Biphenyl-substituted spirocyclic ketoenols

1. A compound of formula (I)

in which

W represents hydrogen or methyl,

X represents fluorine, chlorine, methyl, ethyl, propyl, isopropyl, methoxy, ethoxy, propoxy, isopropoxy, trifluoromethyl, difluoromethoxy or trifluoromethoxy,

Y represents hydrogen, methyl, fluorine or chlorine,

Z represents the radical

V 1 represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy,

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

CKE represents one of the groups

A, B and the carbon atom to which they are attached represent saturated C 6 -cycloalkyl in which one ring member is replaced by oxygen at 3 or 4 position,

G represents hydrogen (a) or represents one of the groups

in which

L represents oxygen or sulphur,

M represents oxygen or sulphur and

E represents a metal ion equivalent or an ammonium ion,

R 1 represents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 2 -alkoxy-C 1 -alkyl, C 1 -C 2 -alkylthio-C 1 -alkyl, each of which is optionally monosubstituted by fluorine or chlorine, or represents cyclopropyl or cyclohexyl, each of which is optionally monosubstituted by fluorine, chlorine, methyl or methoxy,

represents phenyl which 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.

2. A process for preparing compounds of formula (I) according to claim 1 , characterized in that,

(A) in order to obtain a compound of formula (I-1-a)

in which

A, B, W, X, Y and Z are as defined in claim 1 ,

an N-acylamino acid ester of formula (II)

in which

A, B, W, X, Y and Z are as defined in claim 1 ,

and

R 8 represents alkyl

is condensed intramolecularly in the presence of a diluent and in the presence of a base;

(B) in order to obtain a compound of formula (I-2-a)

in which

A, B, W, X, Y and Z are as defined in claim 1 ,

a carboxylic ester of the formula (III)

in which

A, B, W, X, Y and Z are as defined in claim 4 and R 8 is alkyl,

is condensed intramolecularly in the presence of a diluent and in the presence of a base;

(C) in order to obtain a compound of formula (I-1-a), (I-1-b), (I-1-c), (I-1-f), (I-2-a), (I-2-b), (I-2-c), or (I-2-f) shown below,

in which

A, B, E, L, M, W, X, Y, Z, R 1 , and R 2 , are as defined in claim 1 ,

a corresponding compound of formula (I-1′-a), (I-1′-b), (I-1′-c), (I-1′-f), (I-2′-a), (I-2′-b), (I-2′-c), or (I-2′-f), respectively

in which

A, B, G, W, X and Y are as defined in claim 1 , and

Z′ represents chlorine, bromine, or iodine,

is reacted with a boronic acid or a boronic acid derivative of the formula (IV)

in which

R 9 represents hydrogen, C 1 -C 6 -alkyl or C 2 -C 6 -alkanediyl

and

Z is as defined in claim 1 ,

in the presence of a solvent, a base and a catalyst, wherein the catalyst is a palladium salt or a palladium complex;

(D) in order to obtain a compound of formula (I-1-b) or formula (I-2-b) in which A, B, R 1 , W, X, Y and Z are as defined in claim 1 , a compound of the formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1 , is in each case reacted

(α) with an acid halide of formula (V)

in which

R 1 is as defined in claim 1 , and

Hal represents halogen,

or

(β) with a carboxylic anhydride of the formula (VI)

R 1 —CO—O—CO—R 1   (VI)

in which

R 1 is as defined in claim 1 ,

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

(E) in order to obtain a compound of formula (I-1-c) or (I-2-c) in which A, B, R 2 , M, W, X, Y and Z are as defined in claim 1 , and L represents oxygen, a compound of the formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1 , is in each case reacted

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

R 2 -M-CO—Cl  (VII)

in which

R 2 and M are as defined in claim 1 ,

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

(F) in order to obtain a compound of formula (I-1-c) or (I-2-c) in which A, B, R 2 , M, W, X, Y and Z are as defined in claim 1 and L represents sulphur, a compound of formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1 , is in each case reacted

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

in which

M and R 2 are as defined in claim 1 ,

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

(G) in order to obtain a compound of formula (I-1-f) or (I-2-f) in which A, B, E, W, X, Y and Z are as defined in claim 1 , a compound of formula (I-1-a) or (I-2-a) in which A, B, W, X, Y and Z are as defined in claim 1 , is in each case reacted

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

in which

Me represents a mono- or divalent metal,

t represents the number 1 or 2 and

R 10 , R 11 , R 12 independently of one another represent hydrogen or alkyl,

optionally in the presence of a diluent.

3. A pesticide, herbicide, or a combination thereof, comprising at least one compound of the formula (I) according to claim 1 , and an extender, surfactant or combination thereof.

4. A method for controlling animal pests, unwanted vegetation, or combinations thereof, comprising allowing a compound of formula (I) according to claim 1 to act on pests, their habitat, or combinations thereof.

5. A process for preparing pesticides, herbicides, or combinations thereof, comprising mixing a compound of formula (I) according to claim 1 with an extender, a surfactant, or combinations thereof.

6. A compound of formula (I-1-a)

in which

Compound

W

X

Y

F

V 1

V 2

A      B

I-1-a-4

CH 3

CH 3

H

4

H

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

I-1-a-5

CH 3

CH 3

H

4

3-F

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —.

7. A compound of formula (I-1-f)

in which

Com-

pound

W

X

Y

F

V 1

V 2

A      B

E

I-1-f-1

CH 3

CH 3

H

4

H

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

Na +

I-1-f-2

CH 3

CH 3

H

4

H

H

—(CH 2 ) 2 —O—(CH 2 ) 2 —

K + .