EP0796242A1

EP0796242A1 - Substituted carboxylic acid amides and their use as fungicides

Info

Publication number: EP0796242A1
Application number: EP95941029A
Authority: EP
Inventors: Thomas Seitz; Ulrich Heinemann; Klaus Stenzel; Stefan Dutzmann
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1994-12-08
Filing date: 1995-11-27
Publication date: 1997-09-24
Also published as: AU4257096A; JPH11500103A; DE4443641A1; WO1996017825A1

Abstract

Described are carboxylic acid amides of formula (I), as well as their use as pesticides, wherein A1 is hydrogen or alkyl; A2 is hydrogen or alkyl; A3 is hydrogen, alkyl or cyano; Ar1 is in either case optionally substituted arylene or heteroarylene; Ar2 is in either case optionally substituted aryl or heteroaryl; E is one of the groups (a), and G is a single bond, oxygen, sulfur or optionally halogen, hydroxy, alkyl, alkyl halide or cycloalkyl substituted alkandiyl, alkendiyl, alkindiyl or one of the following groups -Q-CQ-, -CQ-Q-, -CH¿2?-Q-; -Q-CH2-, -CQ-Q-CH2-, -CH2-Q-CQ-, -Q-CQ-CH2-, -Q-CQ-Q-CH2-, -N=N-, -S(O)n-, -CH2-S(O)n-, -CQ-, -S(O)n-CH2-, -C(R?7¿)=N-O-, -C(R7)=N-O-CH¿2?, -N(R?8¿)-, -CQ-N(R8)-, -N(R8)-CQ-, -Q-CQ-N(R8)-, -N=C(R7)-Q-CH2-, -CH¿2?-O-N=C(R?7¿)-, -N(R8)-CQ-Q-, -CQ-N(R8)-CQ-Q-, -N(R8)-CQ-Q-CH¿2?, -Q-C(R?7¿)=N-O-CH¿2?- or -N(R?8)-C(R7¿)=N-O-CH¿2?-, wherein n is 0, 1 or 2; Q is oxygen or sulfur; R?7¿ is hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkyl amino, dialkyl amino or cycloalkyl; R8 is hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl, m is 0, 1 or 2, and Z is in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl or heterocyclyl.

Description

SUBSTITUTED CARBON SAUREAMIDS AND THEIR USE AS FUNGICIDES

The invention relates to new substituted carboxamides, a process for their preparation and their use as fungicides.

It is known that certain substituted carboxamides have fungicidal properties (cf. EP-A 398692, EP-A 468775, DE-A 4030038, WO-A 92/13830). However, the action of these compounds is unsatisfactory in many cases.

The new substituted carboxamides of the general formula (I) have now been found

in which

A ^{1 represents} hydrogen or alkyl.

A "represents hydrogen or alkyl.

A ^{J represents} hydrogen, alkyl or cyano. Ar ¹ represents optionally substituted arylene or heteroarylene

Ar stands for optionally substituted aryl or heteroaryl

E stands for a 1-alkene-1,1-diyl grouping, in the 2-position a residue

R ¹ contains, or represents a 2-aza-l-alkene-l, l-diyl grouping which contains a radical R ² in the 2-position, or an optionally substituted one

Imino grouping ("Azamethylene", NR ³ ), or a 3-aza-l-propene-2,3-diyl grouping which has a radical R ⁴ in the 1 position and a radical R in the 3 position ⁵ contains, or stands for a 3-aza-l-propene-2,3-diyl group which contains a radical R ⁴ in the 1-position, or for a 3-thia-l-propene-2,3-diyl -Group, which contains a radical R ⁴ in the 1-position, or stands for an l-aza-l-propene-2,3-diyl group, which has a radical R ⁶ in the 1-position and one in the 3-position Contains radical R ³ , or represents an l-aza-l-propene-2,3-diyl grouping which contains a radical R ⁴ in the 1 position and a radical R ⁵ in the 3 position, or for a 1, 3-Diaza-l-propen-2,3-dιyl grouping, in the 1 position a radical R ⁶ and in

3-position contains a radical R ⁵ , or stands for an l-aza-3-oxa-l-propene-2,3-diyl grouping which contains a radical R ⁶ in the 1-position, or for an l-aza -3-thιa-l-propen-2,3-diyl grouping which contains a radical R ⁶ in the 1 position, where

R ^{1 represents} hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,

, ->

R "stands for hydrogen, amino, cyano or for optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and

R ^{3 represents} hydrogen, cyano or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

R ^{4 represents} hydrogen, halogen, cyano or any optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, R, 5 ^{D represents} alkyl,

R ^{6 represents} hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino.

G for a single bond, for oxygen, sulfur or for each optionally by halogen, hydroxy, alkyl, haloalkyl or

Cycloalkyl substituted alkanediyl, alkenediyl, alkindiyl or one of the groupings below

-Q-CQ-, -CQ-Q-, -CH ₂

-Q-; -Q-CH ₂ -, -CQ-Q-CH ₂ -, -CH, -Q-CQ-, -Q-CQ-CH ₂ -, -Q-CQ-Q-CH, -, -N = N- , -S (O) _n -, -CH ₂ -S (O) _n -, -CQ-,

-S (O) _n -CH ₂ -, -C (R ⁷ ) = NO-, -C (R7) = NO-CH ₂ -, -N (R ⁸ ) -, -CQ-N (R ⁸ ) - ,

-N (R ⁸ ) -CQ-, -Q-CQ-N (R ⁸ ) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ -ON = C (R ⁷ ) -,

-N (R ⁸ ) -CQ-Q-, -CQ-N (R ⁸ ) -CQ-Q-, -N (R ⁸ ) -CQ-Q-CH ₂ -, -QC (R ⁷ ) = NO-

CH ₂ - or -N (R ⁸ ) -C (R ⁷ ) = NO-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

R ^{7 represents} hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and

R ^{8 represents} hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,

m represents the numbers 0, 1 or 2, and

Z for optionally substituted alkyl, alkenyl, alkynyl,

Cycloalkyl, aryl or heterocyclyl.

It was further found that the new substituted carboxamides of the general formula (1) are obtained if carboxylic acid derivatives of the general formula (II) in which

Ar ¹ , E, G and Z have the meaning given above and

R represents hydroxy, halogen or alkoxy,

with an A in the general formula (III)

in which

A ¹ , A ² , A ³ , Ar ² and m have the meaning given above,

- or with a hydrogen halide thereof -

if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent and if appropriate in the presence of a diluent.

Finally, it was found that the new substituted carboxamides of the general formula (I) show very strong fungicidal activity.

The compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as, for. B. E- and Z-, threo- and erythro-, and optical isomers, but optionally also of tautomers are present. Both the E and the Z isomers, as well as the threo- and erythro- as well as the optical isomers, any mixtures of these isomers and the possible tautomeric forms are claimed The invention preferably relates to compounds of the formula (I) in which

A ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms,

A ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms,

A ^{3 represents} hydrogen, alkyl having 1 to 6 carbon atoms or cyano,

Ar ^{1 stands} for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being derived from the the following list is selected:

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or alkynyloxy each having 2 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 Carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts, in each case where appropriate all single or multiple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each substituted twice linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms,

Ar ² for phenyl, naphthyl or for heteroaryl with 3 to 7 ring radicals which are optionally mono- or polysubstituted by identical or different substituents - 6 -

structure, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being selected from the following list: halogen, cyano, nitro, amino, hydroxy, formyl, Carboxy, carbamoyl,

Thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms; each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or haloalkenyloxy, each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts; each optionally single or multiple, identical or different by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different

Halogen atoms substituted, in each case doubly linked alkylene or dioxyalkylene, each having 1 to 6 carbon atoms; Cycloalkyl of 3 to 6 carbon atoms;

Heterocyclyl or heterocyclyl-methyl, each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -; and in each case optionally in the phenyl moiety one or more times, identically or differently

Halogen, cyano and / or straight-chain or branched alkyl with. 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy or haloalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or optionally single or multiple, identical or differently substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each having a double bond alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, substituted ^" phenyl, phenoxy, phenylthio, benzyl, benzyloxy, phenylethyl or phenylethyloxy.

represents one of the following groups:

R ^a R ³

II II

CH, ^N X 2 R ³ II II ^* R ¹ ^H R ² CH ₄ ^• R ⁴ wherein

R ^{1 represents} hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has from 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C ₁ -C ₄ alkoxy,

R ² for hydrogen, amino, cyano or for each optionally by

Halogen, cyano or C _] -C ₄ -alkoxy-substituted alkyl, alkoxy, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radicals, and

R ³ for hydrogen, cyano or for alkyl, alkenyl or alkynyl each optionally substituted by halogen, cyano or C _j - -alkoxy, each having up to 6 carbon atoms or for each optionally by

Halogen, cyano, carboxy, C _| -C ₄ -alkyl or C, -C ₄ -alkoxy-carbonyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part,

R ^{4 represents} hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C, -C ₄ -alkoxy,

R ^{5 represents} alkyl having 1 to 6 carbon atoms,

R ⁶ for hydrogen, amino, cyano or for alkyl, alkoxy, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the

Stands for alkyl residues, and

G for a single bond, for oxygen, sulfur or for alkane diyl, alkenediyl, alkynediyl each optionally substituted by halogen, hydroxy, C, -C ₄ alkyl, C _] -C haloalkyl or C ₃ -C ₆ cycloalkyl, each with up to 4 carbon atoms or one of the following

Groupings

-Q-CQ-, -CQ-Q-, -CH ₂ -Q-; -Q-CH, -, -CQ-Q-CH ₂ -, -CH ₂ -Q-CQ-, -Q-CQ-CH ₂ -, -Q-CQ-Q-CH ₂ -, -N = N- , -S (O) _n -, -CH ₂ -S (O) _n -, -CQ-, -S (O) _n -CH ₂ -, -C (R ⁷ ) = NO-, -C (R ⁷ ) = NO-CH ₂ -, -N (R ⁸ ) -, -CQ-N (R ⁸ ) -, -N (R ⁸ ) -CQ-, -Q-CQ-N (R ⁸ ) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ -ON = C (R ⁷ ) -,

-N (R ⁸ ) -CQ-Q-, -CQ-N (R ⁸ ) -CQ-Q-, -N (R ⁸ ) -CQ-Q-CH ₂ -, -QC (R ⁷ ) = NO- CH ₂ or -N (R ⁸ ) -C (R ⁷ ) = NO-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

R ^{7 represents} hydrogen, cyano, alkyl, alkoxy, alkylthio, alkylamino or dialkylamino optionally substituted by halogen, cyano or C, -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups or each optionally substituted by halogen, cyano , Carboxy, C, -C ₄ alkyl or C, -C ₄ alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and R ° for hydrogen, hydroxy, cyano or for optionally by

Halogen, cyano or C, -C ₄ alkoxy substituted alkyl with 1 to 6

Carbon atoms or for optionally by halogen, cyano,

Carboxy, C ₁ -C ₄ -alkyl or Cl-C4-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,

m represents the numbers 0, 1 or 2 and,

Z for optionally single or multiple, identical or different, by halogen, cyano, hydroxy, amino, C, -C ₄ -alkoxy, C, -C ₄ -alkylthio, C, -C ₄ -alkylsulfonyl or C, -C ₄ -alkylsulfonyl (which can in each case optionally be substituted by halogen) substituted alkyl with 1 to 8 carbon atoms; for alkenyl or alkynyl, each optionally substituted by halogen, each having up to 8 carbon atoms; for each optionally one or more times, identically or differently, by halogen, cyano, carboxy, phenyl (which may be by halogen, cyano, C _] -C ₄ -alkyl, C _] -C ₄ -haloalkyl, C, -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy is substituted), C, - C ₄ -alkyl or C, -C ₄ -alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms; phenyl, naphthyl or heterocyclyl with 3 to 7 ring members, each of which is optionally mono- or polysubstituted by identical or different substituents, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents being given - are preferably selected from the list below:

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkyl- sulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkyl sulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts; each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each substituted twice Alkylene or dioxyalkylene, each with 1 to 6

Carbon atoms; Cycloalkyl of 3 to 6 carbon atoms;

Heterocyclyl or heterocyclyl-methyl each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or

Sulfur -; and in each case optionally in the phenyl, pyridyl or thienyl part, one or more times, identically or differently, by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 up to 9 identical or different halogen atoms and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy or haloalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or optionally simply or multiple, identical or different by halogen and / or straight-chain or branched

Alkyl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each having a double bond, alkylene or dioxyalkylene each having 1 to 6 carbon atoms, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy, benzylthio, phenylethyl or phenylethyloxy.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino. Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

The invention relates in particular to compounds of the formula (I) in which

A ^{1 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

A ^{2 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

A ^{3 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or cyano,

Ar ¹ for optionally substituted ortho-, meta- or para-phenylene, for furandiyl, thiophene diyl, pyrroldiyl, pyrazole diyl, triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, in particular pyridinediyl (pyridinediyl) 3-diyl), pyrimidinediyl, pyridazin-diyl, pyrazinediyl, 1,3,4-triazinediyl or 1,2,3-triazinediyl, the possible substituents being selected in particular from the list below:

Fluorine, chlorine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, methylsulfinyl or methylsulfonyl,

Ar ² for phenyl which is optionally monosubstituted to trisubstituted,

Naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, Pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,3-triazinyl, 1, 2,4-triazinyl, 1,3,5-triazinyl, where the possible substituents are preferably selected from the following list: fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylchlorodifluoromethyl Trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxy carbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, methoximino methyl, methoximino methyl Ethoximinoethyl; each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, Cyclobutyl, cyclopentyl or cyclohexyl, and in each case optionally in the phenyl part once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, or each optionally singly or multiply, identically or differently, by fluorine, chloromethyl, methyl, trifluoromethyl substituted, in each case double-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

represents one of the groupings below

wherein

R ^{1 represents} hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,

R ^{2 represents} hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,

R ^{3 represents} hydrogen, cyano or, in each case optionally by fluorine,

Cyano, methoxy or ethoxy substituted methyl, ethyl n- or i-propyl, n-, i- or s-butyl, for allyl or propargyl or for in each case optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ^{4 represents} hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,

Ethylthio, methylamino, ethylamino or dimethylamino,

R ^{5 represents} methyl, ethyl n- or i-propyl, n-, i- or s-butyl,

R ^{6 represents} hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, and

G for a single bond, for oxygen, sulfur or for each optionally substituted by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, methylene, dimethylene (Ethane-1,2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the groups below

-Q-CQ-, -CQ-Q-, -CH ₂ -Q-; -Q-CH ₂ -, -CQ-Q-CH ₂ -, -CH ₂ -Q-CQ-, -Q-CQ-CH ₂ -, -Q-CQ-Q-CH ₂ -, -N = N- , -S (O) _n -, -CH ₂ -S (O) _n -, -CQ-, -S (O) _n -CH ₂ -, -C (R ⁷ ) = NO-, -C (R ⁷ ) = NO-CH ₂ -, -N (R ⁸ ) -,

-CQ-N (R ⁸ ) -, -N (R ⁸ ) -CQ-, -Q-CQ-N (R ⁸ ) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ - ON = C (R ⁷ ) -, -N (R ⁸ ) -CQ-Q-, -CQ-N (R ⁸ ) -CQ-Q-, -N (R ⁸ ) -CQ-Q-CH ₂ -, -QC (R ⁷ ) = NO-CH ₂ or -N (R ⁸ ) -C (R ⁷ ) = NO-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

R ⁷ for hydrogen, cyano, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methylthio optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy , Ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and

R ^{8 represents} hydrogen, hydroxyl, cyano or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted by fluorine, chlorine, cyano, methoxy or ethoxy or for optionally by fluorine, chlorine, cyano,

Carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,

m represents the numbers 0, 1 or 2 and,

Z for optionally up to five times by fluorine, chlorine, bromine,

Cyano, hydroxy, amino, methoxy, ethoxy, methylthio, ethylthio, Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; for allyl, crotonyl, 1-methyl-allyl, propargyl or 1-methyl-propargyl which are optionally monosubstituted to trisubstituted by fluorine, chlorine or bromine; for each one optionally up to six times by fluorine, chlorine,

Bromine, cyano, carboxy, phenyl (which may be replaced by

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy or trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; for in each case monosubstituted to trisubstituted phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,4-thiadiazolyl, 1 , 3,4-thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxiranyl, oxetanyl, tetrahydrofuryl, perhydropyranyl, pyrrolidinyl, piperidinyl or morpholinyl, where the possible substituents are preferably selected from the following list: fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethyl sulfinyl, methyl sulfonyl or ethyl sulfonyl, trifluoromethyl, trifluoroethyl , Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, Trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino,

Diethylamino, acetyl, propionyl, acetyloxy, methoxy carbonyl, ethoxy carbonyl, methylsulfonyloxy, ethyl sulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximino-methyl, methoximinoethyl or ethoximinoethyl; each optionally single or multiple, identical or different by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-Propyl substituted, in each case two-linked tπmethylene (propane-l, 3-dιyl), methylenedioxy or ethylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case optionally in the phenyl, pyπdyl or thienyl part simply to triple, identical or different by fluorine, chlorine,

Bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy Difluoromethylthio, Difluorchlormethylthio, Trifluormethylthio, or in each case optionally singly or repeatedly, identically or differently by fluorine, chlorine, methyl, trifluoromethyl or ethyl substituted, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio Benzyl, benzyloxy or benzylthio

A particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{J represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar for phenyl, 1,2,4-thiazadolyl, 1, 3,4-thadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, optionally substituted up to three times, identically or differently, Pyπmidinyl, Pyridazinyl, Pyrazinyl stands, the possible substituents are preferably selected from the list below

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or l-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio,

Difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, Methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl,

each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy,

and in each case optionally in the phenyl part once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy , n- or i-Propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, substituted and in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl , Phenoxy, phenylthio, benzyl or benzyloxy,

E represents one of the groupings below

CH V in which

. 1

R and R "each represent methoxy,

G for oxygen, sulfur or for dimethylene (ethane-l, 2-diyl), ethene-l, 2-diyl or one of the following groups, which are each optionally substituted by fluorine, chlorine or bromine

-CQ-Q-, -CH ₂ -Q-, -Q-CH ₂ -, -CQ-Q-CH ₂ -, -Q-CQ-Q-CH ₂ -, -N = N- -S (0) _n -CH ₂ -, -C (R ⁷ ) = N-0-, -C (R ⁷ ) = N-0-CH ₂ - -N (R ⁸ ) -CQ-, -Q-CQ-N (R ^X ) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ -0-N = C (R ⁷ ) -, -N (R) -CQ-Q-, -CQ-NCR ^ - CQ-Q-, -NCR ^ -CQ-Q-CH _j -, -QC (R ⁷ ) = N-0-CH ₂ or -N (R ^s ) -C (R ⁷ ) = N-0-CH ₂ - stands, whereby

n represents the numbers 0, 1 or 2, - 18 -

Q represents oxygen or sulfur,

R ^{7 represents} hydrogen, cyano, methyl, ethyl or cyclopropyl and

R ^{8 represents} hydrogen, methyl, ethyl or cyclopropyl,

m represents 0, 1 or 2 and,

Z for phenyl, 1,2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, which are optionally monosubstituted to trisubstituted in the same or different ways, Pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where the possible substituents are preferably selected from the list below:

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, trifluoromethylthio,

Difluorochloromethylthio, Trifiuormethylsulfinyl or trifluoromethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, methyl, trifluoromethyl or ethyl-substituted, in each case doubly attached methylenedioxy or ethylenedioxy, and in each case optionally in the phenyl, pyridyl or thienyl part single to triple, identical or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy,

Trifluoroethoxy, trifluoromethoxy or in each case optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio.

Compounds of the general formula (Ia) are very particularly preferred,

in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{3 represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, which are optionally monosubstituted to trisubstituted by identical or different substituents, Pyrimidinyl, pyridazinyl, pyrazinyl, the possible substituents preferably being selected from the list below:

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy,

Difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximino or ethy 1, in each case differently by simple or ethy 1, ethoxi mi, 1 or ethoxi mi

Fluorine, chlorine, methyl, trifluoromethyl or ethyl substituted, in each case doubly linked methylenedioxy or ethylenedioxy, and in each case optionally in the phenyl part in one to three times, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-

Propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally one or more times, the same or differently substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case double-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

"~ C ~ E stands for"

^N ^ OCH ₃

m represents 0, 1 or 2 and,

Z ¹ represents phenyl which is optionally monosubstituted to trisubstituted identically or differently, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfony l, trifluoromethyl l , Difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethyl sulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl

Methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case linked methylenedioxy or ethylenedioxy

Compounds of the general formula are also very particularly preferred

(Ib),

in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl, A ^{3 represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxy, trifluoromethyl, methyltrifluoromethyl, methylifluoromethyloxyethyl, trifluoromethyloxyethyl, trifluoromethyloxy, trifluoromethyl, methyltrifluoromethyl, methyltrifluoromethyl, trifluoromethyl, methyltrifunctional Methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, and in the phenyl part in each case optionally monosubstituted to triple, identically or differently by fluorine, chlorine, bromine , Cyano, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally one or more times, identically or differently, by fluorine, Chlorine, methyl, trifluoromethyl or ethyl substituted, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

for stands

^" ^ OCH.

m represents 0, 1 or 2 and,

.->

2r stands for phenyl, pyridyl or pyrimidyl which is optionally monosubstituted to trisubstituted identically or differently, the possible ones Substituents are preferably selected from the list below

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or Ethyl¬ sulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxy carbonyl, methoximinomethyl, ethoximinomethyl, Methoximi noethy 1, ethoximinoethyl , each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case double-linked methylenedioxy or ethylenedioxy,

further particularly preferred are compounds of the general formula (Ic),

in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{J represents} hydrogen, methyl, ethyl or cyano,

Ar for phenyl, 1,2,4-thιadιazolyl, 1,3,4-thiadιazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyπdinyl which is optionally monosubstituted to trisubstituted in the same or different manner, Pynmidinyl, Pyndazinyl, Pyrazinyl stands, wherein the possible substituents are preferably selected from the list below Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, tri fl uo reth ox y, D i fl uorm ethy l thi o, T ri fl uo rm e th yl th io

Difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, each optionally one to four times, the same or different by fluorine, chlorine, methyl, trifluoromethyl or ethylened, in each case two or more, and also linked in two or two, methylene or ethylened, optionally linked, as well as methylene, ethylened, and oxy, respectively, as well as linked in two or two ways, as well as linked, in each case, as well as linked, as well as linked, as well as linked, as well as linked, as well as linked, as well as linked, as well as linked, as well as doubly, respectively, as well as, as well as substituted, optionally Phenyl part single to triple, identical or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally singly or multiply, identically or differently by fluorine, chlorine, methyl, trifluoromethyl or ethyl-substituted, each doubly linked methylenedioxy or ethylenedioxy, substituted phenyl , Phenoxy, phenylthio, benzyl or benzyloxy,

E represents one of the groupings below

^• he

II II in which

CH N.

'r-, 2nd

^' R'. FT

R and R ~ each represent methoxy,

m represents 0, 1 or 2 and,

Z ^J for 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1, 3,4- which are each substituted once or twice, identically or differently.

Oxadiazolyl, pyrimidinyl, or 1,3,5-triazinyl, where the possible

Substituents are preferably selected from the following list Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i- propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, Difluorchlormethyl¬ thio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, and each optionally substituted in the phenyl, pyridyl, or mono- to trisubstituted Thienylteil , identical or different by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, Difluoromethoxy, difluorochloromethoxy,

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediate products required in each case for the preparation.

These radical definitions can be combined with one another as desired, that is also between the specified combinations for preferred compounds.

Formula (II) provides a general definition of the carboxylic acid derivatives required as starting materials for carrying out the process according to the invention. In this formula (II), Ar ¹ , E, G and Z preferably or in particular have those meanings which, in connection with the description of the compounds of the formula (I) according to the invention, are preferred or particularly preferred for Ar ¹ , E, G and Z have been specified, R preferably represents alkoxy having 1 to 4 carbon atoms, in particular methoxy or ethoxy, hydroxyl or chlorine.

The starting materials of the formula (II) are known and / or can be prepared by processes known per se (cf. EP-A 178826, EP-A 242081, EP-A 382375, EP-A 49371 1, EP-A 432503 , DE-A 3938054) - 25 -

Formula (III) provides a general definition of the amines to be used further as starting materials. In formula (III), A ¹ , A ² , A ³ , Ar and m preferably or in particular have the meaning which have been preferred or particularly preferred in connection with the description of the compounds of the formula (I) according to the invention for A ¹ , A ² , A ³ , Ar and m was specified.

The starting materials of the formula (III) are known organic synthesis chemicals and / or can be prepared by processes known per se.

The process according to the invention is optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide , Potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N- Dimethyl-benzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

The process according to the invention is optionally carried out in the presence of a suitable condensing agent. As such, all condensation agents which can usually be used for such amidation reactions are suitable. Examples include acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl chloroformate or methanesulfonyl chloride; Carbodiimides, such as N, N'-dicyclohexylcarbodiimide (DCC) or other customary condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ ) or triphenylphosphine / carbon tetrachloride.

The process according to the invention is optionally carried out in the presence of a diluent. Water and organic solvents are suitable as diluents for carrying out the process according to the invention Consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -20 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 150 ° C.

To carry out the process according to the invention, 1 to 5 moles, preferably 1.0 to 2.5 moles, of amine are generally employed per mole of carboxylic acid derivative of the formula (II).

The reaction is carried out, worked up and isolated by known processes (cf. the preparation examples).

The active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms. The active ingredients are suitable for use as crop protection agents, in particular as fungicides.

Fungicidal agents in crop protection are used to combat plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes

Some pathogens of fungal diseases which fall under the generic names listed above may be mentioned as examples, but not by way of limitation: Pythium species, such as, for example, Pythium ultimum; Phytophthora species, such as, for example, Phytophthora infestans; Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubense; Plasmopara species, such as, for example, Plasmopara viticola;

Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;

Erysiphe species, such as, for example, Erysiphe graminis; Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha; Venturia species, such as, for example, Venturia inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or Pyrenophora graminea (conidial form: Drechslera, synonym: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus (conidial form: Drechslera, synonym: Helminthosporium);

Uromyces species, such as, for example, Uromyces appendiculatus; Puccinia species, such as, for example, Puccinia recondita;

Tilletia species, such as, for example, Tilletia caries;

Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; Pellicularia species, such as, for example, Pellicularia sasakii;

Pyricularia species, such as, for example, Pyricularia oryzae;

Fusarium species, such as, for example, Fusarium culmorum;

Botrytis species, such as, for example, Botrytis cinerea;

Septoria species, such as, for example, Septoria nodorum; Leptosphaeria species, such as, for example, Leptosphaeria nodorum;

Cercospora species, such as, for example, Cercospora canescens;

Alternaria species, such as, for example, Alternaria brassicae;

Pseudocercosporella species, such as Pseudocercosporella herpotrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases allows treatment of above-ground parts of plants and also treatment of plants and seeds and the soil.

The active compounds according to the invention can be used with particularly good results in combating cereal diseases, for example against Erysiphe species, - 28 -

Leptosphaeria, Pyrenophora and Cochliobolus species or of diseases in fruit and vegetable growing, such as against Podospherea species. In addition, the active compounds according to the invention have a particularly good in vitro effect.

Depending on their respective physical and / or chemical properties, the active compounds can be converted into customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV Cold and warm mist formulations.

These formulations are made in a known manner, e.g. by

Mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. also organic solvents as

Auxiliary solvents can be used. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or

Glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g.

Aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; Solid carrier materials are suitable: for example natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates; Solid carriers for granules are possible: for example broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifying and / or foam-generating agents are, for example, nonionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; The following may be used as dispersants: for example lignin sulfite waste liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide,

Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.

The formulations generally contain between 0, 1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to broaden the activity spectrum or to prevent the development of resistance. In many cases, synergistic effects occur.

The following are examples and are preferred for the mixtures:

Fungicides:

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1, 3-thizole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2-

(2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl - (E) - methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole, benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, blasticidin-S,

Bromuconazole, Bupirimate, Buthiobate,

Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, cymoxanil, cyproconazole, cyprofuram, dichlorophen, diclobutrazuan, dicloroflanidol, dicloflanidol, dicloflanlan, dicloflanlan, dicloflanlol, dicloflanlan

Difenoconazole, Dimethirimol, Dimethomorph, Diniconazol, Dinocap, Diphenylamin, Dipyrithion, Ditalimfos, Dithianon, Dodin, Drazoxolon, Edifenphos, Epoxyconazole, Ethirimol, Etridiazol,

Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpicionil, Fenpropidin, Fenpropi-morph, Fentinacetate, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam,

Fludioxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl aluminum, fthalide, fuberidazole, furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodion, Isoprothiolan, Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Mepanip , Metalaxyl, metconazole,

Methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, nickel dimethyldithiocarbamate, nitrothal isopropyl, nuarimol, ofurace, oxadixyl, oxamocarb, oxycarboxin,

Pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb,

Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, tridemoφol, triflumine, triflumine

Triticonazole,

Validamycin A, vinclozolin, zineb, ziram

Bactericides: bronopol, dichlorophene, nitrapyrin, nickel dimethyl dithiocarbamate,

Kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations

Insecticides / acaricides / nematicides:

Abamectin, Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A,

Azinphos M, Azocyclotin,

Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butylpyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan 157

419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhrothrin, Cyhalotinamin, Cyhalotinamin, Cyhalotinin, Cyhalotinin S, demeton-S-methyl, diafenthiuron,

Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoproxosophosquinos, Fenophone, Ephinophosphate, Ephinophosphate Fenobucarb, fenothiocarb,

Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluv- alinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Hexathaftenophloxidos, Hathathafloxidox, Fathionophosphorus Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,

Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,

Methamidophos, methidathione, methiocarb, methomyl, metolcarb, milbemectin,

Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,

Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M, Primiphos A, Profenofos,

Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoat, Pymetrozin, Pyrachlophos, Pyraclofos, Pyraclophos, Pyradaphenthion,

Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,

Quinalphos,

RH 5992,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos,

Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thioethon, Thionazin, Thuringiensin, Tralomethrin, Triarathen, Triazophos,

Triazuron, trichlorfon, triflumuron, trimethacarb,

Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with

Fertilizers and growth regulators are possible.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc.

It is also possible to apply the active ingredients using the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil. The seeds of the plants can also be treated.

In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.

In the seed treatment, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.

When treating the soil, active ingredient concentrations are from 0.00001 to

0.1% by weight, preferably from 0.0001 to 0.02% by weight, is required at the site of action.

Preparation Examples:

example

A mixture of 2.5 g (8 mmol) of 2-methoximino-2- [2- (2-methylphenoxymethyl) phenylj-acetic acid methyl ester and 1.14 g (8 mmol) of 4-chlorobenzylamine is melted at 120 ° for 12 hours C stirred After cooling, the mixture was taken up in dichloromethane, washed once with water, then with 1N hydrochloric acid and then again with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel using petroleum ether / ethyl acetate (5 l)

1.4 g (42% of theory) of N- (4-chlorobenzyl) -2-methoxιmιno-2- [2- (2-methylphenoxymethyl) phenyl] acetic acid amide are obtained as 01 1 H-NMR (CDC1 ₃ , TMS) δ = 3.93, 2.20 ppm

Example 2:

To a solution of 50 g (0.167 mol) of 2-methoximino-2- [2- (2-methylphenoxymethyl) phenyl] acetic acid in 300 ml of tetrahydrofuran are added dropwise in succession at −1 ° C. 23.4 ml (0 , 167 mol) of tri ethyl amine and 22.7 g (0.167 mol) of isobutyl chloroformate and stirred for 2 hours at -10 ° C. A solution of 17.9 g (0.167 mol) of benzylamine in 50 ml of tetrahydrofuran is then added dropwise over the course of 30 minutes, and the mixture is stirred at -10 ° C. for 2 hours and at 20 ° C. for a further 18 hours. The mixture is concentrated in vacuo, taken up in dichloromethane, washed once with water, then with 1N hydrochloric acid and then again with water, dried over sodium sulfate, filtered and concentrated again. The residue is stirred with diisopropyl ether, the crystals thus obtained are filtered off and dried.

52 g (80% of theory) of N-benzyl-2-methoximino-2- [2- (2-methylphenoxymethyl) phenyl] acetic acid amide with a melting point of 68-69 ° C. are obtained.

Example 3:

2.54 g (8 mmol) of 2-methoximino are added dropwise to a mixture of 1.02 g (8 mmol) of 4-chloroaniline and 1.12 ml (8 mmol) of triethylamine in 30 ml of dichloromethane at 20 ° C. in 20 minutes -2- [2- (2-methylphenoxymethyl) phenyl] acetic acid chloride and stirred for 18 hours at 20 ° C. The mixture is poured onto water and washed first with sodium hydrogen carbonate solution and then with water. The organic phase is dried over sodium sulfate, filtered and concentrated again. The residue is chromatographed on silica gel using petroleum ether / ethyl acetate (5: 1).

1.3 g (41% of theory) of N- (4-chlorophenyl) -2-methoximino-2- [2- (2-methylphenoxymethyl) phenyl] acetic acid amide with a melting point of 68-69 ° C. are obtained.

Analogously to Examples 1 to 3 and in accordance with the general description of the production process according to the invention, the compounds listed in Table 1 below can also be prepared, for example:

Table 1

The 'H-NMR spectra were recorded in deuterochloroform (CDC1 ₃ ) or hexacheuterodimethylsulfoxide (DMSO-d ₆ ) with tetramethylsilane (TMS) as the internal standard. The chemical shift is given as the d-value in ppm

The 1H-NMR spectra were recorded in deuterochloroform (CDC1 ₃ ) or hexacheuterodimethylsulfoxide (DMSO-d ₆ ) with tetramethylsilane (TMS) as the internal standard. The chemical shift is given as a d-value in ppm.

The NMR-NMR spectra were recorded in deuterochloroform (CDC1 ₃ ) or hexacheuterodimethyl sulfoxide (DMSO-d ₆ ) with tetramethylsilane (TMS) as the internal standard. The chemical shift is given as a δ value in ppm. Examples of use

Example A

Erysiphe test (wheat) curative

Solvent: 10 parts by weight of 1 N-Methy 1 -py rrol i don

Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To test for curative effectiveness, young plants with spores from

Erysiphe graminis f.sp. tritici pollinated. 48 hours after the inoculation, the plants are sprayed with the active compound preparation in the stated application rate.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and at a relative humidity of approx. 80% in order to

Favor development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, for example, the compound according to Preparation Example (6) shows an efficiency of 100% with an exemplary amount of active ingredient applied of 250 g / ha. Example B

Erysiphe test (wheat) protectiv

Solvent 10 parts by weight of N-methyl-pyrrolidone emulsifier 0.6 parts by weight of alkylaryl polyglycol ether

To test for protective effectiveness, young plants are sprayed with the preparation of active compound in the stated application rate.

After the spray coating has dried on, the plants are covered with spores from Erysiphe graminis f.sp. tritici pollinated.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules

Evaluation is carried out 7 days after the inoculation.

In this test, for example, the compounds according to preparation examples (2), (6), (10) and (11) show an efficiency of 100% at an exemplary active compound application rate of 250 g / ha. Example C

Erysiphe test (barley) / curative

Solvent 10 parts by weight of N-methyl-pyrrohdon

Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, mix 1

Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration

To test for curative activity, young plants are dusted with spores of Erysiphe graminis f sp hordei 48 hours after the inoculation, the plants are sprayed with the preparation of active compound in the stated application rate

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and at a relative humidity of approx. 80% in order to promote the development of mildew pustules

Evaluation is carried out 7 days after the inoculation

In this test, for example, the compound according to preparation example (6) shows an efficiency of 100% with an exemplary active compound application rate of 250 g / ha. Example D

Erysiphe test (barley) protectiv

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier 0.6 parts by weight of alkylaryl polyglycol ether

After the spray coating has dried on, the plants are covered with spores from Erysiphe graminis f.sp. hordei pollinated.

The plants are placed in a greenhouse at a temperature of approx. 20 ° C and a relative humidity of approx. 80% in order to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, for example, the compound according to preparation example (10) shows an efficiency of 100% with an exemplary active ingredient application rate of 250 g / ha. Example E

Podosphaera test (apple) / protectiv

Solvent: 4.7 parts by weight of acetone

Emulsifier 0.3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, mix 1

Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the preparation of active compound to runoff. After the spray coating has dried on, the plants are inoculated by dusting with conidia of the pod mildew pathogen Podosphaera leucotricha.

The plants are placed in a greenhouse at 23 ° C and at a relative humidity of approx. 70%.

Evaluation is carried out 10 days after the inoculation.

In this test e.g. the compounds according to preparation examples (2), (4) and (7) at an active substance concentration of 20 ppm have an efficiency of 89 to 97%.

Claims

1. Carboxamides of the general formula (I)

in which

A ^{1 represents} hydrogen or alkyl.

A ~ represents hydrogen or alkyl.

A ^{"1 represents} hydrogen, alkyl or cyano.

Ar ¹ represents optionally substituted arylene or heteroarylene.

Ar stands for optionally substituted aryl or heteroaryl.

E stands for a 1-alkene-1, 1-diyl grouping in the 2-position

Radical R ¹ contains, or stands for a 2-aza-l-alkene-l, l-diyl grouping which contains a radical R ² in the 2-position, or for an optionally substituted imino grouping ("Azamethylene", N - R- '), or stands for a 3-aza-l-propene-2,3-diyl grouping which contains a radical R ⁴ in the 1 position and a radical R ^D in the 3 position, or for one 3-aza-l-propene-2,3-diyl grouping which contains a R ⁴ radical in the 1-position, or represents a 3-thia-l-propene-2,3-diyl grouping which is in 1 position contains a radical R ⁴ , or represents an l-aza-l-propene-2,3-diyl grouping which is in 1-

Position contains a radical R ⁶ and in the 3-position a radical R ³ , or stands for an l-aza-l-propene-2,3-diyl grouping which has a radical R ⁴ in the 1 position and in the 3 position contains a radical R ⁵ , or represents a 1,3-diaza-l-propene-2,3-diyl grouping which is in 1- - 46 -

Position contains a radical R ⁶ and in the 3-position a radical R ⁵ , or represents an l-aza-3-oxa-l-propene-2,3-diyl grouping which contains a radical R ⁶ in the 1-position , or represents an l-aza-3-thia-l-propen-2,3-diyl grouping which contains a radical R ⁶ in the 1 position, where

R ^{2 represents} hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and

R ^{J stands} for hydrogen, cyano or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

R ^{4 represents} hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,

R ^{5 represents} alkyl,

R ^{6 represents} hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino

for a single bond, for oxygen, sulfur or for alkanediyl, alkenediyl, alkynediyl or one of the following groups, each optionally substituted by halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl

-Q-CQ-, -CQ-Q-, -CH ₂ -Q- -Q-CH ₂ -, -CQ-Q-CH ₂ - -CH ₂ -Q-CQ-, -Q-CQ-CH ₂ - , -Q-CQ-Q-CH ₂ - -N = N-, -S (0) _n - -CH ₂ -S (0) _n -, -CQ-, -S (0) _n -CH ₂ -, -C (R ⁷ ) = N-0- -CCR7) = N-0-CH ₂ - -N (R ⁸ ) -, -CQ-N (R *) -, -N (R ^R ) -CQ-, -Q-CQ-N (R *) -, -N = C (R ⁷ ) -Q-CH2- -CH ₂ -0-N = C (R ⁷ K -N (R ^K ) -CQ-Q- - CQ-N (R ⁸ ) -CQ-Q- -N (R ⁸ ) -CQ-Q-CH ₂ - -QC (R ⁷ ) = N-0-CH ₂ - o ei -N (R ⁸ ) -C (R ⁷ ) = N-θ-C] - -, where - 47 -

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

m represents the numbers 0, 1 or 2, and

Z represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl.

2. Compounds of formula (I) according to claim 1, in which

A ^{1 represents} hydrogen or alkyl having 1 to 6 carbon atoms,

A ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms,

A ^{3 represents} hydrogen, alkyl having 1 to 6 carbon atoms or cyano,

Ar ^{1 stands} for optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being derived from the following the following list are selected:

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl, alkenyloxy or Alkynyloxy each having 2 to 6 carbon atoms, each straight-chain or branched halogen alkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, in each case straight-chain or branched haloalkenyl or haloalkenyloxy

5 each having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoxyminoalkyl each having 1 to 6 carbon atoms in each

10 alkyl parts, each optionally one or more times, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms

15 substituted, each doubly linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms,

Ar is phenyl, naphthyl or heteroaryl with 3 to 7 ring members, each of which is mono- or polysubstituted in the same or different ways, at least one of which is for oxygen

20 is sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being selected from the following list: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl,

25 each straight-chain or branched alkyl, alkoxy, alkylthio,

Alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms,

30 each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or

35 haloalkenyloxy each having 2 to 6 carbon atoms and 1 to

13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts; each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case doubly linked alkylene or dioxyalkylene with 1 to 6 each

Carbon atoms;

Cycloalkyl of 3 to 6 carbon atoms;

Sulfur -; and in each case optionally in the phenyl part once or several times, identically or differently, by halogen, cyano and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4

Carbon atoms and 1 to 9 identical or different

Halogen atoms and / or straight-chain or branched alkoxy or alkylthio with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy or haloalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms and / or optionally single or multiple, identical or different - distinguished by halogen and / or straight-chain or branched

Alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, substituted and in each case doubly linked alkylene or dioxyalkylene, each having 1 to 6 carbon atoms, substituted phenyl, phenoxy, phenylthio,

Benzyl, benzyloxy, phenylethyl or phenylethyloxy represents one of the groupings below

wherein

R ^{1 represents} hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C ₁ -C ₄ alkoxy,

R ~ represents hydrogen, amino, cyano or alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C, -C ₄ -alkoxy, and

R 'for hydrogen, cyano or for alkyl, alkenyl or alkynyl, each optionally substituted by halogen, cyano or C _] -C ₄ alkoxy, each having up to 6 carbon atoms, or for each optionally halogen, cyano, carboxy, C, -C ₄ Alkyl or C _] -C ₄ -alkoxy-carbonyl-substituted cycloalkyl or cycloalkyl alkyl having 3 to 6 carbon atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part,

represents hydrogen, halogen, cyano or alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals, optionally substituted by halogen, cyano or C ₁ -C ₄ alkoxy,

R ^{3 represents} alkyl having 1 to 6 carbon atoms,

R ^{6 is} hydrogen, amino, cyano or alkyl which is optionally substituted by halogen, cyano or C 1 -C ₄ -alkoxy, Alkoxy, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radicals, and

represents a single bond, represents oxygen, sulfur or represents in each case optionally substituted by halogen, hydroxy, C _r C ₄ alkyl, C, -C ₄ - haloalkyl or C ₃ -C ₆ cycloalkyl substituted alkanediyl, Al kendiyl, alkinediyl having in each case up to to 4 carbon atoms or one of the groupings below

-Q-CQ-, -CQ-Q-, -CH ₂ -Q-, -Q-CH ₂ -, -CQ-Q-CH ₂ -, -CH ₂ -Q-CQ-, -Q-CQ-CH ₂ -, -Q-CQ-Q-CH ₂ -, -N = N-, -S (0) _n -, -CH ₂ -S (0) _n -, -CQ-, -S (0) _n - CH ₂ -, -C (R ⁷ ) = N-0-, -C (R ⁷ ) = N-0-CH ₂ -, -NCR *) -, -CQ-NCR *) -,

-N (R ^S ) -CQ-, -Q-CQ-N (R *) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ -0-N = C (R ⁷ ) - , -NCR ^ -CQ-Q-, -CQ-N (R ⁸ ) -CQ-Q-, -N (R ⁸ ) -CQ-Q-CH ₂ -, -QC (R) = N-0-CH ₂ odei -N (R ^κ ) -C (R ⁷ ) = N-0-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

• 7

R for hydrogen, cyano, for optionally by halogen,

Cyano or C, -C ₄ alkoxy substituted alkyl, alkoxy,

Alkylthio, alkylamino or dialkylamino, each with 1 to 6

Carbon atoms in the alkyl groups or for cycloalkyl with 3 to 6 carbon atoms optionally substituted by halogen, cyano, carboxy, C _] -C ₄ alkyl or C, -C ₄ alkoxycarbonyl, and

R represents hydrogen, hydroxyl, cyano or alkyl which has 1 to 6 carbon atoms and is optionally substituted by halogen, cyano or C, -C ₄ -alkoxy or for halogen, cyano, carboxy, C, -C ₄ -alkyl or C1-C4 optionally by halogen Alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms,

m represents the numbers 0, 1 or 2 and,

Z for optionally single or multiple, identical or different by halogen, cyano, hydroxy, amino, C, -C - Alkoxy, C, -C ₄ alkylthio, C, -C ₄ alkylsulfinyl or C _r C ₄ - alkylsulfonyl (which may in each case optionally be substituted by halogen) substituted alkyl having 1 to 8 carbon atoms, 5 for each optionally substituted by halogen

Alkenyl or alkynyl each with up to 8 carbon atoms; for in each case optionally single or multiple, identical or different by halogen, cyano, carboxy, phenyl

10 (which may be replaced by halogen, cyano, C, - ^ -

Alkyl, C _j -C ₄ haloalkyl, C, -C ₄ alkoxy or C - C ₄ - haloalkoxy is substituted), C ₁ -C ₄ alkyl or C _r C ₄ - alkoxycarbonyl substituted cycloalkyl with 3 to 6 carbon atoms, 15 for phenyl, naphthyl or heterocyclyl with 3 to 7 ring members, each of which is optionally mono- or polysubstituted by identical or different substituents, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen , 20 where the possible substituents are preferably selected from the following list: halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, each straight-chain or branched alkyl, alkoxy, alkyl-25 thio, alkylsulfinyl or alkylsulfonyl, each with 1 until 6

Carbon atoms, in each case straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms, in each case straight-chain or branched haloalkyl, 30 haloalkoxy, haloalkylthio, haloalkylsulfinyl or

Haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 6 carbon atoms 35 and 1 to 13 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkyl amino, Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, Alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts; in each case optionally singly or multiply, identically or 5 differently, each substituted twice by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms linked alkylene or dioxyalkylene, each with 1 to 6 carbon atoms;

Cycloalkyl of 3 to 6 carbon atoms; Heterocyclyl or heterocyclyl-methyl, each with 3 to 7 ring members, of which 1 to 3 are identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur -; and in each case optionally in the phenyl, pyridyl or thienyl part, one or more times, identically or differently, by 20 halogen, cyano and / or straight-chain or branched

Alkyl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms 25 and / or straight-chain or branched alkoxy or

Alkylthio with 1 to 4 carbon atoms and / or straight-chain or branched haloalkoxy or haloalkylthio with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms 30 and / or optionally single or multiple, identical or different, by halogen and / or straight-chain or branched Alkyl with 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different 35 halogen atoms substituted, each linked twice

Alkylene or dioxyalkylene each having 1 to 6 carbon atoms, substituted phenyl, pyridyl, thienyl, phenoxy, Phenylthio, benzyl, benzyloxy, benzylthio phenylethyl or phenylethyloxy.

3. Compounds of formula (I) according to claim 1, in which

Ar ¹ for optionally substituted ortho, meta or para

Phenylene, for furandiyl, thiophene diyl, pyrroldiyl, pyrazole diyl, triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, pyridinediyl - (especially pyridine-2,3-diyl), pyrimidinediyl, pyrimidinediyl Is triazinediyl or 1,2,3-triazinediyl, the possible substituents being selected in particular from the list below: fluorine, chlorine, cyano, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, methylsulfinyl or methylsulfonyl,

^• >

Ar for phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, which are optionally mono- to trisubstituted in each case 1,3,4-thiadiazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, with the possible substituents preferably from the following The following are selected:

Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, Difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxy carbonyl, hydroxylomethyloxyethyloxyethyloxyethyloxyethyloxyethylmethyloxyethyloxyethyloxyethylmethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethylmethyloxyethyloxyethyloxyethyloxyethylmethyloxyethylmethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyloxyethyl methyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethylmethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxomethyl Methoximinoethyl or ethoximinoethyl; each optionally singly or multiply, identically or differently by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy, cyclopropyl, Cyclobutyl, cyclopentyl or cyclohexyl, and in each case optionally in the phenyl part once to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, or in each case optionally single or multiple, identical or different, by fluorine, methyl, chlorine, methyl or ethyl-substituted, in each case double-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

represents one of the groupings below

wherein

R ^{1 represents} hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, , 1

R 2 represents hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,

5 R ³ for hydrogen, cyano or for each optionally by

Fluorine, cyano, methoxy or ethoxy substituted methyl, ethyl n- or i-propyl, n-, i- or s-butyl, for allyl or propargyl or for in each case optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n - or i-propyl,

10 methoxy-carbonyl or ethoxy-carbonyl substituted

Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,

R ⁴ for hydrogen, fluorine, chlorine, bromine, cyano or for 15 each optionally by fluorine, chlorine, cyano, methoxy or

Ethoxy substituted methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino or dimethylamino,

R ^{5 represents} methyl, ethyl n- or i-propyl, n-, i- or s-butyl,

20 R ^{6 stands} for hydrogen, amino, cyano or for methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino which is optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, and

G for a single bond, for oxygen, sulfur or for

25 each optionally by fluorine, chlorine, bromine, hydroxy,

Methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted methylene, dimethylene (ethane-l, 2-diyl), ethylene-l, 2-diyl, ethyne-l, 2-diyl or one of the groupings 30 below -Q-CQ-. -CQ-Q- -CH ₂ -Q-, -Q-CH ₂ - -CQ-Q-CH ₂ -, -CH ₂ -Q-CQ-,

-Q-CQ-CH ₂ - -Q-CQ-Q-CH ₂ - -N = N-, -S (0) _n - -CH ₂ -S (0) _n - -CQ-, -S (0) _n -CH ₂ - -C (R ⁷ ) = N-0- -C (R ⁷ ) = N-0-CH ₂ - -N (R ^K ) - - 57 -

-CQ-N (R ^X ) -, -N (R *) - CQ-, -Q-CQ-NCR *) -, -N = C (R ⁷ ) -Q-CH2-, -CH ₂ -0- N = C (R ⁷ ) -, -N (R ^X ) -CQ-Q-, -CQ-N (R ^X ) -CQ-Q-, -N (R) -CQ-Q-CH ₂ -, - QC (R ⁷ ) = N-0-CH ₂ or

-N (R ^κ ) -C (R ⁷ ) = N-0-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

R for hydrogen, cyano, for methyl, ethyl, n- or i-propyl, n-, i- or s- butyl, methoxy, ethoxy, propoxy, butoxy, optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, Methyl thio, ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for each optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl sub¬ substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and

R represents hydrogen, hydroxy, cyano or methyl, ethyl, n- or 1-, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy

Propyl, n-, i-, s- or t-butyl or for cyclopropyl, cyclobutyl, cyclopentyl optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl or cyclohexyl,

m represents the numbers 0, 1 or 2 and,

Z for optionally up to five times by fluorine, chlorine,

Bromine, cyano, hydroxy, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine are substituted) substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; for allyl, crotonyl, 1-methyl-5-allyl, propargyl or 1-methyl-propargyl, each optionally monosubstituted to trisubstituted by fluorine, chlorine or bromine; for in each case optionally up to six times by fluorine, chlorine, bromine, cyano, carboxy, phenyl (which if appropriate by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, trifluoromethyl, 10 methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or

Trifluoromethoxy is substituted), methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; for in each case monosubstituted to trisubstituted 15 phenyl, naphthyl, furyl, thienyl, oxazolyl, isoxazolyl,

Thiazolyl, isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 2,4-thi adiazolyl, 1, 3, 4-thi adi azolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1, 2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, oxiranyl, oxetanyl, tetrahydrofuran, perhydropyranyl, pyrrolidinyl, piperidinyl or

Morpholinyl is available, the possible substituents preferably being selected from the list below:

Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, 25 carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy , n- or i- propoxy, methylthio, ethylthio, n- or i-propylthio, methyl¬ sulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethylthio, trifluoromethylthio, trifluoromethyl, Trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxy-35 carbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonimethyl, methoximino-hydroxonimethyl, oxy-hydroxino-hydroximethyl-oxy methyl, ethoximinomethyl, methoximinoethyl or ethoximinoethyl; each optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- or i-propyl, in each case doubly linked trimethylene (propane-1,3-diyl), methylenedioxy or ethylenedioxy,

Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and in each case optionally in the phenyl, pyridyl or thienyl part in one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloro methoxy, trifluoroethoxy, trifluoromethoxy difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, or in each case, if necessary, differently or singly or differently phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy

4. Compounds of formula (I) according to claim 1, in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{3 represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Ar for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, optionally monosubstituted to trisubstituted by identical or different substituents, Pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, the possible substituents preferably being selected from the list below - 60 -

Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy 5, difluorochloromethoxy, trifluoroethoxy, Difluo- methylthio, trifluoromethylthio, difluorochloromethylthio, trifluoro-methylsulfinyl, or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, Methox- iminoethyl, ethoximinoethyl ,

10 each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy,

and in each case optionally in the phenyl part in one to three times, identical or different by fluorine, chlorine, bromine, cyano, methyl,

15 ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl,

Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or, where appropriate, mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl,

20 each of two-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

E represents one of the groupings below

CH

^

'R ¹ R 2

wherein

25 R and R "each represent methoxy,

G for oxygen, sulfur or for dimethylene optionally substituted by fluorine, chlorine or bromine (Ethane-l, 2-diyl), ethene-l, 2-diyl or one of the groupings below

-CQ-Q-, -CH ₂ -Q-; -Q-CH ₂ -, -CQ-Q-CH ₂ -, -Q-CQ-Q-CH ₂ -, -N = N-, -S (0) _n -CH _> -C (R ⁷ ) = N -0-, -C (R ⁷ ) = N-0-CH ₂ -, -N (R ⁸ ) -CQ-, -Q-CQ-N (R ⁸ ) -, -N = C (R ⁷ ) - Q-CH2-, -CH ₂ -0-N = C (R ⁷ ) -,

-N (R ⁸ ) -CQ-Q-, -CQ-N (R ⁸ ) -CQ-Q-, -N (R ⁸ ) -CQ-Q-CH ₂ -, -QC (R ⁷ ) = N- 0-CH ₂ or -N (R) -C (R ⁷ ) = N-0-CH ₂ -, where

n represents the numbers 0, 1 or 2,

Q represents oxygen or sulfur,

R ^{7 represents} hydrogen, cyano, methyl, ethyl or cyclopropyl and

R ^{8 represents} hydrogen, methyl, ethyl or cyclopropyl,

m represents 0, 1 or 2 and,

Z represents phenyl, 1, 2,4-thiadiazolyl, 1,3,4-thiazadylol, 1, 2,4-oxadiazolyl, 1, 3, 4-oxadiazolyl, pyridinyl, optionally monosubstituted to trisubstituted by identical or different substituents, Pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1, 2,4-triazinyl or 1,3,5-triazinyl, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine , Cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl , ethylsulfinyl, methylsulfonyl or ethylsulfonyl, ethoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro, difluoromethylthio, trifluoromethylthio, Difluorchlormethyl¬ thio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxy carbonyl, ethoxy carbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case optionally easy to four alike, identical or different, substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case double-linked methylenedioxy or ethylenedioxy, and in each case optionally in the phenyl, pyridyl or thienyl part, one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, 1-, s- or t- Butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally substituted one or more times, identically or differently by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case two-linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio

Compounds of the general formula (Ia),

in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{3 represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-dιyl or thιophen-2,3-diyl,

Ar for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, optionally monosubstituted to trisubstituted by identical or different substituents, Pyridinyl, pyrimidinyl,

Pyridazinyl, pyrazinyl, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, Methoxy, ethoxy, n- or i-propoxy. Methylthio, ethylthio, n- or l-propylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl, ethifoxymethyloxyethyl, ethoxymethyloxyethylmethyl, ethoxymethyloxymethyloxymethyloxymethyloxymethyloxoxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyloxymethyl or differently substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, and in each case in the phenyl part in each case simply to triple, identically or differently by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i -Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally one or more times, the same or different by

Fluorine, chlorine, methyl, trifluoromethyl or ethyl substituted, in each case double-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

^{^} C ~ E stands for ^M.

^ OCH,

represents 0, 1 or 2 and,

Z ¹ represents phenyl which is in each case monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, Trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, Ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy,

6. Compounds of the general formula (Ib),

in which

A ^{1 represents} hydrogen or methyl,

A "represents hydrogen, methyl or ethyl,

A ^{3 represents} hydrogen, methyl, ethyl or cyano,

Ar ^{1 represents} ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,

Pyridazinyl, pyrazinyl, where the possible substituents are preferably selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl,

Methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl, trifluoromethylethylmethyloxoxomethyl, ethoxoxy each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, and in each case in the phenyl part, in each case simply to triple, identically or differently by fluorine, chlorine, bromine, cyano, methyl ,

Ethyl, n- or i-propyl, h-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or, if appropriate, simply or several times, identical or different, substituted by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case double-linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

c- stands for II

N Η OCH.

m represents 0, 1 or 2 and,

, "> Z ~ stands for phenyl, pyridyl or pyrimidyl which is optionally monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio,

Ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trift uorethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro-ethoxy, difluoromethylthio, trifluoromethylchlorofluoromethylchlorofluoromethylchlorofluoromethyl, trifluoromethylchlorofluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl or trifluoromethyl

Methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each having two bonds, methylenedioxy or ethylenedioxy, Compounds of the general formula (Ic),

in which

A ^{1 represents} hydrogen or methyl,

A ^{2 represents} hydrogen, methyl or ethyl,

A ^{Λ represents} hydrogen, methyl, ethyl or cyano,

Ar for phenyl, 1,2,4-thionadazolyl, 1,3,4-thadadazolyl, 1,2,4-oxadazolyl, 1, 3,4-oxadazolyl, 1,3,4-oxadazolyl, which is optionally monosubstituted to trisubstituted, identically or differently, Pyridinyl, pynmidinyl, pyndazinyl, pyrazinyl, the possible substituents preferably being selected from the list below fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or l-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy,

Trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethyl methylthio, trifluoromethylthio, difluorochloromethylthio, Tπfluor- methylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, Methox- lminoethyl, ethoximinoethyl, in each case optionally mono- to tetrasubstituted by identical or different fluorine, chlorine, methyl, Trifluoromethyl or ethyl substituted, each linked twice methylenedioxy or ethylenedioxy, and in each case optionally in the phenyl part single to triple, identical or different by fluorine, chlorine, bromine, cyano, methyl,

Ethyl, n- or i-propyl, n-, I-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, difluoro- chloromethoxy, trifluoroethoxy, trifluoromethoxy or, where appropriate, mono- or polysubstituted, identically or differently, fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,

represents one of the groupings below

wherein

CH

V

R and R "each represent methoxy,

m represents 0, 1 or 2 and,

Z for 1,2,4-thiadiazolyl, 1, 3,4-thiadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyrimidinyl, or 1,3, which are each substituted once or twice, identically or differently , 5-triazinyl, the possible substituents preferably being selected from the following list: fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoro- methylthio, trifluoromethylthio, difluorochloromethylthio, trifluoro methylsulfinyl or trifluoromethylsulfonyl, and in each case optionally in the phenyl, pyridyl or thienyl part, one to three times, identically or differently, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or in each case optionally once or several times, identically or differently by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case substituted methylene dioxy or linked twice Ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio.

8. pesticide, characterized by a content of at least one compound of the formula (I) according to claim 1.

9. A method for controlling pests, characterized in that compounds of the formula (I) according to Claim 1 are allowed to act on pests and / or their habitat.

10. Use of compounds of formula (I) according to claims 1 to 7 for combating pests.

1 1 Process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claims 1 to 7 are mixed with extenders and / or surface-active agents.

12. A process for the preparation of carboxamides of the general formula (I), characterized in that carboxylic acid derivatives of the general

Formula (II)

in which

Ar ¹ , E, G and Z have the meaning given in claim 1 and

R represents hydroxy, halogen or alkoxy,

with an amine of the general formula (III)

in which

A ¹ , A ² , A ³ , Ar ² and m have the meaning given above,

or with a hydrogen halide thereof

if appropriate in the presence of an acid acceptor, if appropriate in the presence of a condensing agent and if appropriate in the presence of a diluent