2,4,6-Phenyl-substituted cyclic ketoenols

Abstract

The present invention relates to novel 2,4,6-phenyl-substituted cyclic ketoenols of the formula (I) in which W, X, Y and CKE have the meanings given in the disclosure, to a plurality of processes for their preparation and to their use as pesticides and/or herbicides. The invention further relates to selectively herbicidal compositions containing 2,4,6-phenyl-substituted cyclic ketoenols and a compound which improves crop plant tolerance.

1 - 35 . (canceled) 
     
     
         36 . A compound of formula (I) 
       
         
           
           
               
               
           
         
         in which 
         W represents alkoxy, halogenoalkoxy, alkoxyalkyloxy, alkoxy-bis-alkyloxy, or optionally substituted cycloalkylalkanediyloxythat is optionally interrupted by hetero atoms, 
         X represents alkyl, 
         Y represents chlorine, bromine, or iodine, and 
         CKE represents a group 
       
       
         
           
           
               
               
           
         
         
           in which 
           A represents hydrogen; represents alkyl, alkenyl, alkoxyalkyl, or alkylthioalkyl, each of which is optionally substituted by halogen; represents saturated or unsaturated, optionally substituted cycloalkyl in which one or more ring atoms are optionally replaced by a hetero atom; or represents aryl, arylalkyl, or hetaryl, each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, cyano, or nitro, 
           D represents hydrogen; represents an optionally substituted radical selected from the series consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, and saturated or unsaturated cycloalkyl in which one or more ring members are optionally replaced by hetero atoms; or represents arylalkyl, aryl, hetarylalkyl, or hetaryl, or 
           A and D together with the atoms to which they are bonded represent a saturated or unsaturated cycle that is unsubstituted or substituted in the A,D moiety and optionally contains one or more hetero atoms, and 
           G represents hydrogen (a) or a group 
         
       
       
         
           
           
               
               
           
         
         
           
             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 alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, or poly-alkoxyalkyl, each of which is optionally substituted by halogen; represents cycloalkyl that is optionally interrupted by one or more hetero atoms and is optionally substituted by halogen, alkyl, or alkoxy; or represents optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl, or hetaryloxyalkyl, 
             R 2  represents alkyl, alkenyl, alkoxyalkyl, or polyalkoxyalkyl, each of which is optionally substituted by halogen; or represents optionally substituted cycloalkyl, phenyl, or benzyl, 
             R 3 , R 4  and R 5  independently of one another represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, or cycloalkylthio, each of which is optionally substituted by halogen; or represent optionally substituted phenyl, benzyl, phenoxy, or phenylthio, and 
             R 6  and R 7  independently of one another represent hydrogen; represent alkyl, cycloalkyl, alkenyl, alkoxy, or alkoxyalkyl, each of which is optionally substituted by halogen; represent optionally substituted phenyl; or represent optionally substituted benzyl; or R 6  and R 7  together with the N atom to which they are bonded represent a cycle that is optionally interrupted by oxygen or sulphur. 
           
         
       
     
     
         37 . A compound of formula (I) according to  claim 36  in which
 W represents C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy, C 1 -C 4 -alkoxy-C 2 -C 4 -alkyloxy, C 1 -C 4 -alkoxy-bis-C 2 -C 4 -alkyloxy, or represents C 3 -C 6 -cycloalkyl-C 1 -C 3 -alkanediyloxythat is optionally monosubstituted to trisubstituted by fluorine, chlorine, C 1 -C 3 -alkyl, or C 1 -C 3 -alkoxy and in which one methylene group of the ring is optionally interrupted by oxygen or sulphur, 
 X represents C 1 -C 6 -alkyl, 
 Y represents chlorine, bromine, or iodine, and 
 CKE represents a group 
 
       
         
           
           
               
               
           
         
         
           in which 
           A represents hydrogen; represents C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 1 -C 10 -alkoxy-C 1 -C 8 -alkyl, or C 1 -C 10 -alkylthio-C 1 -C 6 -alkyl, each of which is optionally substituted by halogen; represents C 3 -C 8 -cycloalkyl in which one or two ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur and that is optionally substituted by halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy; or represents phenyl, naphthyl, hetaryl having 5 to 6 ring atoms, phenyl-C 1 -C 6 -alkyl, or naphthyl-C 1 -C 6 -alkyl, each of which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy, cyano, or nitro, 
           D represents hydrogen; represents C 1 -C 12 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, or C 1 -C 10 -alkoxy-C 2 -C 8 -alkyl, each of which is optionally substituted by halogen; represents C 3 -C 8 -cycloalkyl in which a ring member is optionally replaced by oxygen or sulphur and that is optionally substituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkyl; or represents phenyl, hetaryl having 5 or 6 ring atoms, phenyl-C 1 -C 6 -alkyl, or hetaryl-C 1 -C 6 -alkyl having 5 or 6 ring atoms, each of which is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkoxy, cyano, or nitro, or 
           A and D together represent optionally substituted C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl, in which one methylene group is optionally replaced by a carbonyl group, oxygen, or sulphur,
 wherein suitable substituents for A and D together are halogen, hydroxyl, or mercapto, or are C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, C 3 -C 7 -cycloalkyl, phenyl, or benzyloxy, each of which is optionally substituted by halogen; or are a further C 3 -C 6 -alkanediyl, C 3 -C 6 -alkenediyl, or butadienyl group that is itself optionally substituted by C 1 -C 6 -alkyl or in which two adjacent substituents together with the carbon atoms to which they are bonded optionally form a further saturated or unsaturated cycle having 5 or 6 ring atoms that optionally contain oxygen or sulphur or that optionally contains a group 
 
         
       
       
         
           
           
               
               
           
         
         
           
             and 
           
           G represents hydrogen (a) or a group 
         
       
       
         
           
           
               
               
           
         
         
           
             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 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, or poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, each of which is optionally substituted by halogen; represents C 3 -C 8 -cycloalkyl in which one or more ring members that are not directly adjacent are optionally replaced by oxygen and/or sulphur and that is optionally substituted by halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy; represents phenyl that is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -halogenoalkoxy, C 1 -C 6 -alkylthio, or C 1 -C 6 -alkylsulphonyl; represents or phenyl-C 1 -C 6 -alkyl that is optionally substituted by halogen, nitro, cyano, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl, or C 1 -C 6 -halogenoalkoxy; represents 5- or 6-membered hetaryl that is optionally substituted by halogen or C 1 -C 6 -alkyl; represents phenoxy-C 1 -C 6 -alkyl that is optionally substituted by halogen or C 1 -C 6 -alkyl; or represents 5- or 6-membered hetaryloxy-C 1 -C 6 -alkyl that is optionally substituted by halogen, amino or C 1 -C 6 -alkyl, 
             R 2  represents C 1 -C 20 alkyl, C 2 -C 20 -alkenyl, C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, or poly-C 1 -C 8 -alkoxy-C 2 -C 8 -alkyl, each of which is optionally substituted by halogen; or represents C 3 -C 8 -cycloalkyl that is optionally substituted by halogen, C 1 -C 6 -alkyl, or C 1 -C 6 -alkoxy; or represents phenyl or benzyl, each of which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl, or C 1 -C 6 -halogenoalkoxy, 
             R 3  represents C 1 -C 8 -alkyl that is optionally substituted by halogen; or represents phenyl or benzyl, each of which is optionally substituted 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  and R 5  independently of one another represent 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, or C 3 -C 7 -cycloalkylthio, each of which is optionally substituted by halogen; or represents phenyl, phenoxy, or phenylthio, each of which is optionally substituted by halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkylthio, C 1 -C 4 -halogenoalkylthio, C 1 -C 4 -alkyl, or C 1 -C 4 -halogenoalkyl, 
             R 6  and R 7  independently of one another represent hydrogen; represent C 1 -C 8 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 8 -alkoxy, C 3 -C 8 -alkenyl, or C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl, each of which is optionally substituted by halogen; represent phenyl that is optionally substituted by halogen, C 1 -C 8 -halogenoalkyl, C 1 -C 8 -alkyl, or C 1 -C 8 -alkoxy; or represent benzyl that is optionally substituted by halogen, C 1 -C 8 -alkyl, C 1 -C 8 -halogenoalkyl, or C 1 -C 8 -alkoxy; or R 6  and R 7  together represent a C 3 -C 6 -alkylene radical that is optionally substituted by C 1 -C 4 -alkyl and in which one carbon atom is optionally replaced by oxygen or sulphur, 
             R 13  represents hydrogen, C 1 -C 8 -alkyl or C 1 -C 8 -alkoxy, each of which is optionally substituted by halogen, C 3 -C 8 -cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur and which is optionally substituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or phenyl, phenyl-C 1 -C 4 -alkyl or phenyl-C 1 -C 4 -alkoxy, each of which is optionally substituted 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, 
             R 14a  represents hydrogen or C 1 -C 8 -alkyl, or 
             R 13  and R 14a  together represent C 4 -C 6 -alkanediyl, 
             R 15a  and R 16a  are identical or different and represent C 1 -C 6 -alkyl, or 
             R 15a  and R 16a  together represent a C 2 -C 4 -alkanediyl radical that is optionally substituted by C 1 -C 6 -alkyl, by C 1 -C 6 -halogenoalkyl, or by phenyl that is optionally substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -halogenoalkoxy, nitro, or cyano, 
             R 17a  and R 18a  independently of one another represent hydrogen; represent C 1 -C 8 -alkyl that is optionally substituted by halogen; or represent phenyl that is optionally substituted 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, or 
             R 17a  and R 18a  together with the carbon atom to which they are bonded represent a carbonyl group or C 5 -C 7 -cycloalkyl in which one methylene group is optionally replaced by oxygen or sulphur and that is optionally substituted by halogen, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy, and 
             R 19a  and R 20a  independently of one another represent C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 10 -alkoxy, C 1 -C 10 -alkylamino, C 3 -C 10 -alkenylamino, di(C 1 -C 10 -alkyl)amino, or di(C 3 -C 10 -alkenyl)amino. 
           
         
       
     
     
         38 . A compound of formula (I) according to  claim 36  in which
 W represents C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 3 -alkoxy-C 2 -C 3 -alkyloxy, C 1 -C 2 -alkoxy-bis-C 2 -C 3 -alkyloxy or C 3 -C 6 -cycloalkyl-C 1 -C 2 -alkanediyloxy in which one methylene group of the ring can optionally be interrupted by oxygen, 
 X represents C 1 -C 3 -alkyl, 
 Y represents chlorine or bromine, and 
 CKE represents a group 
 
       
         
           
           
               
               
           
         
         
           in which 
           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 monosubstituted to trisubstituted by fluorine or chlorine; represents C 3 -C 6 -cycloalkyl that is optionally monosubstituted or disubstituted by C 1 -C 2 -alkyl, or C 1 -C 2 -alkoxy; or represents phenyl or benzyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 2 -halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkoxy, cyano, or nitro, 
           D represents hydrogen; represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, each of which is optionally monosubstituted to trisubstituted by fluorine; represents C 3 -C 6 -cycloalkyl that is optionally monosubstituted or disubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -halogenoalkyl and in which one methylene group is optionally replaced by oxygen; or when CKE is a group other than group (1), represents phenyl or pyridyl, each of which is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy, or 
           A and D together represent C 3 -C 5 -alkanediyl that is optionally monosubstituted or disubstituted with C 1 -C 2 -alkyl and/or C 1 -C 2 -alkoxy and in which one methylene group is optionally replaced by a carbonyl group except when CKE is group (1), oxygen or sulphur; and 
           G represents hydrogen (a) or a group 
         
       
       
         
           
           
               
               
           
         
         
           
             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 C 1 -C 8 -alkyl, C 2 -C 18 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, or C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl, each of which is optionally monosubstituted to trisubstituted by fluorine or chlorine; represents C 3 -C 6 -cycloalkyl that is optionally monosubstituted or disubstituted by fluorine, chlorine, C 1 -C 2 -alkyl, or C 1 -C 2 -alkoxy and in which one or two ring members that are not directly adjacent are optionally replaced by oxygen; or represents phenyl that is optionally monosubstituted or disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -halogenoalkyl, or C 1 -C 2 -halogenoalkoxy, 
             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 monosubstituted to trisubstituted by fluorine; represents C 3 -C 6 -cycloalkyl that 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 monosubstituted or 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 that is optionally monosubstituted to trisubstituted by fluorine; or represents phenyl that is optionally in each case 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, or 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 -halogenoalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -halogenoalkylthio, 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, or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl; represents phenyl that is optionally monosubstituted by fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 -alkyl, or C 1 -C 4 -alkoxy; or represents benzyl that is optionally monosubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, trifluoromethyl, or C 1 -C 4 -alkoxy, and 
             R 7  represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, or C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, or 
             R 6  and R 7  together represent a C 4 -C 5 -alkylene radical that is optionally substituted by methyl or ethyl and in which one methylene group is optionally replaced by oxygen or sulphur. 
           
         
       
     
     
         39 . A compound of formula (I) according to  claim 36  in which
 W represents methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, methoxy-ethyloxy, ethoxy-ethyloxy, cyclopropyl-methoxy, cyclopentyl-methoxy, or cyclohexyl-methoxy, 
 X represents methyl or ethyl, 
 Y represents chlorine or bromine, and 
 CKE represents a group 
 
       
         
           
           
               
               
           
         
         
           in which 
           A represents hydrogen; represents C 1 -C 4 -alkyl or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, each of which is monosubstituted to trisubstituted by fluorine; represents cyclopropyl, cyclopentyl, or cyclohexyl; or when CKE is a group other than group (5), represents phenyl that is optionally substituted by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano, or nitro, 
           D represents hydrogen; represents C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, each of which is optionally monosubstituted to trisubstituted by fluorine; represents cyclopropyl, cyclopentyl, or cyclohexyl; or when CKE is a group other than group (1), represents phenyl or pyridyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, or trifluoromethyl, or 
           A and D together represent C 3 -C 5 -alkanediyl that is optionally monosubstituted by methyl or methoxy and in which one carbon atom is optionally replaced by oxygen or sulphur; and 
           G represents hydrogen (a) or a group 
         
       
       
         
           
           
               
               
           
         
         
            —SO 2 —R 3  (d), or E (f),
 in which 
 L represents oxygen or sulphur, 
 M represents oxygen or sulphur, 
 E represents an ammonium ion, 
 R 1  represents C 1 -C 6 -alkyl, C 2 -C 17 -alkenyl, C 1 -C 2 -alkoxy-C 1 -alkyl, or C 1 -C 2 -alkylthio-C 1 -alkyl; represents cyclopropyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl, or methoxy; or represents phenyl that is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl, or trifluoromethoxy, 
 R 2  represents C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, phenyl, or benzyl, each of which is optionally monosubstituted by fluorine, and 
 R 3  represents C 1 -C 8 -alkyl. 
 
         
       
     
     
         40 . A compound of formula (I) according to  claim 36  in which
 W represents methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, methoxy-ethyloxy, ethoxy-ethyloxy, or cyclopropylmethoxy, 
 X represents methyl or ethyl, 
 Y represents chlorine, 
 CKE represents a group 
 
       
         
           
           
               
               
           
         
         
           in which 
           A represents hydrogen, methyl, ethyl, cyclopropyl, isopropyl, n-propyl, isobutyl, n-butyl, t-butyl or s-butyl, 
           D represents hydrogen, methyl, ethyl, isopropyl, cyclopropyl, or cyclohexyl, or 
           A and D together represent C 3 -C 5 -alkanediyl, and 
           G represents hydrogen (a) or a group 
         
       
       
         
           
           
               
               
           
         
         
            —SO 2 —R 3  (d), or E (f),
 in which 
 L represents oxygen, 
 M represents oxygen, 
 E represents an ammonium ion (N + (C 6 H 13 ) 4 ), 
 R 1  represents C 1 -C 8 -alkyl, C 1 -C 2 -alkoxy-C 1 -alkyl, or C 2 -C 17 -alkenyl, 
 R 2  represents C 1 -C 8 -alkyl or C 2 -C 6 -alkenyl, and 
 R 3  represents C 1 -C 4 -alkyl. 
 
         
       
     
     
         41 . A process for the preparation of compounds of formula (I) according to  claim 36  comprising
 (A) for compounds of formula (I-8-a) 
 
       
         
           
           
               
               
           
         
         
           in which A, D, W, X, and Y have the meanings given for formula (I) in  claim 36 , 
         
         reacting a compound of formula (X) 
       
       
         
           
           
               
               
           
         
         
           in which A and D have the meanings given for formula (I) in  claim 36 , 
         
         (α) with a compound of formula (VI) 
       
       
         
           
           
               
               
           
         
         
           in which 
           X, Y, and W have the meanings given for formula (I) in  claim 36 , 
           Hal represents halogen, 
           optionally in the presence of a diluent and optionally in the presence of an acid acceptor, or 
         
         (β) with a compound of formula (XI) 
       
       
         
           
           
               
               
           
         
         
           in which 
           W, X, and Y have the meanings given for formula (I) in  claim 36 , 
           U represents NH 2  or O—R 8 , and 
           R 8  represents alkyl, 
           optionally in the presence of a diluent and optionally in the presence of a base, or 
         
         (γ) with a compound of formula (XII) 
       
       
         
           
           
               
               
           
         
         
           in which 
           A, D, W, X, Y, and R 8  have the meanings given for formula (XI), optionally in the presence of a diluent and optionally in the presence of a base, 
         
         or 
         (B) for compounds of formula (I-8-b) 
       
       
         
           
           
               
               
           
         
         in which A, D, R 1 , W, X, and Y have the meanings given for formula (I) in  claim 36 , 
         reacting compounds of formula (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         (α) with an acid chloride of formula (XIII) 
       
       
         
           
           
               
               
           
         
         
           in which 
           R 1  has the meanings given for formula (I) in  claim 36 , 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  has the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of an acid-binding agent; 
 
         or 
         (C) for compounds of formula (I-8-c) 
       
       
         
           
           
               
               
           
         
         in which 
         A, D, R 2 , M, W, X, and Y have the meanings given for formula (I) in  claim 36 , and 
         L represents oxygen, 
         reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         with a chloroformic ester or chloroformic thioester of formula (XV)
   R 2 -M-CO—Cl  (XV)
 
 in which R 2  and M have the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of an acid-binding agent; 
 
         or 
         (D) for compounds of formula (I-8-c) 
       
       
         
           
           
               
               
           
         
         in which 
         A, D, R 2 , M, W, X, and Y have the meanings given for formula (I) in  claim 36 , and 
         L represents sulphur, 
         reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, 
         X and Y have the meanings given for formula (I) in  claim 36 , 
         with a chloromonothioformic ester or chlorodithioformic ester of formula (XVI) 
       
       
         
           
           
               
               
           
         
         
           in which R 2  and M have the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of an acid-binding agent; 
         
         or 
         (E) for compounds of formula (I-8-d) 
       
       
         
           
           
               
               
           
         
         in which A, D, R 3 , W, X and Y have the meanings given for formula (I) in  claim 36 , 
         reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         with a sulphonyl chloride of formula (XVII)
   R 3 —SO 2 —Cl  (XVII)
 
 in which R 3  has the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of an acid-binding agent; 
 
         or 
         (F) for compounds of formula (I-8-e) 
       
       
         
           
           
               
               
           
         
         in which A, D, L, R 4 , R 5 , W, X, and Y have the meanings given for formula (I) in  claim 36 , 
         reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         with a phosphorus compound of formula (XVIII) 
       
       
         
           
           
               
               
           
         
         
           in which 
           L, R 4 , and R 5  have the meanings given for formula (I) in  claim 36 , and 
           Hal represents halogen, 
         
         optionally in the presence of a diluent and optionally in the presence of an acid-binding agent, 
         or 
         (G) for compounds of formula (I-8-f) 
       
       
         
           
           
               
               
           
         
         
           in which A, D, E, W, X and Y have the meanings given for formula (I) in  claim 36 , reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         
         (α) with a metal compound of formula (XIX)
   Me(OR 10 ) t   (XIX)
 
 in which 
 Me represents a mono- or divalent metal, and 
 t represents the number 1 or 2, 
 optionally in the presence of a diluent, or 
 
         (β) with an amine of formulae (XX) 
       
       
         
           
           
               
               
           
         
         
           in which R 10 , R 11  and R 12  independently of one another represent hydrogen or alkyl, 
           optionally in the presence of a diluent, 
         
         or 
         (H) for compounds of formula (I-8-g) 
       
       
         
           
           
               
               
           
         
         in which A, D, L, R 6 , R 7 , W, X, and Y have the meanings given for formula (I) in  claim 36 , 
         reacting compounds of formulas (I-1-a) to (I-8-a) shown above in which A, D, W, X and Y have the meanings given for formula (I) in  claim 36 , 
         (α) with an isocyanate or isothiocyanate of formula (XXI)
   R 6 —N═C=L  (XXI)
 
 in which R 6  and L have the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of a catalyst, or 
 
         (β) with a carbamoyl chloride or thiocarbamoyl chloride of formula (XXII) 
       
       
         
           
           
               
               
           
         
         
           in which L, R 6 , and R 7  have the meanings given for formula (I) in  claim 36 , optionally in the presence of a diluent and optionally in the presence of an acid-binding agent. 
         
       
     
     
         42 . A compound of formula (XXIV) 
       
         
           
           
               
               
           
         
         in which 
         W represents alkoxy, halogenoalkoxy, alkoxyalkyloxy, alkoxy-bis-alkyloxy, or optionally substituted cycloalkylalkanediyloxythat is optionally interrupted by hetero atoms, 
         X represents alkyl, 
         Y represents chlorine, bromine, or iodine, and 
         Z represents a leaving group introduced by a reagent for the activation of carboxylic acids. 
       
     
     
         43 . A compound of formula (XXVII) 
       
         
           
           
               
               
           
         
         in which 
         W represents alkoxy, halogenoalkoxy, alkoxyalkyloxy, alkoxy-bis-alkyloxy, or optionally substituted cycloalkylalkanediyloxythat is optionally interrupted by hetero atoms, 
         X represents alkyl, and 
         Y represents chlorine, bromine, or iodine. 
       
     
     
         44 . A compound of formula (XXXI) 
       
         
           
           
               
               
           
         
         in which 
         W represents alkoxy, halogenoalkoxy, alkoxyalkyloxy, alkoxy-bis-alkyloxy, or optionally substituted cycloalkylalkanediyloxythat is optionally interrupted by hetero atoms, 
         X represents alkyl, 
         Y represents chlorine, bromine, or iodine, and 
         R 8  represents alkyl. 
       
     
     
         45 . A composition with an effective content of an active compound combination comprising the components,
 (a′) one or more substituted cyclic ketoenols of formula (I) according to  claim 36 , and   (b′) one or more compounds that improves crop plant tolerance selected from the group consisting of the compounds 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67, MON-4660), 1-dichloroacetyl-hexahydro-3,3,8a-trimethyl-pyrrolo[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-chloro-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-trichloro-methyl-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 (furilazole, 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-dichloro-methyl-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-quinolin-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-benzo-phenone, 1-bromo-4-chloromethylsulphonyl-benzene, 1-[4-(N-2-methoxybenzoyl-sulphamoyl)-phenyl]-3-methyl-urea (alias N-(2-methoxy-benzoyl)-4-[(methyl-aminocarbonyl)-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)   
       
         
           
           
               
               
           
         
         
           in which X 1  represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4  halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; n represents a number of between 0 and 5; A 1  represents a divalent heterocyclic group of the formulas 
         
       
       
         
           
           
               
               
           
         
         
           R 19  represents hydrogen, cyano, or 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, or 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; and 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, 
         
         a compound of formula (IIb) 
       
       
         
           
           
               
               
           
         
         
           in which X 2  represents hydrogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; X 3  represents hydrogen, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; A 2  represents alkanediyl having 1 or 2 carbon atoms that is optionally substituted by C 1 -C 4 -alkyl and/or C 1 -C 4 -alkoxy-carbonyl; and R 15  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, 
         
         a compound of formula (IIc) 
       
       
         
           
           
               
               
           
         
         
           in which R 16  represents C 1 -C 4 -alkyl that is optionally substituted by fluorine, chlorine and/or bromine; R 17  represents hydrogen, represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, 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, or piperidinyl, each of which is optionally substituted by fluorine, chlorine, and/or bromine, or represents phenyl that is optionally substituted by fluorine, chlorine, and/or bromine or C 1 -C 4 -alkyl; and 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, or piperidinyl, each of which is optionally substituted by fluorine, chlorine, and/or bromine, or represents phenyl that is optionally substituted by fluorine, chlorine, and/or bromine or C 1 -C 4 -alkyl, or R 18  together with R 17  represents 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, 
         
         a compound of formula (IId) 
       
       
         
           
           
               
               
           
         
         
           in which X 4  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; X 5  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; n represents a number of between 0 and 5; R 22  represents hydrogen or C 1 -C 4 -alkyl; R 23  represents hydrogen or C 1 -C 4 -alkyl; and R 24  represents hydrogen, 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, or 
         
         a compound of formula (IIe) 
       
       
         
           
           
               
               
           
         
         
           in which X 4  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; X 5  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulphamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy; n represents a number of between 0 and 5; R 22  represents hydrogen or C 1 -C 4 -alkyl; R 25  represents hydrogen, represents C 1 -C 6 -alkyl that is optionally substituted by cyano, hydroxyl, halogen, or C 1 -C 4 -alkoxy, 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 that is optionally substituted by cyano, halogen, or C 1 -C 4 -alkyl; R 26  represents hydrogen, represents C 1 -C 6 -alkyl that is optionally substituted by cyano, hydroxyl, halogen, or C 1 -C 4 -alkoxy, represents C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, each of which is optionally substituted by cyano or halogen, represents C 3 -C 6 -cycloalkyl which is optionally substituted by cyano, halogen or C 1 -C 4 -alkyl, or represents phenyl that is optionally substituted by nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 -C 4 -alkoxy, or C 1 -C 4 -halogenoalkoxy, or R 26  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. 
         
       
     
     
         46 . A composition according to  claim 45 , in which the compound that improves crop plant tolerance is selected from the group consisting of the compounds cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, the compound 
       
         
           
           
               
               
           
         
       
       and the compound 
       
         
           
           
               
               
           
         
       
     
     
         47 . A composition according to  claim 45  in which the compound that improves crop plant tolerance is cloquintocet-mexyl or mefenpyr-diethyl. 
     
     
         48 . A pesticide and/or herbicide comprising one or more compounds of formula (I) according to  claim 36 . 
     
     
         49 . A method for controlling animal pests comprising allowing an effective amount of one or more compounds of formula (I) according to  claim 36  to act on pests and/or their environment. 
     
     
         50 . A method for controlling undesired vegetation comprising allowing an effective amount of one or more compounds of formula (I) according to  claim 36  to act on plants and/or their environment. 
     
     
         51 . A process for the preparation of a pesticide and/or herbicide comprising mixing one or more compounds of formula (I) according to  claim 36  with one or more extenders and/or surface-active substances. 
     
     
         52 . A method for controlling undesired vegetation comprising allowing an effective amount of a composition according to  claim 45  to act on plants and/or their environment. 
     
     
         53 . A method for controlling undesired vegetation according to  claim 51  in which the compound of formula (I) according to  claim 36  and the compound that improves crop plant tolerance are allowed to act separately at short intervals on plants and/or their environment.