2,4,6-Phenyl-Substituted Cyclic Ketoenols

Abstract

The invention relates to novel 2,4,6-phenyl-substituted cyclic ketoenols of the formula (I), in which CKE, W, X and Y are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides, and also to selective herbicidal compositions comprising firstly the 2,4,6-phenyl-substituted cyclic ketoenols and secondly at least one compound which improves crop plant tolerance.

1 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         in which 
         W represents alkoxy, haloalkoxy, alkoxyalkoxy, alkoxybisalkoxy, bisalkoxyalkoxy or optionally substituted cycloalkylalkanediyloxy which may optionally be interrupted by heteroatoms, 
         X represents halogen, 
         Y represents alkyl, 
         CKE represents 
       
       
         
           
           
               
               
           
         
         
           in which 
         
         A represents hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom, or in each case optionally halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted aryl, arylalkyl or hetaryl, 
         B represents hydrogen, alkyl or alkoxyalkyl, or 
         A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom, 
         G represents hydrogen (a) or represents one of the groups 
       
       
         
           
           
               
               
           
         
         
           in which 
           E represents a metal ion equivalent or an ammonium ion, 
           L represents oxygen or sulphur, 
           M represents oxygen or sulphur, 
           R 1  represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which may be interrupted by at least one heteroatom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, 
           R 2  represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, 
           R 3 , R 4  and R 5  independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, 
           R 6  and R 7  independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with the N atom to which they are attached represent a cycle which is optionally interrupted by oxygen or sulphur. 
         
       
     
     
         2 . A compound of the formula (I) according to  claim 1  in which
 W represents C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 4 -alkoxy-C 2 -C 4 -alkoxy, C 1 -C 4 -alkoxy-bis-C 2 -C 4 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkanediyloxy which is optionally mono- to trisubstituted by fluorine, chlorine, C 1 -C 3 -alkyl or C 1 -C 3 -alkoxy and in which optionally one methylene group of the ring may be interrupted by oxygen or sulphur, 
 X represents halogen, 
 Y represents C 1 -C 4 -alkyl, 
 CKE represents 
 
       
         
           
           
               
               
           
         
         A represents hydrogen or in each case optionally halogen-substituted C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, alkyl, optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen and/or sulphur or represents in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkoxy-, cyano- or nitro-substituted phenyl or naphthyl, hetaryl having 5 to 6 ring atoms, phenyl-C 1 -C 6 -alkyl or naphthyl-C 1 -C 6 -alkyl, 
         B represents hydrogen, C 1 -C 12 -alkyl or C 1 -C 8 -alkoxy-C 1 -C 6 -alkyl, or 
         A, B and the carbon atom to which they are attached represent saturated C 3 -C 10 -cycloalkyl or unsaturated C 5 -C 10 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which are optionally mono- or disubstituted by C 1 -C 8 -alkyl, C 3 -C 10 -cycloalkyl, C 1 -C 8 -haloalkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylthio, halogen or phenyl or 
         A, B and the carbon atom to which they are attached represent C 3 -C 6 -cycloalkyl which is substituted by an alkylenedithioyl or by an alkylenedioxyl or by an alkylenediyl group which optionally contains one or two not directly adjacent oxygen and/or sulphur atoms and which is optionally substituted by C 1 -C 4 -alkyl, which, together with the carbon atom to which it is attached, forms a further five- to eight-membered ring or 
         A, B and the carbon atom to which they are attached represent C 3 -C 8 -cycloalkyl or C 5 -C 8 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent in each case optionally C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy- or halogen-substituted C 2 -C 6 -alkanediyl, C 2 -C 6 -alkenediyl or C 4 -C 6 -alkanedienediyl in which optionally one methylene group is replaced by oxygen or sulphur, 
         G represents hydrogen (a) or represents one of the groups 
       
       
         
           
           
               
               
           
         
         
           in which 
           E represents a metal ion equivalent or an ammonium ion, 
           L represents oxygen or sulphur and 
           M represents oxygen or sulphur, 
         
         represents in each case optionally halogen-substituted C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, C 1 -C 8 -alkylthio-C 1 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl or optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl in which optionally one or more not directly adjacent ring members are replaced by oxygen and/or sulphur,
 represents optionally halogen-, cyano-, nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkyl-, C 1 -C 6 -haloalkoxy-, C 1 -C 6 -alkylthio- or C 1 -C 6 -alkylsulphonyl-substituted phenyl, 
 represents optionally halogen-, nitro-, cyano-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkyl- or C 1 -C 6 -haloalkoxy-substituted phenyl-C 1 -C 6 -alkyl, 
 represents optionally halogen- or C 1 -C 6 -alkyl-substituted 5- or 6-membered hetaryl, 
 represents optionally halogen- or C 1 -C 6 -alkyl-substituted phenoxy-C 1 -C 6 -alkyl or 
 represents optionally halogen-, amino- or C 1 -C 6 -alkyl-substituted 5- or 6-membered hetaryloxy-C 1 -C 6 -alkyl, 
 
         R 2  represents in each case optionally halogen-substituted C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl,
 represents optionally halogen-, C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl or 
 represents in each case optionally halogen-, cyano-, nitro-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 6 -haloalkyl- or C 1 -C 6 -haloalkoxy-substituted phenyl or benzyl, 
 
         R 3  represents optionally halogen-substituted C 1 -C 8 -alkyl or represents in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -haloalkoxy-, cyano- or nitro-substituted phenyl or benzyl, 
         R 4  and R 5  independently of one another represent in each case optionally halogen-substituted C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -alkylamino, di-(C 1 -C 8 -alkyl)amino, C 1 -C 8 -alkylthio, C 2 -C 8 -alkenylthio, C 3 -C 7 -cycloalkylthio or represent in each case optionally halogen-, nitro-, cyano-, C 1 -C 4 -alkoxy-, C 1 -C 4 -haloalkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -haloalkylthio-, C 1 -C 4 -alkyl- or C 1 -C 4 -haloalkyl-substituted phenyl, phenoxy or phenylthio, 
         R 6  and R 7  independently of one another represent hydrogen, represent in each case optionally halogen-substituted C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -alkoxy, C 3 -C 8 -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, represent optionally halogen-, C 1 -C 8 -haloalkyl-, C 1 -C 8 -alkyl- or C 1 -C 8 -alkoxy-substituted phenyl, represent optionally halogen-, C 1 -C 8 -alkyl-, C 1 -C 8 -haloalkyl- or C 1 -C 8 -alkoxy-substituted benzyl or together represent an optionally C 1 -C 4 -alkyl-substituted C 3 -C 6 -alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur. 
       
     
     
         3 . A compound of the formula (I) according to  claim 1  in which
 W represents C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 3 -alkoxy-C 2 -C 3 -alkoxy, C 1 -C 2 -alkoxy-bis-C 2 -C 3 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkanediyloxy in which optionally one methylene group of the ring may be replaced by oxygen, 
 X represents chlorine or bromine, 
 Y represents methyl, ethyl or propyl, 
 CKE represents one of the groups 
 
       
         
           
           
               
               
           
         
         A represents hydrogen, represents C 1 -C 6 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, represents C 3 -C 6 -cycloalkyl which is optionally mono- to disubstituted by C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy 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 2 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkoxy, cyano or nitro, 
         B represents hydrogen, C 1 -C 4 -alkyl or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, or 
         A, B and the carbon atom to which they are attached represent saturated or unsaturated C 5 -C 7 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally mono- to disubstituted by C 1 -C 6 -alkyl, trifluoromethyl or C 1 -C 6 -alkoxy, with the proviso that in this case Q 3  represents hydrogen or methyl, or 
         A, B and the carbon atom to which they are attached represent C 5 -C 6 -cycloalkyl which is optionally substituted by an alkylenedithiol group or by an alkylenedioxyl group or by an alkylenediyl group which optionally contains one or two not directly adjacent oxygen or sulphur atoms and which is optionally substituted by methyl or ethyl, which group, together with the carbon atom to which it is attached, forms a further five- or six-membered ring, with the proviso that in this case Q 3  represents hydrogen or methyl, 
         A, B and the carbon atom to which they are attached represent C 3 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent in each case optionally C 1 -C 2 -alkyl- or C 1 -C 2 -alkoxy-substituted C 2 -C 4 -alkanediyl, C 2 -C 4 -alkenediyl or butadienediyl, with the proviso that in this case Q 3  represents hydrogen or methyl, 
         G represents hydrogen (a) or represents one of the groups 
       
       
         
           
           
               
               
           
         
         
           in which 
           E represents a metal ion equivalent or an ammonium ion, 
           L represents oxygen or sulphur and 
           M represents oxygen or sulphur, 
         
         R 1  represents C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or C 3 -C 6 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy and in which optionally one or two not directly adjacent ring members are replaced by oxygen,
 represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, 
 
         R 2  represents C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine,
 represents C 3 -C 6 -cycloalkyl which is optionally monosubstituted by C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy or 
 represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 3 -alkoxy, trifluoromethyl or trifluoromethoxy, 
 
         R 3  represents C 1 -C 6 -alkyl which is optionally mono- to trisubstituted by fluorine or represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, 
         R 4  represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di-(C 1 -C 6 -alkyl)amino, C 1 -C 6 -alkylthio, C 3 -C 4 -alkenylthio, C 3 -C 6 -cycloalkylthio or represents phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -haloalkylthio, C 1 -C 3 -alkyl or trifluoromethyl, 
         R 5  represents C 1 -C 6 -alkoxy or C 1 -C 6 -alkylthio, 
         R 6  represents hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, represents benzyl which is optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, trifluoromethyl or C 1 -C 4 -alkoxy, 
         R 7  represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, 
         R 6  and R 7  together represent a C 4 -C 5 -alkylene radical which is optionally substituted by methyl or ethyl and in which optionally one methylene group is replaced by oxygen or sulphur. 
       
     
     
         4 . A compound of the formula (I) according to  claim 1  in which
 W represents methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, methoxyethoxy, ethoxyethoxy, cyclopropylmethoxy, cyclopentylmethoxy or cyclohexylmethoxy, 
 X represents chlorine or bromine, 
 Y represents methyl or ethyl, 
 CKE represents 
 A represents hydrogen, represents C 1 -C 4 -alkyl or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, represents cyclopropyl, cyclopentyl or cyclohexyl, 
 B represents hydrogen, methyl or ethyl, or 
 A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 -cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally monosubstituted by methyl, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy, or 
 A, B and the carbon atom to which they are attached represent C 6 -cycloalkyl which is substituted by an alkylenedioxyl group having two not directly adjacent oxygen atoms, or 
 A, B and the carbon atom to which they are attached represent C 5 -C 6 -cycloalkyl or C 5 -C 6 -cycloalkenyl in which two substituents together with the carbon atoms to which they are attached represent C 2 -C 4 -alkanediyl or C 2 -C 4 -alkenediyl or butadienediyl, or 
 G represents hydrogen (a) or represents one of the groups 
 
       
         
           
           
               
               
           
         
         in which 
         E represents an ammonium ion,
 L represents oxygen or sulphur and 
 M represents oxygen or sulphur, 
 
         R 1  represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -alkyl, C 1 -C 2 -alkylthio-C 1 -alkyl or represents C 3 -C 6 -cyclopropyl which is optionally monosubstituted by fluorine, chlorine, methyl or methoxy or represents C 1 -C 4 -alkyl which is monosubstituted by chlorine,
 represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, 
 
         R 2  represents phenyl or benzyl, C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, each of which is optionally mono- to trisubstituted by fluorine, 
         R 3  represents C 1 -C 6 -alkyl. 
       
     
     
         5 . A compound of the formula (I) according to  claim 1  in which
 W represents methoxy, ethoxy, n-propoxy, methoxyethoxy or cyclopropylmethoxy, 
 X represents chlorine, 
 Y represents methyl, 
 CKE represents 
 
       
         
           
           
               
               
           
         
         A represents methyl, isopropyl, isobutyl or cyclopropyl, 
         B represents hydrogen, methyl or ethyl, 
         A, B and the carbon atom to which they are attached represent saturated C 5 -C 6 -cycloalkyl in which optionally one ring atom is replaced by oxygen and which is optionally monosubstituted by methyl or methoxy, 
         G represents hydrogen (a) or represents one of the groups 
       
       
         
           
           
               
               
           
         
         E represents an ammonium ion, 
         R 1  represents C 1 -C 6 -alkyl, C 1 -C 2 -alkoxy-C 1 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkyl which is monosubstituted by chlorine or represents phenyl which is optionally monosubstituted by chlorine, 
         R 2  represents C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl or benzyl, 
         R 3  represents C 1 -C 6 -alkyl. 
       
     
     
         6 . A process for preparing a compound of the formula (I) according to  claim 1 , comprising
 (A) obtaining a compound of formula (I-2-a)   
       
         
           
           
               
               
           
         
         
           in which 
           A, B, W, X and Y are as defined in  claim 1 , 
           by the intramolecular condensation of a compound of formula (III) 
         
       
       
         
           
           
               
               
           
         
         
           in which 
           A, B, W, X, and Y are as defined in  claim 1  and R 8  is alkyl, 
           in the presence of a diluent and in the presence of a base; 
         
         (B) obtaining a compound of formula (I-2-b) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, R 1 , W, X and Y are as defined in  claim 1 , by reacting a compound of formula (I-2-a) in which A, B, W, X and Y are as defined in  claim 1   
           (α) with an acid halide of formula (XIII) 
         
       
       
         
           
           
               
               
           
         
         
           in which 
           R 1  is as defined in  claim 1  and 
           Hal represents halogen, 
           or 
           (β) with a carboxylic anhydride of formula (XIV)
   R 1 —CO—O—CO—R 1   (XIV)
 
 
           in which 
           R 1  is as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (C) obtaining a compound of formula (I-2-c) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, R 2 , M, W, X and Y are as defined in  claim 1  and L represents oxygen, by reacting a compound of formula (I-2-a) 
           with a chloroformic ester or a chloroformic thioester of formula (XV)
   R 2 -M-CO—Cl  (XV)
 
 
           in which 
           R 2  and M are as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (D) obtaining a compound of formula (I-2-c) in which A, B, R 2 , M, W, X and Y are as defined in  claim 1  and L represents sulphur, by reacting a compound of formula (I-2-a)
 with a chloromonothioformic ester or a chlorodithioformic ester of formula (XVI) 
 
       
       
         
           
           
               
               
           
         
         
           in which 
           M and R 2  are as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (E) obtaining a compound of formula (I-2-d) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, R 3 , W, X and Y are as defined in  claim 1 , by reacting a compound of formula (I-2-a) 
           with a sulphonyl chlorides chloride of the formula (XVII)
   R 3 —SO 2 —Cl  (XVII)
 
 
           in which 
           R 3  is as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (F) obtaining a compound of formula (I-2-e) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, L, R 4 , R 5 , W, X and Y are as defined in  claim 1 , by reacting a compound of formula (I-2-a) 
           with a phosphorus compound of formula (XVIII) 
         
       
       
         
           
           
               
               
           
         
         
           in which 
           L, R 4  and R 5  are as defined in  claim 1  and 
           Hal represents halogen, 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (G) obtaining a compound of formula (I-2-f) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, E, W, X and Y are as defined in  claim 1 , by reacting, a compound of formula (I-2-a) 
           with a metal compound or an amine of formulae (XIX) and (XX), respectively, 
         
       
       
         
           
           
               
               
           
         
         
           in which 
           Me represents a mono- or divalent metal, 
           t represents the number 1 or 2 and 
           R 10 , R 11 , R 12  independently of one another represent hydrogen or alkyl, 
           optionally in the presence of a diluent; 
         
         (H) obtaining a compound of formula (I-2-g) 
       
       
         
           
           
               
               
           
         
         
           in which A, B, L, R 6 , R 7 , W, X and Y are as defined in  claim 1 , by reacting a compound of formula (I-2-a) 
           (α) with an isocyanate or an isothiocyanate of formula (XXI)
   R 6 —N═C=L  (XXI)
 
 
           in which 
           R 6  and L are as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of a catalyst, or 
         
         (β) with a carbamoyl chloride or a thiocarbamoyl chloride of formula (XXII) 
       
       
         
           
           
               
               
           
         
         
           in which 
           L, R 6  and R 7  are as defined in  claim 1 , 
           optionally in the presence of a diluent and optionally in the presence of an acid binder; 
         
         (I) obtaining a compound of formula (I-2-a) by reacting a compound of formula (I-2-a′) in which A, B, X and Y are as defined in  claim 1  and W′ represents bromine 
       
       
         
           
           
               
               
           
         
         
           with an alcohol of formula
   W—OH
 
 
           in which 
           W is as defined in  claim 1 , optionally in the presence of a solvent, a Cu(I) salt and a strong base. 
         
       
     
     
         7 - 26 . (canceled) 
     
     
         27 . A pesticide, herbicide or a combination thereof, comprising at least one compound of the formula (I) according to  claim 1 . 
     
     
         28 . A method for controlling animal pests, and/of unwanted vegetation, or a combination thereof, comprising contacting a compound of the formula (I) according to  claim 1  with pests, their habitat, or a combination thereof. 
     
     
         29 . (canceled) 
     
     
         30 . A process for preparing a pesticide, a herbicide, or a combination thereof, comprising mixing a compound of the formula (I) according to  claim 1  with an extender, a surfactant or a combination thereof. 
     
     
         31 . A composition, comprising an effective amount of an active compound combination comprising
 a′) at least one substituted cyclic ketoenol of the formula (I) according to  claim 1     and   (b′) at least one compound which improves crop plant tolerance and which is selected from the group consisting of:
 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloroacetylhexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (dicyclonon, BAS-145138), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine (benoxacor), 1-methyl-hexyl 5-chloio-quinolin-8-oxy-acetate (cloquintocet-mexyl), 3-(2-chloro-benzyl)-1-(1-methyl-1-phenyl-ethyl)-urea (cumyluron), α-(cyanomethoximino)-phenylacetonitrile (cyometrinil), 2,4-dichloro-phenoxyacetic acid (2,4-D), 4-(2,4-dichloro-phenoxy)-butyric acid (2,4-DB), 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea (daimuron, dymron), 3,6-dichloro-2-methoxy-benzoic acid (dicamba), S-1-methyl-1-phenyl-ethyl piperidine-1-thiocarboxylate (dimepiperate), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), ethyl 1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl, phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-α-trifluoro-acetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (farilazole, MON-13900), ethyl 4,5-dihydro-5,5-diphenyl-3-isoxazolecarboxylate (isoxadifen-ethyl), 1-(ethoxycarbonyl)-ethyl-3,6-dichloro-2-methoxybenzoate (lactidichlor), (4-chloro-o-tolyloxy)-acetic acid (MCPA), 2-(4-chloro-o-tolyloxy)-propionic acid (mecoprop), diethyl 1-(2,4-dichloro-phenyl)-4,5-dihydro-5-methyl-1H-pyrazole-3,5-dicarboxylate (mefenpyr-diethyl), 2-dichloromethyl-2-methyl-1,3-dioxolane (MG-191), 2-propenyl-1-oxa-4-azaspiro[4.5]decane 4-carbodithioate (MG-838), 1,8-naphthalic anhydride, α-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 3-dichloroacetyl-2,2-dimethyl-oxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyl-oxazolidine (R-29148), 4-(4-chloro-o-tolyl)-butyric acid, 4-(4-chloro-phenoxy)-butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichloro-phenyl)-5-phenyl-1H-pyrazole-3-carboxylate), ethyl 5-(2,4-dichloro-benzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluoro-phenyl)-5-phenyl-2-isoxazoline-3-carboxylate), 1,3-dimethyl-but-1-yl 5-chloro-quinolin-8-oxy-acetate, 4-allyloxy-butyl 5-chloro-quinolin-8-oxy-acetate, 1-allyloxy-prop-2-yl 5-chloro-quinolin-8-oxy-acetate, methyl 5-chloro-quinoxalin-8-oxy-acetate, ethyl 5-chloro-quinolin-8-oxy-acetate, allyl 5-chloro-quinoxalin-8-oxy-acetate, 2-oxo-prop-1-yl 5-chloro-quinolin-8-oxy-acetate, diethyl 5-chloro-quinolin-8-oxy-malonate, diallyl 5-chloro-quinoxalin-8-oxy-malonate, diethyl 5-chloro-quinolin-8-oxy-malonate), 4-carboxy-chroman-4-yl-acetic acid (AC-304415), 4-chloro-phenoxy-acetic acid, 3,3′-dimethyl-4-methoxy-benzophenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methylamino-carbonyl)-amino]-benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)-phenyl]-3,3-dimethyl-urea, 1-[4-(N-4,5-dimethylbenzoylsulphamoyl)-phenyl]-3-methyl-urea, 1-[4-(N-naphthylsulphamoyl)-phenyl]-3,3-dimethyl-urea, N-(2-methoxy-5-methyl-benzoyl)-4-(cyclopropylaminocarbonyl)-benzenesulphonamide, 
 a compound of formula (IIa) 
   
       
         
           
           
               
               
           
         
         
           a compound of formula (IIb) 
         
       
       
         
           
           
               
               
           
         
         a compound of formula (IIc) 
       
       
         
           
           
               
               
           
         
         where 
         m is 0, 1, 2, 3, 4 or 5, 
         A 1  represents one of the divalent heterocyclic groups outlined hereinbelow, 
       
       
         
           
           
               
               
           
         
         n is 0, 1, 2, 3, 4 or 5, 
         A 2  represents alkanediyl having 1 or 2 carbon atoms which is optionally substituted by C 1 -C 4 -alkyl and/or C 1 -C 4 -alkoxy-carbonyl and/or C 1 -C 4 -alkenyloxy-carbonyl, 
         R 14  represents hydroxyl, mercapto, amino, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di-(C 1 -C 4 -alkyl)amino, 
         R 15  represents hydroxyl, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxy-C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di-(C 1 -C 4 -alkyl)amino, 
         R 16  represents C 1 -C 4 -alkyl which is optionally substituted by fluorine, chlorine and/or bromine, 
         R 17  represents hydrogen, or represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which is optionally substituted by fluorine, chlorine and/or bromine or C 1 -C 4 -alkyl, 
         R 18  represents hydrogen, or represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, dioxolanyl-C 1 -C 4 -alkyl, furyl, furyl-C 1 -C 4 -alkyl, thienyl, thiazolyl, piperidinyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, or represents phenyl which is optionally substituted by fluorine, chlorine and/or bromine or C 1 -C 4 -alkyl, or R 17  and R 18  together also represent C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which is optionally substituted by C 1 -C 4 -alkyl, phenyl, furyl, a fused benzene ring or by two substituents which, together with the C atom to which they are bonded, form a 5- or 6-membered carbocycle, 
         R 19  represents hydrogen, cyano, halogen, or represents C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, 
         R 20  represents hydrogen, or represents C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri(C 1 -C 4 -alkyl)silyl, each of which is optionally substituted by hydroxyl, cyano, halogen or C 1 -C 4 -alkoxy, 
         R 21  represents hydrogen, cyano, halogen, or represents C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl, each of which is optionally substituted by fluorine, chlorine and/or bromine, 
         X 1  represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 
         represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 
         X 3  represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 
         a compound of formula (IId) 
       
       
         
           
           
               
               
           
         
       
       and
 a compound of formula (IIe) 
 
       
         
           
           
               
               
           
         
         where 
         t is 0, 1, 2, 3, 4 or 5, 
         v is 0, 1, 2, 3, 4 or 5, 
         R 22  represents hydrogen or C 1 -C 4 -alkyl, 
         R 23  represents hydrogen or C 1 -C 4 -alkyl, 
         R 24  represents hydrogen, or represents C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di-(C 1 -C 4 -alkyl)amino, each of which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy, or represents C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino, each of which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, 
         R 25  represents hydrogen, or represents C 1 -C 6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or C 1 -C 4 -alkoxy, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, each of which is optionally substituted by cyano or halogen, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, 
         R 26  represents hydrogen, or represents C 1 -C 6 -alkyl which is optionally substituted by cyano, hydroxyl, halogen or C 1 -C 4 -alkoxy, or represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, each of which is optionally substituted by cyano or halogen, or represents C 3 -C 6 -cycloalkyl which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, or represents phenyl which is optionally substituted by nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, or together with R 25  represents C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, each of which is optionally substituted by C 1 -C 4 -alkyl, 
         X 4  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, and 
         X 5  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy. 
       
     
     
         32 . A composition according to  claim 31 , in which the compound which improves crop plant tolerance is selected from:
 cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, compounds IIe-5 or IIe-11   
       
         
           
           
               
               
           
         
       
     
     
         33 . A method for controlling unwanted vegetation, comprising contacting a composition according to  claim 31  on the plants, their habitat, or combinations thereof. 
     
     
         34 . (canceled) 
     
     
         35 . A composition according to  claim 31 , wherein the compound which improves crop plant tolerance is cloquintocet-mexyl or mefenpyr-diethyl.