Pyrazole biphenylcarboxamides

1. A biphenylcarboxamide of the formula (I)

in which

R represents hydrogen, C 1 –C 6 -alkyl, C 3 –C 6 -cycloalkyl, or C 1 –C 6 -halogenoalkyl having 1 to 5 halogen atoms,

Z represents hydrogen, C 1 –C 6 -alkyl, or C 1 –C 6 -halogenoalkyl having 1 to 5 halogen atoms,

X and Y independently of one another each represent halogen, nitro, cyano, hydroxy, carboxyl, C 1 –C 8 -alkyl, C 1 –C 6 -halogenoalkyl having 1 to 5 halogen atoms, C 1 –C 8 -alkoxy, C 1 –C 6 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 –C 8 -alkylthio, C 1 –C 6 -halogenoalkylthio having 1 to 5 halogen atoms, C 2 –C 8 -alkenyloxy, C 2 –C 8 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 –C 8 -alkynyloxy, C 3 –C 8 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 –C 8 -cycloalkyl, C 1 –C 8 -alkoxycarbonyl, C 1 –C 8 -alkylsulphinyl, C 1 –C 8 -alkylsulphonyl, C 1 –C 8 halogenoalkylsulphinyl having 1 to 5 halogen atoms, C 1 –C 8 -halogeno-alkylsulphonyl having 1 to 5 halogen atoms, or C 1 –C 6 -alkoximino-C 1 –C 6 -alkyl,

m represents integers from 0 to 3, with the proviso that X represents identical or different radicals if m represents 2 or 3,

n represents integers from 0 to 4, with the proviso that Y represents identical or different radicals, if n represents 2, 3, or 4, and

A represents a radical of the formula

 in which

(α) R 1 represents hydrogen, cyano, halogen, nitro, C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylthio, C 1 –C 4 -halogenoalkylthio having 1 to 5 halogen atoms, aminocarbonyl, or aminocarbonyl-C 1 –C 4 -alkyl,

R 2 represents hydrogen, cyano, C 1 –C 4 -alkyl, C 1 –C 4 -alkoxy, or C 1 –C 4 -alkylthio, and

R 3 represents hydrogen, C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C 1 –C 4 -alkyl, C 2 –C 6 -alkenyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkylthio-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkylthio-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkoxy-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, or phenyl, or

(β) R 1 represents hydrogen, cyano, halogen, nitro, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylthio, C 1 –C 4 -halogenoalkylthio having 1 to 5 halogen atoms, aminocarbonyl, or aminocarbonyl-C 1 –C 4 -alkyl,

R 2 represents fluorine, and

R 3 represents hydrogen, C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C 1 –C 4 -alkyl, C 2 –C 6 -alkenyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkylthio-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkylthio-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, C 1 –C 4 -alkoxy-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkoxy-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, or phenyl, or

(γ) R 1 represents hydrogen, cyano, halogen, nitro, C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkoxy, C 1 –C 4 -halogenoalkoxy having 1 to 5 halogen atoms, C 1 –C 4 -alkylthio, C 1 –C 4 -halogenoalkylthio having 1 to 5 halogen atoms, aminocarbonyl, or aminocarbonyl-C 1 –C 4 -alkyl,

R 2 represents fluorine, and

R 3 represents hydrogen, C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C 1 –C 4 -alkyl, C 2 –C 6 -alkenyl, C 3 –C 6 -cycloalkyl, C 1 –C 4 -alkylthio-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkylthio-C 1 –C 4 -alkyl having 1 to 5 halogen atoms, C 1 –C 4 alkoxy-C 1 –C 4 -alkyl, C 1 –C 4 -halogenoalkoxy-C 1 –C 4 -alkyl having 1 to 5 halogen atoms or phenyl.

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

R represents hydrogen, C 1 –C 4 -alkyl, or C 3 –C 6 -Cycloalkyl, or C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms,

Z represents hydrogen, C 1 –C 4 -alkyl, or C 1 –C 4 -halogenoalkyl having 1 to 5 halogen atoms,

X and Y independently of one another each represent fluorine, chlorine, bromine, nitro, cyano, hydroxy, carboxyl, C 1 –C 6 -alkyl, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, C 1 –C 6 -alkoxy, C 1 –C 2 -halogenoalkoxy having 1 to 5 fluorine, chlorine and/or bromine atoms, C 1 –C 6 -alkylthio, C 1 –C 2 -halogenoalkylthio having 1 to 5 fluorine, chlorine, and/or bromine atoms, C 2 –C 6 -alkenyloxy, C 2 –C 6 -halogenoalkenyloxy having 1 to 5 halogen atoms, C 3 –C 6 -alkynyloxy, C 3 –C 6 -halogenoalkynyloxy having 1 to 5 halogen atoms, C 3 –C 7 -cycloalkyl, C 1 –C 4 -alkoxycarbonyl, C 1 –C 6 -alkylsulphinyl, C 1 –C 6 -alkyl-sulphonyl, C 1 –C 6 -halogenoalkylsulphinyl having 1 to 5 halogen atoms, C 1 –C 6 -halogenoalkylsulphonyl having 1 to 5 halogen atoms, or C 1 –C 4 -alkoximino-C 1 –C 4 -alkyl,

m represents integers from 0 to 3, with the proviso that X represents identical or different radicals if m represents 2 or 3,

n represents integers from 0 to 4, with the proviso that Y represents identical or different radicals if n represents 2, 3, or 4, and

A represents a radical of the formula

 in which

(α) R 1 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C 1 –C 2 -halogenoalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl, or aminocarbonylethyl,

R 2 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio, and

R 3 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, or phenyl, or

(β) R 1 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C 1 –C 2 -halogenoalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, amino-carbonyl, aminocarbonylmethyl, or aminocarbonylethyl,

R 2 represents fluorine, and

R 3 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, or phenyl, or

(γ) R 1 represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, cyclopropyl, methoxy, ethoxy, C 1 –C 2 -halogenoalkoxy having 1 to 5 fluorine, chlorine, and/or bromine atoms, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl, or aminocarbonylethyl,

R 2 represents fluorine, and

R 3 represents hydrogen, C 1 –C 2 -halogenoalkyl having 1 to 5 fluorine, chlorine, and/or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, or phenyl.

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

R represents hydrogen or C 1 –C 4 -alkyl,

Z represents hydrogen or C 1 –C 4 -alkyl,

X and Y independently of one another each represent fluorine, chlorine, bromine, nitro, cyano, hydroxy, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, tert-butyl, trichloromethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, trifluoromethylthio, difluorochloromethylthio, allyloxy, propargyloxy, cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, or ethoximinoethyl,

m represents integers from 0 to 3, with the proviso that X represents identical or different radicals if m represents 2 or 3,

n represents the numbers 0 to 4, with the proviso that Y represents identical or different radicals if n represents 2, 3, or 4, and

A represents a radical of the formula

 in which

(α) R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio, or difluoromethylthio,

R 2 represents hydrogen, methyl, ethyl, methoxy, ethoxy, methylthio, or ethylthio, and

R 3 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl, or phenyl, or

(β) R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio, or difluoromethylthio, and

R 2 represents fluorine, and

R 3 represents hydrogen, methyl, ethyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl, or phenyl, or

(γ) R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio, or difluoromethylthio,

R 2 represents fluorine, and

R 3 represents hydrogen, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl, or phenyl.

4. A process for preparing a biphenylcarboxamide of the formula (I) according to claim 1 comprising

(a) reading a carboxylic acid derivative of the formula (II)

 in which

A is as defined for formula (I) in claim 1 , and

G represents halogen, hydroxy, or C 1 –C 6 -alkoxy, with an aniline derivative of the formula (III)

 in which R, Z, X, Y, m, and n are each as defined for formula (I) in claim 1 , optionally in the presence of a catalyst, optionally in the presence of an acid binder, and optionally in the presence of a diluent, or

(b) reacting a carboxamide derivative of the formula (IV)

 in which A, X, and m are each as defined for formula (I) in claim 1 , with a boronic acid derivative of the formula (V)

 in which

R, Z, Y, and n are each as defined for formula (I) in claim 1 , and

G 1 and G 2 each represent hydrogen or together represent tetramethylethylene, optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(c) reacting a carboxamide-boronic acid derivative of the formula (VI)

 in which

A, X, and m are each as defined for formula (I) in claim 1 , and

G 1 and G 2 each represent hydrogen or together represent tetramethylethylene, with a phenyloxime derivative of the formula (VII)

 in which R, Z, Y, and n are each as defined for formula (I) in claim 1 , optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(d) reacting biphenylacyl derivative of the formula (VIII)

in which A, R, X, Y, m, and n are each as defined for formula (I) in claim 1 , with an alkoxamine of the formula (IX)

Z-O—NH 2 x HCl  (IX)

in which each Z is as defined for formula (I) in claim 1 , optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(e) reading a hydroxyamine derivative of the formula (I-a)

in which A, R, X, Y, m, and n are each as defined for formula (I) in claim 1 , with a compound of the formula (x)

Z 1 -E  (x)

 in which

Z 1 represents C 1 –C 6 -alkyl, and

E represents chlorine, bromine, iodine, methanesulphonyl, or p-toluenesulphonyl, or

Z 1 and E together represent (di-C 1 –C 6 -alkyl) sulphate, optionally in the presence of an acid binder and optionally in the presence of a diluent, or

(f) reacting a carboxamide derivative of the formula (IV)

 in which A, X, and m are each as defined for formula (I) in claim 1 , with a phenyloxime derivative of the formula (VII)

 in which R, Z, Y, and n are each as defined for formula (I) in claim 1 , in the presence of a palladium or platinum catalyst and in the presence of 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane, and optionally in the presence of an acid binder and optionally in the presence of a diluent.

5. A composition for controlling undesirable microorganisms comprising an effective amount of one or more biphenylcarboxamides of the formula (I) according to claim 1 and extenders and/or surfactants.

6. A method for controlling undesirable microorganisms comprising applying a biphenylcarboxamide of the formula (I) according to claim 1 to the microorganisms and/or their habitat.