mono- to pentasubstituted by halogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkinyl, C 1 -C 8 -alkoxy, C 2 -C 8 -alkenyloxy, C 3 -C 8 -alkinyloxy, C 1 -C 8 -alkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -halogeno-alkoxy, C 2 -C 8 -halogeno-alkenyloxy, C 1 -C 2 -alkylidenediyl-dioxy, C 1 -C 2 -halogenoalkylidenediyl-dioxy, halogeno-C 1 -C 4 -alkylthio, halogeno-C 1 -C 4 -alkylsulfinyl, halogeno-C 1 -C 4 -alkylsulfonyl, hydroxyl, mercapto, nitro, cyano, amino, or by the groups     a) -L-CO—R 7 ,                           or represents Ar 2 , where Ar 2  represents Ar 1  which is additionally substituted by phenyl, naphthyl, five- or six-membered hetaryl, phenyl-C 1 -C 4 -alkyl, phenoxy, phenyl-S(O) g —, five- or six-membered hetaryloxy or hetaryl-S(O) g , where these substituents for their part are in each case optionally mono- to tetrasubstituted by halogen, C 1 -C 6  alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, nitro or cyano, and    K represents oxygen or sulphur,    L represents oxygen or sulphur,    X represents CN,                          Y represents halogen, —C 1 -C 6 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 6 -alkoxy, represents phenyl, phenyl-di-C 4 alkyl, five- or six-membered hetaryl or five- or six-membered hetaryl-C 1 -C 4 -alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro, or represents the groups                           two adjacent Y n  represent a 5- to 8-membered, saturated or unsaturated cycle which may be interrupted by 1 to 3 heteroatoms from the group consisting of N, O, S and which may optionally be mono- to trisubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro, and    Z represents hydrogen, represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 8 -alkyl, cyano-C 1 -C 6 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkinyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkoxy-C 1 -C 4 -alkyl, represents phenoxy-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkyloxy-C 1 -C 4 -alkyl, phenylthio-C 1 -C 4 -alkyl, phenyl-C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, phenyl, phenyl-C 1 -C 4 -alkyl, five- or six-membered hetaryl, five- or six-membered hetaryl-C 1 -C 4 -alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogeno-alkoxy, nitro or cyano, or represents the groups                           or cyano,    g represents 0 to 2,    l represents 0 to 2,    R 1  represents hydrogen (but not for the radicals —CO 2 R 1  and —SO 2 R 1 ), represents in each case fluorine- and/or chlorine-substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 3 -C 6 -alkinyl, represents in each case optionally fluorine-, chlorine-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-substituted C 3 -C 8 -cycloalkyl or C 5 -C 8 -cycloalkenyl in which optionally one methylene group may be interrupted by oxygen or sulphur, or represents phenyl, pyridyl, thienyl, pyrimidyl, thiazolyl, phenyl-C 1 -C 4 -alkyl, pyridyl-C 1 -C 2 -alkyl, thiazolyl-C 1 -C 2 -alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro,    R 2  represents hydrogen, represents in each case optionally, fluorine- and/or chlorine-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy or represents phenyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -alkoxy, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro, or    R 1 , R 2  together with the nitrogen atom to which they are attached represent an optionally C 1 -C 4 -alkyl-substituted five- to eight-membered cycle in which optionally one methylene group may be replaced by oxygen or sulphur,    R 3  represents hydrogen, optionally halogen-substituted C 1 -C 6 -alkyl or represents phenyl or phenyl-C 1 -C 2 -alkyl each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro,    R 4  represents hydrogen or C 1 -C 6 -alkyl,    R 5 , R 6  independently of one another each represent hydrogen or optionally fluorine- and/or chlorine-substituted C 1 -C 4 -alkyl,    R 7  represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 3 -C 10 -alkinyl, C 1 -C 10 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 4 -alkyl, in each case optionally fluorine- and/or chlorine-, C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-substituted C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkyloxy in which optionally one methylene group may be replaced by oxygen or sulphur, represents phenyl, phenoxy, benzyloxy, five- or six-membered hetaryl or phenyl-C 1 -C 4 -alkyl, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alcyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogeno-alkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro, or, in the case of the radicals a) and c) mentioned under Ar, also represents a group                           or, for the radical g), also represents hydroxyl,    R 8  represents hydrogen or C 1 -C 4 -alkyl,    R 9  represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted C 1 -C 10 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkinyl, C 1 -C 10 -alkoxy, C 3 -C 8 -alkenyl-oxy, optionally fluorine-, chlorine-, C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-substituted C 3 -C 8 -cycloalkyl in which optionally one methylene group may be replaced by oxygen or sulphur, represents phenyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 2 -alkoxy, each of which is optionally mono- to tetrasubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogenoalkoxy, cyano or nitro,    R 10  represents hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -alkenyl, or    R 9 , R 10  together with the nitrogen atom to which they are attached represent an optionally C 1 -C 4 -alkyl-substituted five- to eight-membered cycle m which optionally one methylene group may be replaced by oxygen or sulphur, and    m represents 1 to 3, and    n depending on m, represents 0 to 3.    
     
     
         3 . Compounds according to  claim 1 , characterized in that 
 K represents oxygen or sulphur,    Ar represents Ar 1 , where Ar 1  represents phenyl, naphthyl, quinolinyl, thienyl, pyrimidyl, furanyl, thiazolyl, benzothiazolyl, oxazolyl, pyrazolyl or pyridyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkinyloxy, C 1 -C 6 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -halogeno-alkoxy, C 2 -C 4 -halogenoalkenyloxy, C 1 -C 2 -alkylidenediyl-dioxy, C 1 -C 2 -halogenoalkylidenediyl-dioxy, halogeno-C 1 -C 2 -alkylthio, halogeno-C 1 -C 2 -alkylsulfinyl, halogeno-C 1 -C 2 -alkylsulfonyl, hydroxyl, mercapto, nitro, cyano, amino or by one of the following groups                           or represents Ar 2 , where Ar 2  represents Ar 1  which is additionally substituted by phenyl, pyridyl, pyrimidyl, thienyl, furanyl, thiazolyl, tetrazolyl, triazolyl, benzyl, phenoxy, phenyl-S(O) g —, pyridyloxy, pyrimidyloxy, thiazolyloxy, pyridyl-S(O) g —, pyrimidyl-S(O) g — or thiazolyl-S(O) g —, where these substituents for their part are optionally mono- to tri-substituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, nitro or cyano, where g represents 0 to 2, and    L represents oxygen or sulphur,    X represents CN,                          Y represents fluorine, C 1 -C 4 -alkyl, C 1 -C 2 -halogenoalkyl, C 1 -C 4 -alkoxy, represents phenyl, phenyl-C 1 -C 2 -alkyl, thiazolylmethyl, pyridylmethyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C 1 -C 4 -allyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, cyano or nitro, or represents the groups 
 —CO 2 R 1  or  
                     
    two adjacent Y n  furthermore represent a 5- to 6-membered, saturated or unsaturated cycle which may be interrupted by a heteroatom from the group consisting of N, O, S and which may optionally be mono- to disubstituted by fluorine, chlorine, bromine, methyl, t-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, and    Z represents hydrogen, represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 6 -alkyl, cyano-C 1 -C 3 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 8 -alkinyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -halogeno-C 1 -C 2 -alkyl, represents phenoxy-C 1 -C 2 -alkyl, phenyl-C 1 -C 2 -alkyloxy-C 1 -C 2 -alkyl, phenylthio-C 1 -C 2 -alkyl, phenyl-C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl, phenyl-C 1 -C 2 -alkyl, phenyl, pyridyl-C 1 -C 2 -alkyl, thiazolyl-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, nitro or cyano, or represents the groups                           or cyano,    l represents 0 to 1,    R 1  represents hydrogen (but not for the radicals —CO 2 R 1  and O 2 R 1 ), represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 4 -alkinyl, represents optionally fluorine-, chlorine-, C 1 -C 2 -alkyl-, C 1 -C 2 -alkoxy-substituted C 3 -C 6 -cycloalkyl or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, cyano or nitro,    R 2  represents hydrogen, represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkinyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyloxy or represents phenyl, benzyl or benzyloxy, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, C 1 -C 2 -halogenoalkoxy, cyano or nitro, or    R 1 , R 2  together with the nitrogen atom to which they are attached represent an optionally C 1 -C 2 -alkyl-substituted five- or six-membered cycle in which optionally one methylene group may be replaced by oxygen,    R 3  represents hydrogen, represents C 1 -C 4 -alkyl or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro,    R 4 , R 5 , R 6  each represents hydrogen, methyl or ethyl,    R 7  represents in each case optionally fluorine- and/or chlorine-substituted C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, in each case optionally fluorine- and/or chlorine-, C—C 2 -alkyl-, C 1 -C 2 -alkoxy-substituted C 3 -C 6 -cycloalkyl in which optionally one methylene group may be replaced by oxygen, represents phenyl, phenoxy, benzyloxy, thienyl, furanyl, pyridyl, pyrimidyl, thiazolyl, pyrazolyl or phenyl-C 1 -C 2 -alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro, or, in the case of the radicals a) and c) mentioned under Ar, also represents a group                           for the radical g), also represents hydroxyl,    R 8  represents hydrogen,    R 9  represents hydrogen, in each case optionally fluorine- and/or chlorine-substituted C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkinyl, C 1 -C 6 -alkoxy, C 3 -C 6 -cycloalkyl, in which optionally one methylene group may be replaced by oxygen, represents phenyl or phenyl-C 1 -C 2 -alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, cyano or nitro,    R 10  represents hydrogen or C 1 -C 4 -alkyl, or    R 9 , R 10  together with the nitrogen atom to which they are attached represent an optionally C 1 -C 2 -alkyl-substituted five- to six-membered cycle in which optionally one methylene group may be replaced by oxygen, and    m represents 0 to 1, and    n depending on m, represents 0 to 2.    
     
     
         4 . Compounds according to  claim 1 , characterized in that 
 K represents oxygen or sulphur,    Ar represents Ar 1 , where Ar 1  represents phenyl, thienyl, pyrimidyl, furanyl or pyridyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, propoxy, i-propoxy, s-, n-, i- or t-butoxy, allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, hydroxyl, mercapto, nitro, cyano, amino or by one of the following groups                           or represents Ar 2 , where Ar 2  represents Ar 1  which is additionally substituted by phenyl, pyridyl, thienyl, tetrazolyl, triazolyl or phenoxy, where these substituents for their part are optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, s-, n-, i- or t-butyl, methoxy, ethoxy, i-propoxy, s-, n- or t-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, and    L represents oxygen or sulphur,    X represents —CN, —CO—NH 2 ,                          Y represents methyl, phenyl which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, or represents the group 
 —CO 2 R 1 , or  
    two adjacent Y n  represent a six-membered unsaturated cycle which may optionally be monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, and    Z represents hydrogen, methyl, ethyl, allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, methoxymethyl, ethoxymethyl, represents phenyl, benzyl, pyridylmethyl, thiazolylmethyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy, cyano or nitro, or represents the groups                           or cyano,    R 1  represents hydrogen (but not for the radicals O 2 R 1  and —SO 2 R 1 ), methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, allyl, propargyl, cyclopropyl, cyclopentyl, cyclohexyl, represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,    R 2  represents hydrogen, methyl, ethyl, propyl, isopropyl, allyl, propargyl, methoxy, ethoxy, allyloxy or represents benzyloxy which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or    R 1 , R 2  together with the nitrogen atom to which they are attached represent a pyrrolidine, piperidine, thiazine or morpholine radical,    R 3 , R 5  each represent hydrogen, methyl or ethyl,    R 7  represents methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, vinyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, n-, s-, i- or t-butyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cyclopentyloxy, cyclohexyloxy, represents phenyl, pyridyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, n-, s-, i- or t-butyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or, in the case of the radicals a) and c) mentioned under Ar, also represents a group                           , for the radical g), also represents hydroxyl,    R 9  represents hydrogen, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, cyclopropyl, cyclopentyl, cyclohexyl, represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,    R 10  represents hydrogen, methyl or ethyl, or    R 9 , R 10  together with the nitrogen atom to which they are attached represent a pyrrolidine, piperidine or morpholine radical, and    m represents 1 to 3, and    n depending on m, represents 0 to 1.    
     
     
         5 . Compounds according to  claim 1 , characterized in that 
 K represents oxygen or sulphur,    Ar represents Ar 1 , where Ar 1  represents phenyl, thienyl, pyrimidyl or pyridyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, methallyloxy, 2-butenyloxy, propargyloxy, 2-butinyloxy, methylthio, ethylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, methylenedioxy, difluoromethylenedioxy, tetrafluoroethylenedioxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, hydroxyl, mercapto, nitro, cyano, amino,     or represents Ar 2 , where Ar 2  represents Ar 2  which is additionally substituted by phenyl or phenoxy, where these substituents for their part are optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, isopropyl, n-, s-, i- or t-butyl, methoxy, ethoxy, isopropoxy, n-, s-, i- or t-butoxy, trifluoromethyl, trifluoromethoxy, nitro or cyano, and    X represents CN,    Z represents hydrogen or methyl,    m represents 1 to 3, and    n represents 0.    
     
     
         6 . Process for preparing compounds according to any of  claims 1  to  5 , characterized in that 
 (A) in the case where K represents oxygen and Z represents hydrogen,  
  compounds of the formula (II)  
                     
  in which  
  Ar and X are each as defined in any of  claims 1  to  5 ,  
  are reacted with compounds of the formula (III)  
                     
  in which 
 Y, m, n are each as defined in any of  claims 1  to  5 , and  
 W represents O or S(O) g , where g represents 0 or 2, and  
 R 11  represents alkyl or benzyl,  
 
  if appropriate in the presence of a diluent and if appropriate in the presence of a base or a metal compound of the formula (IIIa)  
 Me(V) 2   (IIIa)  
  in which 
 Me represents a divalent transition metal atom and  
 V represents a chelate ligand,  
 
  or in that  
 (B) in the case where K represents oxygen and Z represents hydrogen,  
  compounds of the formula (IV)  
                     
  in which 
 Ar and X are each as defined in any of  claims 1  to  5  and  
 Hal represents halogen,  
  are reacted with compounds of the formula (V)  
                     
 
  in which 
 Y, m and n are each as defined in any of  claims 1  to  5 ,  
 
  if appropriate in the presence of a diluent to give compounds of the formula (VI)  
                     
  in which 
 Ar, X, Y, m and n are each as defined in any of  claims 1  to  5 ,  
 
  which are reacted further, if appropriate in the presence of a base and if appropriate in the presence of a trivalent phosphorus compound, with elimination of sulphur and hydrogen halide, to give compounds of the formula (I)  
  in which 
 Ar, X, Y, m and n are each as defined in any of  claims 1  to  5  and  
 Z represents hydrogen,  
 
  or that  
 (C) in the case where K represents oxygen and Z does not represent hydrogen  
  compounds of the formula (VII)  
                     
  in which 
 Y, m and n are each as defined in any of  claims 1  to  5 ,  
 
  are reacted with halogenating agents, if appropriate in the presence of a diluent, to give compound of the formula (VIII)  
                     
  in which 
 Y, Z, m and n are each as defined in any of  claims 1  to  5   
  and Z does not represent hydrogen, and  
 Hal represents halogen,  
 
  which are then reacted with compounds of the formula (II)  
                     
  in which 
 Ar, X are each as defined in any of  claims 1  to  5 ,  
 
  if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,  
  or in that  
 (D) in the case where K represents oxygen and Z does not represent hydrogen,  
  compounds of the formula (I-a)  
                     
  in which 
 Ar, X, Y, m and n are each as defined in. any of claims  1  to S are reacted with  
  alkylating agents, acylating agents, sulphonylating agents or condensing agents of the formula (IX)  
 Z-G  (IX),  
  in which  
 G represents a leaving group such as halogen, sulphonate or alkoxy,  
 
  if appropriate in the presence of a solvent and if appropriate in the presence of a base,  
  or in that  
 (E) in the case where Ar represents Ar 2  according to any of  claims 1  to  5 ,  
  compounds of the formula (I 1 )  
                     
  in which 
 Ar 1 , X, Y, Z, m and n are each as defined in any of  claims 1  to  5  and  
 Hal represents halogen,  
 
  are reacted with boronic acids of the formula (X)  
 Ar 2 -B(OH) 2   (X),  
  in which 
 Ar 2  is as defined in any of  claims 2  to  5 ,  
 Ar 2′  represents the substituents which were mentioned in  claim 1  as additional substituents for Ar 1 ,  
 
  in the presence of a solvent, if appropriate in the presence of a base and/or a noble metal complex,  
  or in that  
 (F) compounds of the formula (I)  
                     
  in which 
 Ar, X, Y, Z, m and n are each as defined in any of  claims 1  to  5 , and  
 K represents oxygen,  
 
  are reacted in the presence of a sulphurizing agent in the presnce of a solvent.  
 Herbicidal, acaricidal and/or insecticidal compositions, characterized in that they comprise at least one compound according to any of  claims 1  to  5 .  
 
     
     
         8 . Use of compounds according to any of  claims 1  to  5  for controlling undesirable vegetation and/or animal pests.  
     
     
         9 . Compounds of the formula (V)  
       
         
           
           
               
               
           
         
       
       in which Y n  represents optionally substituted phenyl and m=1 or 2,  
       except for the compounds 5-phenyl-pyrrolidine-2-thione and 5-(3,4-dimethoxyphenyl)-pyrrolidine-2-thione.  
     
     
         10 . Compounds of the formula (II-1-b)  
       
         
           
           
               
               
           
         
       
       where 
 T is as defined in the table below:  
                         T           3-Cl, 4-F     4-Cl, 3-F     3,5-(CF 3 ) 2       2,4-Cl 2 , 5-F     3,5-Cl 2 , 4-F     4-Cl, 2-F     3-CF 3 , 5-CH 3       3-Cl, 4,5-F 2       4-CN, 2,5-F 2       2,3-F 2       3-F, 4-CF 3       3,4-O—CF 2 —O     3-NO 2 , 5-CF 3       4-Cl, 2,5-F 2       3,4,5-(OC 2 H 5 ) 3       4-Br, 2-F     2,6-Cl 2 , 4-CF 3       2-F, 4-NO 2       2,4-Cl 2 , 5-NO 2       4-Cl, 2-F, 5-NO 2       2,4-F 2 , 5-NO 2       4-Br, 2-F, 5-NO 2       2-F, 4-CF 3       4-OCF 3 , 3-NO 2       4-Cl, 2-NO 2       2-F, 3-CF 3       2-Cl, 6-F     2-Cl, 3-CF 3       3,4-O—(CF 2 ) 2 —O—     2-Cl, 4-SCH 3       2-Cl, 4-SO 2 CH 3                                                                     
 
     
     
         11 . Compounds of the formula (II-2-b)  
       
         
           
           
               
               
           
         
       
       where T is as defined in the table below:  
       
         
           
                 
               
                     
                 
                     
                 
                   T 
                 
                     
                 
                   2,6-Cl 2   
                 
                   2,6-Cl 2 , 4-CH 3   
                 
                   6-Cl