2,6-Diethyl-4-Methylphenyl-Substituted Tetramic Acid Derivatives

Abstract

The invention relates to novel 2,6-diethyl-4-methylphenyl-substituted tetramic acid derivatives of the formula (I) in which A, B, D and G 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 selectively herbicidal compositions comprising, firstly, the 2,6-diethyl-4-methylphenyl-substituted tetramic acid derivatives of the formula (I) and, secondly, at least one crop plant tolerance promoter compound.

1 . A compound of the formula (I) 
     
       
         
         
             
             
         
       
       in which 
       A represents hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl or alkylthioalkyl or optionally substituted cycloalkyl, 
       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 C 3 -C 8 -ring which optionally contains at least one heteroatom and which is optionally substituted and 
       D represents hydrogen, 
       or 
       A represents hydrogen or alkyl, 
       B represents hydrogen and 
       D represents an optionally substituted radical selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and cycloalkyl, or 
       A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which optionally contains at least one oxygen or sulfur atom in the A,D moiety or which is optionally substituted by alkyl, alkoxy or haloalkyl, and 
       G represents one of the groups 
     
     
       
         
         
             
             
         
       
       
         in which 
         E represents a metal ion equivalent or an ammonium iron, 
         L represents oxygen or sulfur, 
         M represents oxygen or sulfur, 
       
       R 1  represents in each case optionally substituted primary or secondary alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, or in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl, or in each case optionally substituted phenyl or heteroaryl, 
       R 2  represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxy-alkyl or polyalkoxyalkyl, or 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 or cycloalkylthio, or 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, in each case optionally substituted phenyl or benzyl or together with the N-atom to which they are attached form an optionally substituted cycle which optionally contains oxygen or sulfur. 
     
   
   
       2 . A compound according to  claim 1  in which
 A represents hydrogen, C 1 -C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkoxy-C 1 -C 4 -alkyl or C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by halogen, or C 3 -C 8 -cycloalkyl which is optionally mono- to trisubstituted by halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy,   B represents hydrogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy-C 1 -C 2 -alkyl, or   A, B and the carbon atom to which they are attached represent saturated C 3 -C 8 -cycloalkyl or unsaturated C 5 -C 8 -cycloalkyl in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally substituted by C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl or C 1 -C 6 -alkoxy, and   D represents hydrogen,   or   A represents hydrogen or C 1 -C 8 -alkyl,   B represents hydrogen and   D represents C 1 -C 8 -alkyl, C 1 -C 8 -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 4 -alkyl or C 1 -C 6 alkylthio-C 2 -C 4 -alkyl, each of which is optionally mono- to pentasubstituted by halogen, or represents C 3 -C 8 -cycloalkyl which is optionally mono- to trisubstituted by halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkyl, or   A and D together represent a C 3 -C 6 -alkanediyl or C 3 -C 6 -alkenediyl group in which in each case optionally one methylene group is replaced by oxygen or sulfur and which is in each case mono- to disubstituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkyl or by a further C 3 -C 6 -alkanediyl, C 3 -C 6 -alkenediyl- or C 4 -C 6 -alkanedienediyl group which forms a fused-on ring,   G represents one of the groups   
     
       
         
         
             
             
         
       
       
         in which 
         E represents a metal ion equivalent or an ammonium iron, 
         L represents oxygen or sulfur and 
         M represents oxygen or sulfur, 
       
       R 1  represents primary or secondary C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl or poly-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally mono- to heptasubstituted by halogen, mono- to disubstituted by cyano, monosubstituted by COR 13 , C═N—OR 13 , CO 2 R 13   
     
     
       
         
         
             
             
         
       
       
         or represents C 3 -C 8 -cycloalkyl which is optionally mono- to trisubstituted by halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen or sulfur, 
         represents phenyl, phenyl-C 1 -C 2 -alkyl or phenyl-C 1 -C 2 -alkenyl, each of which is optionally mono- to trisubstituted by 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, C 1 -C 6 -alkylsulfinyl or C 1 -C 6 -alkylsulfonyl, 
         represents 5- or 6-membered heteroaryl which is optionally mono- to disubstituted by halogen or C 1 -C 6 -alkyl substituents and which has one or two heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen, 
       
       R 2  represents C 1 -C 20 -alkyl, C 2 -C 20 -alkenyl, C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl or poly-C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl, each of which is optionally mono- to trisubstituted by halogen,
 or represents C 3 -C 8 -cycloalkyl which is optionally mono- to disubstituted by halogen, C 1 -C 6 -alkyl or C 1 -C 6 -alkoxy or 
 represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl or C 1 -C 6 -haloalkoxy, 
 
       R 3  represents C 1 -C 8 -alkyl which is optionally mono- to polysubstituted by halogen, or phenyl or benzyl, each of which is optionally mono- to disubstituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, 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 or C 2 -C 8 -alkenyl-thio, each of which is optionally mono- to trisubstituted by halogen, or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to trisubstituted by 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, 
       R 6  and R 7  independently of one another represent hydrogen, 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 2 -C 8 -alkyl, each of which is optionally mono- or trisubstituted by halogen, or represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by halogen, C 1 -C 8 -alkyl, C 1 -C 8 -haloalkyl or C 1 -C 8 -alkoxy, or together represent a C 3 -C 6 -alkylene radical which is optionally mono- to disubstituted by C 1 -C 4 -alkyl and in which optionally one methylene group is replaced by oxygen or sulfur, 
       R 13  represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by halogen, or represents C 3 -C 6 -cycloalkyl which is optionally mono- to disubstituted by halogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen, or 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, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, cyano or nitro, 
       R 13′  represents hydrogen, C 1 -C 6 -alkyl or C 3 -C 6 -alkenyl. 
     
   
   
       3 . A compound according to  claim 1  in which
 A represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 3 -alkyl or C 1 -C 4 -alkylthio-C 1 -C 3 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents 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,   B represents hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, or   A, B and the carbon atom to which they are attached represent saturated C 3 -C 7 -cycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally mono- to disubstituted by C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl or C 1 -C 4 -alkoxy, and   D represents hydrogen,   or   A represents hydrogen or C 1 -C 6 -alkyl,   B represents hydrogen and   D represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl or C 1 -C 4 -alkylthio-C 2 -C 3 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents C 3 -C 6 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or trifluoromethyl, or   A and D together represent a C 3 -C 5 -alkanediyl group in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by C 1 -C 2 -alkyl, C 1 -C 2 -alkoxy or trifluoromethyl,   or A and D together with the atoms to which they are attached represent one of the groups AD-1 to AD-10   
     
       
         
         
             
             
         
       
       G represents one of the groups 
     
     
       
         
         
             
             
         
       
       
         in which 
         E represents a metal ion equivalent or an ammonium ion, 
         L represents oxygen or sulfur and 
         M represents oxygen or sulfur, 
       
       R 1  represents primary or secondary C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 -alkyl or poly-C 1 -C 3 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to pentasubstituted by fluorine or chlorine, monosubstituted by cyano or, monosubstituted by CO—R 13 , C═N—OR 13  or CO 2 R 13 , or represents 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 methylene groups are replaced by oxygen, 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 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy, or 
 represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 2 -alkyl, 
 
       R 2  represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl, C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl or poly-C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or
 represents C 3 -C 7 -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, methoxy, trifluoromethyl or trifluoromethoxy, 
 
       R 3  represents C 1 -C 4 -alkyl which is optionally mono- to trisubstituted by fluorine or chlorine or represents phenyl or benzyl, each of 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  and R 5  independently of one another represent 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 or C 3 -C 4 -alkenylthio, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represent phenyl, phenoxy or phenylthio, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 -alkoxy, trifluoromethoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -alkyl or trifluoromethyl, 
       R 6  and R 7  independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 6 -alkenyl or C 1 -C 6 -alkoxy-C 2 -C 6 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, trifluoromethyl, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or together represent a C 5 -C 6 -alkylene radical which is optionally mono- to disubstituted by methyl in which optionally one methylene group is replaced by oxygen, 
       R 13  represents C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl, or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, or represents C 3 -C 6 -cycloalkyl in each optionally one methylene group is replaced by oxygen. 
     
   
   
       4 . A compound according to  claim 1  in which
 A represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, cyclo-propyl, cyclopentyl or cyclohexyl,   B represents hydrogen, methyl or ethyl, or   A, B and the carbon atom to which they are attached represent saturated C 6 -cycloalkyl in which optionally one methylene group is replaced by oxygen and which is optionally substituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, n-propoxy, n-butoxy or isobutoxy, and   D represents hydrogen,   or   A represents hydrogen, methyl or ethyl,   B represents hydrogen, and   D represents methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, cyclopropyl, cyclopentyl or cyclohexyl, or   A and D together represent a C 3 -C 4 -alkanediyl group in which optionally one methylene group is replaced by oxygen or sulfur and which is optionally mono- to disubstituted by methyl or methoxy, or   
     A and D together with the atoms to which they are attached represent the groups below: 
     
       
         
         
             
             
         
       
       G represents one of the groups 
     
     
       
         
         
             
             
         
       
       
         L represents oxygen and 
         M represents oxygen or sulfur, 
       
       R 1  represents primary or secondary C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl or poly-C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy, or
 represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl or trifluoromethoxy, or 
 represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl, 
 
       R 2  represents C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 3 -alkoxy-C 2 -C 3 -alkyl, cyclopentyl or cyclohexyl,
 or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, 
 
       R 4  represents C 1 -C 6 -alkoxy, 
       R 5  represents C 1 -C 6 -alkoxy, 
       R 6  represents hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or allyl, or represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl, 
       R 7  represents methyl, ethyl, n-propyl, isopropyl or allyl, 
       R 6  and R 7  together represent a C 5 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen. 
     
   
   
       5 . A compound according to  claim 1  in which
 A represents methyl, ethyl or cyclopropyl,   B represents methyl or ethyl, or   A, B and the carbon atom to which they are attached represent saturated C 6 -cycloalkyl which is optionally substituted by methyl or methoxy,   D represents hydrogen,   or   A represents methyl or ethyl,   B represents hydrogen,   D represents methyl, ethyl or cyclopropyl, or   A and D together represent a C 3 -C 4 -alkanediyl group which is optionally monosubstituted by methoxy, or   A and D together with the atoms to which they are attached represent the groups AD-1 and AD-2,   
     
       
         
         
             
             
         
       
       G represents one of the groups 
     
     
       
         
         
             
             
         
       
       R 1  represents primary or secondary C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, C 1 -C 2 -alkylthio-C 1 -C 2 -alkyl or poly-C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy, or
 represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl or trifluoromethoxy, or 
 represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl, 
 
       R 2  represents C 1 -C 8 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 3 -alkoxy-C 2 -C 3 -alkyl, cyclopentyl or cyclohexyl, or
 or represents phenyl or benzyl, each of which is optionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy, 
 
       R 4  represents C 1 -C 6 -alkoxy, and 
       R 5  represents C 1 -C 6 -alkoxy. 
     
   
   
       6 . A process for preparing a compound according to  claim 1  comprising
 (A) obtaining a compound of the formula (I-b)   
     
       
         
         
             
             
         
       
       
         in which A, B, D and R 1  are as defined in  claim 1  by reacting a compound of the formula (I-a) 
       
     
     
       
         
         
             
             
         
       
       
         in which 
         A, B and D are as defined in  claim 1   
       
       a) with an acid halide of the formula (II) 
     
     
       
         
         
             
             
         
       
       
         in which 
         R 1  is as defined above and 
         Hal represents halogen 
         or 
       
       b) with a carboxylic anhydride of the formula (III)
   R 1 —CO—O—CO—R 1   (III) 
 in which 
 R 1  is as defined above, 
 optionally in the presence of a diluent and optionally in the presence of an acid binder, or 
 
       (B) obtaining a compound of the formula (I-c) 
     
     
       
         
         
             
             
         
       
       
         in which A, B, D, R 2  and M are as defined in  claim 1  and L represents oxygen by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
         with a chloroformic ester or a chloroformic thioester of the formula (IV)
   R 2 -M-CO—Cl  (IV) 
 
         in which 
         R 2  and M are as defined above, 
         optionally in the presence of a diluent and optionally in the presence of an acid binder, or 
       
       (C) obtaining a compound of the formula (I-c) by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
       a) with a chloromonothioformic ester or a chlorodithioformic ester of the formula (V) 
     
     
       
         
         
             
             
         
       
       
         in which 
         M and R 2  are as defined above, 
         optionally in the presence of a diluent and optionally in the presence of an acid binder, 
         or 
       
       b) with carbon disulfide and then with a compound of the formula (VI)
   R 2 —Hal  (VI) 
 in which 
 R 2  is as defined above and 
 Hal represents chlorine, bromine or iodine, 
 optionally in the presence of a diluent and optionally in the presence of a base, or 
 
       D) obtaining a compound of the formula (I-d) 
     
     
       
         
         
             
             
         
       
       
         in which A, B, D and R 3  are as defined in  claim 1  by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
         with a sulfonyl chloride of the formula (VII)
   R 3 —SO 2 —Cl  (VII) 
 
         in which 
         R 3  is as defined above, 
         optionally in the presence of a diluent and optionally in the presence of an acid binder, or 
       
       (E) obtaining a compound of the formula (I-e) 
     
     
       
         
         
             
             
         
       
       
         in which A, B, D, L, R 4  and R 5  are as defined in  claim 1  by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
         with a phosphorus compound of the formula (VIII), 
       
     
     
       
         
         
             
             
         
       
       
         in which 
         L, R 4  and R 5  are as defined above and 
         Hal represents halogen, 
         optionally in the presence of a diluent and optionally in the presence of an acid binder, or 
       
       (F) obtaining a compound of the formula (I-f) 
     
     
       
         
         
             
             
         
       
       
         in which A, B, D and E are as defined in  claim 1  by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
         with a metal compound or an amine of the formulae (IX) or (X), 
       
     
     
       
         
         
             
             
         
       
       
         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, 
         or 
       
       (G) obtaining a compound of the formula (I-g) 
     
     
       
         
         
             
             
         
       
       
         in which A, B, D, L, R 6  and R 7  are as defined in  claim 1  by reacting a compound of the formula (I-a) shown above in which A, B and D are as defined above 
       
       a) with an isocyanate or an isothiocyanate of the formula (XI),
   R 6 —N═C=L  (XI) 
 in which 
 R 6  and L are as defined above, 
 optionally in the presence of a diluent and optionally in the presence of a catalyst, 
 or 
 
       b) with a carbamoyl chloride or a thiocarbamoyl chloride of the formula (XII), 
     
     
       
         
         
             
             
         
       
       
         in which 
         L, R 6  and R 7  are as defined above, 
         optionally in the presence of a diluent and optionally in the presence of an acid binder. 
       
     
   
   
       7 . A composition comprising an effective amount of an active compound combination comprising, as components,
 a′) at least one compound according to  claim 1     or   b′) at least one substituted cyclic ketoenol of the formula (I-a)   
     
       
         
         
             
             
         
       
       in which 
       A represents hydrogen, C 2 -C 10 -alkyl, C 1 -C 6 -haloalkyl, in each case optionally halogen-substituted alkenyl, alkoxyalkyl or alkylthioalkyl, or optionally substituted cycloalkyl, 
       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 C 3 -C 8 -ring which is substituted by alkyl, alkoxy or haloalkyl, or a C 5 -C 8 -ring which contains at least one heteroatom and which is optionally substituted, and 
       D represents hydrogen 
       or 
       A represents hydrogen or alkyl, 
       B represents hydrogen and 
       D represents an optionally substituted radical selected from the group consisting of C 2 -C 10 -alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and substituted cycloalkyl, or 
       A and D together with the atoms to which they are attached represent a saturated or unsaturated cycle which optionally contains at least one oxygen or sulfur atom in the A,D-moiety and which is optionally substituted by alkyl, alkoxy or haloalkyl, 
       and 
       (c′) at least one crop plant tolerance promoter compound selected from the group consisting of:
 4-dichloroacetyl-1-oxa-4-azaspiro[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-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethyl 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-propenylacetamide (dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (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-dichoro-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-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-di-methyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid (AC-304415), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulfonylbenzene, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide), 1-[4-(N-2-methoxy-benzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethyl-benzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthylsulfamoyl)-phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide, 
 
       or one of the following compounds, 
       of formula (IIa) 
     
     
       
         
         
             
             
         
       
       or of formula (IIb) 
     
     
       
         
         
             
             
         
       
       or of formula (IIc) 
     
     
       
         
         
             
             
         
       
       where 
       m represents a number 0, 1, 2, 3, 4 or 5, 
       A 1  represents one of the divalent heterocyclic groupings shown below 
     
     
       
         
         
             
             
         
       
       n represents a number 0, 1, 2, 3, 4 or 5, 
       A 2  represents optionally C 1 -C 4 -alkyl- or C 1 -C 4 -alkoxy-carbonyl- or C 1 -C 4 -alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms, 
       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 optionally fluorine-, chlorine- or bromine-substituted C 1 -C 4 -alkyl, 
       R 17  represents hydrogen, in each case optionally fluorine-, chlorine- or bromine-substituted 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, piperidinyl, or optionally fluorine-, chlorine-, bromine- or C 1 -C 4 -alkyl-substituted phenyl, 
       R 18  represents hydrogen, in each case optionally fluorine-, chlorine- or bromine-substituted 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, piperidinyl, or optionally fluorine-, chlorine-, bromine- or C 1 -C 4 -alkyl-substituted phenyl, or 
       R 17  and R 18  together 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 attached, form a 5- or 6-membered carbocycle, 
       R 19  represents hydrogen, cyano, halogen, or in each case optionally fluorine-, chlorine- or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl, 
       R 20  represents hydrogen, in each case optionally hydroxyl-, cyano-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl or tri(C 1 -C 4 -alkyl)silyl, 
       R 21  represents hydrogen, cyano, halogen, or in each case optionally fluorine-, chlorine- or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl, 
       X 1  represents nitro, cyano, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 
       X 2  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, 
       or a compound, of the formula (IId) 
     
     
       
         
         
             
             
         
       
       or of the formula (IIe) 
     
     
       
         
         
             
             
         
       
       where 
       t represents a number 0, 1, 2, 3, 4 or 5, 
       v represents a number 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, in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted 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, or in each case optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino, 
       R 25  represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, or optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, 
       R 26  represents hydrogen, optionally cyano-, hydroxyl-, halogen- or C 1 -C 4 -alkoxy-substituted C 1 -C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 -alkenyl or C 3 -C 6 -alkynyl, optionally cyano-, halogen- or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, or optionally nitro-, cyano-, halogen-, C 1 -C 4 -alkyl-, C 1 -C 4 -haloalkyl-, C 1 -C 4 -alkoxy- or C 1 -C 4 -haloalkoxy-substituted phenyl, or together with R 25  represents in each case optionally C 1 -C 4 -alkyl-substituted C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl, 
       X 4  represents nitro, cyano, carboxyl, carbamoyl, formyl, sulfamoyl, 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, sulfamoyl, hydroxyl, amino, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy, 
       or combinations thereof. 
     
   
   
       8 . A composition according to  claim 7  in which the crop plant tolerance promoter compound is selected from the group consisting of:
 cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron,   
     
       
         
         
             
             
         
       
     
   
   
       9 . A composition according to  claim 8 , in which the crop plant tolerance promoter compound is cloquintocet-mexyl. 
   
   
       10 . A composition according to  claim 8 , in which the crop plant tolerance promoter compound is mefenpyr-diethyl. 
   
   
       11 . (canceled) 
   
   
       12 . A pesticide or herbicide, comprising a compound according to  claim 1 . 
   
   
       13 . A method for controlling animal pests or unwanted vegetation comprising contacting pests or their habitat with a compound according to  claim 1 . 
   
   
       14 . (canceled) 
   
   
       15 . A process for preparing pesticides or herbicides, comprising mixing a compound according to  claim 1  with an extender or a surfactant. 
   
   
       16 . A method for controlling unwanted vegetation, comprising contacting unwanted vegetation with a composition according to  claim 7 . 
   
   
       17 . (canceled) 
   
   
       18 . A method for controlling unwanted vegetation, comprising contacting plants or their habitat with a compound according to  claim 1  and a crop plant tolerance promoter compound selected from the group consisting of: 
     4-dichloroacetyl-1-oxa-4-azaspiro[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-methylhexyl 5-chloroquinoline-8-oxyacetate (cloquintocet-mexyl), 3-(2-chlorobenzyl)-1-(1-methyl-1-phenylethyl)urea (cumyluron), α-(cyanomethoximino)phenylacetonitrile (cyometrinil), 2,4-dichlorophenoxyacetic acid (2,4-D), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), 1-(1-methyl-1-phenylethyl)-3-(4-methylphenyl)urea (daimuron, dymron), 3,6-dichloro-2-methoxybenzoic acid (dicamba), S-1-methyl-1-phenylethyl 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-propenylacetamide (dichlormid), 4,6-dichloro-2-phenylpyrimidine (fenclorim), ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazole-ethyl), phenylmethyl 2-chloro-4-trifluoromethylthiazole-5-carboxylate (flurazole), 4-chloro-N-(1,3-dioxolan-2-ylmethoxy)-α-trifluoroacetophenone oxime (fluxofenim), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyloxazolidine (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-dichorophenyl)-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-ylmethoximino)phenylacetonitrile (oxabetrinil), 2,2-dichloro-N-(1,3-dioxolan-2-ylmethyl)-N-(2-propenyl)acetamide (PPG-1292), 3-dichloroacetyl-2,2-di-methyloxazolidine (R-28725), 3-dichloroacetyl-2,2,5-trimethyloxazolidine (R-29148), 4-(4-chloro-o-tolyl)butyric acid, 4-(4-chlorophenoxy)butyric acid, diphenylmethoxyacetic acid, methyl diphenylmethoxyacetate, ethyl diphenylmethoxyacetate, methyl 1-(2-chlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-methyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropyl-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)-1H-pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenyl-1H-pyrazole-3-carboxylate, ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate, ethyl 5-phenyl-2-isoxazoline-3-carboxylate, ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate, 1,3-dimethylbut-1-yl 5-chloroquinoline-8-oxyacetate, 4-allyloxybutyl 5-chloroquinoline-8-oxyacetate, 1-allyloxyprop-2-yl 5-chloroquinoline-8-oxyacetate, methyl 5-chloroquinoxaline-8-oxyacetate, ethyl 5-chloroquinoline-8-oxyacetate, allyl 5-chloroquinoxaline-8-oxyacetate, 2-oxoprop-1-yl 5-chloroquinoline-8-oxyacetate, diethyl 5-chloroquinoline-8-oxymalonate, diallyl 5-chloroquinoxaline-8-oxymalonate, diethyl 5-chloroquinoline-8-oxymalonate, 4-carboxychroman-4-ylacetic acid (AC-304415), 4-chlorophenoxyacetic acid, 3,3′-dimethyl-4-methoxybenzophenone, 1-bromo-4-chloromethylsulfonylbenzene, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea (also known as N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide), 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthylsulfamoyl)-phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbonyl)benzenesulfonamide, 
     separately in close temporal succession. 
   
   
       19 . A method for preparing 2,6-diethyl-4-methylphenylacetic acid, comprising reacting 2,6-diethyl-2-methylbromobenzene with tert-butyl acetate, optionally in the presence of a base, a phosphine ligand, a palladium compound and a diluent, and then reacting with an acid. 
   
   
       20 . A process for preparing 2,6-diethyl-4-methylphenylacetic acid, comprising reacting 2,6-diethyl-4-methylphenylmalononitrile with an acid, optionally in the presence of a diluent.