KR100772457B1 - Biphenyl carboxamides - Google Patents

Abstract

The present invention relates to novel biphenylcarboxamides of the general formula (I), a number of methods for their preparation and their use for controlling unwanted microorganisms, and novel intermediates and methods for the preparation thereof:

Where

A, R, Z, X, Y, m and n are each as defined in the specification.

Description

Biphenyl carboxamides             

The present invention relates to novel biphenylcarboxamides, a number of methods for their preparation, and their use for controlling unwanted microorganisms.

It is already known that many carboxanilides are fungicidal (see WO 93/11 117, WO 99/09 013, WO 00/14 071, EP-A 0 545 099 and EP-A 0 589 301). . The activity of these materials is good, but often they are not satisfactory.

According to the present invention a novel biphenylcarboxamide of the general formula (I) was found:

Where

R represents hydrogen, C _1-6 -alkyl, C _3-6 -cycloalkyl or C _1-6 -halogenoalkyl having 1 to 5 halogen atoms,

Z is hydrogen, C _1-6 - represents a halogeno-alkyl, - C _1-6 alkyl, having 1 to 5 halogen atoms,

X and Y are each independently halogen, nitro, cyano, hydroxy, carboxyl, C _1-8 -alkyl, C _1-6 -halogenoalkyl having 1 to 5 halogen atoms, C _1-8 -alkoxy , C _1-6 -halogenoalkoxy having 1 to 5 halogen atoms, C _1-8 -alkylthio, C _1-6 -halogenoalkylthio having 1 to 5 halogen atoms, C _2-8 -al alkenyloxy, C _2-8 with 1 to 5 halogen atoms halogeno noal alkenyloxy, C _{3-8-alkynyloxy,} C _3-8 with 1 to 5 halogen atoms halogeno alkynyloxy, C _3-8 - cycloalkyl, C _1-8 - alkoxycarbonyl, C _1-8 - alkyl sulfinyl, C _{1-8-alkylsulfonyl,} C _1-8 with 1 to 5 halogen atoms halogenoalkyl alkyl sulfinyl, C _1-8 with 1 to 5 halogen atoms or C _1-6 halogenoalkyl sulfonyl-Al kokseuyi unexposed -C _1-6 - represents alkyl,

m represents an integer of 0 to 3, when m represents 2 or 3, X represents the same or different radicals,

n represents an integer of 0 to 4, and when n represents 2, 3 or 4, Y represents the same or different radicals,

의 래디칼을 나타내며,A is an expression

Represents the radical of,

From here,             

α) R ¹ is hydrogen, cyano, halogen, nitro, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - halogenoalkyl, C _3-6 - cycloalkyl, C _1-4 -halogeno alkoxy, C _1-4 - - alkylthio, C _1-4 with 1 to 5 halogen atoms halogeno alkylthio, aminocarbonyl or alkoxy group, with 1 to 5 halogen atoms having a C _1-4 Aminocarbonyl-Ci_ ₄ -alkyl,

R ² represents hydrogen, chlorine, bromine, iodine, cyano, C _1-4 -alkyl, C _1-4 -alkoxy or C _1-4 -alkylthio,

R ³ is hydrogen, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms halogenoalkyl, hydroxy, -C _1-4 - alkyl, C _2-6 - alkenyl, C _{3- 6} -cycloalkyl, C _1-4 - alkylthio -C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms-halogeno alkylthio -C _1-4 - alkyl, C _1-4 - Alkoxy-C _1-4 -alkyl, C _1-4 -halogenoalkoxy-C _1-4 -alkyl or having 1 to 5 halogen atoms, or

β) R ¹ is hydrogen, cyano, halogen, nitro, C _2-4 -alkyl, C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, C _3-6 -cycloalkyl, C _1-4 -halogeno alkoxy, C _1-4 - - alkylthio, C _1-4 with 1 to 5 halogen atoms halogeno alkylthio, aminocarbonyl or alkoxy group, with 1 to 5 halogen atoms having a C _1-4 Aminocarbonyl-Ci_ ₄ -alkyl,

R ² represents fluorine,

R ³ is hydrogen, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms halogenoalkyl, hydroxy, -C _1-4 - alkyl, C _2-6 - alkenyl, C _{3- 6} -cycloalkyl, C _1-4 - alkylthio -C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms-halogeno alkylthio -C _1-4 - alkyl, C _1-4 - Alkoxy-C _1-4 -alkyl, C _1-4 -halogenoalkoxy-C _1-4 -alkyl or having 1 to 5 halogen atoms, or

γ) R ¹ is hydrogen, cyano, halogen, nitro, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - halogenoalkyl, C _3-6 - cycloalkyl, C _1-4 -halogeno alkoxy, C _1-4 - - alkylthio, C _1-4 with 1 to 5 halogen atoms halogeno alkylthio, aminocarbonyl or alkoxy group, with 1 to 5 halogen atoms having a C _1-4 Aminocarbonyl-Ci_ ₄ -alkyl,

R ² represents fluorine,

R ³ is hydrogen, C _2-4 -alkyl, C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, hydroxy-C _1-4 -alkyl, C _2-6 -alkenyl, C _{3- 6} -cycloalkyl, C _1-4 - alkylthio -C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms-halogeno alkylthio -C _1-4 - alkyl, C _1-4 - Alkoxy-C _1-4 -alkyl, C _1-4 -halogenoalkoxy-C _1-4 -alkyl or phenyl having 1 to 5 halogen atoms,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ⁴ and R ⁵ independently of each other represent hydrogen, halogen, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ⁶ represents halogen, cyano, C _1-4 -alkyl or C _1-4 -halogenoalkoxy having 1 to 5 halogen atoms, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ⁷ and R ⁸ independently of each other represent hydrogen, halogen, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ⁹ represents hydrogen, C _1-4 -alkyl or halogen, or

의 래디칼을 나타내고, A is an expression

Represents the radical,

From here,

R ¹⁰ is hydrogen, halogen, hydroxy, cyano, C _1-6 -alkyl, C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, C _1-4 -having 1 to 5 halogen atoms Halogenoalkoxy or C _1-4 -halogenoalkylthio having 1 to 5 halogen atoms, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ¹¹ is halogen, hydroxy, cyano, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - halogenoalkyl, C _1-4 - alkoxy, C _1-4 - alkylthio, C _1-4 -halogenoalkylthio having 1 to 5 halogen atoms or C _1-4 -halogenoalkoxy having 1 to 5 halogen atoms,

R ¹² is hydrogen, halogen, cyano, C _1-4 - alkyl, a C _1-4 with 1 to 5 halogen atoms halogenoalkyl, C _1-4 - alkoxy, C _{1-4-alkylthio,} 1 C _1-4 -halogenoalkoxy, C _1-4 -alkylsulfinyl or C _1-4 -alkylsulfonyl having from 5 to 5 halogen atoms, or

의 래디칼을 나타내고, A is an expression

Represents the radical,

From here,

R ¹³ is C _1-4 - represents a halogeno-alkyl, - C _1-4 alkyl, having 1 to 5 halogen atoms,

R ¹⁴ represents C _1-4 -alkyl,

X ¹ represents a sulfur atom, SO, SO ₂ or CH ₂ ,

p represents 0, 1 or 2, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ¹⁵ is C _1-4 - alkyl or C _1-4 having 1 to 5 halogen atoms or represent halogenoalkyl,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ¹⁶ is C _1-4 - alkyl or C _1-4 having 1 to 5 halogen atoms or represent halogenoalkyl,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ¹⁷ represents halogen, cyano, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ¹⁸ represents hydrogen, halogen, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ¹⁹ is hydrogen, cyano, C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - halogenoalkyl, C _1-4 - alkoxy -C _1-4 - alkyl, hydroxy -C _1-4 -alkyl, C _1-4 -alkylsulfonyl, di (C _1-4 -alkyl) aminosulfonyl or C _1-6 -alkylcarbonyl, or optionally substituted phenylsulfonyl or benzoyl Or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ²⁰ and R ²¹ independently of each other represent hydrogen, halogen, amino, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ²² represents hydrogen, halogen, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ²³ and R ²⁴ independently of each other represent hydrogen, halogen, amino, nitro, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

R ²⁵ represents hydrogen, halogen, C _1-4 -alkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ²⁶ is hydrogen, halogen, amino, C _1-4 -alkylamino, di- (C _1-4 -alkyl) amino, cyano, C _1-4 -alkyl or C _1- having 1 to 5 halogen atoms ₄ -halogenoalkyl,

R ²⁷ is halogen, C _1-4 - or represent halogenoalkyl, - C _1-4 alkyl, having 1 to 5 halogen atoms,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ²⁸ is hydrogen, halogen, amino, C _1-4 -alkylamino, di- (C _1-4 -alkyl) amino, cyano, C _1-4 -alkyl or C _1- having 1 to 5 halogen atoms ₄ -halogenoalkyl,

R ²⁹ is halogen, C _1-4 - or represent halogenoalkyl, - C _1-4 alkyl, having 1 to 5 halogen atoms,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ³⁰ is halogen, C _1-4 - or represent halogenoalkyl, - C _1-4 alkyl, having 1 to 5 halogen atoms,

의 래디칼을 나타내고, A is an expression

Represents the radical,

From here,

R ³¹ represents hydrogen or C _1-4 -alkyl,

R ³² represents halogen or C _1-4 -alkyl, or

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ³³ is C _1-4 - alkyl or C _1-4 having 1 to 5 halogen atoms or represent halogenoalkyl,

의 래디칼을 나타내고,A is an expression

Represents the radical,

From here,

R ³⁴ represents hydrogen, halogen or C _1-4 -alkyl.

Further, according to the present invention, biphenylcarboxamide of general formula (I)

a) reacting a carboxylic acid derivative of the general formula (II) with an aniline derivative of the general formula (III) below optionally in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent ,

b) reacting the carboxamide derivative of formula (IV) with the boronic acid derivative of formula (V) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent,

c) Carboxamide-boronic acid derivatives of the general formula (VI) with phenyloxime derivatives of the general formula (VII) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a diluent React,

d) reacting a biphenylacyl derivative of the general formula (VIII) below with an alkoxamine of the general formula (IX), optionally in the presence of an acid binder and optionally in the presence of a diluent,

e) reacting a hydroxyamine derivative of the general formula (I-a) with a compound of the general formula (X), optionally in the presence of an acid binder and optionally in the presence of a diluent,

f) Carboxamide derivatives of the following general formula (IV) are prepared in the presence of palladium or platinum catalyst, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- It was found to be obtained by reacting with a phenyloxime derivative of the general formula (VII) in the presence of bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder and optionally in the presence of a diluent. :

Where

A, R, Z, X, Y, m and n are each as defined above,

G represents halogen, hydroxy or C _1-6 -alkoxy,

G ¹ and G ² each represent hydrogen or together represent tetramethylethylene,

Z ¹ represents C _1-6 -alkyl,

E represents chlorine, bromine, iodine, methanesulfonyl or p-toluenesulfonyl, or

Z ¹ and E together represent di-C _1-6 -alkyl sulfate.

Finally, it has been found that the novel biphenylcarboxamides of general formula (I) exhibit very good bactericidal properties and can be used to control unwanted microorganisms in both crop protection and material protection.

Surprisingly, the biphenylcarboxamides of general formula (I) according to the invention exhibit far superior fungicidal activity than the prior active compounds which are the most structurally similar and have the same propensity to action.

Formula (I) provides a general definition of biphenylcarboxamide according to the present invention.

R preferably represents hydrogen, C _1-4 -alkyl, C _3-6 -cycloalkyl or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms,

Z is preferably hydrogen, C _1-4 - represents a halogeno-alkyl, - C _1--4 alkyl, having 1 to 5 halogen atoms,

X and Y are each independently preferably a fluorine, chlorine, bromine, nitro, cyano, hydroxy, carboxyl, C _1-6 each other -alkyl, C ₁ having 1 to 5 fluorine, chlorine and / or bromine atom _-2 -halogenoalkyl, C _1-6 -alkoxy, C _1-2 -halogenoalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms, C _1-6 -alkylthio, 1 to 5 fluorine , chlorine and / or bromine atom with a C _1-2 - halogenoalkyl alkylthio, C _{2-6-alkenyloxy,} C _2-6 with 1 to 5 halogen atoms-halogeno noal alkenyloxy, C _{3- 6} -alkynyloxy, C _3-6 -halogenoalkynyloxy having 1 to 5 halogen atoms, C _3-7 -cycloalkyl, C _1-4 -alkoxycarbonyl, C _1-6 -alkylsulfinyl , C _{1-6-alkylsulfonyl,} C _1-6 with 1 to 5 halogen atoms halogeno alkylsulfonyl or C _{1-halogeno-alkyl} sulfinyl, C _1-6 with 1 to 5 halogen atoms _-4- al kokseuyi unexposed -C _1-4 - alkyl Get out,

m preferably represents an integer of 0 to 3, when m represents 2 or 3, X represents the same or different radicals,

n preferably represents an integer of 0 to 4, and when n represents 2, 3 or 4, Y represents the same or different radicals,

의 래디칼을 나타내며,A is preferably a formula

Represents the radical of,

From here,

α) R ¹ is hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, C _1-2 -halogenoalkyl, cyclopropyl having 1 to 5 fluorine, chlorine and / or bromine atoms , Methoxy, ethoxy, C _1-2 -halogenoalkoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbo with 1 to 5 fluorine, chlorine and / or bromine atoms Nil, aminocarbonylmethyl or aminocarbonylethyl,

R ² represents hydrogen, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio,

R ³ is hydrogen, methyl, ethyl, n-propyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclo Propyl, cyclopentyl, cyclohexyl or phenyl,

β) R ¹ is hydrogen, cyano, fluorine, chlorine, bromine, iodine, ethyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, cyclopropyl, methi Methoxy, ethoxy, C _1-2 -halogenoalkoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbonyl, having 1 to 5 fluorine, chlorine and / or bromine atoms, Aminocarbonylmethyl or aminocarbonylethyl,

R ² represents fluorine,

R ³ is hydrogen, methyl, ethyl, n-propyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, Or cyclopentyl, cyclohexyl or phenyl,

γ) R ¹ is hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, C _1-2 -halogenoalkyl, cyclopropyl having 1 to 5 fluorine, chlorine and / or bromine atoms , Methoxy, ethoxy, C _1-2 -halogenoalkoxy, methylthio, ethylthio, trifluoromethylthio, difluoromethylthio, aminocarbo with 1 to 5 fluorine, chlorine and / or bromine atoms Nil, aminocarbonylmethyl or aminocarbonylethyl,

R ² represents fluorine,

R ³ is hydrogen, ethyl, n-propyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, cyclopentyl , Cyclohexyl or phenyl,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ⁴ and R ⁵ independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ⁶ represents fluorine, chlorine, bromine, cyano, methyl, ethyl, or C _1-2 -halogenoalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ⁷ and R ⁸ independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ⁹ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹⁰ is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C _1-4 -alkyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, 1 to 5 fluorine, chlorine and / or bromine atom with a C _1-2 - alkoxy or halogenoalkyl with 1 to 5 fluorine, chlorine and / or bromine atom with a C _1-2 - halogenoalkyl, or represent alkylthio,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹¹ is fluorine, chlorine, bromine, iodine, hydroxy, cyano, C _1-4 -alkyl, C _1-2 -halogenoalkyl, having 1 to 5 fluorine, chlorine and / or bromine atoms, methoxy, Ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, or C _1-2 -halogenoalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ¹² is hydrogen, fluorine, chlorine, bromine, iodine, cyano, C _1-4 -alkyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, methoxy, Methoxy, methylthio, ethylthio, C _1-2 -halogenoalkoxy, C _1-2 -alkylsulfinyl or C _1-2 -alkylsulfonyl having 1 to 5 fluorine, chlorine and / or bromine atoms Or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹³ represents methyl, ethyl or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ¹⁴ represents methyl or ethyl,

X ¹ represents a sulfur atom, SO, SO ₂ or CH ₂ ,

p represents 0, 1 or 2, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹⁵ represents methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹⁶ represents methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ¹⁷ represents fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ¹⁸ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ¹⁹ is hydrogen, methyl, ethyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, C _1-2 -alkoxy-C _1-2 -alkyl, hydroxymethyl, Hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ²⁰ and R ²¹ independently of each other represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

R ²² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ²³ and R ²⁴ independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms; Indicates,

R ²⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ²⁶ is hydrogen, fluorine, chlorine, bromine, amino, C _1-4 -alkylamino, di- (C _1-4 -alkyl) amino, cyano, methyl, ethyl, or 1 to 5 fluorine, chlorine and / Or C _1-2 -halogenoalkyl having a bromine atom,

R ²⁷ represents fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ²⁸ is hydrogen, fluorine, chlorine, bromine, amino, C _1-4 -alkylamino, di- (C _1-4 -alkyl) amino, cyano, methyl, ethyl, or 1 to 5 fluorine, chlorine and / Or C _1-2 -halogenoalkyl having a bromine atom,

R ²⁹ represents fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ³⁰ represents fluorine, chlorine, bromine, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ³¹ represents hydrogen, methyl or ethyl,

R ³² represents fluorine, chlorine, bromine, methyl or ethyl, or

의 래디칼을 나타내고,A is also preferably a formula

Represents the radical,

From here,

R ³³ represents methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms,

의 래디칼을 나타내고, A is also preferably a formula

Represents the radical,

From here,

R ³⁴ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

R particularly preferably represents hydrogen or C _1-4 -alkyl,

Z particularly preferably represents hydrogen or C _1-4 -alkyl,

X and Y are each independently of each other particularly preferably fluorine, chlorine, bromine, nitro, cyano, hydroxy, carboxyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl , t-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 particularly preferably represents an integer from 0 to 3, when m represents 2 or 3, X represents the same or different radicals,

n particularly preferably represents an integer of 0 to 4, when n represents 2, 3 or 4, Y represents the same or different radicals,

의 래디칼을 나타내며, A is particularly preferably a formula

Represents the radical of,

From here,

α) R ¹ is 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, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio,

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

β) R ¹ is hydrogen, fluorine, chlorine, bromine, iodine, ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, methoxy , Ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio;

R ² represents fluorine,

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

γ) R ¹ is hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, mono fluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, cyclopropyl, Methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio;

R ² represents fluorine,

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

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ⁴ and R ⁵ independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl,

R ⁶ represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy, or

의 래디칼을 나타내고, A is also particularly preferably formula

Represents the radical,

From here,

R ⁷ and R ⁸ independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl,

R ⁹ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹⁰ is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, difluoromethyl , Trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, trifluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethylthio, di Fluorochloromethylthio or trichloromethylthio, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹¹ is fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, trifluoromethyl, Difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy, di Fluorochloromethoxy or trichloromethoxy,

R ¹² is hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, trifluoromethyl, difluoromethyl, di Fluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulfinyl or methylsulfonyl Or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹³ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ¹⁴ represents methyl or ethyl,

X ¹ represents a sulfur atom, SO, SO ₂ or CH ₂ ,

p represents 0, 1 or 2, or             

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹⁵ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹⁶ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ¹⁷ represents fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ¹⁸ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl,

R ¹⁹ represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ²⁰ and R ²¹ independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ²² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ²³ and R ²⁴ independently of each other represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ²⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ²⁶ represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ²⁷ represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ²⁸ represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

R ²⁹ represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ³⁰ represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ³¹ represents hydrogen, methyl or ethyl,

R ³² represents fluorine, chlorine, bromine, methyl or ethyl, or

의 래디칼을 나타내고,A is also particularly preferably formula

Represents the radical,

From here,

R ³³ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl,

의 래디칼을 나타내고, A is also particularly preferably formula

Represents the radical,

From here,

R ³⁴ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl.

Preferred or particularly preferred are compounds with substituents mentioned as preferred or particularly preferred.

For example, saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, including those bonded with hetero atoms, such as in alkoxy, may be as straight or branched as possible in each case.

The optionally substituted radical may be mono- or polysubstituted, and when polysubstituted, the substituents may be the same or different. A plurality of radicals having the same index, for example m may be the same or different if m is greater than one.

Halogen-substituted radicals such as halogenoalkyl may be mono- or multi-halogenated. In the case of plural halogenation, the halogen atoms may be the same or different. Halogen here represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

However, the general or preferred radical definitions or descriptions mentioned above may also be combined with one another as desired, ie they comprise a combination between each range and a preferred range. These definitions apply to the final product and corresponding precursors and intermediates. In addition, individual definitions may not apply.

When 2-methyl-4-trifluoromethyl-1,3-thiazole-5-carbonyl chloride and 2- (4-methoximinomethylphenyl) aniline are used as starting materials, the process according to the invention ( The process of a) can be represented by the following scheme:

When using a catalyst with 2'-bromo-1,3-dimethylpyrrole-4-carboxanilide and 4-methoximinoethylphenylboronic acid as starting materials, the process of process (b) according to the present invention is Can be represented as:

In the case of using 2-[(1,4-dimethylpyrrole-3-yl) carbonylamino] phenyl-boronic acid and 1-bromo-4-methoximinoethylbenzene as a starting material and a catalyst, The process of method (c) can be represented by the following scheme:

When using 2 '-(4-acetylphenyl) -4'-fluoro-1-methyl-3-trifluoromethylpyrazole-4-carboxanilide and methoxamine hydrochloride as starting materials, the present invention The process of method (d) according to can be represented by the following scheme:

When 2 '-(4-hydroxyiminoethyl) -phenyl-1,3-dimethylpyrazole-4-carboxanilide and methyl bromide are used as starting materials, the process of the process (e) according to the present invention is as follows. It can be represented by the scheme:

2'-bromo-5-fluorothiazole-4-carboxanilide and 1-bromo-4-methoximinomethylbenzene as starting materials, catalysts and 4,4,4 ', 4'5,5,5 When using ', 5'-octamethyl-2,2'-bis-1,3,2-dioxaborolane, the process of process (f) according to the invention can be represented by the following scheme:

Process and Intermediate Description

Formula (II) provides a general definition of the carboxylic acid derivative required as starting material for carrying out process (a) according to the invention. In this general formula, A preferably has the meaning mentioned above as preferred or particularly preferred for this radical in connection with the description of the substance of general formula (I) according to the invention. G preferably denotes chlorine, bromine, hydroxy, methoxy or ethoxy, particularly preferably chlorine, hydroxy or methoxy.

Carboxylic acid derivatives of formula (II) are known or can be prepared by known methods (see WO 93/11 117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589 313). .

Formula (III) provides a general definition of the aniline derivative required as a reactive component for carrying out process (a) according to the invention. In this general formula, R, Z, X, Y, m and n are each preferably mentioned above as preferred or particularly preferred for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention. Has meaning.

The aniline derivatives of formula (III) are novel. Some of these can be prepared by known methods (see EP-A 0 545 099 and EP-A 0 589 301).

Aniline derivatives of general formula (III)

g) the boron of formula (V) wherein the 2-halogenaniline derivative of formula (XI) is optionally in the presence of an acid binder and optionally in the presence of an inert organic diluent and optionally in the presence of a catalyst React with acid derivatives,             

h) The phenyloxime derivatives of the general formula (VII) wherein aniline boronic acid of the general formula (XII) is optionally present in the presence of an acid binder and optionally in the presence of an inert organic diluent and optionally in the presence of a catalyst Obtained by reaction with:

Where

X, m, R, Z, Y, n, G ¹ and G ² are each as defined above,

Hal represents halogen.

Formula (XI) provides a general definition of 2-halogenoaniline derivatives necessary as reactive components for carrying out process (g) according to the invention. In this general formula, X and m each preferably have the meaning mentioned as preferred or particularly preferred above for this radical or index in connection with the description of the substance of general formula (I) according to the invention. Hal preferably denotes fluorine, chlorine or bromine, in particular chlorine or bromine.

2-halogenoaniline derivatives of formula (XI) are commercially available or can be prepared by reducing the corresponding nitro compounds.

Formula (XII) provides a general definition of aniline boronic acid which is necessary as a reactive component for carrying out process (h) according to the invention. In this general formula, X and m each preferably have the meanings mentioned above as preferred or particularly preferred for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention. G ¹ and G ² preferably each represent hydrogen or together represent tetramethylethylene.

Aniline boronic acid of formula (XII) is commercially available.

Formula (IV) provides a general definition of the carboxamide derivatives necessary as starting materials for carrying out the methods (b) and (f) according to the invention. In this general formula, A, X and m each preferably have the meanings mentioned above as preferred or particularly preferred for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention.

Carboxamide derivatives of formula (IV) are known or can be prepared by known methods (see WO 91/01311, EP-A 0 371 950).             

Formula (V) provides a general definition of the boronic acid derivatives necessary to prepare reactive moieties when carrying out methods (b) and (g) according to the invention. In this general formula, R, Z, Y and n each preferably have the meaning mentioned as preferred or particularly preferred above for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention. G ¹ and G ² preferably each represent hydrogen or together represent tetramethylethylene.

Boronic acid derivatives of general formula (V) are novel,

i) Alkoxyamines of the general formula (IX) wherein phenylboronic acid of general formula (XIII) is optionally present in the presence of an acid binder and optionally inert organic diluents and optionally in the presence of a catalyst Obtained by reaction with:

Where

R, Y, n, G ¹ , G ² and Z are each as defined above.

Formula (XIII) provides a general definition of phenylboronic acid which is necessary as a reactive component for carrying out process (i) according to the invention. In this general formula, R, Y and n each preferably have the meanings mentioned above as preferred or particularly preferred for these radicals and exponents in connection with the description of the substances of general formula (I) according to the invention. G ¹ and G ² preferably each represent hydrogen or together represent tetramethylethylene.

Aniline boronic acid of formula (XIII) is commercially available.

Formula (VI) provides a general definition of the carboxamide-boronic acid derivative required as a reactive component for carrying out process (c) according to the invention. In this general formula, A, X and m each preferably have the meanings mentioned above as preferred or particularly preferred for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention. G ¹ and G ² preferably each represent hydrogen or together represent tetramethylethylene.

Carboxamide-boronic acid derivatives of formula (VI) are novel. These are

j) Reaction of the carboxylic acid derivative of the general formula (II) with the aniline boronic acid of the general formula (XII) in the presence of an acid binder and optionally in the presence of an inert organic diluent and optionally in the presence of a catalyst Obtained by:

Where             

A, G, X, m, G ¹ and G ² are each as defined above.

Formula (VII) provides a general definition of phenyloxime derivatives necessary as starting materials for carrying out the processes (c) and (f) according to the invention. In this general formula, R, Z, Y and n each preferably have the meaning mentioned as preferred or particularly preferred above for these radicals and indices in connection with the description of the substances of general formula (I) according to the invention.

Phenyloxime derivatives of formula (VII) are known or can be prepared by known methods (Synth. Commun. 2000, 30, 665-669, Synth. Commun. 1999, 29, 1697-1701).

Formula (VIII) provides a general definition of biphenylacyl derivatives necessary as starting materials for carrying out process (d) according to the invention. In this general formula, A, R, X, Y, m and n preferably each have the meaning mentioned above as preferred or particularly preferred for these radicals in connection with the description of the substances of general formula (I) according to the invention. Have

Biphenylacyl derivatives of general formula (VIII) are novel. These are

k) obtained by reacting a carboxylic acid derivative of formula (II) with a 2-benzaldehyde-aniline derivative of formula (XIV) in the presence of an acid binder and optionally in the presence of an inert organic diluent: :

Where

A, G, R, X, Y, m and n are as defined above, respectively.

Formula (XIV) provides a general definition of 2-benzaldehyde-aniline derivatives which are required as reactive components for carrying out process (k) according to the invention. In this general formula, R, X, Y, m and n each preferably have the meanings mentioned above as preferred or particularly preferred for these radicals in connection with the description of the substances of general formula (I) according to the invention.

The 2-benzaldehyde-aniline derivatives of formula (XIV) are novel. These are

l) Aniline derivatives of the general formula (XI) are obtained by reacting with phenylboronic acid derivatives of the general formula (XIII) in the presence of an acid binder and optionally in the presence of an inert organic diluent:

Where

X, m, R, Y, n, G ¹ and G ² are each as defined above,

Hal represents halogen.

Aniline derivatives of the general formula (XI) which are necessary as reactives for carrying out method (l) have already been described with reference to method (g).

Phenylboronic acid derivatives of the general formula (XIII) which are required as reactive components to carry out method (l) have already been described with reference to method (i).

Formula (IX) provides a general definition of the alkoxamines necessary as reactive components for carrying out the methods (d) and (i) according to the invention. In this general formula, Z preferably has the meaning mentioned above as preferred or particularly preferred for this radical in connection with the description of the substance of general formula (I) according to the invention. Preference is given to using the hydrochlorides mentioned in the description. However, it is also possible to use free alkoxamines in the process according to the invention.

Alkoxamines of formula (IX) are commercially available.

Formula (I-a) according to the present invention provides a general definition of the hydroxyamine derivative required as starting material for carrying out process (e) according to the invention. In this general formula, A, R, X, Y, m and n preferably each have the meaning mentioned above as preferred or particularly preferred for these radicals in connection with the description of the substances of general formula (I) according to the invention. Have

The hydroxyamine derivatives of general formula (I-a) can be prepared by one of the processes (a), (b), (c), (d) or (f) according to the invention mentioned above.

Formula (X) provides a general definition of the compound required as a reactive component for carrying out process (e) according to the invention. In this general formula, Z ¹ preferably represents C _1-4 -alkyl, particularly preferably methyl or ethyl. E preferably represents chlorine, bromine, iodine, methanesulfonyl or p-toluenesulfonyl. E particularly preferably represents chlorine or bromine.

Compounds of formula (X) are commercially available.

Acid binders suitable for carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention are in each case all inorganic and organic bases customary for such reactions. These are preferably alkaline earth metal or alkali metal hydroxides, for example sodium hydroxide, calcium hydroxide, potassium hydroxide, ammonium hydroxide, alkali metal carbonates such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkali metal or alkali Earth metal acetates such as sodium acetate, potassium acetate, calcium acetate, and also tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diaza bicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU) are used. However, it is also possible to carry out the above processes without additional acid binders or to use excess amine components so that they can act simultaneously as acid binders.

Suitable diluents for carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention are in each case all customary inert organic solvents. These preferably include optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, or decalin; Chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or Anisole; Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethylsulfoxide or sulfones such as sulfolane are used.

When carrying out the processes (a), (b), (c), (d), (e) and (f) according to the invention, the reaction temperature can in each case be varied within a relatively wide range. In general, these processes are carried out at temperatures of 0 to 140 ° C, preferably 10 to 120 ° C.             

The processes (a), (b), (c), (d), (e) and (f) according to the invention are generally carried out at atmospheric pressure in each case, but in each case can also be carried out under elevated or reduced pressure. have.

When carrying out process (a) according to the invention, generally 1 mole or excess of aniline derivatives of general formula (III) and 1-3 moles of acid binder are used per mole of acid halide of general formula (II). However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water, the organic phase is separated and dried, and then concentrated under reduced pressure. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

When carrying out process (b) according to the invention, generally 1 mole or excess boronic acid derivative of formula (V) and 1 to 5 moles of acid binder are used per mole of carboxamide of formula (IV) do. However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water and the precipitate is separated and dried. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

When carrying out process (c) according to the invention, generally 1 mole or excess of phenyloxime derivative of general formula (VII) and 1 to 10 moles per mole of carboxamide-boronic acid derivative of general formula (VI) Acid binders and catalysts of 0.5 to 5 mol% are used. However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water and the precipitate is separated and dried. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

When carrying out process (d) according to the invention, generally one mole or excess of alkoxamine of formula (IX) and 1 to 5 moles of acid binder per mole of biphenylacyl derivative of formula (VIII) Used. However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water and the precipitate is separated, washed with water and diisopropyl ether, and then dried. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

When carrying out process (e) according to the invention, generally 1 mole or excess of reagent of formula (X) and 1 to 5 moles of acid binder are used per mole of hydroxyamine derivative of general formula (la). . However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water and the precipitate is separated and dried. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

When carrying out process (f) according to the invention, it is generally carried out with 1 mole or excess of phenyloxime derivative of general formula (VII) and 1 to 5 moles of acid binder per mole of carboxamide derivative of general formula (IV) 1 to 5 moles of catalyst are used. However, the reaction components may be used in other ratios. Post-treatment is carried out in a conventional manner. In general, the reaction mixture is treated with water and the precipitate is separated and dried. If desired, it is possible to remove impurities that may still be present from the residual residue by conventional methods such as chromatography or recrystallization.

The materials according to the invention exhibit strong microbicidal activity and can be used to control unwanted microorganisms, for example fungi and bacteria, in crop protection and material protection.

Fungicides include Plasmodiophoromycetes , Oomycetes , Chytridiomycetes , Zygomycetes and Ascomycetes in crop protection. , Basidiomycetes and Deuteromycetes can be used to rescue.

Fungicides may be used to remedy the pseudo mono Ada years old child (Pseudomonoadaceae), Li Jovi Asia (Rhizobiaceae), Enterobacter bacteria years old child (Enterobacteriaceae), Corey four bacteria years old child (Corynebacteriaceae) and Streptomyces setae years old child (Streptomycetaceae) in crop protection .

Some examples of pathogens that cause fungal and bacterial diseases of the genus above are mentioned below, but not limited to:

Xanthomonas species, for example Xanthomonas campestris fib . Orissa ( Xanthomonas campestris pv. Oryzae );

Pseudomonas (Pseudomonas) species, such as blood V Pseudomonas when Manly. Lacrymans ( Pseudomonas syringae pv. Lachrymans );

Erwinia species, for example Erwinia amylovora ;

Pythium species, for example Pythium ultimum ;

Phytophthora species, for example Phytophthora infestans ;

Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis ;

Plasmopara species, for example Plasmopara viticola ;

Bremia species, for example Bremia lactucae

Peronospora species, for example Peronospora pisi or Peronospora brassicae ;

Erysiphe species, for example Erysiphe graminis ;

Sphaerotheca species, for example Sphaerotheca fuliginea ;

Podosphaera species, for example Podosphaera leucotricha ;

Venturia species, for example Venturia inaequalis ;

Pyrenophora species, for example Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera ), isoform: Helmintosporium ( Helminthosporium ));

Cochliobolus species, for example Cochliobolus sativus (conidia form: Dresslera, isoform: Helmintosporium);

Uromyces species, for example Uromyces appendiculatus ;

Puccinia species, for example Puccinia recondita ;

Sclerotinia species, for example Sclerotinia sclerotiorum ;

Tilletia species, for example Tilletia caries ;

Ustilago species, for example Ustilago nuda or Ustilago avenae ;

Pellicularia species, for example Pellicularia sasakii ;

Pyricularia species, for example Pyricularia oryzae ;

Fusarium (Fusarium) species, such as Fusarium cool morum (Fusarium culmorum);

Botrytis species, for example Botrytis cinerea ;

Septoria species, for example Septoria nodorum ;

Leptosphaeria species, for example Leptosphaeria nodorum ;

Cercospora species, for example Cercospora canescens ;

Alternaria species, for example Alternaria brassica and

Pseudocercosporella species, for example Pseudocercosporella herpotrichoides .

Because the plants are tolerable to the active compounds at the concentrations necessary to control plant diseases, it is possible to treat the plant's ground, breeding stems and seeds, and soil.

The active compounds according to the invention are diseases of vines and fruit trees and diseases that occur during vegetable growth, such as Venturia , Botrytis , Sclerotinia , Rhizoctonia , unsi Cronulla (Uncinula), to the relief Rotterdam car (Sphaerotheca), grape spa Era (Podosphaera), Alterna Liao (Alternaria) and sat Collet tree glutamicum (Colletotrichum) species in the spa and in particular exhibit excellent results. Rice diseases such as Pyricularia and Pellicularia species can likewise be well controlled.

The active compounds according to the invention can also be used to increase crop yields. In addition, they are low toxicity and exhibit tolerability to plants.

According to the invention, all plants and parts of plants can be treated. By plants is meant all plants and plant populations, such as unwanted or unwanted wild plants or crops (including naturally occurring crops). Crops include plant varieties and transgenic plants, which may or may not be protected by cultivar rights, by conventional plant breeding and optimization methods, by biotechnology and genetic engineering methods, or by these methods. It may be a plant obtainable in combination. Some of the plants are to be understood as meaning all the above-ground and underground parts and organs of the plant, for example, shoots, leaves, flowers and roots, examples of which are leaves, needles, stems and trunks. ), Flowers, fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Some of the plants also include harvested plants and nutritional and reproductive materials, such as seedlings, tubers, rhizomes, cuttings and seeds.

The compounds according to the invention can be used to protect industrial materials from invasion and destruction by unwanted microorganisms.

Industrial material is to be understood herein to mean non-living materials prepared for industrial use. For example, industrial materials which are intended to be protected by the active compounds according to the invention from changes or destruction by microorganisms are adhesives, sizes, paper, plywood, textiles, leather, wood, paints, plastic products, cooling lubricants. And other materials that can be invaded or destroyed by microorganisms. Included within the scope of the material to be protected may also refer to parts of the production plant, for example cooling water circuits, which may be adversely affected by the growth of microorganisms. Industrial materials that may be mentioned within the scope of the invention are preferably adhesives, sizes, paper, plywood, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.

Microorganisms capable of degrading or changing industrial materials can be mentioned, for example, bacteria, fungi, yeast, algae and slime organisms. The active compounds according to the invention preferably act on fungi, in particular filamentous fungi, wood discoloration and wood destruction fungi (bacsidomycetes) and on modified organisms and algae.

Microorganisms of the following genus may be mentioned by way of example:

Alternaria , for example Alternaria tenuis

Aspergillus , for example Aspergillus niger

Kaeto hate (Chaetomium), for example kaeto hatred Globo breath (Chaetomium globosum),

Coniophora , for example Coniophora puetana ,

Lentinus , for example Lentinus tigrinus ,

Penicillium , for example Penicillium glaucum ,

Polyporus , for example Polyporus versicolor ,

Aureobasidium , for example Aureobasidium pullulans ,

'S nucleoside poma (Sclerophoma), for example, scan nucleoside poma pita EO pillar (Sclerophoma pityophila),

Trichoderma (Trichoderma), for example, to irregularities in Trichoderma (Trichoderma viride),

Escherichia , for example Escherichia coli ,

Pseudomonas (Pseudomonas), for example Pseudomonas rugi ah industrial (Pseudomonas aeruginosa) and

Staphylococcus , for example Staphylococcus aureus .

The active compounds, depending on their particular physical and / or chemical properties, are conventional formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in polymeric and seed coating compositions. And ULV cold and warm agents.

These formulations are known methods, for example by mixing the active compounds with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers. To prepare. If the extender used is water, an organic solvent can also be used as an auxiliary solvent. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide or dimethylsulfoxide, or water. Liquefied gaseous extenders or carriers refer to liquids that are gaseous at standard temperatures and atmospheric pressures and are, for example, halogenated hydrocarbons or aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as finely divided silica, alumina and silicates. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, or synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty alcohol ethers such as polyoxyethylene fatty acid esters, alkylaryl polyglycol ethers, alkylsulfonates, alkylsulphates, aryls Sulfonates or protein hydrolysates. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.             

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or natural and synthetic phospholipids such as cephalin and lecithin Can be. As other additives, mineral oil and vegetable oil may be used.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic pigments such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; You can also use the same micronutrients.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

The active compounds according to the invention are themselves or in their preparations, for example, as a mixture with known fungicides, fungicides, acaricides, nematicides or insecticides, for example in order to broaden the activity spectrum or prevent the development of resistance. Can be used. In many cases a synergistic effect is observed, ie the activity of the mixture exceeds the activity of the individual components.

Examples of suitable mixing partners are the following compounds:

Fungicides:

Aldimorph, Ampropyl Force, Ampropyl Force Potassium, Andoprim, Anilazine, Azaconazole, Azoxystrobin,

Benalacyl, Benodanil, Benomil, Benzamacryl, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Vitertanol, Blastisidin-S, Bromuconazole, Buprimate, Bu Thioate,

Calcium Polysulfide, Capsaicin, Captapol, Captan, Carbendazim, Carboxin, Carbon, Quinomethionate, Clobenthiazone, Chlorfenazole, Chloronev, Chloropicrine, Chlothalonil, Clozolinate, Chlozila Cones, cupraneb, cymoxanyl, cyproconazole, cyprodinyl, cypropuram,

Debaccarb, dichlorophene, diclobutrazole, diclofloanid, diclomezin, dichloran, dietofencarb, difenokonazole, dimethymolol, dimethomorph, dinicoazole, dinicoazole- M, dinocap, diphenylamine, dipyrithione, dietalifoss, dithianon, dodemorph, dodine, drazoxolone,

Edifene Force, Epoxyconazole, Etaconazole, Ethirimol, Etridiazole,

Sofasadon, phenafanil, phenarimol, fenbuconazole, fenfuram, phenytropane, fenpiclonyl, phenpropidine, fenpropormorph, fentin acetate, fentin hydroxide, ferbam, perimzone, flua Last, Flumetober, Fluoride, Fluquinconazole, Fluprimidol, Flusilazole, Flusulfamid, Flutolanil, Flutriafol, Polpet, Pocetyl-aluminum, Pocetyl-sodium, Phthalide , Fuberidazole, furalacyl, furametpyr, furcarbonyl, furconazole, furconazole-cis, purmecyclox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalyl, imibenconazole, iminottadine, iminottadine albesylate, iminottadine triacetate, iodocarb, ifconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, iso Ballet,

Kasugamycin, cresoxime-methyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures,

Mancoper, Mancozeb, Manev, Meperimzone, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metomeclam, Metsulfobox, Mildiomycin , Michaelrobutanyl, michaelrozoline,

Nickel dimethyldithiocarbamate, nitrotal-isopropyl, noarimol,

Opuras, oxadixyl, oxamocarb, oxolinic acid, oxycarboxime, oxypentin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, fimaricin, piperaline, polyoxine, polyoxolim, probenazole, prochloraz, prosaimidone, propamocarb, Propanosine-sodium, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxipur,

Quinconazole, quintogen (PCNB), quinoxyphene,

Sulfur and sulfur preparations,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, triclamid, tricyclazole, tridemorph, trifluzazole, tripolin, triticonazole,

Uniconazole,

Validamycin A, vinclozoline, viniconazole,

Zarylamide, Genev, Zara, and also

Dagger G, OK-8705, OK-8801,

α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,

α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

α- (5-methyl-1,3-dioxan-5-yl) -β-[[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazole-1-ethanol ,

(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,

(E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,

1-isopropyl {2-methyl-1-[[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamate,

1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) ethanone O- (phenylmethyl) -oxime,

1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,

1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

1-[(diiodomethyl) sulfonyl] -4-methylbenzene,             

1-[[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,

1-[[2- (4-chlorophenyl) -3-phenyloxyranyl] methyl] -1 H-1,2,4-triazole,

1- [1- [2-[(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1 H-imidazole,

1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,

2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,

2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,

2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide,

2,6-dichloro-N-[[4- (trifluoromethyl) phenyl] methyl] benzamide,

2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,

2-[(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,

2-[[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] amino] -4-methoxy-1 H-pyrrolo [ 2,3-d] pyrimidine-5-carbonitrile,

2-aminobutane,

2-bromo-2- (bromomethyl) pentanedinitrile,

2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,

2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,             

2-phenylphenol (OPP),

3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,

3,5-dichloro-N- [cyano-[(1-methyl-2-propynyl) oxy] methyl] benzamide,

3- (1,1-dimethylpropyl) -1-oxo-1H-indene-2-carbonitrile,

3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,

4-chloro-2-cyano-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfonamide,

4-methyltetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4,5] decan-2-methanamine,

8-hydroxyquinoline sulfate,

9H-xanthene-2-[(phenylamino) carbonyl] -9-carboxylic acid hydrazide,

Bis- (1-methylethyl) -3-methyl-4-[(3-methylbenzoyl) oxy] -2,5-thiophendicarboxylate,

Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol,

Cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,

Ethyl [(4-chlorophenyl) azo] cyanoacetate,

Potassium bicarbonate,

Methane tetrathiol sodium salt,

Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,

Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alanineate,

Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alanineate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) -acetamide,

N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) -acetamide,

N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitrobenzenesulfonamide,

N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,

N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,

N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetamide,

N- (6-methoxy) -3-pyridinyl-cyclopropanecarboxamide,

N- [2,2,2-trichloro-1-[(chloroacetyl) amino] ethyl] benzamide,

N- [3-chloro-4,5-bis (2-propynyloxy) phenyl) -N'-methoxymethaneimideamide,

N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,

O-methyl S-phenyl phenylpropylphosphoramidothioate,

S-methyl 1,2,3-benzothiadiazole-7-carbothioate,             

Spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran-3'-one.

disinfectant:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, Acetate, Acetamiprid, Acrinatrin, Alanicarb, Aldicarb, Aldoxicarb, Alphacypermethrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Aza Metifos, azinfos A, azinfos M, azocyclotin,

Bacillus popilia, Bacillus sp. Erythose, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Buberia bassiana, Buberia tenella, Bendiocab, Benpuracab, Bensultop, Benzosimate, Beta Cyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin, BPMC, bromophos A, bufencarb, buprofezin, butathiophos, butocarboxime, butylpyridaben,

Cadusafos, cabaril, cabofuran, cabofennotion, cabosulphan, cartop, chloretocarb, chlorethoxy force, chlorfenapyr, chlorfenbinfos, chlorfluazuron, chlormephos, chlorpyrufos, chlor Pyriphos M, clovapotrin, cis-resmethrin, cispermethrin, clocitrin, clotocarb, clofenthezin, cyanophosph, cycloprene, cycloprotrin, cyfluthrin, cyhalothrin, cy Hexatin, cypermethrin, cyromargin,             

Deltamethrin, Demethone M, Demethone S, Demethone-S-methyl, Diapentiuuron, Diazinon, Dichlorbose, Diflubenzuron, Dimethoate, Dimethylbinfos, Diophenolran, Disulfotone, Docusat Sodium, dofenaphine,

Eflusilanate, emamectin, empentrin, endosulfan, entomorphora species, esfenvalerate, thiophencarb, ethion, etoprophos, etofenprox, ethoxazole, ethrimfoss,

Fenamifos, phenaquinone, fenbutatin oxide, phenythrothione, phenothiocarb, phenoxa cream, phenoxycarb, phenpropatrine, fenpyrad, phenpyrithine, fenpyrroxate, fenvallate, blood Pronyl, fluazinam, fluazuron, flubrocithinate, flucycloroxinone, flucitalinate, flufenoxuron, flutginine, fluvalinate, phonophos, phosphmethylene, phosphthiazate, Pufenfenrox, furateocarb,

Granulosis virus,

Halofenozide, HCH, heptenophos, hexaflumuron, hexiaxose, hydroprene,

Imidacloprid, isosaphos, isopenfos, isoxation, ivermectin,

Nuclea polyhedrosis virus,

Lambda-cyhalothrin, lufenuron,

Malathion, Mecarbam, Metaldehyde, Metamidose, Metadium Anisopliia, Metadium Flavoviride, Methidadion, Methiocarb, Methyl, Methoxyfenozide, Metholcarb, Metoxa Diazon, Melvinforce, Milvemectin, Monocrotoforce,             

Naled, nitenpyram, nithiazine, novaluron,

Ometoate, oxamyl, oxydemethone M,

Paesilomyses pumosorusus, parathion A, parathion M, permethrin, pentoate, forate, posalon, phosphmet, phosphamidone, bombardment, pyrimicab, pyrimifos A, pyrimifos M, Propenophos, promecarb, propoxur, prothiophos, protoate, pymetrozine, pyraclophos, pyrethmetrin, pyrethrum, pyridaben, pyridation, pyrimidipene, pyriproxyfen,

Quinal Force, Ribavirin,

Salitione, cebufoss, silafluorene, spinosad, sulfotep, sulfpropos,

Tau-Fluvalinate, Tebufenozide, Tebufenpyrad, Tebupyrimifos, Teflubenzuron, Tefluthrin, Temephos, Temivinforce, Terbufos, Tetrachlorbinfos, Tetacypermethrin, Tia Methoxam, thiapronyl, thiatriphos, thiocyclam hydrogen oxalate, thiodicarb, thiophanox, thuringiencin, tralositerin, tralomethrin, triarate, triamate, triazo Force, triazurone, triclofenidine, trichlorphone, triflumuron, trimetacarb,

Vamidothione, vinylliprol, vertilium recany,

YI 5302, zeta-cypermethrin, zolapropos,

(1R-cis)-[5- (phenylmethyl) -3-furanyl] -methyl-3-[(dihydro-2-oxo-3 (2H) -furanylidene) -methyl] -2,2- Dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl) -methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,             

1-[(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2 (1H) -imine,

2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl] -4,5-dihydro-oxazole,

2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione,

2-chloro-N-[[[4- (1-phenylethoxy) -phenyl] -amino] -carbonyl] -benzamide,

2-chloro-N-[[[4- (2,2-dichloro-1,1-difluoroethoxy) -phenyl] -amino] -carbonyl] -benzamide,

3-methylphenyl propylcarbamate,

4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-2-phenoxy-benzene,

4-chloro-2- (1,1-dimethylethyl) -5-[[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone,

4-chloro-2- (2-chloro-2-methylpropyl) -5-[(6-iodo-3-pyridinyl) methoxy] -3 (2H) -pyridazinone,

4-chloro-5-[(6-chloro-3-pyridinyl) methoxy] -2- (3,4-dichlorophenyl) -3 (2H) -pyridazinone,

Bacillus thuringiensis strain EG-2348,

2-benzoyl-1- (1,1-dimethylethyl) hydrazinobenzoic acid,

2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [4.5] dec-3-en-4-yl butanoate,             

[3-[(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide,

Dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde,

Ethyl [2-[[1,6-dihydro-6-oxo-1- (phenylmethyl) -4-pyridazinyl] oxy] ethyl] -carbamate,

N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine,

N- (4-chlorophenyl) -3- [4- (difluoromethoxy) phenyl] -4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide,

N-[(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine,

N-methyl-N '-(1-methyl-2-propenyl) -1,2-hydrazinedicarbothioamide,

N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide,

N-methyl-N'-2-propenyl-1,2-hydrazinedicarbothioamide,

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate.

Other known active compounds, such as herbicides, or mixtures with fertilizers and growth regulators are also possible.

In addition, the compounds of the general formula (I) according to the present invention show very good antibacterial activity. These are especially dermatophytes, yeast, fungi and yisanggyun, such as Candida (Candida) species, such as Candida albicans (Candida albicans), Candida glabrata (Candida glabrata), epi more fur tone (Epidermophyton) species, such as epi more Epidermophyton floccosum , Aspergillus species, such as Aspergillus nigrt and Aspergillus fumigatus , Trichophyton species, such as Trichophyton menta It exhibits a very broad spectrum of antimicrobial activity against Trichophyton mentagrophytes , Microsporon species such as Microsporon canis and audouinii .

These fungal lists do not limit the fungal spectrum to be applied in any way and are listed for illustrative purposes only.

The active compounds can be used on their own, in the form of their preparations, or in the preparations prepared from them, such as ready-to-use solutions, suspensions, hydrating powders, pastes, soluble powders, powders and granules. This applies by conventional methods such as watering, spraying, misting, spraying, spraying, foaming, spraying and the like. In addition, the active compounds may be applied by a microvolume method or the active compound preparation or the active compound itself may be injected into the soil. Seeds of plants may also be treated.

When the active compounds according to the invention are used as fungicides, the application rate can vary within a relatively wide range depending on the application form. When treating a part of the plant, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 10 to 1,000 g / dL. For seed dressings, the application rate of the active compound is generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the application rate of the active compound is generally 0.1 to 10,000 g / dL, preferably 1 to 5,000 g / dL.             

Compositions used to protect industrial materials generally contain the active compound in an amount of 1 to 95% by weight, preferably 10 to 75% by weight.

The concentration of use of the active compound according to the invention depends on the wettability and incidence of the microorganism to be controlled and the composition of the substance to be protected. The optimum rate of use can be determined by a series of tests. In general, the use concentration is from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.

If necessary, broaden the activity spectrum, or add other antimicrobial active compounds, fungicides, fungicides, herbicides, insecticides or other active compounds to achieve a particular effect, for example, additional protection against insects. It is possible to increase the activity and activity spectrum of the active compounds used according to the invention, or compositions, concentrates or very general preparations which can be prepared from them. These mixtures may have a broader activity spectrum than the compounds according to the invention.

Examples of preparation and use of the active compounds according to the invention are illustrated in the following examples.

Manufacturing Example

Example 1

Method (a):

At room temperature, a solution of 0.59 g (0.0026 mol) of 2- (4-methoximinomethylphenyl) aniline in 25 ml of toluene was treated with 0.26 g (0.0026 mol) triethylamine. While stirring the mixture, a solution of 0.6 g (0.0026 mol) of 2-methyl-4-trifluoromethylthiazole-5-carbonyl chloride in 5 ml of toluene was added at room temperature. After the addition was completed, the reaction mixture was heated to 50 ° C. and stirred at this temperature for 2 hours. As a workup, the reaction mixture was cooled to room temperature and mixed with water. The organic phase was separated, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel using 3: 1 cyclohexane: ethyl acetate as mobile phase. The eluate was concentrated to 0.81 g (74% of theory) of 2 '-(4-methoximinomethylphenyl) -2-methyl-4-trifluoromethylthiazole-5-carboxanilide having a melting point of 122 to 123 ° C. Obtained as a solid.             

Preparation of Starting Material

At room temperature, 2.9 g (0.017 mol) of 2-bromoaniline, 0.68 g of tetrakis- (triphenylphosphine) palladium, 5.5 g (0.031 mol) of 4-methoximinomethylphenyl-boronic acid and 1,2-dimethoxy A mixture of 40 ml of ethane was treated with a solution of 8.2 g (0.077 mol) of sodium carbonate in 35 ml of water. The reaction mixture was heated to reflux and boiled for 12 hours. As a workup, the reaction mixture was cooled to room temperature and extracted with diethyl ether. The organic phase was separated and mixed with water. The organic phase was separated again and dried over sodium sulphate and finally concentrated under reduced pressure. The residue was chromatographed on silica gel using 3: 1 cyclohexane: ethyl acetate as mobile phase. The eluate was concentrated to give 3.8 g (98.8% of theory for 2-bromoaniline) in oil form of 2- (4-methoximinomethylphenyl) -aniline.

¹ H-NMR spectrum (DMSO / TMS): δ = 3.90 (3H) ppm.

A mixture of 5.0 g (0.033 mol) of 4-formylphenylboronic acid, 3.4 g (0.041 mol) of methoxylamine hydrochloride, 3.4 g (0.041 mol) of sodium acetate, 40 ml of methanol and 10 ml of water was mixed for 12 hours at room temperature. Was stirred. As a workup, the reaction mixture was stirred with water, the resulting precipitate was suction filtered and washed with water and then dried at 50 ° C. under reduced pressure. 5.56 g (93.1% of theory) of 4-methoximinomethylphenyl-boronic acid were obtained as colorless crystals having a melting point of 199 to 200 ° C.

The biphenylcarboxamides of formula (I) listed in the table below were also prepared by the abovementioned methods.             

Table 1

The logP values given in Table 1 were measured in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (high performance liquid chromatography) on reverse phase column (C 18). Temperature: 43 ° C.

(a) Mobile phase for determination in acidic range: 0.1% aqueous phosphoric acid, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile—the corresponding measurement results are indicated in Table 1 as ^a) .

(b) mobile phase for measurement in the neutral range: 0.01 molar aqueous phosphate buffer, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile—corresponding measurement results are shown in Table 1 as ^b) .

Calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms) where the logP values were known (measured logP values by residence time using linear interpolation between two consecutive alkanones).

UV spectra of 200-400 nm were used to determine the lambda max value as the maximum of the chromatographic signal.

Example of use

Example A

Grape Spaera Test (Apple) / Protection

Solvent: 24.5 parts by weight of acetone             

         24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After the spray coating was dried, the plants were inoculated with an aqueous spore suspension of Podosphaera leucotricha , an apple powdery mildew causative agent. The plants were then placed in a greenhouse at about 23 ° C. and about 70% relative atmospheric humidity.

Evaluation was carried out 10 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

In this test, for example, the compounds according to the invention in the following preparation examples showed better activity than the compounds of the prior art:             

Table A: Grape Spaera Test (Apple) / Protection

Example B

Spa Erotica Test (cucumber) / protection

Solvent: 24.5 parts by weight of acetone

         24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After the spray coating was dried, the plants were inoculated with an aqueous spore suspension of Sphaerotheca fuliginea . The plants were then placed in a greenhouse at about 23 ° C. and about 70% relative atmospheric humidity.

Evaluation was carried out 10 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

In this test, for example, the compounds according to the invention in the following preparation examples showed better activity than the compounds of the prior art:             

Table B: Spaerotheca Test (cucumber) / protection

Example C

Venturi Test (Apple) / Protection

Solvent: 24.5 parts by weight of acetone

         24.5 parts by weight of dimethylacetamide

Emulsifier: 1.0 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the formulation of the active compound at the specified application rate. After the spray coating was dried, the plants were inoculated with an aqueous conidia suspension of Venturia inaequalis , the causative agent of apple disease, and placed in a culture chamber at about 20 ° C. and 100% relative atmospheric humidity for one day.

The plants were then placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity.

Evaluation was performed 12 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

In this test, for example, the compounds according to the invention in the following preparation examples showed better activity than the compounds of the prior art:             

Table C: Venturi Test (Apple) / Protection

Example D

Puknia (Wheat) / Protection

Solvent: 25 parts by weight of N, N-dimethylacetamide

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young plants were sprayed with the active compound preparation at the specified application rate. After the spray coating was dried, the plants were sprayed with a conidia suspension of Puccinia recondita . The plants were then left for 48 hours in a culture chamber at 20 ° C. and 100% relative atmospheric humidity.

Subsequently, the plants were placed in a greenhouse at about 20 ° C. and 80% relative atmospheric humidity to spread rust foam.

Evaluation was carried out 10 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

In this test, for example, the compounds according to the invention in the following preparation examples showed better activity than the compounds of the prior art:             

Table D: Pukine Test (Wheat) / Protection

Example E

Alternaria (tomato) / protection

Solvent: 49 parts by weight of N, N-dimethylformamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above, and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

To test for protective activity, young tomato plants were sprayed with the active compound preparation at the specified application rate. One day after the treatment, the plants were inoculated with a spore suspension of Alternaria solani and left for 24 hours at 20 ° C. and 100% relative atmospheric humidity. The plants were then left at a temperature of 20 ° C. and 96% relative atmospheric humidity.

Evaluation was carried out 7 days after the inoculation. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

In this test, for example, the compounds according to the invention in the following preparation examples showed better activity than the compounds of the prior art:             

Table E: Alternaria Test (Tomato) / Protection

Example F

Inhibition test for giant colonies of Vassiidiomycetes

From colonies of Gloeophyllum trabeum , Coniophora puteana , Poria placenta , Lentinus tigrinus and Coriolus versicolor Mycelium was removed and incubated at 26 ° C. on agar medium containing malt extract peptone. The degree of inhibition of mycelial growth on the medium containing the active compound was compared with the growth of the species on the medium without the active compound, and was graded by percent inhibition.

In this test, for example, the compounds according to the invention in the following preparation examples showed good activity:             

Table F: Inhibition Tests for Giant Colonies of Vassiidiomycetes

Claims (20)

Biphenylcarboxamide of general formula (I):

Where R represents hydrogen or C _1-6 -alkyl, Z represents hydrogen or C _1-6 -alkyl, X and Y independently of each other represent halogen, C _1-8 -alkyl, or C _1-6 -alkoxyimino-C _1-6 -alkyl, m represents an integer of 0 or 1, n represents an integer of 0 or 1, A is an expression

Represents the radical of, From here, α) R ¹ is C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - represents cycloalkyl, - halogenoalkyl, or C _3-6 R ² represents hydrogen, chlorine, bromine or iodine, R ³ represents C _1-4 -alkyl, or β) R ¹ represents C _2-4 -alkyl, C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, or C _3-6 -cycloalkyl, R ² represents fluorine, R ³ represents C _1-4 -alkyl, or γ) R ¹ is C _1-4 - alkyl, C _1-4 with 1 to 5 halogen atoms - represents cycloalkyl, - halogenoalkyl, or C _3-6 R ² represents fluorine, R ³ represents C _2-4 -alkyl, or A is an expression

Represents the radical, From here, R ⁴ and R ⁵ each independently represent hydrogen, R ⁶ represents halogen or C _1-4 -alkyl, or A is an expression

Represents the radical, From here, R ⁷ and R ⁸ independently of each other represent hydrogen or halogen, R ⁹ represents hydrogen, C _1-4 -alkyl or halogen, or A is an expression

Represents the radical, From here, R ¹⁰ represents halogen, C _1-6 -alkyl, or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, or A is an expression

Represents the radical, From here, R ¹¹ represents halogen, hydroxy, C _1-4 -alkyl, or C _1-4 -alkoxy, R ¹² represents hydrogen or C _1-4 -alkoxy, or A is an expression

Represents the radical, From here, R ¹³ represents C _1-4 -alkyl, X ¹ represents a sulfur atom, p represents 0, or A is an expression

Represents the radical, From here, R ¹⁷ represents C _1-4 -alkyl, or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, R ¹⁸ represents hydrogen, R ¹⁹ represents C _1-4 -alkyl, or A is an expression

Represents the radical, From here, R ²⁰ and R ²¹ independently of each other represent hydrogen or C _1-4 -alkyl, R ²² is C _1-4 - alkyl or C _1-4 having 1 to 5 halogen atoms or represent halogenoalkyl, A is an expression

Represents the radical, From here, R ²³ and R ²⁴ independently of each other represent hydrogen, halogen, nitro, C _1-4 -alkyl, or C _1-4 -halogenoalkyl having 1 to 5 halogen atoms, R ²⁵ represents hydrogen, or A is an expression

Represents the radical, From here, R ²⁶ represents halogen, di- (C _1-4 -alkyl) amino, or C _1-4 -alkyl, R ²⁷ is C _1-4 - alkyl or C _1-4 having 1 to 5 halogen atoms or represent halogenoalkyl, A is an expression

Represents the radical, From here, R ³³ represents C _1-4 -alkyl. The method of claim 1, R represents hydrogen or C _1-4 -alkyl, Z represents hydrogen or C _1-4 -alkyl, X and Y independently of each other represent fluorine, chlorine, bromine, C _1-6 -alkyl, or C _1-4 -alkoxyimino-C _1-4 -alkyl, m represents an integer of 0 or 1, n represents an integer of 0 or 1, A is an expression

Represents the radical of, From here, α) R ¹ represents methyl, ethyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or cyclopropyl, R ² represents hydrogen, chlorine, bromine or iodine, R ³ represents methyl, ethyl, n-propyl or isopropyl, or β) R ¹ represents ethyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or cyclopropyl, R ² represents fluorine, R ³ represents methyl, ethyl, n-propyl, or isopropyl, or γ) R ¹ represents methyl, ethyl, isopropyl, C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or cyclopropyl, R ² represents fluorine, R ³ represents ethyl, n-propyl or isopropyl, or A is an expression

Represents the radical, From here, R ⁴ and R ⁵ each independently represent hydrogen, R ⁶ represents fluorine, chlorine, bromine, methyl or ethyl, or A is an expression

Represents the radical, From here, R ⁷ and R ⁸ independently of each other represent hydrogen, fluorine, chlorine or bromine, R ⁹ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A is an expression

Represents the radical, From here, R ¹⁰ represents fluorine, chlorine, bromine, iodine, C _1-4 -alkyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A is an expression

Represents the radical, From here, R ¹¹ represents fluorine, chlorine, bromine, iodine, hydroxy, C _1-4 -alkyl, methoxy or ethoxy, R ¹² represents hydrogen, methoxy or ethoxy, or A is an expression

Represents the radical, From here, R ¹³ represents methyl or ethyl, X ¹ represents a sulfur atom, p represents 0, or A is an expression

Represents the radical, From here, R ¹⁷ represents methyl, ethyl, isopropyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ¹⁸ represents hydrogen, R ¹⁹ represents methyl or ethyl, or A is an expression

Represents the radical, From here, R ²⁰ and R ²¹ independently of each other represent hydrogen, methyl or ethyl, R ²² represents methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A is an expression

Represents the radical, From here, R ²³ and R ²⁴ independently of each other represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ²⁵ represents hydrogen, or A is an expression

Represents the radical, From here, R ²⁶ represents fluorine, chlorine, bromine, di- (Ci_ ₄ -alkyl) amino, methyl or ethyl, R ²⁷ represents methyl, ethyl, or C _1-2 -halogenoalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A is an expression

Represents the radical, From here, R ³³ represents biphenylcarboxamide of formula (I) representing methyl or ethyl. The method of claim 1, R represents hydrogen or C _1-4 -alkyl, Z represents hydrogen or C _1-4 -alkyl, X and Y are independently of each other fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, i-butyl, t-butyl, methoximinomethyl, ethoximinomethyl , Methoximinoethyl or ethoximinoethyl, m represents an integer of 0 or 1, n represents an integer of 0 or 1, A is an expression

Represents the radical of, From here, α) R ¹ represents methyl, ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl or cyclopropyl, R ² represents hydrogen, chlorine, bromine or iodine, R ³ represents methyl or ethyl, or β) R ¹ represents ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl or cyclopropyl, R ² represents fluorine, R ³ represents methyl or ethyl, or γ) R ¹ represents methyl, ethyl, isopropyl, monofluoromethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl or cyclopropyl, R ² represents fluorine, R ³ represents ethyl, or A is an expression

Represents the radical, From here, R ⁴ and R ⁵ each independently represent hydrogen, R ⁶ represents fluorine, chlorine, bromine or methyl, or A is an expression

Represents the radical, From here, R ⁷ and R ⁸ independently of each other represent hydrogen, fluorine, chlorine or bromine, R ⁹ represents hydrogen, fluorine, chlorine, bromine, methyl or ethyl, or A is an expression

Represents the radical, From here, R ¹⁰ is fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, difluoromethyl, trifluoromethyl, difluoro Chloromethyl or trichloromethyl, or A is an expression

Represents the radical, From here, R ¹¹ represents fluorine, chlorine, bromine, iodine, hydroxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyl, t-butyl, methoxy or ethoxy, R ¹² represents hydrogen, methoxy or ethoxy, or A is an expression

Represents the radical, From here, R ¹³ represents methyl or ethyl, X ¹ represents a sulfur atom, p represents 0, or A is an expression

Represents the radical, From here, R ¹⁷ represents methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, R ¹⁸ represents hydrogen, R ¹⁹ represents methyl or ethyl, or A is an expression

Represents the radical, From here, R ²⁰ and R ²¹ independently of each other represent hydrogen, methyl or ethyl, R ²² represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, A is an expression

Represents the radical, From here, R ²³ and R ²⁴ independently of each other represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, R ²⁵ represents hydrogen, or A is an expression

Represents the radical, From here, R ²⁶ represents fluorine, chlorine, bromine, dimethylamino, methyl or ethyl, R ²⁷ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, A is an expression

Represents the radical, From here, R ³³ represents biphenylcarboxamide of formula (I) representing methyl or ethyl. a) reacting a carboxylic acid derivative of the general formula (II) with an aniline derivative of the following general formula (III) in the presence of a catalyst, optionally in the presence of an acid binder and optionally in the presence of a A process for preparing biphenylcarboxamide of formula (I) according to claim 1 characterized by:

Where A, R, Z, X, Y, m and n are each as defined in claim 1, G represents halogen, hydroxy or C _1-6 -alkoxy. Aniline derivatives of general formula (III):

Where R, Z, X, Y, m and n are each as defined in claim 1. g) 2-halogenoaniline derivatives of the general formula (XI) of the following general formula (V) in the presence of an acid binder, optionally in the presence of an inert organic diluent and React with boronic acid derivatives, h) Aniline boronic acid of the general formula (XII) wherein the phenyloxime derivative of the general formula (VII) is optionally present in the presence of an acid binder, optionally in the presence of an inert organic diluent and A process for preparing an aniline derivative of formula (III) according to claim 5 characterized by reacting with:

Where X, m, R, Z, Y and n are each as defined in claim 1, Hal stands for halogen, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. Boronic Acid Derivatives of Formula (V):

Where R, Z, Y and n are each as defined in claim 1, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. i) Alkoxyamines of the general formula (IX), wherein phenylboronic acid of the general formula (XIII) is optionally present in the presence of an acid binder, optionally in the presence of an inert organic diluent and A process for preparing a boronic acid derivative of formula (V) according to claim 7 characterized in that for reacting with:

Where R, Y, n And Z are each as defined in claim 1, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. Carboxamide-boronic acid derivatives of general formula (VI):

Where A, X And m are each as defined in claim 1, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. j) Reaction of the carboxylic acid derivative of the general formula (II) with aniline boronic acid of the general formula (XII) A process for preparing a carboxamide-boronic acid derivative of formula (VI) according to claim 9 characterized by

Where A, X and m are each as defined in claim 1, G represents halogen, hydroxy or C _1-6 -alkoxy, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. Biphenylacyl Derivatives of Formula (VIII):

Where A, R, X, Y, m and n are each as defined in claim 1. k) reacting a carboxylic acid derivative of formula (II) with a 2-benzaldehyde-aniline derivative of formula (XIV) in the presence of an acid binder and optionally in the presence of an inert organic diluent To prepare a biphenylacyl derivative of the general formula (VIII) according to claim 11

Where A, R, X, Y, m and n are each as defined in claim 1, G represents halogen, hydroxy or C _1-6 -alkoxy. 2-benzaldehyde-aniline derivatives of general formula (XIV):

Where R, X, Y, m and n are each as defined in claim 1. l) reacting an aniline derivative of formula (XI) with a phenylboronic acid derivative of formula (XIII), optionally in the presence of an acid binder and optionally in the presence of an inert organic diluent Process for preparing 2-benzaldehyde-aniline derivatives of general formula (XIV) according to claim 13

Where X, m, R, Y and n are each as defined in claim 1, Hal stands for halogen, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. A composition for controlling fungi and bacteria, characterized by containing at least one biphenylcarboxamide of formula (I) according to claim 1 together with an extender and / or a surfactant. delete A method for controlling fungi and bacteria, characterized in that the biphenylcarboxamide of formula (I) according to claim 1 is applied to fungi, bacteria and / or their habitats. A process for preparing a composition for controlling fungi and bacteria, characterized by mixing biphenylcarboxamide of formula (I) according to claim 1 with an extender and / or a surfactant. b) reacting the carboxamide derivative of formula (IV) with the boronic acid derivative of formula (V), optionally in the presence of an acid binder and optionally in the presence of a diluent, c) reacting a carboxamide-boronic acid derivative of formula (VI) with a phenyloxime derivative of formula (VII), optionally in the presence of an acid binder and optionally in the presence of a diluent, f) Carboxamide derivatives of the following general formula (IV) are prepared in the presence of palladium or platinum catalyst, 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'- Reacting with a phenyloxime derivative of the general formula (VII) in the presence of bis-1,3,2-dioxaborolane, optionally in the presence of an acid binder and optionally in the presence of a diluent Method for preparing biphenylcarboxamide of general formula (I) according to claim 1:

Where A, R, Z, X, Y, m and n are each as defined in claim 1, G ¹ and G ² each represent hydrogen or together represent tetramethylethylene. d) reacting a biphenylacyl derivative of the general formula (VIII) below with an alkoxamine of the general formula (IX), optionally in the presence of an acid binder and optionally in the presence of a diluent, e) reacting a hydroxyamine derivative of the general formula (Ia) with a compound of the general formula (X) in the presence of an acid binder and optionally in the presence of a diluent Process for preparing biphenylcarboxamide of formula (I) according to

Where A, R, Z, X, Y, m and n are each as defined in claim 1, Z ¹ represents C _1-6 -alkyl, E represents chlorine, bromine, iodine, methanesulfonyl or p-toluenesulfonyl, or Z ¹ and E together represent (di-C _1-6 -alkyl) sulfate.