KR20060136459A - N-(2-(Hydroxymethyl)phenyl)-1H-pyrazole-4-carboxamide derivatives and related compounds as microbicidal active ingredients for phyto-protection and the protection of materials - Google Patents

Abstract

Novel carboxamides of formula (I), a number of methods for their preparation, their use for controlling unwanted microorganisms, new intermediates and methods for their preparation are disclosed:

Where

R ¹ , M, L ¹ , Q, L ² , R and A are as defined in the specification.

Description

N- (2- (hydroxymethyl) phenyl) -1H-pyrazole-4-carboxamide derivatives and related compounds as bactericidal active ingredients for plant protection and material protection {N- (2- (Hydroxymethyl) phenyl) -1H-pyrazole-4-carboxamide derivatives and related compounds as microbicidal active ingredients for phyto-protection and the protection of materials}

The present invention relates to novel carboxamides, many methods for their synthesis and their use for controlling unwanted microorganisms.

Many carboxamides have already been known to have bactericidal properties (see for example WO 03/010149, WO 02/059086, EP-A 0 824 099, EP-A 0 737 682, EP-A 0 591). 699, EP-A 0 589 301, EP-A 0 545 099, DE-A 24 09 011, DE-A 20 06 472, JP-A 2001-302605, JP-A 10-251240, JP-A 8-176112 , JP-A 8-92223 and JP-A 53-72823. That is, many alkyl carboxamides with unsubstituted alkyl moieties such as N-allyl-N- [2- (1,3-dimethylbutyl) phenyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide is known from WO 02/059086, and N- [2- (1,3-dimethylbutyl) phenyl] -2,4-dimethyl-1,3-thiazole-5 Carboxamides are known from EP-A 0 824 099, 5-Fluoro-1,3-dimethyl-N- [2- (1,3,3-trimethylbutyl) phenyl] -1 H-pyrazole-4 Carboxamides are known from WO 03/010149. The effect of these compounds is excellent; In many cases, for example, it is not satisfactory at low application rates.

The present invention provides novel carboxamides of formula (I):

Where

R ¹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₈ -alkyl) carbonyl, (C ₁ -C ₈ -alkoxy) carbonyl, (C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -Cycloalkyl) carbonyl; (C ₁ -C ₆ -haloalkyl) carbonyl, (C ₁ -C ₆ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ ,

R ² is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ with 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₈ -halocycloalkyl,

R ³ and R ⁴ independently of one another in each occurrence are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₈ -haloalkyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or

R ³ and R ⁴ may also, together with the nitrogen atom to which they are attached, have one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ and halogen and C ₁ -C ₄ -alkyl A heterocycle of saturated 5 to 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of

R ⁵ and R ⁶ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl; In each case represent C ₁ -C ₈ -haloalkyl or C ₃ -C ₈ -halocycloalkyl having 1 to 9 fluorine, chlorine and / or bromine atoms,

R ⁵ and R ⁶ may also, together with the nitrogen atom to which they are attached, have one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ and include halogen and C ₁ -C ₄ -alkyl A heterocycle of saturated 5 to 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of

R ⁷ represents hydrogen or C ₁ -C ₆ -alkyl,

M is represented by a substituted phenyl, pyridine, pyrimidine, pyridazine or pyrazine ring by R ⁸ in each case, or represents a thiazole ring substituted by R ^8-A,

R ⁸ represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, or

R ⁸ represents methoxy,

R ^8-A represents hydrogen, methyl, methylthio or trifluoromethyl,

L ¹ represents C ₁ -C ₁₀ -alkylene (alkanediyl),

Q represents O, S, SO, SO ₂ or NR ⁹ ,

L ² represents a direct bond, SiR ¹⁰ R ¹¹ or CO,

R is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl Or C ₃ -C ₆ -cycloalkyl,

R ⁹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl or C ₃ -C ₆ -cyclo Alkyl,

R ¹⁰ and R ¹¹ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkyl Thio-C ₁ -C ₄ -alkyl or C ₁ -C ₆ -haloalkyl,

A represents a group of formula (A1):

From here,

R ¹² is hydrogen, cyano, halogen, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₃ -C ₆ -cycloalkyl, in each case 1 C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy or C ₁ -C ₄ -haloalkylthio, aminocarbonyl or aminocarbonyl-C ₁ -C ₄ -alkyl having from 5 to 5 halogen atoms ,

R ¹³ represents hydrogen, halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio,

R ¹⁴ is hydrogen, C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, C ₂ -C ₆ -alkenyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkylthio -C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, in each case C ₁ -C ₄ -haloalkyl, having 1 to 5 halogen atoms, C ₁ -C ₄ -Haloalkylthio-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkoxy-C ₁ -C ₄ -alkyl or phenyl

A represents a group of formula (A2):

From here,

R ¹⁵ and R ¹⁶ independently of one another represent hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ¹⁷ represents halogen, cyano, C ₁ -C ₄ -alkyl, or C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy having 1 to 5 halogen atoms in each case, or

A represents a group of formula (A3):

From here,

R ¹⁸ and R ¹⁹ independently of one another represent hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ²⁰ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or

A represents a group of formula (A4):

From here,

R ²¹ is hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ -alkyl, or C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy having 1 to 5 halogen atoms in each case Or C ₁ -C ₄ -haloalthio,

A represents a group of formula (A5):

From here,

R ²² is halogen, hydroxy, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, in each case C ₁ -having 1 to 5 halogen atoms C ₄ -haloalkyl, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -haloalkoxy, or

R ²³ is hydrogen, halogen, cyano, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio having 1 to 5 halogen atoms, in each case C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy, or C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl, or

A represents a group of formula (A6):

From here,

R ²⁴ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ²⁵ represents C ₁ -C ₄ -alkyl,

Q ¹ represents S (sulfur), SO, SO ₂ or CH ₂ ,

p represents 0, 1 or 2, and when p is 2, R ²⁵ represents the same or different group, or

A represents a group of formula (A7):

From here,

R ²⁶ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A8):

From here,

R ²⁷ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or

A represents a group of formula (A9):

From here,

R ²⁸ and R ²⁹ independently of one another represent hydrogen, halogen, amino, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ³⁰ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or

A represents a group of formula (A10):

From here,

R ³¹ and R ³² independently of one another represent hydrogen, halogen, amino, nitro, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ³³ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A11):

From here,

R ³⁴ is hydrogen, halogen, amino, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ -alkyl) amino, cyano, C ₁ -C ₄ -alkyl or having 1 to 5 halogen atoms C ₁ -C ₄ -haloalkyl,

R ³⁵ represents halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A12):

From here,

R ³⁶ has hydrogen, halogen, amino, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ -alkyl) amino, cyano, C ₁ -C ₄ -alkyl or having 1 to 5 halogen atoms C ₁ -C ₄ -haloalkyl,

R ³⁷ represents halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or

A represents a group of formula (A13):

From here,

R ³⁸ represents hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A14):

From here,

R ³⁹ represents hydrogen or C ₁ -C ₄ -alkyl,

R ⁴⁰ represents halogen or C ₁ -C ₄ -alkyl, or

A represents a group of formula (A15):

From here,

R ⁴¹ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A16):

From here,

R ⁴² represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A17):

From here,

R ⁴³ is halogen, hydroxy, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, in each case 1 to 5 C ₁ -C ₄ has a halogen atom - Haloalkyl, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -haloalkoxy, or

A represents a group of formula (A18):

From here,

R ⁴⁴ is hydrogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, hydroxy Oxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl, di (C ₁ -C ₄ -alkyl) aminosulfonyl, C ₁ -C ₆ -alkylcarbonyl or optionally substituted in each case Phenylsulfonyl or benzoyl,

R ⁴⁵ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ⁴⁶ represents hydrogen, halogen, cyano, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

R ⁴⁷ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms,

A represents a group of formula (A19):

From here,

R ⁴⁸ represents C ₁ -C ₄ -alkyl,

Provided that when L ² is a direct bond, R is not alkoxy.

Further, the carboxamide of formula (I)

a) Aniline of formula (III) in the presence of a carboxylic acid derivative of formula (II), optionally in the presence of a catalyst, optionally in the presence of a condensation agent, optionally in the presence of an acid binder and optionally in the presence of a diluent React with derivatives,

b) reacting the carboxamide of formula (IV) with a compound of formula (V) in the presence of a base and in the presence of a dilution medium, or

c) It has been found that the carboxamide of formula (I-a) is obtained by reacting with a halide of formula (VI) in the presence of a base and in the presence of a dilution medium:

Where

A, R ¹ , M, Q, L ² and R are as defined above,

X ¹ represents halogen or hydroxy,

L ³ represents hydrogen or C ₁ -C ₉ -alkyl,

Y represents halogen, triflate (trifluoromethylsulfonyl), mesylate (methylsulfonyl) or tosylate (4-methylphenylsulfonyl),

X ² represents chlorine, bromine or iodine,

R ^{1 -A} is C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl or halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₈ -alkyl) carbonyl, (C ₁ -C ₈ -alkoxy) carbonyl, (C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -Cycloalkyl) carbonyl; (C ₁ -C ₆ -haloalkyl) carbonyl, (C ₁ -C ₆ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ ,

Wherein R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are as defined above.

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

The compounds according to the invention may exist in several possible different isomers, in particular stereoisomeric forms, for example E and Z, threo and erythro and also optical isomers and optionally mixtures of tautomers. According to the invention, both the E and Z isomers, and also the stereo and erythroisomers and optical isomers, any mixtures of these isomers and possible tautomeric forms are all claimed.

Carboxamides according to the invention are generally defined by formula (I). Hereinafter, definitions of the preferred groups of the formulas mentioned above and hereinafter are given. These definitions apply to the final product of formula (I) and correspondingly all intermediate products.

R ¹ is preferably hydrogen; C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C _6- Cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₆ -alkyl) carbonyl, (C ₁ -C ₄ -alkoxy) carbonyl, (C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -Cycloalkyl) carbonyl; (C ₁ -C ₄ -haloalkyl) carbonyl, (C ₁ -C ₄ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ .

R ¹ is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, pentyl, hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulphi Nyl, n-, iso-, sec- or t-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methoxy Methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, formyl, -CH ₂ -CHO,-(CH ₂ ) ₂ -CHO, -CH ₂ -CO- CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ ,-(CH ₂ ) ₂ -CO-CH ₃ ,-(CH ₂ ) ₂ -CO-CH ₂ CH ₃ ,-(CH ₂ ) ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ -CO ₂ CH ₃ , -CH ₂ -CO ₂ CH ₂ CH ₃ ,- CH ₂ -CO ₂ CH (CH ₃ ) ₂ ,-(CH ₂ ) ₂ -CO ₂ CH ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CH ₃ ,-(CH ₂ ) ₂ -CO ₂ CH (CH ₃ ) ₂ , -CH ₂ -CO-CF ₃ , -CH ₂ -CO-CCl ₃ , -CH ₂ -CO-CH ₂ CF ₃ , -CH ₂ -CO-CH ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO-CH ₂ CF ₃ ,-(CH ₂ ) ₂ -CO-CH ₂ CCl ₃ , -CH ₂ -CO ₂ CH ₂ CF ₃ , -CH ₂ -CO ₂ CF ₂ CF ₃ , -CH ₂ -CO ₂ CH ₂ CCl ₃ , -CH ₂ -CO ₂ CCl ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CF ₃ ,-(CH ₂ ) ₂ -CO ₂ CF ₂ CF ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO ₂ -CCl ₂ CCl ₃ , methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, t-butylcarbonyl, methoxy Carbonyl, ethoxycarbonyl, t-butoxycarbonyl, cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or —CH ₂ NR ⁵ R ⁶ is represented.

R ¹ is most preferably hydrogen, methyl, methoxymethyl, formyl, -CH ₂ -CHO,-(CH ₂ ) ₂ -CHO, -CH ₂ -CO-CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ , -C (= O) CHO, -C (= O) C (= O) CH ₃ , -C (= O) C (= O) CH ₂ OCH ₃ , —C (═O) CO ₂ CH ₃ or —C (═O) CO ₂ CH ₂ CH ₃ .

R ² is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl.

R ² is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, t-butyl, methoxy, ethoxy, n- or isopropoxy, t-butoxy, methoxymethyl, cyclopropyl, trifluoro Chloromethyl or trifluoromethoxy.

R ³ and R ⁴ are independently of each other preferably hydrogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl.

R ³ and R ⁴ together with the nitrogen atom to which they are attached may also contain one or two additional nonadjacent heteroatoms, preferably selected from the group consisting of oxygen, sulfur and NR ⁷ , and halogen and C ₁ − It represents a heterocycle of saturated 5 or 6 ring atoms which is preferably one to tetrasubstituted by the same or different substituents selected from the group consisting of C ₄ -alkyl.

R ³ and R ⁴ independently of one another are particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, Ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl or trifluoromethoxymethyl.

R ³ and R ⁴ together with the nitrogen atom to which they are attached are particularly preferably one- to tetrasubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and methyl, morpholines, thiomors Saturated heterocycle selected from the group consisting of poline and piperazine, wherein piperazine may be substituted at the second nitrogen atom by R ⁹ .

R ⁵ and R ⁶ independently of one another preferably hydrogen, C ₁ -C ₆ -alkyl, C ₃ -C ₆ -cycloalkyl, or C in each case having 1 to 9 fluorine, chlorine and / or bromine atoms ₁ -C ₄ -haloalkyl or C ₃ -C ₆ -halocycloalkyl.

R ⁵ and R ⁶ together with the nitrogen atom to which they are attached may also contain one or two additional nonadjacent heteroatoms, preferably selected from the group consisting of oxygen, sulfur and NR ⁷ , and halogen and C ₁ − Represents a heterocycle of saturated 5 or 6 ring atoms which is preferably mono- to tetrasubstituted by the same or different substituents selected from the group consisting of C ₄ -alkyl,

R ⁵ and R ⁶ independently of one another are particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, Ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl or trifluoromethoxymethyl.

R ⁵ and R ⁶ together with the nitrogen atom to which they are attached are particularly preferably mono- to tetrasubstituted by the same or different substituents selected from the group consisting of fluorine, chlorine, bromine and methyl, morpholine, thiomorpholine And a saturated heterocycle selected from the group consisting of piperazine, wherein piperazine may be substituted at a second nitrogen atom by R ⁷ .

R ⁷ preferably represents hydrogen or C ₁ -C ₄ -alkyl.

R ⁷ particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl.

M preferably represents one of the following cyclics:

From here,

The bond marked * is attached to the amide.

M particularly preferably represents a cyclic selected from M-1, M-2, M-3, M-6, M-7, M-10 or M-11.

M also particularly preferably represents a cyclic selected from M-1, M-2, M-3, M-4, M-5, M-6, M-10 or M-11.

M most preferably represents cyclic M-1.

M also most preferably represents heterocycle M-2.

M also most preferably represents heterocycle M-3.

M also most preferably represents heterocycle M-6.

M also most preferably represents heterocycle M-7.

M also most preferably represents heterocycle M-10.

M also most preferably represents heterocycle M-11.

R ⁸ preferably represents hydrogen.

R ⁸ is also preferably fluorine when M represents M-1, particularly preferably in the 4-, 5- or 6-position, most particularly preferably in the 4- or 6-position, especially the 4-position Represents fluorine.

R ⁸ also preferably represents chlorine when M represents M-1, particularly preferably chlorine in the 4- or 6-position.

R ⁸ also preferably represents methyl, particularly when M represents M-1, methyl group in the 3-position and also particularly preferably the 4-position.

R ⁸ also preferably represents methoxy, particularly preferably the methoxy group in the 4-position, when M represents M-1.

R ⁸ also preferably represents trifluoromethyl, particularly preferably trifluoromethyl group in the 4- or 6-position when M represents M-1.

R ⁸ is also preferably fluorine when M represents M-2, M-3, M-4 or M-5, particularly preferably 6-position (M-2, M-3), or 3- Fluorine in the position (M-4, M-5) is shown.

R ⁸ is also preferably chlorine when M represents M-2, M-3, M-4 or M-5, particularly preferably 6-position (M-2, M-3), or 3- Chlorine at positions M-4 and M-5.

R ⁸ is also preferably methyl when M represents M-2, M-3, M-4 or M-5, particularly preferably 4-position (M-2), or 3-position (M- 3, M-4, M-5).

R ⁸ preferably also represents methyl, particularly preferably the methyl group in the 3-position when M represents M-6.

R ⁸ also preferably represents trifluoromethyl, particularly preferably trifluoromethyl group, when M represents M-6.

R ⁸ is also preferably chlorine when M represents M-7, M-8 or M-9, particularly preferably 5-position (M-7, M-8), or 3-position (M- Chlorine in 9).

R ⁸ is also preferably methyl when M represents M-7, M-8 or M-9, particularly preferably 5-position (M-7, M-8), or 3-position (M- The methyl group in 9) is shown.

R ⁸ also preferably denotes methyl, particularly preferably the methyl group in the 4-position when M represents M-12.

R ⁸ also preferably represents trifluoromethyl, particularly preferably the trifluoromethyl group in the 4-position when M represents M-12.

R ⁸ preferably also represents methyl, particularly preferably the methyl group in the 3-position when M represents M-13.

R ⁸ also preferably represents trifluoromethyl, particularly preferably trifluoromethyl group, when M represents M-13.

R ⁸ also preferably denotes methyl, particularly preferably the methyl group at the 3-position when M represents M-14.

R ⁸ also preferably represents trifluoromethyl, particularly preferably trifluoromethyl group, when M represents M-14.

R ^8-A preferably represents hydrogen.

R ^8-A also preferably represents methyl.

R ^8-A also preferably represents trifluoromethyl.

L ¹ preferably denotes C ₁ -C ₆ -alkylene (alkanediyl).

L ¹ particularly preferably represents —CH ₂ —, —CH (CH ₃ ) — or — (CH ₂ ) ₂ C (CH ₃ ) ₂ —.

L ¹ also particularly preferably represents — (CH ₂ ) ₂ —.

Q preferably represents O.

Q also preferably represents S.

Q also preferably represents SO.

Q also preferably represents SO ₂ .

Q also preferably represents NR ⁹ , particularly preferably NH.

L ² preferably represents a direct bond.

L ² also preferably denotes SiR ¹⁰ R ¹¹ .

L ² also preferably represents CO.

R is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkylthio-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -cycloalkyl.

R also preferably represents C ₁ -C ₄ -haloalkyl.

R is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxy, ethoxy, n- or isopropoxy, n-, iso-, sec- or t-butoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl.

R also particularly preferably represents C ₁ -C ₂ -haloalkyl, cyclopentyl or cyclohexyl having 1-methylbutyl, 1 to 5 fluorine, chlorine or bromine atoms.

R most preferably represents hydrogen, methyl, ethyl, n- or isopropyl, iso- or t-butyl, methoxy, isopropoxy, iso- or t-butoxy, methoxymethyl or methylthiomethyl.

R also most preferably represents sec-butyl, 1-methylbutyl, dichloromethyl, cyclopropyl, cyclopentyl or cyclohexyl.

R particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, iso- or t-butyl, methoxy, isopropoxy, iso- or t-butoxy.

R also particularly preferably represents sec-butyl or 1-methylbutyl.

R ⁹ is preferably hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkylthio-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -cycloalkyl is represented.

R ⁹ is particularly preferably hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthio Methyl, ethylthiomethyl, methylthioethyl, ethylthioethyl or cyclopropyl.

R ⁹ most particularly preferably represents hydrogen, methyl, ethyl, n- or isopropyl, iso- or t-butyl, methoxymethyl or methylthiomethyl.

R ⁹ particularly preferably represents hydrogen or methyl.

R ¹⁰ and R ¹¹ are independently of each other preferably C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₁ -C _3- Alkylthio-C ₁ -C ₃ -alkyl is indicated.

R ¹⁰ and R ¹¹ independently of one another are particularly preferably methyl, ethyl, methoxy, ethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl Or ethylthioethyl.

R ¹⁰ and R ¹¹ independently of one another most particularly preferably represent methyl, methoxy, methoxymethyl or methylthiomethyl.

R ¹⁰ and R ¹¹ particularly preferably represent methyl in each case.

A preferably represents one of groups A1, A2, A3, A4, A5, A6, A9, A10, A11, A12, A17 and A18.

A particularly preferably represents one of groups A1, A2, A4, A5, A6, A9, A11, A16, A17, A18.

A most particularly preferably represents radical A1.

A also most particularly preferably represents radical A4.

A also most particularly preferably represents radical A5.

A also most particularly preferably represents radical A6.

A also most particularly preferably represents radical A9.

A also most particularly preferably represents radical A11.

A also most particularly preferably represents radical A16.

A also most particularly preferably represents radical A18.

R ¹² preferably is hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, in each case 1 to 5 fluorine, C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonyl having chlorine and / or bromine atoms Ethyl.

R ¹² is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl, Trichloromethyl, dichloromethyl, cyclopropyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, methylthio, ethylthio, trifluoromethylthio or difluoromethylthio.

R ¹² is most particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, methyl, isopropyl, monofluoromethyl, monofluoroethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloro Romethyl.

R ¹² particularly preferably represents methyl, difluoromethyl, trifluoromethyl or 1-fluoroethyl.

R ¹³ preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.

R ¹³ particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or methyl.

R ¹³ most particularly preferably represents hydrogen, fluorine, chlorine or methyl.

R ¹⁴ is preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, C ₁ -C ₂ -haloalkyl, hydroxymethyl, hydroxyethyl, having 1 to 5 fluorine, chlorine and / or bromine atoms, Cyclopropyl, cyclopentyl, cyclohexyl or phenyl.

R ¹⁴ particularly preferably represents hydrogen, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, hydroxymethyl, hydroxyethyl or phenyl.

R ¹⁴ most particularly preferably represents hydrogen, methyl, trifluoromethyl or phenyl.

R ¹⁴ particularly preferably represents methyl.

R ¹⁵ and R ¹⁶ independently of one another preferably represent C ₁ -C ₂ -haloalkyl having hydrogen, fluorine, chlorine, bromine, methyl, ethyl or 1 to 5 fluorine, chlorine and / or bromine atoms.

R ¹⁵ and R ¹⁶ independently of each other particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl, difluorochloromethyl or trichloromethyl.

R ¹⁵ and R ¹⁶ independently of each other most particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, trifluoromethyl or trichloromethyl.

R ¹⁵ and R ¹⁶ particularly preferably represent hydrogen in each case.

R ¹⁷ is preferably fluorine, chlorine, bromine, cyano, methyl, ethyl, in each case C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ having 1 to 5 fluorine, chlorine and / or bromine atoms -Haloalkoxy.

R ¹⁷ particularly preferably represents fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy or trichloromethoxy.

R ¹⁷ most particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or trifluoromethoxy.

R ¹⁷ particularly preferably represents methyl.

R ¹⁸ and R ^l9 is independently preferably a hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or 1 to 5 fluorine, chlorine and / or C ₁ -C ₂ having a bromine atom - represents a haloalkyl.

R ¹⁸ and R ^l9 represents a methyl, independently of each other, particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoro methyl, trifluoromethyl, chloromethyl or trichloromethyl-difluoro.

R ¹⁸ and R independently represents a methyl ^l9 most particularly preferably hydrogen, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, methyl, methyl or trifluoromethyl trichloromethyl each other.

R ¹⁸ and R ^l9 will be particularly preferably a hydrogen in each case.

R ²⁰ preferably denotes C ₁ -C ₂ -haloalkyl having hydrogen, fluorine, chlorine, bromine, methyl, ethyl or 1 to 5 fluorine, chlorine and / or bromine atoms.

R ²⁰ particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.

R ²⁰ most particularly preferably represents methyl.

R ²¹ is preferably hydrogen, F, Cl, Br, I, hydroxy, cyano, C ₁ -C ₄ - ₁ C with an alkyl, 1 to 5 fluorine, chlorine and / or bromine atoms in each case C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy or C ₁ -C ₂ -haloalkylthio.

R ²¹ is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, di Fluoromethyl, trifluoromethyl, difluorochloromethyl, trichloromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, trifluoromethylthio, difluoromethyl Thio, difluorochloromethylthio or trichloromethylthio.

R ²¹ most particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, difluoromethyl, trifluoromethyl or trichloromethyl.

R ²¹ particularly preferably represents iodine, methyl, difluoromethyl or trifluoromethyl.

R ²² is preferably fluorine, chlorine, bromine, iodine, hydroxy, cyano, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethyl Thio, in each case C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ²² is particularly preferably fluorine, chlorine, bromine, iodine, hydroxy, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, trifluoro Methyl, difluoromethyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, trifluoromethoxy, difluoromethoxy , Difluorochloromethoxy or trichloromethoxy.

R ²² most particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ²³ is preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, in each case 1 to 5 fluorine, chlorine and Or C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy, C ₁ -C ₂ -alkylsulfinyl or C ₁ -C ₂ -alkylsulfonyl having a bromine atom.

R ²³ is particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, cyano, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, trifluoromethyl, difluoro Methyl, difluorochloromethyl, trichloromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trichloromethoxy, methylsulfinyl or methyl Sulfonyl.

R ²³ is most particularly preferably hydrogen, fluorine, chlorine, bromine, iodine, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, trifluoromethyl, difluoromethyl, Trichloromethyl, methylsulfinyl or methylsulfonyl.

R ²³ particularly preferably represents hydrogen.

R ²⁴ preferably represents methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ²⁴ particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ²⁵ preferably denotes methyl or ethyl.

R ²⁵ particularly preferably represents methyl.

Q ¹ preferably represents S (sulfur), SO ₂ or CH ₂ .

Q ¹ particularly preferably represents S (sulfur) or CH ₂ .

Q ¹ most particularly preferably represents S (sulfur).

p preferably represents 0 or 1;

p particularly preferably represents 0.

R ²⁶ preferably represents methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ²⁶ particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ²⁶ most particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ²⁷ preferably denotes C ₁ -C ₂ -haloalkyl having methyl, ethyl or 1 to 5 fluorine, chlorine and / or bromine atoms.

R ²⁷ particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ²⁷ most particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ²⁸ and R ²⁹ independently of one another preferably represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms .

R ²⁸ and R ²⁹ independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ²⁸ and R ²⁹ independently of one another most particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ²⁸ and R ²⁹ particularly preferably represent hydrogen in each case.

R ³⁰ preferably denotes C ₁ -C ₂ -haloalkyl having hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or 1 to 5 fluorine, chlorine and / or bromine atoms.

R ³⁰ particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³⁰ most particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁰ particularly preferably represents methyl.

R ³¹ and R ³² are independently of each other preferably hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms Indicates.

R ³¹ and R ³² independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³¹ and R ³² independently of one another most particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³¹ and R ³² particularly preferably represent hydrogen in each case.

R ³³ preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ³³ particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³³ most particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³³ particularly preferably represents methyl.

R ³⁴ is preferably hydrogen, fluorine, chlorine, bromine, amino, C ₁ -C ₄ -alkylamino, di (C ₁ -C ₄ -alkyl) amino, cyano, methyl, ethyl or 1 to 5 fluorine, C ₁ -C ₂ -haloalkyl having chlorine and / or bromine atoms.

R ³⁴ is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl Indicates.

R ³⁴ most particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁴ particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.

R ³⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ³⁵ particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³⁵ most particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁵ particularly preferably represents methyl, trifluoromethyl or difluoromethyl.

R ³⁶ is preferably hydrogen, fluorine, chlorine, bromine, amino, C ₁ -C ₄ -alkylamino, di (C ₁ -C ₄ -alkyl) amino, cyano, methyl, ethyl or 1 to 5 fluorine, C ₁ -C ₂ -haloalkyl having chlorine and / or bromine atoms.

R ³⁶ is particularly preferably hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, cyano, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl Indicates.

R ³⁶ most particularly preferably represents hydrogen, fluorine, chlorine, bromine, amino, methylamino, dimethylamino, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁶ particularly preferably represents amino, methylamino, dimethylamino, methyl or trifluoromethyl.

R ³⁷ preferably denotes C ₁ -C ₂ -haloalkyl having fluorine, chlorine, bromine, methyl, ethyl or 1 to 5 fluorine, chlorine and / or bromine atoms.

R ³⁷ particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³⁷ most particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁷ particularly preferably represents methyl, trifluoromethyl or difluoromethyl.

R ³⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ³⁸ particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ³⁸ most particularly preferably represents fluorine, chlorine, bromine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ³⁹ preferably denotes hydrogen, methyl or ethyl.

R ³⁹ particularly preferably represents methyl.

R ⁴⁰ preferably represents fluorine, chlorine, bromine, methyl or ethyl.

R ⁴⁰ particularly preferably represents fluorine, chlorine or methyl.

R ⁴¹ preferably represents methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴¹ particularly preferably represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ⁴¹ most particularly preferably represents methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ⁴¹ particularly preferably represents methyl or trifluoromethyl.

R ⁴² preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴² particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl or trifluoromethyl.

R ⁴³ is preferably fluorine, chlorine, bromine, iodine, hydroxy, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, or C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴³ is particularly preferably fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, trifluoromethyl, difluoromethyl , Difluorochloromethyl and trichloromethyl are shown.

R ⁴³ most particularly preferably represents fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ⁴⁴ is preferably hydrogen, methyl, ethyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl having 1 to 5 fluorine, chlorine and / or bromine atoms , Hydroxymethyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl.

R ⁴⁴ particularly preferably represents hydrogen, methyl, ethyl, trifluoromethyl, methoxymethyl, ethoxymethyl, hydroxymethyl or hydroxyethyl.

R ⁴⁴ most particularly preferably represents methyl or methoxymethyl.

R ⁴⁵ preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴⁵ particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl or trichloromethyl.

R ⁴⁵ most particularly preferably represents hydrogen or methyl.

R ⁴⁶ preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴⁶ particularly preferably represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl.

R ⁴⁶ most particularly preferably represents hydrogen, methyl, difluoromethyl or trifluoromethyl.

R ⁴⁷ preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms.

R ⁴⁷ particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine, methyl or trifluoromethyl.

R ⁴⁷ most particularly preferably represents hydrogen.

R ⁴⁸ preferably denotes methyl, ethyl, n-propyl or isopropyl.

R ⁴⁸ particularly preferably represents methyl or ethyl.

Preferred embodiments are compounds corresponding to formula (I) in which all groups have in each case the preferred meaning cited above.

Particularly preferred embodiments are compounds corresponding to formula (I) in which all groups have in each case the particularly preferred meaning cited above.

New carboxamides of the following groups are preferred, each of which is considered to be part of a compound corresponding to formula (I) cited above.

Group 1: carboxamide of formula (I-a):

Where

M, L ¹ , Q, L ² , R and A are as defined above.

Group 2: carboxamide of formula (I-b):

Where

R ^{1 -A} , M, L ¹ , Q, L ² , R and A are as defined above.

R ^{1 -A} is preferably C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C _3- Alkyl, C ₃ -C ₆ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₆ -alkyl) carbonyl, (C ₁ -C ₄ -alkoxy) carbonyl, (C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -Cycloalkyl) carbonyl; (C ₁ -C ₄ -haloalkyl) carbonyl, (C ₁ -C ₄ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ .

R ^1-A is particularly preferably methyl, ethyl, n- or isopropyl, n-, iso-, sec- or t-butyl, pentyl, hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulphi Nyl, n-, iso-, sec- or t-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec- or t-butylsulfonyl, methoxy Methyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylthio, difluorochloromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, formyl, -CH ₂ -CHO,-(CH ₂ ) ₂ -CHO, -CH ₂ -CO- CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ ,-(CH ₂ ) ₂ -CO-CH ₃ ,-(CH ₂ ) ₂ -CO-CH ₂ CH ₃ ,-(CH ₂ ) ₂ -CO-CH (CH ₃ ) ₂ , -CH ₂ -CO ₂ CH ₃ , -CH ₂ -CO ₂ CH ₂ CH ₃ , -CH ₂ -C O ₂ CH (CH ₃ ) ₂ ,-(CH ₂ ) ₂ -CO ₂ CH ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CH ₃ ,-(CH ₂ ) ₂ -CO ₂ CH (CH ₃ ) ₂ , -CH ₂ -CO-CF ₃ , -CH ₂ -CO-CCl ₃ , -CH ₂ -CO-CH ₂ CF ₃ , -CH ₂ -CO-CH ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO- CH ₂ CF ₃ ,-(CH ₂ ) ₂ -CO-CH ₂ CCl ₃ , -CH ₂ -CO ₂ CH ₂ CF ₃ , -CH ₂ -CO ₂ CF ₂ CF ₃ , -CH ₂ -CO ₂ CH ₂ CCl ₃ , -CH ₂ -CO ₂ CCl ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CF ₃ ,-(CH ₂ ) ₂ -CO ₂ CF ₂ CF ₃ ,-(CH ₂ ) ₂ -CO ₂ CH ₂ CCl ₃ ,-(CH ₂ ) ₂ -CO ₂ -CCl ₂ CCl ₃ , methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, t-butylcarbonyl, methoxycarbonyl, Ethoxycarbonyl, t-butoxycarbonyl, cyclopropylcarbonyl, trifluoromethylcarbonyl, trifluoromethoxycarbonyl, -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ Or -CH ₂ NR ⁵ R ⁶ .

R ^1-A is most particularly preferably methyl, methoxymethyl, formyl, -CH ₂ -CHO,-(CH ₂ ) ₂ -CHO, -CH ₂ -CO-CH ₃ , -CH ₂ -CO-CH ₂ CH ₃ , -CH ₂ -CO-CH (CH ₃ ) ₂ , -C (= O) CHO, -C (= O) C (= O) CH ₃ , -C (= O) C (= O) CH ₂ OCH ₃ , —C (═O) CO ₂ CH ₃ or —C (═O) CO ₂ CH ₂ CH ₃ .

Group 3: carboxamide of formula (I-c):

Where

R ¹ , R ⁸ , L ¹ , Q, L ² , R and A are as defined above.

Preferred embodiments are carboxamides of formula (Ic) in which R ¹ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ic) in which R ⁸ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ic) in which R ¹ and R ⁸ each represent hydrogen.

Group 4: carboxamide of formula (I-d):

Where

R ¹ , R ⁸ , L ¹ , Q, L ² , R and A are as defined above.

Preferred embodiments are carboxamides of formula (Id) wherein R ¹ represents hydrogen.

Preferred embodiments are carboxamides of formula (Id) wherein R ⁸ represents hydrogen.

Preferred embodiments are carboxamides of formula (Id) in which R ¹ and R ⁸ each represent hydrogen.

Group 5: carboxamide of formula (I-e):

Where

R ¹ , R ⁸ , L ¹ , Q, L ² , R and A are as defined above.

Preferred embodiments are carboxamides of formula (Ie) in which R ¹ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ie) in which R ⁸ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ie) in which R ¹ and R ⁸ each represent hydrogen.

Group 6: carboxamide of formula (I-f):

Where

R ¹ , R ⁸ , L ¹ , Q, L ² , R and A are as defined above.

Preferred embodiments are carboxamides of formula (If) wherein R ¹ represents hydrogen.

Preferred embodiments are carboxamides of formula (If) in which R ⁸ represents hydrogen.

Preferred embodiments are carboxamides of formula (If) in which R ¹ and R ⁸ each represent hydrogen.

Group 7: carboxamide of formula (I-g):

Where

R ¹ , R ⁸ , L ¹ , Q, L ² , R and A are as defined above.

Preferred embodiments are carboxamides of formula (Ig) in which R ¹ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ig) wherein R ⁸ represents hydrogen.

Preferred embodiments are carboxamides of formula (Ig) in which R ¹ and R ⁸ each represent hydrogen.

Emphasis is given to compounds of formula (I) in which R ¹ represents hydrogen (and groups 1 to 7).

Emphasis is given to compounds of formula (I) in which R ¹ represents formyl (and groups 1 to 7).

R ¹ represents —C (═O) C (═O) R ² , with R ² accentuating the compounds of formula (I) as defined above (and groups 1 to 7).

For example, saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can be as straight or branched as possible in each case, including those bonded with heteroatoms such as in alkoxy. Likewise, double bond hydrocarbon groups, such as alkylene (alkanediyl), can in each case be as straight or branched as possible.

The optionally substituted radical may be mono- or polysubstituted, and when polysubstituted, the substituents may be the same or different. Thus, the definition "dialkylamino" also includes asymmetrically substituted amino groups, such as methylethylamino.

Halogen-substituted radicals, such as for example haloalkyl, are mono- or polyhalogenated. In the case of polyhalogenated halogen atoms may be the same or different. Here, halogen represents fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.

However, the definitions and / or descriptions of the general or preferred radicals given above may be combined with one another between each range and the preferred range as necessary. These definitions apply to both the final product and, correspondingly, to precursors and intermediates. In particular, the definitions mentioned in groups 1 to 6 may be combined with definitions such as general, preferred or particularly preferred, where all combinations of preferred regions are possible in each case.

Description of the process according to the invention for synthesizing hexylcarboxanilide and intermediate products of formula (I)

Method (a)

When using 2-trifluoromethylbenzoyl chloride and {2- [1- (isopropylsulfonyl) ethyl] phenyl} amine as starting materials, the process of the method (a) according to the present invention can be represented by the following scheme. Can:

Carboxylic acid derivatives required as starting materials for carrying out process (a) according to the invention are generally defined by formula (II). In this formula (II), A is preferably, particularly preferably or most particularly preferably mentioned above as preferred, particularly preferred or very particularly preferred for A with respect to the description of the compounds of formula (I) according to the invention. Has a meaning. X ¹ preferably represents chlorine, bromine or hydroxy.

Most of the carboxylic acid derivatives of formula (II) are known and / or can be synthesized by known methods (see WO 93/11117, EP-A 0 545 099, EP-A 0 589 301 and EP-A 0 589). 313).

Aniline derivatives which are also necessary as starting materials for carrying out process (a) according to the invention are generally defined by formula (III). In this formula (III), R ¹ , M, Q, L ² and R are preferably, particularly preferably or most particularly preferably for these radicals in connection with the description of the compounds of formula (I) according to the invention. Each has the meanings mentioned above as being preferred, particularly preferred or very particularly preferred. L ³ preferably denotes hydrogen or C ₁ -C ₅ -alkyl, particularly preferably hydrogen or methyl.

The aniline derivatives of formula (III) are novel.

Aniline derivatives of formula (III-a)

d) It has been found that the aniline derivatives of formula (III-b) are obtained by reacting with a halide of formula (VI) in the presence of a base and optionally in the presence of a dilution medium:

Where

R ^{1 -A} , M, Q, L ² , R, L ³ and X ² are as defined above.

Aniline derivatives of formula (III-b)

e) It has been found that the nitro compound of formula (VII) is obtained by reacting in the presence of a metal and a reducing agent, optionally in the presence of a diluent and optionally in the presence of a reaction medium:

Where

M, Q, L ² , R and L ³ are as defined above.

Nitro compounds required as starting materials for carrying out process (e) according to the invention are generally defined by formula (VII). In this formula (VII), M, Q, L ² , R and L ³ are preferably, particularly preferably or most particularly preferably with reference to the description of the compounds of formula (I) or (III) according to the invention Each of these radicals has the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

The nitro compound of formula (VII) is

f) It has been found that the nitro compound of formula (VII) is obtained by reaction with a compound of formula (IX) in the presence of a base and optionally in the presence of a dilution medium:

Where

M, Q, L ² , R and L ³ are as defined above,

X represents chlorine, bromine or iodine.

Nitro compounds required as starting materials for carrying out process (f) according to the invention are generally defined by formula (VII). In this formula (VII), M and L ³ are preferably, particularly preferably or most particularly preferably respectively preferred for these radicals in connection with the description of the compounds of formula (I) or (III) according to the invention It has the meaning mentioned above as particularly preferred or very particularly preferred. X preferably represents chlorine.

Compounds required as starting materials for carrying out process (f) according to the invention are generally defined by formula (IX). In this formula (IX), Q, L ² and R are preferably, particularly preferably or most particularly preferably for these radicals in connection with the description of the compounds of formula (I) or (III) according to the invention, respectively. It has the meaning mentioned above as being preferred, particularly preferred or very particularly preferred.

Compounds of formula (IX) are known or may be obtained according to known methods.

The nitro compound of formula (VII-a)

g) It has been found that the nitro compound of formula (VII-b) is obtained by reacting in the presence of an oxidizing agent, optionally in the presence of a diluent and optionally in the presence of a reaction medium:

Where

M, L ² , R and L ³ are as defined above,

n represents 1 or 2.

The nitro compound of formula (VII-c) is

h) It was found that the nitro compound of formula (VII-d) is obtained by reacting in the presence of a base and in the presence of a dilution medium:

Where

M, L ² , R and n are as defined above,

L ⁴ represents C ₁ -C ₉ -alkyl, in particular C ₁ -C ₅ -alkyl, particularly preferably methyl.

Halides of formula (X) are known.

Compounds of formula (VII-a), (VII-b), (VII-c) and (VII-d) are subgroups of nitro compounds of formula (VII) and are included in the general description of these compounds. Thus, definitions such as preferred, particularly preferred or very particularly preferred apply.

The nitro compound of formula (VII) is

j) It has been found that the hydroxy derivatives of formula (XI) are obtained by halogenating, optionally in the presence of diluents, optionally in the presence of acid acceptors and optionally in the presence of catalysts:

Where

M and L ³ are as defined above.

The hydroxy derivatives required as starting materials for carrying out process (j) according to the invention are generally defined by formula (XI). In this formula (XI), M and L ³ are preferably, particularly preferably or most particularly preferably respectively preferred for these radicals in connection with the description of the compounds of the formula (I) or (III) according to the invention It has the meaning mentioned above as particularly preferred or very particularly preferred.

Hydroxy derivatives of formula (XI)

k) It has been found that the acylated aromatics of formula (XII) are obtained by reacting in the presence of a reducing agent, optionally in the presence of a diluent, optionally in the presence of an acid and optionally in the presence of a catalyst:

Where

M and L ³ are as defined above.

Aniline derivatives of formula (III) can also be obtained in a manner analogous to known methods (see EP-A 0 737 682).

Method (b)

When using N- [2- (hydroxymethyl) phenyl] -1-methyl-3- (trifluoromethyl) -1H-pyrazole-4-carboxamide and 2-iodopropane as starting materials, The process of process (b) according to the invention can be represented by the following scheme:

Carboxamides required as starting materials for carrying out process (b) according to the invention are generally defined by formula (IV). In this formula (IV), M ² , L ¹ , Q and A are each preferably preferred for these radicals in connection with the description of the compounds of formula (I) according to the invention, particularly preferably or most particularly preferably. Or particularly as preferred or very particularly preferred.

Compounds required as starting materials for carrying out process (b) according to the invention are generally defined by formula (V). In this formula (V), L ² and R are preferably, particularly preferably or most particularly preferably respectively preferred, particularly preferred or very preferred for these radicals in connection with the description of the compounds of formula (I) according to the invention. As particularly preferred, they have the meanings mentioned above. Y is preferably chlorine, bromine, iodine, triflate (trifluoromethylsulfonyl), mesylate (methylsulfonyl) or tosylate (4-methylphenylsulfonyl), particularly preferably bromine, iodine or triflate (Trifluoromethylsulfonyl) is shown.

Compounds of formula (V) are known or may be obtained according to known methods. Carboxamides of formula (IV) are novel. These are

m) Aniline of formula (XIII) in which the carboxylic acid derivative of formula (II) is optionally in the presence of a catalyst, optionally in the presence of a condensation agent, optionally in the presence of an acid binder and optionally in the presence of a diluent It has been found that it is obtained by reacting with a derivative:

Where

A, M, L ¹ and Q are as defined above,

X ¹ represents halogen or hydroxy.

Carboxylic acid derivatives of formula (II) which are necessary as starting materials for carrying out process (m) according to the invention have been described above in connection with process (a) according to the invention.

Aniline derivatives required as starting materials for carrying out process (m) according to the invention are generally defined by formula (XIII). In this formula (XIII), M, L ¹ and Q are preferably, particularly preferably or most particularly preferably respectively preferred or particularly preferred for these radicals in connection with the description of the compounds of formula (I) according to the invention. Or very particularly preferred as mentioned above.

Aniline derivatives of formula (XIII) are known or may be obtained according to known methods.

Method (c)

As starting materials 3- (difluoromethyl) -N- {2-[(isopropylthio) methyl] phenyl} -1-methyl-1H-pyrazole-4-carboxamide and ethylchloro (oxo) acetate If used, the process of process (c) according to the invention can be represented by the following scheme:

Hexylcarboxanilides required as starting materials for carrying out process (c) according to the invention are generally defined by formula (la). In this formula (Ia), M, L ¹ , Q, L ² , R and A are preferably, particularly preferably or most particularly preferably these radicals in connection with the description of the compounds of formula (I) according to the invention Each have the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

Hexylcarboxanilides of formula (Ia) are also compounds according to the invention and are subject to patents of the present application. These can be obtained by process (a) according to the invention (R ¹ = hydrogen).

The halides required as starting materials for carrying out process (c) according to the invention are generally defined by formula (VI). In this formula (VI), R ^1-A is preferably, particularly preferably and most particularly preferably respectively preferred, particularly preferred or very preferred for this radical in connection with the description of the compound of formula (Ib) according to the invention. As particularly preferred, they have the meanings mentioned above. X ² preferably represents chlorine or bromine.

Halides of formula (VI) are known.

Reaction conditions

All inert organic solvents can be considered as diluents for carrying out the processes (a) and (m) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

Processes (a) and (m) according to the invention are optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases can be used by themselves. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium t-butylate, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributyl Amine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi Cyclononene (DBN) or diazabicycloundecene (DBU).

Processes (a) and (m) according to the invention are optionally carried out in the presence of a suitable condensing agent. Suitable condensing agents are all condensing agents conventionally used for such amidation reactions. Examples thereof include acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, oxalyl chloride or thionyl chloride; Anhydride formers such as chloroformic acid ethyl ester, chloroformic acid ethyl ester, chloroformic acid methyl ester, chloroformic acid isopropyl ester, chloroformic acid isobutyl ester or methanesulfonyl chloride; Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC), or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2- Ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine / tetrachloromethane or bromotripyrrolidinophosphonium hexafluorophosphate may be mentioned.

Processes (a) and (m) are optionally carried out in the presence of a catalyst. Examples thereof may be mentioned 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.

When carrying out the processes (a) and (m) according to the invention, the reaction temperature can be varied in a wide range. In general, these processes are carried out at temperatures of 0 to 150 ° C, preferably 0 to 80 ° C.

When carrying out process (a) according to the invention for the preparation of compounds of formula (I), generally 0.2 to 5 moles, preferably 0.5 to 2 moles of formula (III) per mole of carboxylic acid derivative of formula (II) Aniline derivatives) are used.

When carrying out process (m) according to the invention for the preparation of compounds of formula (IV), generally 0.2 to 5 moles, preferably 0.5 to 2 moles of formula (XIII) per mole of carboxylic acid derivative of formula (II) Aniline derivatives).

All inert organic solvents can be considered as diluents for carrying out the processes (b), (c), (d) and (h) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

Processes according to the invention Processes (b), (c), (d) and (h) are carried out in the presence of a base. All conventional inorganic or organic bases can be used. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium t-butylate, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributyl Amine, N, N-dimethyl aniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi Cyclononene (DBN) or diazabicycloundecene (DBU).

Process according to the invention When carrying out the processes (b), (c), (d) and (h), the reaction temperature can be varied in a wide range. In general, these processes are carried out at temperatures of 0 to 150 ° C, preferably 20 to 110 ° C.

When carrying out process (b) according to the invention for the preparation of compounds of formula (I), generally 0.2 to 5 moles, preferably 0.5 to 2 moles of the formula (1) per mole of carboxamide of formula (IV) The compound of V) is used.

When carrying out process (c) according to the invention for preparing compounds of formula (I), generally 0.2 to 5 moles, preferably 0.5 to 2 moles per mole of hexylcarboxanilide of formula (Ia) The halide of (VI) is used.

When carrying out process (d) according to the invention for the preparation of compounds of formula (III-a), generally 0.2 to 5 moles, preferably 0.5 to 2 moles per mole of aniline derivatives of formula (III-b) Halides of formula (VI) are used.

When carrying out process (h) according to the invention for the preparation of compounds of formula (VII-c), generally 0.2 to 5 moles, preferably 0.5 to 2 moles per mole of nitro compound of formula (VII-d) Halides of formula (X) are used.

All inert organic solvents can be considered as diluents for carrying out process (e) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols such as methanol, ethanol, n- or isopropanol, n-, iso-, sec- or t-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether , Diethylene glycol monoethyl ether, triethylene glycol, mixtures thereof with water or pure water.

Process (e) according to the invention is carried out in the presence of a metal. Preferred among them are transition metals such as palladium, platinum, rhodium, nickel (Rani nickel), iron, cobalt, ruthenium, iridium, zinc or osmium. The metal may be bonded to a substrate, such as carbon, resin, zeolite, alkali or alkaline earth sulfate, as desired.

Process (e) according to the invention is carried out in the presence of a reducing agent. Preferred materials for these are elemental hydrogen, formate salts, preferably alkali formate salts such as sodium formate, ammonium formate or metal hydrides or metal hydrides such as lithium aluminum hydride and sodium borohydride.

Process (e) according to the invention can be carried out in the presence of an acid. Preferred materials for these are organic acids such as formic acid, acetic acid, ascorbic acid, inorganic acids such as hydrochloric acid or sulfuric acid.

Process (e) according to the invention can be carried out in the presence of a base. Preferred materials for these are organic bases such as aqueous solutions of pyridine, alkali or alkaline earth metal hydroxides such as sodium or barium hydroxide.

When carrying out process (e) according to the invention, the reaction temperature can be varied in a wide range. In general, this process is carried out at temperatures of -80 to 300 ° C, preferably 0 to 200 ° C.

When using elemental hydrogen, process (e) according to the invention is carried out under hydrogen pressure of 0.5 to 200 bar, preferably 1 to 100 bar.

When carrying out process (e) according to the invention for the preparation of compounds of formula (III-b), generally 0.8 to 1000 moles, preferably 1 to 500 moles of reducing agent per mole of nitro compound of formula (VII) (Ammonium formate, hydride, etc.) are used.

All inert organic solvents can be considered as diluents for carrying out process (f) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

Process according to the invention Process (f) is carried out in the presence of a base. All conventional inorganic or organic bases can be used. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium t-butylate, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributyl Amine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi Cyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out process (f) according to the invention, the reaction temperature can be varied in a wide range. In general, this process is carried out at temperatures of 0 to 200 ° C, preferably 20 to 150 ° C.

When carrying out process (f) according to the invention for preparing compounds of formula (VII), generally 0.2 to 5 moles, preferably 0.5 to 2 moles of formula (IX) per mole of nitro compound of formula (VII) ) Compounds are used.

All inert organic solvents can be considered as diluents for carrying out process (g) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane.

Process according to the invention Process (g) is carried out in the presence of an oxidizing agent. All organic and inorganic oxidizing agents, preferably oxygen elements, ozone, peroxides such as hydrogen peroxide, m-chloroperbenzoic acid, benzoyl peroxide, t-butyl peroxide; Sodium hypochlorite; Chromium salts such as chromium oxide (VI), chromic acid, sodium dichromate, pyridinium chlorochromate; Manganese salts such as potassium permanganate, manganese dioxide; Selenium dioxide; Iodate and puriodate; Potassium peroxodisulfate can be used.

Process (g) according to the invention is carried out in the presence of an acid. Preferred materials for these are organic acids such as formic acid, acetic acid, ascorbic acid, inorganic acids such as hydrochloric acid or sulfuric acid.

Process (g) according to the invention can be carried out in the presence of a base. Preferred materials for these are organic bases such as aqueous solutions of pyridine, alkali or alkaline earth metal hydroxides such as sodium or barium hydroxide.

When carrying out process (g) according to the invention, the reaction temperature can be varied in a wide range. In general, this process is carried out at temperatures of -80 to 300 ° C, preferably 0 to 200 ° C.

When carrying out process (g) according to the invention for preparing compounds of formula (VII-a), it is generally from 0.6 to 10 moles, preferably from 0.8 to 5 moles per mole of nitro compound of formula (VII-b) Oxidant is used.

All inert organic solvents can be considered as diluents for carrying out process (j) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide.

Process (j) according to the invention is optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases can be used. These preferably include alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium t-butylate, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate, and also tertiary amines such as trimethylamine, triethylamine, tributyl Amine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi Cyclononene (DBN) or diazabicycloundecene (DBU).

Process (j) according to the invention is optionally carried out in the presence of a suitable halogenating agent. As the halogenating agent, those conventionally used for such halogenation reactions can be considered. Examples thereof include halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as chloroformic acid ethyl ester, chloroformic acid methyl ester, chloroformic acid isopropyl ester, chloroformic acid isobutyl ester or methanesulfonyl chloride; Or other conventional condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), tri Phenylphosphine / tetrachloromethane or bromotripyrrolidinophosphonium hexafluorophosphate may be mentioned.

Process (j) is optionally carried out in the presence of a catalyst. Examples thereof may be mentioned 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.

When carrying out process (j) according to the invention, the reaction temperature can be varied in a wide range. In general, this process is carried out at temperatures of 0 to 200 ° C, preferably 0 to 150 ° C.

When carrying out process (g) according to the invention for preparing compounds of formula (VII), generally 0.2 to 10 moles, preferably 0.5 to 5 moles of halogenating agent per mole of hydroxy derivative of formula (XI) Used.

All inert organic solvents can be considered as diluents for carrying out process (k) according to the invention. These preferably include aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Alcohols such as methanol, ethanol, isopropanol.

Process according to the invention Process (k) is carried out in the presence of a suitable reducing agent. For this purpose, all conventional inorganic or organic reducing agents can be used. These preferably include alkaline earth metal or alkali metal hydrides such as sodium hydride or complex hydrides such as lithium aluminum hydride, sodium borohydride, sodium cyano borohydride, diisobutyl aluminum hydride, borane, diborane or Borane complexes such as borane-pyridine, silanes such as triethylsilane, metals such as sodium, lithium, zinc, iron or hydrogen.

Process (k) according to the invention is carried out in the presence of a suitable acid or Lewis acid. All typical acids / Lewis acids used for acid / Lewis acid-mediated reduction can be used. Examples include hydrochloric acid, acetic acid, trifluoroacetic acid, boron trifluoride or boron trifluoride complexes such as boron trifluoride etherate, aluminum trichloride, cerium trichloride, inorganic or organic titanium compounds such as titanium tetrachloride, titanium tetraisopropylate do.

Process (k) according to the invention is optionally carried out in the presence of a catalyst. These are mentioned by way of example of metals or metal salts, in particular transition metals such as platinum, palladium, nickel (Rani nickel), iridium, rhodium, osmium, iron, ruthenium, cobalt. These metals or metal salts may also be bound or applied to a substrate or surface or substrate material such as carbon.

When carrying out process (k) according to the invention, the reaction temperature can be varied in a wide range. In general, this process is carried out at temperatures of 0 to 200 ° C, preferably 0 to 150 ° C.

When elemental hydrogen is used as reducing agent in the process (k) according to the invention, the pressure can be varied within a wide range. In general, it is carried out under a pressure of 1 to 300 bar, preferably 1 to 100 bar.

When carrying out process (k) according to the invention for the preparation of compounds of formula (XI), generally 0.2 to 10 moles, preferably 0.5 to 5 moles of reducing agent per mole of acylated aromatics of formula (XII) Used.

Unless stated otherwise, all the processes according to the invention are generally carried out at atmospheric pressure. However, it is also possible in each case to carry out under elevated or reduced pressure-generally 0.1 to 10 bar.

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 ;

Avoid Leno Fora (Pyrenophora) species, for example, blood Reno Fora Te Les (Pyrenophora teres) or blood Reno Fora Gras Minya (Pyrenophora gr amines a) (min living person Type: Dre rest sled LA (Drechslera), homozygous: Hell Minto 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 ;

Rhizoctonia species, for example Rhizoctonia solani .

The active substances according to the invention also show very good strengthening action in plants. Thus, they can be used to confer plant protection against attack by unwanted microorganisms.

Here, a plant fortifying (resistance-inducing) compound should be understood to mean a substance capable of stimulating a plant's defense system so that when plants are inoculated with unwanted microorganisms, the plant is significantly resistant to these microorganisms. do.

In this case, unwanted microorganisms should be understood to mean phytopathogenic fungi, bacteria and viruses. Thus, the compounds according to the invention can be used to protect plants from invasion by the aforementioned pathogens for a period of time after treatment. The period of protection is generally 1 to 10 days, preferably 1 to 7 days after treatment of the plant with the active substance.

The plants are tolerated to the active substance at the concentrations necessary to control plant diseases, thus allowing the treatment of the plant's ground, breeding stems and seeds, and soil.

In this case, the active substances according to the invention are used for the control of grain diseases, for example Puchinia species, and diseases that appear in the cultivation of grapes, fruits and vegetables, for example Botrytis, Venturi or Alternaria species. If used, it can be used particularly successfully.

The active substances according to the invention can also be used to increase crop yields. In addition, they are low toxicity and exhibit excellent plant compatibility.

If desired, the active substances according to the invention can also be used at certain concentrations and application rates and also as herbicides, for controlling plant growth or for controlling animal pests. If desired, they can also be used as intermediates or precursors for synthesizing other active substances.

All plants and plant parts can be treated according to the invention. Plant is to be understood here as meaning all plants and plant populations, such as desired or unwanted wild plants (weeds) or crops (including naturally occurring crops). Crops include plant cultivars and transgenic plants, which may or may not be protected by plant breeder's endorsement, by conventional breeding and optimization methods, by biotechnology and genetic engineering methods, or by these methods It may be a plant obtained by combining. 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, stalks, stems. ), Flowers, fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Some of the plants also include harvesting materials, and nutritional and reproductive materials, such as seedlings, tubers, rhizomes, cuttings and seeds.

Treatment of plants and parts of plants with active substances according to the invention is carried out by conventional treatment methods, for example by dipping, spraying, evaporating exposure, spraying, spraying, spraying, and in the case of propagating materials, in particular seed It is also carried out by applying one or multiple coatings to act directly or on its environment, habitat or storage space.

The compounds according to the invention can be used to protect the material from being infected and destroyed by unwanted microorganisms.

Industrial materials here are to be understood as meaning non-living materials prepared for industrial use. For example, industrial materials intended to be protected by the active substances according to the invention from changes or destruction by microorganisms are adhesives, glues, paper, cardboard, textiles, leather, wood, paints, plastic products, cooling lubricants. And other substances that can be infected or destroyed by microorganisms. Within the scope of the material to be protected, mention may also be made of parts of the production equipment, such as cooling water circuits, which may be damaged by the growth of microorganisms. Industrial materials that may be mentioned within the scope of the present invention are preferably adhesives, glues, paper, cardboard, 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 substances according to the invention preferably act on fungi, in particular filamentous fungi, wood discoloration and wood destruction fungi (vasidiomycetes) 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 substances may be prepared according to their particular physical and / or chemical properties, such as conventional formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in polymeric and seed coating compositions. It can be converted to very small volume coolants and warmers.

These formulations are known methods, for example, using surfactants, ie emulsifiers and / or dispersants and / or foam formers, to extend the active material with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carrier materials. It is prepared by mixing. If the extender used is water, for example organic solvents can also be used as auxiliary solvents. 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 petroleum 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 mean liquids which are gaseous at room temperature and atmospheric pressure, for example halogenated hydrocarbons and also 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 solid carriers 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 acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates or protein hydrolysates. Lignin, sulfite waste liquor and methylcellulose can be considered as dispersants.

The formulations also contain adhesives 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. Include. Other additives may be mineral and vegetable oils.

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; The same micronutrients may be used.

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

The active substance according to the invention can also be used on its own or as a mixture with known fungicides, fungicides, acaricides, nematicides or insecticides, for example in order to prevent broadening or developing resistance in the activity spectrum. May exist. In many cases a synergistic effect is obtained, ie the effect of the mixture exceeds the effect of the individual components.

Examples of supplemental formulation ingredients include the following compounds:

Fungicides:

2-phenylphenol, 8-hydroxyquinoline sulfate,

Acibenzola-S-methyl, Aldimorph, Amidoflumet, Ampropyl force, Ampropyl force-potassium, Andoprim, Anilazin, Azaconazole, Azoxystrobin,

Benalacyl, Benalacyl-M, Benodanil, Benomyl, Ventiavalicab-Isopropyl, Benzamacryl, Benzamacryl-Isobutyl, Villanaphos, Vinapacryl, Biphenyl, Vitertanol, Blastisidin- S, bromuconazole, burimate, butiobate, butylamine,

Calcium-polysulfide, capsaicin, captapol, captan, carbendazim, carboxycin, capropamide, carbon, quinomethionate, clobenthiazone, chlorfenazole, chloroneb, chlorotalonyl, clozolinate , Clozilacon, cyazopamide, cyflufenamide, cymoxanyl, cyproconazole, cyprodinyl, cyprofuram,

Dagger G, devacarb, diclofluanide, diclones, dichlorophene, diclocemet, diclomezin, dichloran, dietofencarb, difenokazole, diflumethorim, dimethirimol, dimetho Morph, Dimoxistrobin, Diconazole, Diconazole-M, Dinocap, Diphenylamine, Dipyrithione, Ditalimfoss, Dithianon, Dodine, Dragoxolone,

Edifene Force, Epoxyconazole, Ethaboxam, Ethirimole, Etridazole,

Soxaxadon, phenamidone, phenananil, phenarimol, fenbuconazole, fenfuram, phenhexamide, phenytropan, phenoxanyl, fenpiclonyl, phenpropidine, phenpropimod, ferbam, Fluazinam, Flubenzimin, Fludioxonyl, Flumetober, Flumorph, Fluoromid, Fluoxastrobin, Fluquinconazole, Fluprimidol, Flusilazole, Flusulfamid, Flutolanil , Flutriafol, polpet, pocetyl-Al, pocetyl-sodium, fuberidazole, furalacyl, furametpyr, purcarbanyl, purmecyclolox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalyl, imibenconazole, iminottadine triacetate, iminottadine albesylate, iodocarb, ifconazole, iprobenfos, iprodione, iprovalicab, irumamycin, isoprothiolane, isovale Dion,

Kasugamycin, Cresoxime-Methyl,

Mancozeb, maneb, meperimzone, mepanipyrim, mepronil, metallaxyl, metallaxyl-M, metconazole, metasulfocarb, metfuroxam, metiram, metomistrobin, metsulfobox, Mildiomycin, Michael Robutanil, Michael Rozoline,

Natamycin, nicobifen, nitrotal-isopropyl, nobiflumuron, noarimol,

Opuras, orissastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxycin, oxypentetiin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, phthalide, picoxistrobin, piperaline, polyoxine, polyoxorim, provenazole, prochloraz, procymidone, pro Pamocarb, propanosine-sodium, propiconazole, propineb, proquinazide, prothioconazole, pyraclostrobin, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxipur Pyrronitrin,

Quinconazole, quinoxifen, quintogen,

Cymeconazole, spiroxamine, sulfur,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Tifluzamide, Thiophanate-methyl, Thiram, Thioxymide, Tollclofos-methyl , Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, tricyclamide, tricyclazole, tridemorph, trixystrobin, triflumizol, tripolin, tri Ticonazole,

Uniconazole,

Validamycin A, vinclozoline,

Geneb, Zeram, Joksamid,

(2S) -N- [2- [4-[[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2-[(methylsul Phonyl) amino] butanamide,

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

2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine,

2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide,

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

3,4,5-trichloro-2,6-pyridine dicarbonitrile,

Actinate,

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

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

Potassium carbonate,

N- (6-methoxy-3-pyridinyl) cyclopropane carboxamide,

N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decan-3-amine,

Sodium tetrathiocarbonate, and

Copper salts and preparations, such as Bordeaux mixtures, copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, cupraneb, copper oxide, mancopper, auxin-copper.

disinfectant:

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

Pesticides / Acaricides / Nematicides:

1. Acetylcholine esterase (AChE) inhibitors.

1.1 carbamate, for example

Alanicarb, Aldicarb, Aldoxicarb, Alixicarb, Aminocarb, Azametifoss, Bendiocarb, Benfuracarb, Buppencarb, Butacarb, Butokkasimsim, Butoxycarbsim, Cabaril, Cabofuran, Cabo Sulfan, cloetocarb, coomafoss, cyanofenfoss, cyanofoss, dimethyllan, ethiophencarb, phenobucarb, phenothiocarb, formmethate, furathiocarb, isoprocarb, metham-sodium, methiocarb , Metomil, metholcarb, oxamyl, pyrimikab, promecarb, propoxur, thiodicarb, thiophanox, triamate, trimethcarb, XMC, xylylcarb,

1.2 organic phosphates, for example

Acetate, Azametifoss, Ajinfoss (-methyl, -ethyl), Bromophos-ethyl, Brompfenbinfoss (-methyl), Butadithiofoss, Cardusafoss, Carbophenothione, Chloethoxyfoss, Chlor Penvinforce, Chlormephos, Chlorpyriphos (-methyl, -ethyl), Coomaphos, Cyanophene Force, Cyanophos, Chlorfenbinphos, Demethone-S-methyl, Demethone-S-methylsulfone, Diali Phos, diazinon, diclofenvinthion, dichlorbos / DDVP, dicrotophos, dimethoate, dimethylbinfos, dioxabenzophos, disulfotone, EPN, ethion, etoprophos, etrimpos, Pampur, Penamifoss, Phenythrothione, Pensulfothione, Pention, Flupyrazophos, Phonophos, Formomolion, Phosmethyllan, Phosthiazate, Heptenophos, Iodofenfoss, Iprobenfoss , Isazofos, isofenfoss, isopropyl O-salicylate, isoxation, malathion, mecarbam, methacrypo , Metamidofos, metidathione, mevinfoss, monocrotophos, naled, ometoate, oxydemethone-methyl, parathion (-methyl, -ethyl), pentoate, forate, posalon, posmet, Phosphomidone, Phosphocarb, Bombide, Pyrimiphos (-methyl, -ethyl), Propenophos, Propaphos, Propetafoss, Prothiophos, Protoate, Pycloclofos, Pyridapentione, Pyri Dation, Quinal Force, Cebu Force, Sulpotep, Sulprophos, Tebupyrimphos, Temephos, Terbufoss, Tetrachlorbinfos, Tiomethone, Triazophos, Trichlorpon, Bamidothione,

2. Sodium Channel Regulators / Voltage-Dependent Sodium Channel Blockers

2.1 pyrethroids, for example

Acrinatrin, alletrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioaletrin, bioaletrin-S-cyclopentyl-isomer, bioethanomethrin, bio Permethrin, bioresmethrin, clovapotrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocitrin, cycloprotrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta- , Theta-, zeta-), cyphenothrin, DDT, deltamethrin, empentrin (1R-isomer), espen valerate, etofenprox, fenfluthrin, phenpropatrine, phenpytrin, Penvalerate, flubrocithinate, flucitrinate, flufenprox, flumethrin, fluvalinate, fufenfenrox, gamma-cyhalothrin, imiprotrin, cathetrin, ramma-cyhalo Tririne, metofluthrin, permethrin (cis-, trans-), phenothrin (1R-trans isomer), Lalettrin, profluthrin, protrifenbut, pyresmethrin, resmetrin, RU 15525, silafluorene, tau-fluvalinate, tefluthrin, traletrine, tetramethrin (1R-isomer), Tralomethrin, transflutrin, ZXI 8901, pyrethrin (pyrethrum),

2.2 oxadiazines such as indoxacarb,

3. Acetylcholine Receptor Agonists / antagonists

3.1 chloronicotinyl / neicotinoids, for example

Acetamiprid, clothianidine, dinotefuran, imidacloprid, nitenpyram, nithiazine, tiacloprid, thiamethoxam,

3.2 nicotine, bensultap, katap,

4. Acetylcholine Receptor Modulator

4.1 Spinosine, for example spinosad

5. GABA-Regulating Chloride Channel Antagonists

5.1 cyclodiene organic chlorine, for example

Campechlor, chlorodan, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxycyclo,

5.2 fiprole, for example

Acetoprole, etiprole, fipronil, vaniliprole,

6. Chloride Channel Activator

6.1 mectin, for example

Abamectin, Avermectin, Emamectin, Emamectin Benzoate, Ivermectin, Milvemectin, Milbemycin,

7. Larva hormone mimetics, eg

Diphenols, epopenonane, phenoxycarb, hydroprene, quinoprene, metoprene, pyriproxyfen, triprene,

8. Ecdyson agonists / disruptors

8.1 diacylhydrazines, for example

Chromafenozide, halofenozide, methoxyfenozide, tebufenozide,

9. Chitin Biosynthesis Inhibitors

9.1 benzoylurea, for example

Bistrifluron, Clofluazuron, Diflubenzuron, Fluazuron, Flucycloloxone, Flufenoxlon, Hexaflumuron, Lufenuron, Novaluron, Nobifluuron, Fenfluron, Tflubenzuron , Triple lumuron,

9.2 Buprofezin

9.3 Cyclo Margin,

10. Oxidative phosphorylation inhibitors, ATP disruptors

10.1 diafenthiuron,

10.2 organic tin, for example azocyclotin, cyhexatin, fenbutatin oxide,

11. oxidative phosphorylation inhibitors by blocking H-proton gradients,

11.1 pyrrole, for example chlorfenapyr,

11.2 dinitrophenols such as vinapacryl, dinobutone, dinocap, DNOC,

12. I-side electron transfer inhibitor

12.1 METIs, for example penazaquine, penpyroximate, pyrimidipene, pyridaben, tebufenpyrad, tolfenpyrad,

12.2 hydramethylnon,

12.3 decopol,

13. II-Side Electron Transfer Inhibitor

13.1 rotenone,

14. III-Side Electron Transfer Inhibitor

14.1 acequinosyl, fluacrypyrim,

15. Insect Vesicle Microbial Disintegrant

Bacillus thuringiensis strains,

16. fat synthesis inhibitors,

16.1 tetronic acid, for example spirodiclofen, spiromesifen,

16.2 Tetramic acid, for example 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] de-3-sen-4-yl ethyl carbonate (aka carboxylic acid , 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] de-3-sen-4-yl ethyl ester, CAS-Reg.-No .: 382608- 10-8) and carboxylic acid, cis-3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] de-3-sen-4-yl ethyl ester, CAS -Reg.-No .: 203313-25-1),

17, carboxamides, for example flornicamid,

18. octopaminergic agonist, for example amitraz,

19, magnesium-promoting ATPase inhibitors such as propargite,

20. phthalamide, for example N ² - [1,1- dimethyl-2- (methylsulfonyl) ethyl] -3-iodo -N ¹ - [2- methyl-4- [1,2,2, 2-tetrafluoro-1- (trifluoromethyl) ethyl] phenyl] -1,2-benzenedicarboxamide (CAS-Reg.-No .: 272451-65-7),

21. Neracetoxin analogues such as thiocyclam hydrogen oxalate, thiosulfato-sodium,

22. Biological agents, hormones or pheromones, eg

Azadirachtin, Bacillus species, Burberry species, Codmon species, Metadium species, Paesilomyces species, Turingienxins, Verticillium species,

23. Active substances of unknown or nonspecific mechanism of action,

23.1 fumigants such as aluminum phosphide, methyl bromide, sulryl fluoride,

23.2 Selective food intake inhibitors such as cryolite, floricamid, pimetrozin,

23.3 mite growth inhibitors, for example clofentezin, ethoxazole, hexiaxox,

23.4 Amidoflumet, benclothiaz, benzoxmate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzylate, chloropicrine, clothiazobene, cycloprene , Cyflumetophene, dicyclanyl, phenoxa cream, phentrifanyl, flubenzimine, flufenerim, flutenzin, gosiflure, hydrammethylnon, japonilure, methoxadione, petroleum, Piperonyl butoxide, potassium oleate, pyridalyl, pyriprolol, sulfluramid, tetradipon, tetrasul, traarate, verbutin,

Compound 3-methylphenyl propylcarbamate (chumaside Z),

Compound 3- (5-chloro-3-pyridinyl) -8- (2,2,2-trifluoroethyl) -8-azabicyclo [3.2.1] octane-3-carbonitrile (CAS Reg. 185982-80-3) and the corresponding 3-endo-isomer (CAS Reg. No. 185984-60-5) (WO-96 / 37494, WO-98 / 25923),

And formulations containing insecticidal plant extracts, nematodes, fungi or viruses.

It is also possible to mix it with other known active ingredients such as herbicides, fertilizers, growth regulators, anti-mitigating agents or signaling substances.

The compounds of formula (I) according to the invention also show very good antibacterial effects. These particular skin fungi (dermatophyte) and yeasts, molds and more fungi (e.g. Candida albicans (Candida albicans), Candida glabrata (Candida species (Candida species), such as Candida glabrata)) and epi Dermo python flow kosum ( Aspergillus species such as Epidermophyton floccosum , Aspergillus noger and Aspergillus fumigatus , and Trichophyton species such as Trichophyton mentagrophyte Trichophyton species , Microsporon canis and Microsporon species such as audouinii have a very broad spectrum of antimicrobial action. These fungal lists do not limit the recordable antimicrobial spectrum in any way, but are for illustrative purposes only.

The active substances can be used on their own, in the form of their preparations, or in embodiments prepared from them such as ready-to-use solutions, suspensions, hydrating powders, pastes, soluble powders, powders and granules. This applies by conventional means, for example by pouring, spraying, showering, spraying, misting, foaming, spraying and the like. In addition, the active substance can be applied by a microvolume method or the active substance preparation or the active ingredient itself can be injected into the soil. Seeds of plants can be treated.

When the active substance according to the invention is used as a fungicide, the application amount may vary within a wide range depending on the application form. When treating plant parts, the application rate of the active substance is generally from 0.1 to 10,000 g / dL, preferably from 10 to 1,000 g / dL. When treating seed, the application amount of the active substance is generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, the amount of active substance used is generally 0.1 to 10,000 g / dL, preferably 1 to 5,000 g / dL.

As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, naturally occurring plant types and varieties and those parts and those obtained by conventional biological breeding methods such as hybrid breeding or protoplast fusion are treated. In another preferred embodiment, genetically engineered transgenic plants and plant types (genetically modified organisms) and these parts are treated with conventional methods, where appropriate. The terms "part", "part of the plant" or "plant part" have been described above.

In each case plants of the plant type which are commercially available or in use are particularly preferably treated according to the invention. The term "plant type" is to be understood as a plant having new properties that can be obtained by conventional breeding techniques, mutagenesis or recombinant DNA techniques. They may be of type, breed, biotype or genotype.

Depending on the plant variety or type, their location and growing conditions (soil, climate, growth period, nutrients), an additive ("raising") effect may also be produced by treatment according to the present invention. Thus, for example, reduction in the application rate of substances and preparations which can be used according to the invention and / or broadening the activity spectrum and / or increasing activity, improving plant growth, increasing hot or cold resistance, drought, or water or soil salinity Expected effects such as increased resistance to, increased flowering, increased harvesting, increased maturity, increased crop yields, improved quality and / or nutritional value of harvested products, and improved shelf life and / or treatability of harvested products. It may appear abnormal.

Transgenic plants or plant types (ie those obtained genetically) which are preferably treated according to the invention are those which accept genetic material that confers useful properties (“characteristics”) that are particularly advantageous to these plants at the time of genetic modification. Contains plants. Examples of such properties include improved plant growth, increased high or low temperature resistance, drought, or increased resistance to water or soil salts, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality of harvested products, and / or Increased nutritional value, and increased shelf life and / or processability of harvested products. Further particular mention of such properties is an increase in the plant's defense against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses and also an increase in the plant's tolerability against certain herbicidally active substances. Examples of transgenic plants may include important crop plants, for example cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, oilseeds, and also fruit plants (opening apples, pears, citrus fruits and grape fruits). Corn, soybeans, potatoes, cotton, tobacco and oilseeds. Highlighted properties are in particular genetic material derived from toxins formed in plants, in particular Bacillus thuringiensis (eg genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c) , Increased protection of plants against insects, arachnids, nematodes and snails due to toxins formed in plants (hereinafter referred to as "Bt plants") by Cry2Ab, Cry3Bb and CryIF and combinations thereof. Also of particular emphasis is the increased defense of plants against fungi, bacteria and viruses due to systemically acquired resistance (SAR), cystemine, phytoalexin, eliminator and resistance genes and correspondingly expressed proteins and toxins. . Another particularly highlighted property is also the increased plant resistance to certain herbicidally active substances, for example imidazolinone, sulfonylurea, glyphosate or phosphinothricin (eg the "PAT" gene). In each case genes conferring the desired properties of interest can also be present in transgenic plants in mutual combinations. Examples of "Bt plants" include YIELD GARD ^® (e.g. corn, cotton, soybean), KnockOut ^® (e.g. corn), StarLink ^® (e.g. corn), Bollgard ^® (e.g. cotton), Nucotn ^® (e.g. cotton) And corn varieties, cotton varieties, soybean varieties and potato varieties which are commercially available under the NewLeaf ^® (eg potato) brand name. Examples of herbicide-tolerant plants include Roundup Ready ^® (glyphosate tolerant, eg corn, cotton, soybean), Liberty Link ^® (phosphinothricin tolerant, e.g. oilseed rape), IMI ^® (imidazolinone tolerant) And corn varieties, cotton varieties and soybean varieties available under the trade name STS ^® (sulfonylurea tolerant such as corn). Examples of herbicide-tolerant plants (plants bred by conventional methods for herbicide tolerability) may also be mentioned varieties sold under the name Clearfield ^® (eg corn). Of course, the above description also applies to plant varieties which have the above-described genetic properties or which remain to be developed, with plants to be developed and / or marketed in the future.

The plants listed above can be treated particularly advantageously according to the invention with a compound of formula (I) or a mixture of active ingredients according to the invention. The preferred ranges mentioned above for the active substances also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned herein.

Hereinafter, the preparation and use of the active substances according to the invention are described by way of examples.

Synthetic Example

Synthesis of Compound No. 40

To a solution of 0.27 g (1.5 mmol) 2- [1- (isopropylamino) ethyl] aniline (III-4) and 0.42 ml (3.0 mmol) triethylamine in 5 ml dichloromethane in 10 dichloromethane 0.27 g (1.5 mmol) of 5-fluoro-1,3-dimethyl-lH-pyrazole-4-carbonyl chloride solution was added dropwise. The reaction mixture was stirred at 50 ° C. for 2 hours and then at room temperature for 16 hours. After the reaction mixture was added to water, the organic phase was dried over magnesium sulfate and then concentrated in vacuo to work up. 0.27 g (56% of theory) of 5-fluoro-N- {2- [1- (isopropylamino) ethyl] phenyl} -1,3-dimethyl by column chromatography (hexane / acetone 4: 1) -1H pyrazole-4-carboxamide [log P (pH 2.3) = 0.58] was obtained.

Synthesis of Compound No. 60

156.0 mg (3.9 mmol) of 60% sodium hydride in oil was added to 897.8 mg (3.0 mmol) N- [2- (hydroxymethyl) phenyl] -1-methyl-3- (trifluoro) in 2 ml dimethyl formamide at room temperature. To a solution of rhomethyl) -1H-pyrazole-4-carboxamide (IV-1). After 30 minutes, 0.6 ml (6.0 mmol) of 2-iodopropane were added. The reaction mixture was stirred at 100 ° C. for 6 hours and then at room temperature for 16 hours. The mixture was then diluted with 1 ml of methanol, added to water and extracted with ethyl acetate; After drying the organic phase over magnesium sulfate, the desiccant was filtered and concentrated in vacuo. 100.0 mg (9.7% of theory) of N- [2- (isopropoxymethyl) phenyl] -1-methyl-3- (trifluoromethyl) by column chromatography (cyclohexane / ethyl acetate 3: 1) -lH-pyrazole-4-carboxamide [logP (pH 2.3) = 2.85] was obtained.

Similarly to Examples 1 and 2 and in accordance with the general description of the synthetic methods (a) to (m) of the present invention, compounds of formula (I) listed in Table 1 below were also obtained.

Table 1

^a ) The bond represented by ( ^"*" ) is attached to the amide.

Synthesis of Starting Material of Formula (III)

Example (III-1)

44 g (0.188 mol) of 1- [1- (isopropylthio) ethyl] -2-nitrobenzene (VII-1) are dissolved in 250 ml of ethanol and mixed with 3 g of Raney nickel, followed by autoclave Hydrogenated at room temperature with 3 bars of hydrogen for 6 hours at. After 6 hours, 3 g Raney nickel was added and hydrogenation continued for 3 hours at 3 bar hydrogen at room temperature. The catalyst is then filtered off and the solvent is removed in vacuo. The crude product was purified by column chromatography (silica gel, hexane / methyl t-butyl ether 3: 1). 32 g (97.3% purity by HPLC, 84.4% of theory) of 2- [1- (isopropylthio) ethyl] aniline were obtained as a yellow oil [logP (pH 2.3) = 2.45].

Example (III-2)

Into a 500 ml three-necked flask equipped with a stirrer and a thermometer was introduced 16.2 g (60.5 mmol) of 1- [1- (isopropylsulfonyl) ethyl] -2-nitrobenzene (VII-4) in 160 ml of methanol, and 160 After stirring with ml of concentrated hydrochloric acid, 31.5 g of powdered tin (265.2 mmol) was added in portions at 20-40 ° C. The mixture was stirred at 40 ° C. for about 1 hour. The reaction was cooled, filtered and then mixed with 1575 ml ice-cold 10% aqueous sodium hydroxide solution. Then extracted twice with dichloromethane, dried over sodium sulfate and then the solvent was removed in vacuo. 13.3 g (95.8% purity by HPLC, 92.6% of theory) of 2- [1- (isopropylsulfonyl) ethyl] aniline [logP (pH 2.3) = 1.28] were obtained.

Example (III-3)

Into a 500 ml three-necked flask equipped with a stirrer and a thermometer was introduced 11.8 g (55.6 mmol) of 1- [1- (isopropylthio) methyl] -2-nitrobenzene (VII-2) in 150 ml of methanol and 150 ml After stirring with concentrated hydrochloric acid, 17.6 g of powdered tin (148.5 mmol) was added little by little at 20-40 ° C. The mixture was stirred at 40 ° C. for about 1 hour. The reaction was cooled, filtered and mixed with 1300 ml of ice cooled 10% aqueous sodium hydroxide solution. Then extracted twice with dichloromethane, dried over sodium sulfate and then the solvent was removed in vacuo. The crude product was purified on 3: 1 hexanes / methyl t-butyl ether on silica gel. 4.6 g (94.6% purity by HPLC, 43.2% of theory) of 2- [1- (isopropylthio) methyl] aniline [logP (pH 2.3) = 1.94] were obtained as a yellow oil.

Example (III-4)

A solution of 5 g N- [1- (2-nitrophenyl) ethyl] propan-2-amine (VII-5) (24 mmol) in 30 ml methanol is mixed with 0.5 g Raney nickel and 5 hours in an autoclave Hydrogenated at 50 ° C. with 50 bar of hydrogen. After cooling, the catalyst was filtered off and the solvent was removed in vacuo. 2.8 g (purity 98.1% by HPLC, 64.2% of theory) of 2- [1- (isopropylamino) ethyl] aniline [logP (pH 2.3) = 0.05] were obtained.

Synthesis of Starting Material of Formula (IV)

Example (IV-1)

A solution of 34.5 g (0.16 mol) of 1-methyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl chloride in 50 ml tetrahydrofuran at room temperature was 20.0 g (0.16) in 250 ml tetrahydrofuran. mol) of 2-aminophenylmethanol and 36 ml (0.26 mol) of triethylamine were added dropwise. After the exothermic reaction had settled, the reaction was refluxed for 6 hours and then further stirred at room temperature for 48 hours. The reaction mixture was added to about 250 ml of water, extracted with ethyl acetate, washed with 2N hydrochloric acid, dried over magnesium sulfate and then concentrated in vacuo. 33.8 g (69% of theory) of N- [2- (hydroxymethyl) phenyl] -methyl-3- (trifluoromethyl) -1H-pyra by column chromatography (gradient: cyclohexane / ethyl acetate) Sol-4-carboxamide [logP (pH 2.3) = 1.55] was obtained.

Synthesis of Starting Material of Formula (VII)

Example (VII-1)

In a 1 L three-necked flask equipped with a stirrer, dropping funnel and thermometer, 63 g of 1- (1-chloroethyl) -2-nitrobenzene (VIII-l) (purity 99.4%, 0.337 mol) in 20 ml acetonitrile was added. Add dropwise to 34.8 g (0.354 mol) sodium 2-propanethiolate in 450 ml acetonitrile at 30-40 ° C. The suspension is further stirred at 40 ° C. for 16 h, then cooled and the solvent is removed in vacuo. The residual residue was dissolved in dichloromethane, washed, dried over sodium sulfate and the solvent removed in vacuo. The crude product was purified by column chromatography (silica gel, 29: 1 hexanes / acetone) to give 48 g (98.8% purity by HPLC, 62.4% of theory) of 1- [1- (isopropylthio) ethyl] -2 Nitrobenzene was obtained as a yellow oil [logP (pH 2.3) = 3.89].

Example (VII-2)

In a 250 ml three-necked flask equipped with a stirrer, a dropping funnel and a thermometer, 17.2 g (0.1 mol) of 2-nitrobenzyl chloride in 20 ml acetonitrile was cooled in 75 ml acetonitrile while maintaining the temperature at 30-40 ° C. 10.3 g (0.105 mol) of sodium 2-propanethiolate was added dropwise. The suspension was further stirred at 40-50 ° C. for 16 h. To complete the reaction, 6 g (0.061 mol) of sodium 2-propanethiolate was added and then further stirred at 40-50 ° C. for 24 hours. The reaction was cooled and the solvent removed in vacuo. The residue was dissolved in methyl t-butyl ether, washed and dried over sodium sulfate. Sodium sulfate was removed by filtration and the solution was concentrated in vacuo. The crude product was purified by column chromatography (silica gel, 50: 1 cyclohexane / ethyl acetate) to give 11.8 g (92% purity by HPLC, 51.2% of theory) of 1- [1- (isopropylthio) methyl] 2-nitrobenzene was obtained as a brown oil [logP (pH 2.3) = 3.28].

Example (VII-3)

Into a 1 L three-neck flask equipped with a stirrer, dropping funnel and thermometer was introduced 32.8 g 1- [1- (isopropylthio) methyl] -2-nitrobenzene (VII-2) (0.155 mol) in 465 ml dichloromethane. 14.3 g of formic acid (0.31 mol) and 1.6 g of ammonium molybdate were then added with stirring. 45.3 g (0.466 mol) of 35% aqueous hydrogen peroxide solution was added dropwise with rapid stirring at room temperature. The mixture was further stirred for 16 hours. The organic phase was then removed, washed once with dilute sodium hydrogen sulfite solution and once with water, then the organic solution was dried over sodium sulfate. The solvent was distilled under vacuum and the residue was stirred with diethyl ether, then the precipitated product was filtered off and dried. 30.5 g (99% purity by HPLC, 80% of theory) of 1-[(isopropylsulfonyl) methyl] -2-nitrobenzene were obtained as a yellow solid [logP (pH 2.3) = 1.63].

Example (VII-4)

Into a 1 L three-neck flask equipped with a stirrer, dropping funnel and thermometer was introduced 18.9 g (77.7 mmol) of 1-[(isopropylsulfonyl) methyl] -2-nitrobenzene (VII-3) in 390 ml acetonitrile. 90.1 g (652 mnmol) of potassium carbonate, 0.26 g of 18-crown-6 and 12.1 g (85.5 mmol) of iodomethane were added sequentially. The reaction was stirred at reflux for 4 h, then 2.5 g of iodomethane (17.6 mmol) was added and then further stirred at reflux for 4 h. The reaction was cooled and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with water and then dried over sodium sulfate. After removing the solvent, the crude product was purified by column chromatography (silica gel, 7: 3 hexanes / acetone). 16.2 g (purity 96.1% by HPLC, 77.9% of theory) of 1- [1-isopropylsulfonyl) ethyl] -2-nitrobenzene [logP (pH 2.3) = 1.99] was obtained.

Example (VII-5)

13.8 g of 1- (1-chloroethyl) -2-nitrobenzene (VIII-1) (purity 98.3%, 73.1 mol) and 43.2 g (731 mmol) of isopropylamine at 60 ° C. and high pressure in an autoclave Stir for 24 hours. After cooling the reaction mixture, excess isopropylamine was removed in vacuo and the crude product was purified on 4: 1 cyclohexane / ethyl acetate on silica gel. 5 g (purity 94.4%, 31% of theory) of N- [1- (2-nitrophenyl) ethyl] propan-2-amine were obtained as an oil [logP (pH 2.3) = 0.55].

Synthesis of Starting Material of Formula (VIII)

Example (VIII-1)

In a 6 L three-necked flask equipped with a stirrer, dropping funnel and thermometer, 311 g of 1- (2-nitrophenyl) ethanol (XI-1) (purity 95.8%, 1.78 mol) was dissolved in 3000 ml dimethyl formamide. 921.4 g (7.13 mol) of diisopropylethylamine were added in one portion, stirred for 5 minutes, and then 612.5 g (5.35 mol) of methanesulfonyl chloride were added dropwise with moderate cooling at 20 to 35 ° C. After the reaction was completed, the mixture was stirred at room temperature for 90 hours, and then the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed three times with water, dried over sodium sulfate and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, 9: 1 hexanes / acetone). 219 g (100% purity by HPLC, 66.2% of theory) of 1- (1-chloroethyl) -2-nitrobenzene were obtained as a brown oil [logP (pH 2.3) = 2.87].

Synthesis of Starting Material of Formula (XI)

Example (XI-1)

320 g (1.938 mol) of 2-nitroacetophenone in 3200 ml methanol were introduced into a 6 L three-necked flask equipped with a stirrer, dropping funnel, thermometer and bubble counter, and 73.3 g (1.938 mol) of sodium in 288 ml water. Borohydride was added dropwise with moderate cooling at 30-40 ° C. After the reaction was completed, the mixture was further stirred at room temperature for 16 hours. The reaction was neutralized with dilute hydrochloric acid and the solvent was worked up by removal on a rotary evaporator. The residue was dissolved in dichloromethane, washed with water, dried over sodium sulfate and the solvent removed in vacuo. 311 g (95.1% pure by HPLC, 91.3% of theory) of 1- (2-nitrophenyl) ethanol [logP (pH 2.3) = 1.49] were obtained as a pale oil.

The logP values given were determined by HPLC (high performance liquid chromatography) using a reversed phase column (C 18) according to EEC Directive 79/831 Annex V.A8. Temperature: 43 ° C.

Eluent for determination in acidic range (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; Linear gradient from 10% acetonitrile to 90% acetonitrile.

The calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms) with known logP values (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.

Application Example

Example A

Grape Spaera Test (Apple) / Protection

Solvent: 24.5 parts by weight of acetone

         24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active ingredient.

To test for protective activity, young plants were sprayed with the active substance formulation at the specified application rate. After drying of the spray coating, 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% effectiveness means that no infection was observed.

Table A

Grape Spaera Test (Apple) / Protection

Example B

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 substance is mixed with the aforementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active ingredient.

To test for protective activity, young plants were sprayed with a formulation of the active substance at the specified application rate. After drying of the spray coating, the plants were inoculated with an aqueous conidia suspension of the apple strains ( Venturia inaequalis ) and then placed in a culture room 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 carried out 10 days after the inoculation. 0% means efficacy corresponding to the control, and 100% effectiveness means that no infection was observed.

TABLE B

Venturi Test (Apple) / Protection

Example C

Botrytis Test (Bean) / Protection

Solvent: 24.5 parts by weight of acetone

               24.5 parts by weight of dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

An effective active ingredient formulation is prepared by mixing 1 part by weight of the active ingredient with the solvents and emulsifiers in the amounts mentioned above and diluting the concentrate with water to the desired concentration.

To test for protective activity, young plants are sprayed with the formulations of the active ingredient in the indicated amounts. After drying of the spray coating, two pieces of small agar, clustered with Botrytis cinerea, were placed on each leaf. Inoculated plants were placed in the dark at about 20 ° C. and 100% relative atmospheric humidity.

Two days after inoculation, the lesion area size on the leaves was evaluated. 0% means efficacy corresponding to the control, and 100% efficacy means that no infection was observed.

Table C

Botrytis Test (Bean) / Protection

Example D

Pukenia Test (Wheat) / Protection

Solvent: 50 parts by weight of N, N-dimethylacetamide

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active ingredient.

To test for protective activity, young plants were sprayed with the active substance formulation at the specified application rate. After drying of the spray coating, 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.

The plants were then placed in a greenhouse at about 20 ° C. and 80% relative atmospheric humidity to facilitate the spread of rust foam.

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

Table D

Pukenia Test (Wheat) / Protection

Table D-continued

Pukenia Test (Wheat) / Protection

Table D-continued

Pukenia Test (Wheat) / Protection

Example E

Alternaria test (tomato) / protection

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

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration to prepare a suitable formulation of the active ingredient.

To test for protective activity, young tomato plants were sprayed with the active substance formulation at the specified application rate. One day after plant treatment, the plants were sprayed with a spore suspension of Alternaria solani . The plants were then placed in a greenhouse at 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% effectiveness means that no infection was observed.

Table E

Alternaria test (tomato) / protection

Claims (9)

Carboxamides of Formula (I):

Where R ¹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₈ -alkyl) carbonyl, (C ₁ -C ₈ -alkoxy) carbonyl, (C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -Cycloalkyl) carbonyl; (C ₁ -C ₆ -haloalkyl) carbonyl, (C ₁ -C ₆ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ , R ² is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₆ -haloalkyl, C ₁ -C ₆ -haloalkoxy, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ with 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₈ -halocycloalkyl, R ³ and R ⁴ independently of one another in each occurrence are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; C ₁ -C ₈ -haloalkyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or R ³ and R ⁴ may also, together with the nitrogen atom to which they are attached, have one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ and halogen and C ₁ -C ₄ -alkyl A heterocycle of saturated 5 to 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of R ⁵ and R ⁶ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₃ -C ₈ -cycloalkyl; In each case 1 to 9 fluorine, chlorine and / or C ₁ -C ₈ having a bromine atom -haloalkyl or C ₃ - C ₈ - cycloalkyl, or represents a halo, R ⁵ and R ⁶ may also, together with the nitrogen atom to which they are attached, have one or two additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ and include halogen and C ₁ -C ₄ -alkyl A heterocycle of saturated 5 to 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of R ⁷ represents hydrogen or C ₁ -C ₆ -alkyl, M is represented by a substituted phenyl, pyridine, pyrimidine, pyridazine or pyrazine ring by R ⁸ in each case, or represents a thiazole ring substituted by R ^8-A, R ⁸ represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, or R ⁸ represents methoxy, R ^8-A represents hydrogen, methyl, methylthio or trifluoromethyl, L ¹ represents C ₁ -C ₁₀ -alkylene (alkanediyl), Q represents O, S, SO, SO ₂ or NR ⁹ , L ² represents a direct bond, SiR ¹⁰ R ¹¹ or CO, R is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, C ₂ -C ₈ - alkenyl, C ₂ -C ₈ - alkynyl, C ₁ -C ₆ - haloalkyl, C ₂ -C ₆ - haloalkenyl, C ₂ -C ₆ - haloalkynyl, or C ₃ -C ₆ -cycloalkyl, R ⁹ is hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylthio-C ₁ -C ₄ -alkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, C ₁ -C ₆ -haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₂ -C ₆ -haloalkynyl or C ₃ -C ₆ -cyclo Alkyl, R ¹⁰ and R ¹¹ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₈ -alkoxy, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkyl Thio-C ₁ -C ₄ -alkyl or C ₁ -C ₆ -haloalkyl, A represents a group of formula (A1):

From here, R ¹² is hydrogen, cyano, halogen, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₃ -C ₆ -cycloalkyl, in each case 1 C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy or C ₁ -C ₄ -haloalkylthio, aminocarbonyl or aminocarbonyl-C ₁ -C ₄ -alkyl having from 5 to 5 halogen atoms , R ¹³ represents hydrogen, halogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio, R ¹⁴ is hydrogen, C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, C ₂ -C ₆ -alkenyl, C ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -alkylthio -C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, in each case C ₁ -C ₄ -haloalkyl, having 1 to 5 halogen atoms, C ₁ -C ₄ -Haloalkylthio-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkoxy-C ₁ -C ₄ -alkyl or phenyl A represents a group of formula (A2):

From here, R ¹⁵ and R ¹⁶ independently of one another represent hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ¹⁷ represents halogen, cyano, C ₁ -C ₄ -alkyl, or C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy having 1 to 5 halogen atoms in each case, or A represents a group of formula (A3):

From here, R ¹⁸ and R ¹⁹ independently of one another represent hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ²⁰ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or A represents a group of formula (A4):

From here, R ²¹ is hydrogen, halogen, hydroxy, cyano, C ₁ -C ₆ -alkyl, or C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy having 1 to 5 halogen atoms in each case Or C ₁ -C ₄ -haloalthio, A represents a group of formula (A5):

From here, R ²² is halogen, hydroxy, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, in each case C ₁ -having 1 to 5 halogen atoms C ₄ -haloalkyl, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -haloalkoxy, or R ²³ is hydrogen, halogen, cyano, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio having 1 to 5 halogen atoms, in each case C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy, or C ₁ -C ₄ -alkylsulfinyl or C ₁ -C ₄ -alkylsulfonyl, or A represents a group of formula (A6):

From here, R ²⁴ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ²⁵ represents C ₁ -C ₄ -alkyl, Q ¹ represents S (sulfur), SO, SO ₂ or CH ₂ , p represents 0, 1 or 2, and when p is 2, R ²⁵ represents the same or different group, or A represents a group of formula (A7):

From here, R ²⁶ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A8):

From here, R ²⁷ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or A represents a group of formula (A9):

From here, R ²⁸ and R ²⁹ independently of one another represent hydrogen, halogen, amino, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ³⁰ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or A represents a group of formula (A10):

From here, R ³¹ and R ³² independently of one another represent hydrogen, halogen, amino, nitro, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ³³ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A11):

From here, R ³⁴ is hydrogen, halogen, amino, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ -alkyl) amino, cyano, C ₁ -C ₄ -alkyl or having 1 to 5 halogen atoms C ₁ -C ₄ -haloalkyl, R ³⁵ represents halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A12):

From here, R ³⁶ has hydrogen, halogen, amino, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ -alkyl) amino, cyano, C ₁ -C ₄ -alkyl or having 1 to 5 halogen atoms C ₁ -C ₄ -haloalkyl, R ³⁷ represents halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, or A represents a group of formula (A13):

From here, R ³⁸ represents hydrogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A14):

From here, R ³⁹ represents hydrogen or C ₁ -C ₄ -alkyl, R ⁴⁰ represents halogen or C ₁ -C ₄ -alkyl, or A represents a group of formula (A15):

From here, R ⁴¹ represents C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A16):

From here, R ⁴² represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A17):

From here, R ⁴³ is halogen, hydroxy, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkylthio, in each case 1 to 5 C ₁ -C ₄ has a halogen atom - Haloalkyl, C ₁ -C ₄ -haloalkylthio or C ₁ -C ₄ -haloalkoxy, or A represents a group of formula (A18):

From here, R ⁴⁴ is hydrogen, cyano, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, hydroxy Oxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkylsulfonyl, di (C ₁ -C ₄ -alkyl) aminosulfonyl, C ₁ -C ₆ -alkylcarbonyl or optionally substituted in each case Phenylsulfonyl or benzoyl, R ⁴⁵ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ⁴⁶ represents hydrogen, halogen, cyano, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, R ⁴⁷ represents hydrogen, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl having 1 to 5 halogen atoms, A represents a group of formula (A19):

From here, R ⁴⁸ represents C ₁ -C ₄ -alkyl. The method of claim 1, When L ² represents a direct bond, R is not alkoxy; carboxamide of formula (I). The method according to claim 1 or 2, R ¹ is hydrogen; C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C _6- Cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₆ -alkyl) carbonyl, (C ₁ -C ₄ -alkoxy) carbonyl, (C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -Cycloalkyl) carbonyl; In each case having 1 to 9 fluorine, chlorine and / or bromine atom (C ₁ -C ₄ - roal to kill) carbonyl, (C ₁ -C ₄ - haloalkoxy) carbonyl, (halo -C ₁ - C ₃ -alkoxy-C ₁ -C ₃ -alkyl) carbonyl, (C ₃ -C ₆ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ , R ² is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -haloalkoxy, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ having 1 to 9 fluorine, chlorine and / or bromine atoms in each case -Alkyl or C ₃ -C ₆ -halocycloalkyl, R ³ and R ⁴ independently of one another are hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₃ -C ₆ -cycloalkyl; C ₁ -C ₄ -haloalkyl, halo-C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -having 1 to 9 fluorine, chlorine and / or bromine atoms in each case Halocycloalkyl, or R ³ and R ⁴ may also contain 1 or 2 additional nonadjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ together with the nitrogen atom to which they are attached, halogen and C ₁ -C _4- A heterocycle of saturated 5 or 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of alkyl, R ⁵ and R ⁶ are each independently hydrogen, C ₁ -C ₆ - alkyl, C ₃ -C ₆ - cycloalkyl, or with one to nine fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₄ -haloalkyl or C ₃ -C ₆ -halocycloalkyl, or R ⁵ and R ⁶ may also contain 1 or 2 additional non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur and NR ⁷ together with the nitrogen atom to which they are attached, halogen and C ₁ -C _4- A heterocycle of saturated 5 or 8 ring atoms mono- or polysubstituted by the same or different substituents selected from the group consisting of alkyl, R ⁷ represents hydrogen or C ₁ -C ₄ -alkyl, M represents one of the following cyclics:

From here, Bonds marked with * are attached to the amide, R ⁸ represents hydrogen, fluorine, chlorine, methyl, isopropyl, methylthio or trifluoromethyl, or represents methoxy, R ^{8 -A} represents hydrogen, methyl, methylthio or trifluoromethyl, L ¹ represents C ₁ -C ₁₀ -alkylene (alkanediyl), Q represents O, S, SO, SO ₂ or NR ⁹ , L ² represents a direct bond, SiR ¹⁰ R ¹¹ or CO, R is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkylthio-C ₁ -C ₃ -Alkyl, C ₁ -C ₄ -haloalkyl or C ₃ -C ₆ -cycloalkyl, R ⁹ is hydrogen, C ₁ -C ₆ -alkyl, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl, C ₁ -C ₃ -alkylthio-C ₁ -C ₃ -alkyl or C ₃ -C ₆ -cycloalkyl, R ¹⁰ and R ¹¹ independently of _one another are C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy, C ₁ -C ₃ -alkoxy-C ₁ -C ₃ -alkyl or C ₁ -C ₃ -alkylthio- C ₁ -C ₃ -alkyl, A represents a group of formula (A1):

From here, R ¹² is hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, isopropyl, methoxy, ethoxy, methylthio, ethylthio, cyclopropyl, in each case 1 to 5 fluorine, chlorine and / Or C ₁ -C ₂ -haloalkyl, C ₁ -C ₂ -haloalkoxy, trifluoromethylthio, difluoromethylthio, aminocarbonyl, aminocarbonylmethyl or aminocarbonylethyl with bromine atom , R ¹³ represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio, R ¹⁴ is hydrogen, methyl, ethyl, n-propyl, isopropyl, C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, hydroxymethyl, hydroxyethyl, cyclopropyl, Or cyclopentyl, cyclohexyl or phenyl, A represents a group of formula (A2):

From here, R ¹⁵ and R ¹⁶ independently of each other represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ¹⁷ is fluorine, chlorine, bromine, cyano, methyl, ethyl, in each case C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms , Or A represents a group of formula (A3):

From here, R ¹⁸ and R ^l9 are each independently hydrogen, fluorine, chlorine, bromine, methyl, ethyl, or 1 to 5 fluorine, chlorine and / or bromine, C ₁ -C ₂ with the atoms represents a haloalkyl, R ²⁰ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A4):

From here, R ²¹ is hydrogen, fluorine, chlorine, bromine, iodine, hydroxy, cyano, C ₁ -C ₄ -alkyl, in each case C ₁ -C ₂ -having 1 to 5 fluorine, chlorine and / or bromine atoms Haloalkyl, C ₁ -C ₂ -haloalkoxy or C ₁ -C ₂ -haloalkylthio, or A represents a group of formula (A5):

From here, R ²² is fluorine, chlorine, bromine, iodine, hydroxy, cyano, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, each In the case C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy having 1 to 5 fluorine, chlorine and / or bromine atoms, R ²³ is hydrogen, fluorine, chlorine, bromine, iodine, cyano, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, in each case 1 to 5 fluorine, chlorine and / or bromine C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy, C ₁ -C ₂ -alkylsulfinyl or C ₁ -C ₂ -alkylsulfonyl having an atom, or A represents a group of formula (A6):

From here, R ²⁴ represents methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ²⁵ represents methyl or ethyl, Q ¹ represents S (sulfur), SO ₂ or CH ₂ , p represents 0 or 1, or A represents a group of formula (A7):

From here, R ²⁶ represents methyl, ethyl, or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A8):

From here, R ²⁷ represents methyl, ethyl, trifluoromethyl, difluoromethyl, difluorochloromethyl or trichloromethyl, or A represents a group of formula (A9):

From here, R ²⁸ and R ²⁹ independently represent hydrogen, fluorine, chlorine, bromine, amino, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ³⁰ represents hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or A represents a group of formula (A10):

From here, R ³¹ and R ³² independently of one another represent hydrogen, fluorine, chlorine, bromine, amino, nitro, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms , R ³³ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A11):

From here, R ³⁴ is hydrogen, fluorine, chlorine, bromine, amino, C ₁ -C ₄ -alkylamino, di (C ₁ -C ₄ -alkyl) amino, cyano, methyl, ethyl or 1 to 5 fluorine, chlorine and / Or C ₁ -C ₂ -haloalkyl having a bromine atom, R ³⁵ represents fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A12):

From here, R ³⁶ is hydrogen, fluorine, chlorine, bromine, amino, C ₁ -C ₄ -alkylamino, di (C ₁ -C ₄ -alkyl) amino, cyano, methyl, ethyl or 1 to 5 fluorine, chlorine and / Or C ₁ -C ₂ -haloalkyl having a bromine atom, R ³⁷ represents fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A13):

From here, R ³⁸ represents fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or A represents a group of formula (A14):

From here, R ³⁹ represents hydrogen, methyl or ethyl, R ⁴⁰ represents fluorine, chlorine, bromine, methyl or ethyl, or A represents a group of formula (A15):

From here, R ⁴¹ represents methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A16):

From here, R ⁴² represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, A represents a group of formula (A17):

From here, R ⁴³ is fluorine, chlorine, bromine, iodine, hydroxy, C ₁ -C ₄ -alkyl, methoxy, ethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, or 1 to 5 C ₁ -C ₂ -haloalkyl or C ₁ -C ₂ -haloalkoxy having ₂ fluorine, chlorine and / or bromine atoms, A represents a group of formula (A18):

From here, R ⁴⁴ is hydrogen, methyl, ethyl, C ₁ -C ₂ -haloalkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, hydroxy having 1 to 5 fluorine, chlorine and / or bromine atoms Methyl, hydroxyethyl, methylsulfonyl or dimethylaminosulfonyl, R ⁴⁵ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ⁴⁶ represents hydrogen, fluorine, chlorine, bromine, cyano, methyl, ethyl, isopropyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, R ⁴⁷ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl or C ₁ -C ₂ -haloalkyl having 1 to 5 fluorine, chlorine and / or bromine atoms, or A represents a group of formula (A19):

From here, R ⁴⁸ is carboxamide of formula (I) representing methyl, ethyl, n-propyl or isopropyl. a) Aniline of formula (III) in the presence of a carboxylic acid derivative of formula (II), optionally in the presence of a catalyst, optionally in the presence of a condensation agent, optionally in the presence of an acid binder and optionally in the presence of a diluent React with derivatives, b) reacting the carboxamide of formula (IV) with a compound of formula (V) in the presence of a base and in the presence of a dilution medium, or c) synthesizing the carboxamide of formula (I) according to claim 1, characterized in that the carboxamide of formula (Ia) is reacted with a halide of formula (VI) in the presence of a base and in the presence of a dilution medium. How to:

Where A, R ¹ , M, Q, L ² and R are as defined in claim 1, X ¹ represents halogen or hydroxy, L ³ represents hydrogen or C ₁ -C ₉ -alkyl, Y represents halogen, triflate (trifluoromethylsulfonyl), mesylate (methylsulfonyl) or tosylate (4-methylphenylsulfonyl), X ² represents chlorine, bromine or iodine, R ^{1 -A} is C ₁ -C ₈ -alkyl, C ₁ -C ₆ -alkylsulfinyl, C ₁ -C ₆ -alkylsulfonyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, C ₃ -C ₈ -cycloalkyl; Having 1 to 9 fluorine, chlorine and / or bromine atoms in each case C ₁ -C ₆ - haloalkyl, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - haloalkyl sulfinyl, C ₁ - C ₄ -haloalkylsulfonyl, halo-C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl or C ₃ -C ₈ -halocycloalkyl; Formyl, formyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl, (C ₁ -C ₃ -alkoxy) carbonyl-C ₁ -C ₃ -alkyl; Halo- (C ₁ -C ₃ -alkyl) carbonyl-C ₁ -C ₃ -alkyl or halo- (C ₁ -C ₃ -alkoxy) having 1 to 13 fluorine, chlorine and / or bromine atoms in each case Carbonyl-C ₁ -C ₃ -alkyl; (C ₁ -C ₈ -alkyl) carbonyl, (C ₁ -C ₈ -alkoxy) carbonyl, (C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -Cycloalkyl) carbonyl; (C ₁ -C ₆ -haloalkyl) carbonyl, (C ₁ -C ₆ -haloalkoxy) carbonyl, (halo-C ₁ -C) having 1 to 9 fluorine, chlorine and / or bromine atoms in each case ₄ -alkoxy-C ₁ -C ₄ -alkyl) carbonyl, (C ₃ -C ₈ -halocycloalkyl) carbonyl; Or -C (= 0) C (= 0) R ² , -CONR ³ R ⁴ or -CH ₂ NR ⁵ R ⁶ , Wherein R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are as defined in claim 1. A medium for the control of unwanted microorganisms, characterized in that it contains at least one carboxamide of formula (I) according to claim 1 together with an extender and / or a surfactant. Use of the carboxamide of formula (I) according to claim 1 for controlling unwanted microorganisms. A method of controlling unwanted microorganisms, characterized by applying the carboxamide of formula (I) according to claim 1 to microorganisms and / or their environment. A method for synthesizing a substance for controlling unwanted microorganisms, characterized by mixing the carboxamide of formula (I) according to claim 1 with an extender and / or a surfactant. Aniline derivatives of formula (III):

Where R ¹ , M, Q, L ² and R are as defined in claim 1, L ³ represents hydrogen or C ₁ -C ₉ -alkyl.