IP Library › Granted Patent US 8,138,119

Granted Patent B2

US 8,138,119 · App. 12/083,691 · Granted Mar 20, 2012

Alkoxyalkyl spirocyclic tetramic acids and tetronic acids

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Quick Facts

Patent No.: US 8,138,119
App. No.: 12/083,691
Granted: Mar 20, 2012
Kind: B2

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Abstract

The invention relates to novel alkoxyalkyl spirocyclic tetramic and tetronic acids of the formula (I), in which A, B, D, Q 1 , Q 2 , Q 3 , Q 4 , G, W, X, Y and Z are as defined above, to a plurality of processes and intermediates for their preparation and to their use as pesticides and/or herbicides and/or microbicides, and also to selective herbicidal compositions comprising, firstly, the alkoxyalkyl spirocyclic tetramic and tetronic acids and, secondly, at least one crop plant compatibility-improving compound.

Claims (531)

1. A compound of formula (I)

in which

W represents hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkyl, haloalkoxy or cyano,

X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkoxyalkoxy, haloalkyl, haloalkoxy or cyano,

Y represents hydrogen, halogen, alkyl, alkoxy, cyano, haloalkyl, haloalkoxy; or represents in each case optionally substituted phenyl or heteroaryl,

Z represents hydrogen, halogen, alkyl, haloalkyl, cyano, alkoxy or haloalkoxy,

A represents hydrogen; represents in each case optionally halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkylalkyl in which optionally at least one ring atom is replaced by a heteroatom; or represents in each case optionally halogen-, alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, cyano- or nitro-substituted aryl, arylalkyl, heteroaryl or heteroarylalkyl,

B represents hydrogen, alkyl or alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or alkyl, or

A and Q 1 together with the atoms to which they are attached represent a saturated or unsaturated ring which contains at least one heteroatom and is unsubstituted or substituted in the A,Q moiety,

m represents 0, 1 or 2,

n represents 0 or 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R 1 represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl; represents in each case optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl or heterocyclyl; or represents in each case optionally substituted phenyl, phenylalkyl, heteroaryl, phenoxyalkyl or heteroaryloxyalky,

R 2 represents in each case optionally halogen- or cyano-substituted alkyl, alkenyl, alkoxyalkyl or 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 or cycloalkylthio; or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,

R 6 and R 7 independently of one another represent hydrogen; represent in each case optionally halogen- or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxy-alkyl; or represent in each case optionally substituted phenyl or benzyl, or together with the N atom to which they are attached form an optionally substituted ring which optionally contains oxygen or sulphur.

2. A compound of formula (I) according to claim 1 in which

W represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalky, C 1 -C 4 -haloalkoxy or cyano,

X represents hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkoxy-C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy or cyano,

Y represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, cyano, C 1 -C 4 -haloalkyl, haloalkoxy; or represents V 1 - and V 2 -substituted phenyl or pyridyl,

V 1 represents halogen, C 1 -C 12 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, cyano or nitro,

V 2 represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkyl, or

V 1 and V 2 together represent C 3 -C 4 -alkanediyl optionally substituted by halogen and/or C 1 -C 2 -alkyl and optionally interrupted by one or two oxygen atoms,

Z represents hydrogen, halogen, C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, cyano, C 1 -C 6 -alkoxy or C 1 -C 4 -haloalkoxy,

A represents hydrogen or in each case optionally halogen-substituted C 1 -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl, optionally halogen- , C 1 -C 6 -alkyl- or C 1 -C 6 -alkoxy-substituted C 3 -C 8 -cycloalkyl-C 1 -C 4 -alkyl in which optionally one or two not directly adjacent ring members are replaced by oxygen, sulphur, or a combination of oxygen and 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, heteroaryl having 5 to 6 ring atoms, phenyl-C 1 -C 4 -alkyl or heteroaryl-C 1 -C 4 -alkyl having 5 to 6 ring atoms,

B represents hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or C 1 -C 2 -alkyl, or

A and Q 1 together with the atoms to which they are attached represent a saturated 5- to 6-membered ring which is interrupted by at least one heteroatom and is optionally substituted by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or C 1 -C 4 -haloalkyl,

m represents 0, 1 or 2,

n represents 0 or 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur and

M represents oxygen or sulphur,

R 1 represents in each case optionally halogen- or cyano-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 or poly-C 1 -C 8 -alkoxy-C 1 -C 8 -alkyl; represents 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 methylene groups are replaced by oxygen, sulphur, or a combination of oxygen and 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 heteroaryl having one or two heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen;

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 heteroaryloxy-C 1 -C 6 -alkyl having one or two heteroatoms selected from the group consisting of oxygen, sulphur and nitrogen,

R 2 represents in each case optionally halogen- or cyano-substituted 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;

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 in each case optionally halogen-, C 1 -C 6 -alkyl-, C 1 -C 6 -alkoxy-, C 1 -C 4 -haloalky-, 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 or C 3 -C 8 -alkenylthio; 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 phenyl-thio,

R 6 and R 7 independently of one another represent hydrogen, represent in each case optionally halogen- or cyano-substituted 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; represent in each case optionally halogen-, C 1 -C 8 -alkyl-, C 1 -C 8 -haloalkyl- or C 1 -C 8 alkoxy-substituted phenyl or benzyl; or R 6 and R 7 together represent an optionally C 1 -C 6 -alkyl-substituted C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

3. A compound of formula (I) according to claim 1 in which

W represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy,

X represents chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 3 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano,

Y in the 4-position represents hydrogen, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, cyano, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

Z represents hydrogen,

A represents hydrogen, represents C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, 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-C 1 -C 2 -alkyl 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 2 -alkyl or C 1 -C 2 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or methyl, or

A and Q 1 together with the atoms to which they are attached represent a saturated 5- to 6-membered ring which is interrupted by at least one oxygen atom and which is optionally substituted by methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl or trifluoromethyl,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R 1 represents C 1 -C 16 -alkyl, C 2 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio-C 1 -C 4 -alkyl or poly-C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine; represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulphur;

represents phenyl which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl, C 1 -C 3 -haloalkoxy, C 1 -C 4 -alkylthio or C 1 -C 4 -alkylsulphonyl;

represents phenyl-C 1 -C 4 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy;

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl;

represents phenoxy-C 1 -C 5 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl; or

represents pyridyloxy-C 1 -C 5 -alkyl, pyrimidyloxy-C 1 -C 5 -alkyl or thiazolyloxy-C 1 -C 5 -alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, amino or C 1 -C 4 -alkyl,

R 2 represents C 1 -C 16 -alkyl, C 2 -C 16 -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 fluorine or chlorine,

represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or

represents phenyl or benzyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy,

R 3 represents C 1 -C 6 -alkyl which is optionally mono- to trisubstituted by fluorine or chlorine; or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkoxy, C 1 -C 2 -haloalkyl, 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, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -haloalkylthio, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl,

R 6 and R 7 independently of one another represent hydrogen; represent 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 2 -C 6 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine; represent phenyl or benzyl, each of which is optionally mono- to trisubstituted by fluorine, chlorine, bromine, C 1 -C 5 -haloalkyl, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy; or R 6 and R 7 together represent an optionally C 1 -C 4 -alkyl-substituted C 3 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

4. A compound of formula (I) according to claim 1 in which

W represents hydrogen, chlorine, bromine, methyl, ethyl, methoxy, ethoxy or trifluoromethyl,

X represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,

Y in the 4-position represents hydrogen, chlorine, bromine, iodine, methoxy, trifluoromethyl or trifluoromethoxy,

Z represents hydrogen,

A represents hydrogen, represents C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl, C 3 -C 4 -alkynyl or C 1 -C 2 -alkoxy-C 1 -C 2 -alkyl, each of which is optionally mono- to trisubstituted by fluorine; or represents cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen, or

A and Q 1 together with the atoms to which they are attached represent a saturated 5- to 6-membered ring which is interrupted by at least one oxygen atom and is optionally substituted by methyl or ethyl,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur, and

M represents oxygen or sulphur,

R 1 represents 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, each of which is optionally mono- to trisubstituted by fluorine or chlorine; represents C 3 -C 6 -cycloalkyl which is optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy;

represents phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, 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 10 -alkyl, C 2 -C 10 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;

represents cyclopentyl or cyclohexyl;

or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,

R 3 represents methyl, ethyl, propyl or isopropyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine; or represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,

R 4 and R 5 independently of one another represent C 1 -C 4 -alkoxy or C 1 -C 4 -alkylthio; or represent phenyl, phenoxy or phenylthio, each of which is optionally monosubstituted by fluorine, chlorine, bromine, nitro, cyano, methyl, methoxy, trifluoromethyl or trifluoromethoxy,

R 6 and R 7 independently of one another represent hydrogen, represent C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl; represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl; or R 6 and R 7 together represent a C 5 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

5. A compound of formula (I) according to claim 1 in which

W represents chlorine, methyl or ethyl,

X represents chlorine, methyl, ethyl, methoxy or ethoxy,

Y in the 4-position represents chlorine, bromine, iodine or methoxy,

Z represents hydrogen,

A represents C 1 -C 4 -alkyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

R 1 represents C 1 -C 10 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or cyclopropyl,

R 2 represents C 1 -C 10 -alkyl or benzyl.

6. A process for preparing a compound of formula (I) according to claim 1 , comprising

(A) obtaining a compound of formula (I-1-a)

in which

A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 ,

by the intramolecular condensation of a compound of formula (II)

in which

A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 ,

and

R 8 represents alkyl,

in the presence of a diluent and a base,

(B) obtaining a compound of formula (I-2-a)

in which

A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 ,

by the intramolecular condensation of a compound of formula (III)

in which

A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y, Z and R 8 are as defined in claim 1 , in the presence of a diluent and a base,

in which R 1 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 , by reacting a compound of formulae (I-1-a) or (I-2-a),

a) with a compound of formula (IV)

in which

R 1 is as defined above, and

Hal represents halogen,

b) with a carboxylic anhydride of formula (V)

R 1 —CO—O—CO—R 1 (V)

in which

R 1 is as defined above,

optionally in the presence of a diluent and an acid binder,

(D) obtaining a compound of formulae (I-1-c) or (I-2-c)

in which R 2 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 and L represents oxygen, by reacting a compound of formulae (I-1-a) or (I-2-a),

with a chloroformic ester or a chloroformic thioester of formula (VI)

R 2 -M-CO—Cl (VI)

in which

R 2 and M are as defined above,

optionally in the presence of a diluent and an acid binder,

(E) obtaining a compound of formulae (I-1-c) or (I-2-c) in which R 2 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , M, W, X, Y and Z are as defined in claim 1 and L represents sulphur, by reacting a compound of formulae (I-1-a) or (I-2-a),

with a chloromonothioformic ester or a chlorodithioformic ester of formula (VII)

in which

M and R 2 are as defined above,

optionally in the presence of a diluent and an acid binder,

(F) obtaining a compound of formulae (I-1-d) or (I-2-d)

in which R 3 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 , by reacting a compound of formulae (I-1-a) or (I-2-a),

with a sulphonyl chloride of formula (VIII)

R 3 —SO 2 —Cl (VIII)

in which

R 3 is as defined above,

optionally in the presence of a diluent and an acid binder,

(G) obtaining a compound of formulae (I-1-e) or (I-2-e)

in which L, R 4 , R 5 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 , by reacting a compound of formulae (1-1-a) or (I-2-a),

with a phosphorus compound of formula (IX)

in which

L, R 4 and R 5 are as defined above, and

Hal represents halogen,

optionally in the presence of a diluent and an acid binder,

(H) obtaining a compound of formulae (I-1-f) or (I-2-f)

in which E, A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 , by reacting a compound of formulae (I-1-a) or (I-2-a),

with a metal compound or an amine of formulae (X) and (XI), respectively,

in which

Me represents a mono- or divalent metal,

t represents 1 or 2, and

R 10 , R 11 , R 12 independently of one another represents hydrogen or alkyl, optionally in the presence of a diluent,

(I) obtaining a compound of formulae (I-1-g) or (I-2-g)

in which L, R 6 , R 7 , A, B, m, n, Q 1 , Q 2 , Q 3 , Q 4 , W, X, Y and Z are as defined in claim 1 , by reacting a compound of formulae (I-1-a) or (I-2-a),

a) with an isocyanate or isothiocyanate of formula (XII)

R 6 —N═C=L (XII)

in which

R 6 and L are as defined above,

optionally in the presence of a diluent and a catalyst, or

b) with a carbamoyl chloride or a thiocarbamoyl chloride of formula (XIII)

in which

L, R 6 and R 7 are as defined above,

optionally in the presence of a diluent and an acid binder.

7. A composition comprising an effective amount of an active compound combination comprising,

(a′) least one compound of formula (I) according to claim 1

and

(b′) at least one crop plant compatibility-improving 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-(cyanomethox-imino)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-dimethyloxazolidine (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-fluoro-phenyl)-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-chloromethylsulphonylbenzene, 1[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea (N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulphonamide), 1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoyl-sulphamoyl)phenyl]-3-methylurea, 1-[4-(N-naphthylsulphamoyl)phenyl]-3,3-dimethylurea, N-(2-methoxy-5-methylbenzoyl)-4-(cyclopropylaminocarbony)benzenesulphonamide,

a compound of formula (IIa)

a compound of formula (IIb)

a compound of formula (IIc)

where

m represents 0, 1, 2, 3, 4 or 5,

A 1 represents one of the divalent heterocyclic groupings shown below

n represents 0, 1, 2, 3, 4 or 5,

A 2 represents optionally C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-carbonyl-, or C 1 -C 4 -alkenyloxycarbonyl-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 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, or represents optionally fluorine-, chlorine- and/or 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 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, or represents optionally fluorine-, chlorine- and/or bromine- or C 1 -C 1 -alkyl-substituted phenyl, R 17 and R 18 also 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 represents 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 represents 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 -alkoxy or C 1 -C 4 -haloalkoxy,

X 3 represents hydrogen, cyano, nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy,

a compound or formula (IId)

a compound of formula (IIe)

where

t represents 0, 1, 2, 3, 4 or 5,

v represents 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)-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, 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.

8. A pesticide, herbicide or fungicide composition comprising at least one compound of formula (I) according to claim 1 .

9. A method for controlling animal pests, unwanted vegetation, or fungi, comprising contacting said pests, vegetation, fungi or their habitat with a compound of formula (I) according to claim 1 .

10. A process of preparing a pesticide, herbicide or fungicide composition, comprising mixing a compound of formula (I) according to claim 1 with an extender, a surfactant, or a combination thereof.

11. The composition according to claim 7 , in which the crop plant compatibility-improving compound is selected from the group consisting of

cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazole, fenclorim, cumyluron, dymron, a compound of formula IIe-5,

and a compound of formula IIe-11,

12. The composition according to claim 11 , in which the crop plant compatibility-improving compound is mefenpyr-diethyl.

13. The composition according to claim 11 , in which the crop plant compatibility-improving compound is the compound IIe-5.

14. A method for controlling unwanted vegetation, comprising contacting said vegetation on or its habitat with a composition according to claim 7 .

15. A method for controlling unwanted vegetation, comprising contacting said vegetation or its habitat with a compound of formula (I) according to claim 1 and a crop plant compatibility-improving compound according to claim 7 separately in close temporal succession or as a mixture.

16. A compound of formula (H)

in which

V in the 3′ or 4′-position represents

in which

A represents in each case optionally halogen-substituted alkyl, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl, saturated or unsaturated, optionally substituted cycloalkylalkyl 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, heteroaryl or heteroarylalkyl,

Q 1 and Q 2 independently of one another represent hydrogen or alkyl, or

A and Q 1 together with the atoms to which they are attached represent a saturated or unsaturated ring which contains at least one heteroatom and is unsubstituted or substituted in the A,Q moiety,

m represents 0, 1 or 2.

17. A compound of formula (I) according to claim 1 in which

W represents hydrogen, fluorine, chlorine, bromine or C 1 -C 4 -alkyl,

X represents chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano,

Y in the 4-position represents the radical

Z represents hydrogen,

V 1 represents fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, cyano or nitro,

V 2 represents hydrogen, fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkyl, or

V 1 and V 2 together also represent —O—CH 2 —O— or —O—CF 2 —O—,

B represents hydrogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or methyl, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

represents phenyl-C 1 -C 4 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy;

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl;

represents phenoxy-C 1 -C 5 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl; or

represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or

18. A compound of formula (I) according to claim 1 in which

W represents hydrogen, fluorine, chlorine, bromine or C 1 -C 4 -alkyl,

X represents chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano,

Y in the 5-position represents the radical

Z in the 4-position represents hydrogen,

V 1 represents fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy, cyano or nitro,

V 2 represents hydrogen, fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkyl, or

V 1 and V 2 together likewise represent —O—CH 2 —O— or —O—CF 2 —O—,

B represents hydrogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or methyl, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

represents phenyl-C 1 -C 4 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy;

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, fulanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl;

represents phenoxy-C 1 -C 5 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl; or

represents pyridyloxy-C 1 -C 5 -alkyl, pyrimidyloxy-C 1 -C 5 alkyl or thiazolyloxy -C 1 -C 5 -alkyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine, amino or C 1 -C 4 -alkyl,

represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or

19. A compound of formula (I) according to claim 1 in which

W represents hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, fluorine, chlorine, bromine or trifluoromethyl,

X represents chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 3 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano,

Y in the 4-position represents C 1 -C 4 -alkyl,

Z represents hydrogen,

B represents hydrogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or methyl, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur

M represents oxygen or sulphur,

represents phenyl-C 1 -C 4 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy;

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl;

represents phenoxy-C 1 -C 5 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl; or

represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or

20. A compound of formula (I) according to claim 1 in which

W represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy,

X represents chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 2 -haloalkyl, C 1 -C 2 -haloalkoxy or cyano,

Y in the 4-position represents hydrogen,

chlorine, bromine, iodine, C 1 -C 4

-alkyl, C 1 -C 2 -haloalkyl or C 1 -C 2 -haloalkoxy,

Z in the 3- or 5-position represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 2 -haloalkoxy,

B represents hydrogen, C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 independently of one another represent hydrogen or methyl, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur,

M represents oxygen or sulphur,

R 1 represents C 1 -C 16 -alkyl, C 2 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 6 -alkylthio-C 3 -C 4 -alkyl or poly-C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine; represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 5 -alkyl or C 1 -C 5 -alkoxy and in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and/or sulphur;

represents phenyl-C 1 -C 4 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -haloalkyl or C 1 -C 3 -haloalkoxy;

represents pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl;

represents phenoxy-C 1 -C 5 -alkyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl; or

represents C 3 -C 7 -cycloalkyl which is optionally mono- to disubstituted by fluorine, chlorine, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; or

21. A compound of formula (I) according to claim 1 in which

W represents hydrogen, chlorine, bromine, methyl or ethyl,

X represents chlorine, bromine, methyl, ethyl, propyl, methoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,

Y in the 4-position represents the radical

Z represents hydrogen,

V 1 represents fluorine, chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy or cyano,

V 2 represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur, and

M represents oxygen or sulphur,

represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,

R 2 represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;

represents cyclopentyl or cyclohexyl;

or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,

R 6 and R 7 independently of one another represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl; represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl; or R 6 and R 7 together represent a C 5 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

22. A compound of formula (I) according to claim 1 in which

W represents hydrogen, chlorine or methyl,

X represents chlorine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy or cyano,

Y in the 5-position represents the radical

Z in the 4-position represents hydrogen,

V 1 represents fluorine, chlorine, methyl, methoxy, trifluoromethyl, trifluoromethoxy or cyano,

V 2 represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur, and

M represents oxygen or sulphur,

represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,

R 2 represents C 1 -C 10 alkyl, C 2 -C 10 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;

represents cyclopentyl or cyclohexyl;

or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,

23. A compound of formula (I) according to claim 1 in which

W represents hydrogen, methyl, ethyl, methoxy, ethoxy, chlorine or bromine,

X represents chlorine, bromine, iodine, methyl, ethyl, propyl, methoxy, ethoxy, propoxy, methoxyethoxy, ethoxyethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,

Y in the 4-position represents methyl or ethyl,

Z represents hydrogen,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur, and

M represents oxygen or sulphur,

represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,

R 2 represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;

represents cyclopentyl or cyclohexyl;

or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,

R 6 and R 7 independently of one another represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 alkoxy, C 3 -C 4 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl; represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl; or R 6 and R 7 together represent a C 5 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

24. A compound of formula (I) according to claim 1 in which

W represents hydrogen, chlorine, bromine, methyl or ethyl,

X represents chlorine, bromine, iodine, methyl, ethyl, methoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

Y in the 4-position represents hydrogen,

chlorine, bromine, methyl or

ethyl,

Z in the 3- or 5-position represents fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl or trifluoromethoxy,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen, or

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

E represents a metal ion or an ammonium ion,

L represents oxygen or sulphur, and

M represents oxygen or sulphur,

represents furanyl, thienyl or pyridyl, each of which is optionally monosubstituted by chlorine, bromine or methyl,

R 2 represents C 1 -C 10 -alkyl, C 2 -C 10 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl, each of which is optionally mono- to trisubstituted by fluorine or chlorine;

represents cyclopentyl or cyclohexyl;

or represents phenyl or benzyl, each of which is optionally mono- to disubstituted by fluorine, chlorine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,

R 6 and R 7 independently of one another represent hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 3 -C 4 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 -alkyl; represent phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, methoxy or trifluoromethyl; or R 6 and R 2 together represent a C 5 -C 6 -alkylene radical in which optionally one methylene group is replaced by oxygen or sulphur.

25. A compound of formula (I) according to claim 1 in which

W represents hydrogen or methyl,

X represents chlorine or methyl,

Y in the 5-position represents

Z in the 4-position represents hydrogen,

A represents C 1 -C 4 -alkyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a)

in which

R 1 represents C 1 -C 10 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or cyclopropyl,

R 2 represents C 1 -C 10 -alkyl or benzyl.

26. A compound of formula (I) according to claim 1 in which

W represents methyl, ethyl or methoxy,

X represents chlorine, bromine, methyl, ethyl or methoxy,

Y in the 4-position represents methyl,

Z represents hydrogen,

A represents C 1 -C 4 -alkyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

R 1 represents C 1 -C 10 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or cyclopropyl,

R 2 represents C 1 -C 10 -alkyl or benzyl.

27. A compound of formula (I) according to claim 1 in which,

W represents hydrogen or methyl,

X represents bromine, methyl or methoxy,

Y in the 4-position represents

hydrogen, chlorine or methyl,

Z in the 3- or 5-position represents methyl,

A represents C 1 -C 4 -alkyl,

B represents hydrogen,

D represents NH or oxygen,

Q 1 , Q 2 , Q 3 and Q 4 represent hydrogen,

m represents 0 or 1,

n represents 1,

G represents hydrogen (a),

in which

R 1 represents C 1 -C 10 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 2 -alkyl or cyclopropyl,

R 2 represents C 1 -C 10 -alkyl or benzyl.

Assignments (2)

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 23, 2015

From: BAYER CROPSCIENCE AG

To: BAYER INTELLECTUAL PROPERTY GMBH

Reel/Frame 035005/0367 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 16, 2009

From: FISCHER, REINER, DR.; GAERTZEN, OLIVER, DR.; LEHR, STEFAN, DR.; FEUCHT, DIETER, DR.; MALSAM, OLGA, DR.; DREWES, MARK WILHELM, DR.; FRANKEN, EVA-MARIA, DR.; ARNOLD, CHRISTIAN, DR.; AULER, THOMAS, DR.; HILLS, MARTIN JEFFREY; KEHNE, DR. HEINZ; ROSINGER, CHRIS HUGH, DR.; BRETSCHNEIDER, THOMAS, DR.; BOJACK, GUIDO, DR.; DITTGEN, JAN, DR.

To: BAYER CROPSCIENCE AG

Reel/Frame 022556/0606 →