DE4443641A1 - Substituted carboxamides - Google Patents

Abstract

Described are carboxylic acid amides of formula (I), as well as their use as pesticides, wherein A<1> is hydrogen or alkyl; A<2> is hydrogen or alkyl; A<3> is hydrogen, alkyl or cyano; Ar<1> is in either case optionally substituted arylene or heteroarylene; Ar<2> 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-, -CH2-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-CH2, -N(R<8>)-, -CQ-N(R<8>)-, -N(R<8>)-CQ-, -Q-CQ-N(R<8>)-, -N=C(R<7>)-Q-CH2-, -CH2-O-N=C(R<7>)-, -N(R<8>)-CQ-Q-, -CQ-N(R<8>)-CQ-Q-, -N(R<8>)-CQ-Q-CH2, -Q-C(R<7>)=N-O-CH2- or -N(R<8>)-C(R<7>)=N-O-CH2-, 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; R<8> 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

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

It is known that certain substituted carboxamides are fungicidal have shafts (cf. EP-A 398692, EP-A 468775, DE-A 40 30 038, WO-A 92/13830). However, the effect of these compounds is in many cases unsatisfactory.

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

in which
A¹ represents hydrogen or alkyl.
A² represents hydrogen or alkyl.
A³ represents hydrogen, alkyl or cyano.
Ar¹ stands for optionally substituted arylene or heteroarylene.
Ar² stands for optionally substituted aryl or heteroaryl.
E represents a 1-alkene-1,1-diyl grouping which contains a radical R 1 in the 2-position, or represents a 2-aza-1-alkene-1,1-diyl grouping which is in 2- Position contains a radical R², or represents an optionally substituted imino group ("Azamethylene", N-R³), or represents a 3-aza-1-propene-2,3-diyl group, which is in the 1-position contains a radical R⁴ and in the 3-position a radical R⁵, or represents a 3-oza-1-propene-2,3-diyl grouping which contains a radical R⁴ in the 1-position, or represents a 3-thia 1-propen-2,3-diyl grouping which contains a radical R⁴ in the 1-position, or represents a 1-aza-1-propene-2,3-diyl grouping which has a radical in the 1-position R⁶ and in the 3-position contains a radical R⁵, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R⁴ in the 1-position and a radical R⁵ in the 3-position, or stands for a 1,3-diaza-1-propene-2,3-diyl grouping, in the 1-position a radical R⁶ and contains a R⁵ radical in the 3-position, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a R⁶ radical in the 1-position, or represents a 1-aza- 3-thia-1-propene-2,3-diyl grouping, which contains a radical R⁶ in the 1-position, wherein
R¹ represents hydrogen, halogen, cyano or any optionally substituted alkyl, alkoxy, alkylthio, alkylamino or di alkylamino,
R² stands for hydrogen, amino, cyano or for optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
R³ represents hydrogen, cyano or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
R⁴ represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R⁵ represents alkyl,
R⁶ represents hydrogen, amino, cyano or optionally substituted alkyl, alkoxy, alkylamino or dialkylamino.
G for a single bond, for oxygen, sulfur or for alkanediyl, alkenediyl, alkynediyl or one of the following groups, each optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl
-Q-CQ-, -CQ-Q-, -CH₂
-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 (R⁷) = NO-, -C (R7) = NO-CH₂-, -N (R⁸) -, -CQ-N (R⁸) -,
-N (R⁸) -CQ-, -Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO- CH₂- or -N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R⁸ represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
m represents the numbers 0, 1 or 2, and
Z represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl.

It was also found that the new substituted carboxamides general formula (I) is obtained when carboxylic acid derivatives of the general Formula (II)

in which
Ar¹, E, G and Z have the meaning given above and
R represents hydroxy, halogen or alkoxy,
with an amine of the general formula (III)

in which
A¹, A², A³, Ar² 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 general formula (I) show very strong fungicidal activity.  

The compounds according to the invention can optionally be mixed various possible isomeric forms, in particular stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E- and the Z- Isomers, as well as the threo- and erythro- as well as the optical isomers, be arbitrary mixtures of these isomers, as well as the possible tautomeric forms claimed.

The invention preferably relates to compounds of the formula (I) in which
A¹ represents hydrogen or alkyl having 1 to 6 carbon atoms,
A² represents hydrogen or alkyl having 1 to 6 carbon atoms,
A³ represents hydrogen, alkyl having 1 to 6 carbon atoms or cyano,
Ar¹ represents in each case optionally substituted phenylene or naphthylene or for heteroarylene with 5 or 6 ring members, of which at least one is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being from the list below 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 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 NEN halogen atoms, each 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, in each case optionally times or more, the same or different, halogen-substituted 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 by two linked alkylene or Dioxyalkylene with 1 to 6 carbon atoms each,
Ar² for phenyl, naphthyl or heteroaryl with 3 to 7 rings, each of which is optionally mono- or polysubstituted, the same or differently, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
each straight-chain or branched alkyl, alkoxy, alkylthio, alkyl sulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;
each straight-chain or branched alkenyl or alkenyloxy, each with 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;
each straight-chain or branched alkylamino, dialkylamino, alkyl carbonyl, 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 double-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 part once or several times, identically or differently
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 having 1 to 4 carbon atoms
and / or straight-chain or branched haloalkoxy or haloalkylthio having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or 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 double-linked Alkylene or dioxyalkylene each having 1 to 6 carbon atoms, substituted phenyl, phenoxy, phenylthio, benzyl, benzyloxy, phenylethyl or phenylethyloxy.
E represents one of the groupings below:

wherein
R¹ stands for hydrogen, halogen, cyano or for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C₁-C jeweilsalkoxy, each having 1 to 6 carbon atoms in the alkyl radicals,
R² stands for hydrogen, amino, cyano or for alkyl, alkoxy, alkyl amino or dialkylamino, each optionally substituted by halogen, cyano or C₁-C Alkalkoxy, each having 1 to 6 carbon atoms in the alkyl radicals, and
R³ for hydrogen, cyano or for alkyl, alkenyl or alkynyl each optionally substituted by halogen, cyano or C₁-C₄alkoxy, each having up to 6 carbon atoms or for each optionally halogen, cyano, carboxy, C₁-C₄alkyl or C₁- C₄-alkoxycarbonyl-substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part,
R⁴ 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 C₁-C₄alkoxy,
R⁵ represents alkyl having 1 to 6 carbon atoms,
R⁶ represents hydrogen, amino, cyano or alkyl, alkoxy, alkyl amino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C₁-C₄alkoxy, and
G for a single bond, for oxygen, sulfur or for in each case optionally substituted by halogen, hydroxy, C₁-Ci-alkyl, C₁-C₄-haloalkyl or C₃-C₆-cycloalkyl, alkanediyl, alkenediyl, alkindiyl, each having up to 4 carbon atoms or one of the groupings below
-Q-CQ-, -CQ-Q-, -CH₂-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 (R⁷) = NO-, -C (R⁷) = NO-CH₂-, -N (R⁸) -, -CQ-N (R⁸) -,
-N (R⁸) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO- CH₂ or -N ( R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ for hydrogen, cyano, optionally substituted by halogen, cyano or C₁-C₄alkoxy alkyl, alkoxy, alkylthio, alkyl amino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for each optionally by halogen, cyano, carboxy, C₁ -C₄-alkyl or C₁-C₄-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and
R⁸ for hydrogen, hydroxy, cyano or for optionally substituted by halogen, cyano or C₁-C₄-alkoxy-substituted alkyl having 1 to 6 carbon atoms or for optionally by halogen, cyano, carboxy, C₁-C₄-alkyl or C₁-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, the same or different, by halogen, cyano, hydroxy, amino, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl (which are each optionally substituted by halogen can) substituted alkyl of 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, the same or different, by halogen, cyano, carboxy, phenyl (which may be by halogen, cyano, C₁-C₄-alkyl, C₁-C₄-halogen alkyl, C₁-C₄-alkoxy or C₁-C₄- Haloalkoxy is substituted), C₁-C₄-alkyl or C₁-C₄-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, carb amoyl, 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;
each 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;
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 singly or multiply, 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 each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
Heterocyclyl or heterocyclyl-methyl with 3 to 7 rings each, 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
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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or optionally singly or multiply 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 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 are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with Heteroatoms, such as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branches.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

The invention relates in particular to compounds of the formula (I) in which
A¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
A² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
A³ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or cyano,
Ar¹ for each 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-diyl (in particular ), Pyrimidinediyl, pyridazine 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,
Ar² 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, where the possible substituents are preferably from the list below 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, trifluorethoxy, trifluoromethylthioiflormifluoromifluoromifluoromifluoromethyl , Ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxy carbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, 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 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 substituted one or more times, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl substituted methyl, in each case substituted by two Ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,
E represents one of the groupings below

wherein
R1 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,
R² represents hydrogen, amino, cyano or methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
R³ for hydrogen, cyano or for methyl, ethyl n- or i-propyl, n-, i- or s-butyl, optionally substituted by fluorine, cyano, methoxy or ethoxy, 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,
R⁴ 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,
R⁵ represents methyl, ethyl n- or i-propyl, n-, i- or s-butyl,
R⁶ 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 methylene, dimethylene (ethane-1.) Which is optionally substituted by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl , 2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the groups below
-Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-,
-Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O) _n -, -CH₂S (O) _n , -CQ-,
-S (O) _n -CH₂, -C (R⁷) = NO-, -C (R⁷) = NO-CH₂-, -N (R⁸) -,
-CQ-N (R⁸) -, -N (R⁸) -CQ-, -Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-,
-CH₂-ON = C (R⁷) -, -N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-,
-N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO-CH₂ or
-N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ represents hydrogen, cyano, 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 or cyclopropyl, cyclobutyl , Cyclopentyl or cyclohexyl, and
R⁸ for hydrogen, hydroxy, cyano or for any given by fluorine, chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for optionally cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxy-carbonyl,
m represents the numbers 0, 1 or 2 and,
Z for methyl which is optionally mono- to pentasubstituted 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), 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 optionally one to six times by fluorine, chlorine, bromine, cyano, carboxy, phenyl (which optionally 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, the possible substituents preferably being selected from the list below:
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, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoro ethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoro-methylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl , Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximino methyl, methoximinoethyl;
each optionally singly or multiply, identical or different 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, 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 difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, or each optionally single or multiple, the same or different, trifluoromethyl, fluorine, chlorine Ethyl-substituted, in each case double-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
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidinyl, each optionally monosubstituted to trisubstituted in the same or different ways , Pyridazinyl, pyrazinyl, 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 ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, ethylifluoromethyl, ethoxymethyloxymethyloxy, methylifoxyloxymethyloxy,
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, trifluoromoxy or in each case optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each substituted by two linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E represents one of the groupings below

wherein
R¹ and R² each represent methoxy,
G for oxygen, sulfur or for in each case optionally substituted by fluorine, chlorine or bromine, dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or one of the following groups
-CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -Q-CQ-Q-CH₂-, -N = N-,
-S (O) _n -CH₂-, -C (R⁷) = NO-, -C (R⁷) = NO-CH₂-, -N (R⁸) -CQ-,
-Q-CQ-N (R⁸) -, NC (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-,
-QC (R⁷) = NO-CH₂ or -N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ represents hydrogen, cyano, methyl, ethyl or cyclopropyl and
R⁸ 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, pyrimidinyl, each optionally monosubstituted to trisubstituted in the same or different ways , 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 ethyl sulfonyl, trifluoromethyl, trifluoroethyl, 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, 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 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
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidinyl, each optionally monosubstituted to trisubstituted in the same or different ways , Pyridazinyl, pyrazinyl, 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 ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethifluoromethyloxyethyl, ethoxymethyloxyethyl, ethoxymethyloxyethyl, methylifoxyloxymethyloxy, methylifoxy
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, trifluoromoxy or in each case optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each substituted by two linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E for

stands
m represents 0, 1 or 2 and,
Z¹ represents phenyl which is optionally 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 ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethifluoromethyloxyethyl, ethoxymethyloxyethyl, ethoxymethyloxyethyl, methylifoxyloxymethyloxy, methylifoxy
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy,
compounds of the general formula (Ib) are also very particularly preferred,

in which
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidinyl, each optionally monosubstituted to trisubstituted in the same or different ways , Pyridazinyl, pyrazinyl, 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 ethyl sulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethifluoromethyloxyethyl, ethoxymethyloxyethyl, ethoxymethyloxyethyl, methylifoxyloxymethyloxy, methylifoxy
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, trifluoromoxy or in each case optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each substituted by two linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E for

stands
m represents 0, 1 or 2 and,
Z² stands for phenyl, pyridyl or pyrimidyl which may be 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 ethyl sulfonyl, trifluoromethyl, trifluoroethyl, 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,
further particularly preferred are compounds of the general formula (Ic),

in which
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar² for each optionally monosubstituted to triple, identical or differently substituted phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidinyl , Pyridazinyl, pyrazinyl, the possible substituents preferably being selected from the following payment:
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, trifluoromethyloxyethyl, ethifylmethyloxethyl, ethoxymethyloxymethyloxyethyloxyethyloxymethyloxoxy, methylifoxyloxymethyloxoxy, methylifoxy
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 singly or multiply, 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,
E represents one of the groupings below

wherein
R¹ and R² each represent methoxy,
m represents 0, 1 or 2 and,
Z³ for 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyrimidinyl, or 1,3, each substituted once or twice, identically or differently , 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethyltrifluoromethyl, trifluoromethyl
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 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.

The radicals listed above or specified in preferred ranges definitions apply to both the end products of formula (I) and correspondingly for the respective starting materials or Intermediates.

These residual definitions can be among themselves, that is, between the specified combinations for preferred connections, any combination will.

The starting materials for carrying out the process according to the invention The required carboxylic acid derivatives are generally defined by the formula (II). In Ar¹, E, G and Z of this formula (II) preferably or in particular have those ge meanings already related to the description of the he Compounds of formula (I) according to the invention as preferred or ins particularly preferred for Ar 1, E, G and Z; R is preferably  for alkoxy with 1 to 4 carbon atoms, in particular for methoxy or ethoxy, for hydroxy or chlorine.

The starting materials of formula (II) are known and / or can be per se known processes can be produced (cf. EP-A 178826, EP-A 242081, EP-A 382375, EP-A 493711, EP-A 432503, DE-A 39 38 054).

The amines to be used further as starting materials are represented by the formula (III) generally defined. In formula (III), A¹, A², A³, Ar² and m preferably have or in particular the meaning already in connection with the Be writing the compounds of formula (I) according to the invention as preferred or was specified as particularly preferred for A¹, A², A³, Ar² and m.

The starting materials of formula (III) are known organic synthesis chemicals and / or can be produced by methods known per se will.

The process according to the invention is optionally used in the presence of a ten acid acceptor performed. All the usual inorganic ones come as such or organic bases in question. 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 me ethylate, sodium ethylate, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, Ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium ace tat, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, and tertiary amines, such as trimethylamine, tri ethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), di azabicyclonones (DBN) or diazabicycloundecene (DBU).

If appropriate, the process according to the invention is suitable in the presence of a Neten condensing agent performed. As such, everyone usually comes condensing agents that can be used for such amidation reactions. Acid halide formers such as phosgene, phosphorus tribromide, Phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl  chloride; Anhydride formers such as ethyl chloroformate, chloroformate methyl ester or methanesulfonyl chloride; Carbodiimides such as N, N'-dicydohexyl carbodiimide (DCC) or other common condensing agents such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbo nyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride.

The process according to the invention is optionally carried out in the presence of a Diluent carried out. As a diluent to carry out the The method according to the invention includes water and organic solvents Consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as gasoline, Benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, Cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ether like Diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dime ethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethyl formamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or Hexamethylphosphoric triamide; Esters such as methyl acetate or acetic acid reethyl esters, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol, ethylene glycol monomethyl ether, ethylene glycol mo noethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally works one at temperatures between -20 ° C and + 200 ° C, preferably at temperature ren between 0 ° C and 150 ° C.

To carry out the process according to the invention, one starts out per mole Carboxylic acid derivative of the formula (II) in general 1 to 5 mol, preferably 1.0 up to 2.5 moles of amine.

Carrying out the reaction, working up and isolating the reaction products takes place according to known methods (cf. the production examples).  

The active compounds according to the invention have a strong microbicidal action and can be useful to combat unwanted microorganisms be used. The active ingredients are for use as pesticides, particularly suitable as fungicides.

Fungicides in crop protection are used to combat plas modiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Some pathogens of fungal diseases that 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, Pyricuiaria 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, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of the plant necessary concentrations, allows treatment from above plant parts, as well as a treatment of plant and seed and of the floor.

The active compounds according to the invention can be used with particularly good success Control of cereal diseases, such as against Erysiphe species, Leptosphaeria, Pyrenophora and Cochliobolus species or diseases in Fruit and vegetable cultivation, such as used against Podospherea species will. In addition, the active compounds according to the invention show a particularly good one in vitro effect.

The active ingredients can depend on their respective physical and / or chemical properties converted into customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, Granules, aerosols, very fine encapsulations in polymeric substances and in Envelopes for seeds, as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents, under Pressurized liquefied gases and / or solid carriers, if necessary using surface-active agents, ie emulsifiers and / or Dispersing agents and / or foaming agents. In case of use of water as an extender can e.g. B. also organic solvents Auxiliary solvents can be used. As liquid solvents come in essential in question: aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethy 18529 00070 552 001000280000000200012000285911841800040 0002004443641 00004 18410lene, or methylene chloride, aliphatic hydrocarbons, such as  Cyclohexane or paraffins, e.g. B. 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; with liquefied gaseous extenders or carriers are meant such liquids which are gaseous at normal temperature and pressure, e.g. B. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide; as solid carriers come into question: B. natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silica, alumina and silicates; as solid carriers for granules come into question: z. B. 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; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and Protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 Weight percent active ingredient, preferably between 0.5 and 90%.  

The active compounds according to the invention can be used as such or in their Formulations also in a mixture with known fungicides, bactericides, Acaricides, nematicides or insecticides can be used, e.g. B. that To broaden the spectrum of activity or to prevent the development of resistance. In 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-carboxa-nilide; 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,
Dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone,
Edifenphos, epoxyconazole, ethirimol, etridiazole,
Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropi-morph, Fentinacetate, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolafolidol, Futinaflidol, Folut Furalaxyl, furmecyclox,
Guazatine,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan,
Kasugamycin, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, nuanmol,
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, tecnazene, tetraconazole, thiabendazole, Thicyofen, thiophanate-methyl, thiram, Tolclophos-methyl, tolylfluanid, triadimefon, Triadi menol, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Validamycin A, vinclozolin,
Zineb, ziram

Bactericides:
Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, 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, Cartap, CGA 157 419, CGA 184699, Chlorethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clofhrinhrin, Clofintrinhrin, Clofinhrin, Clofinhrin, Clofintrinin Cyhalothrin, cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethopro phos, Etofenprox, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenproothate, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufone
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin, Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin,
Naled, NC 184, M 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, Pyrophophos, Pyroflosophroat, Pym 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, Thio methon, Thionazin, Thuringiensin, Tralomethrononium, Triaromenontronium, Triaromenhroniaz, Triaratheniazin, Triaratheniazon
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 substances can be used as such, in the form of their formulations or in the form thereof prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules are used will. The application is done in the usual way, e.g. B. by pouring, Spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to use the active ingredients according to the UItra low volume method apply or the drug preparation or the drug itself in the Inject soil. The seeds of the plants can also be treated.

When treating parts of plants, the active substance concentrations can be in the application forms can be varied in a larger area: 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 are generally from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.

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 at the site of action required.

Manufacturing examples example 1

A mixture of 2.5 g (8 mmol) of 2-methoximino-2- [2- (2-methylphenoxymethyl) - phenyl] -acetic acid methyl ester and 1.14 g (8 mmol) 4-chlorobenzylamine is in the Melt stirred at 120 ° C for 12 hours. After cooling in dichloromethane taken up, once with water, then with IN hydrochloric acid and then again with Washed water, dried over sodium sulfate and filtered. The filtrate is in the Concentrated vacuum and the residue with petroleum ether / ethyl acetate (5: 1) on silica gel chromatographed.

1.4 g (42% of theory) of N- (4-chlorobenzyl) -2-methoximino-2- [2- (2- methylphenoxymethyl) phenyl] acetic acid amide as an oil.

1 H-NMR (CDCl₃, TMS): δ = 3.93; 2.20 ppm  

Example 2

To a solution of 50 g (0.167 mol) of 2-methoximino-2- [2- (2-methylphenoxyme thyl) phenyl] acetic acid in 300 ml of tetrahydrofuran is added dropwise in succession -10 ° C 23.4 ml (0.167 mol) triethylamine and 22.7 g (0.167 mol) Isobutyl chloroformate and stirred for 2 hours at -10 ° C. Then drips a solution of 17.9 g (0.167 mol) of benzylamine in 50 ml of tetrahydrofuran within 30 minutes, stirring for 2 hours at -10 ° C and another 18 hours 20 ° C. The mixture is concentrated in vacuo, taken up in dichloromethane, once with water, then with 1N hydrochloric acid and then again with water washed, dried over sodium sulfate, filtered and concentrated again. Of the The residue is stirred with diisopropyl ether, the crystals thus obtained filtered off and dried.

52 g (80% of theory) of N-benzyl-2-methoximino-2- [2- (2-methyl phenoxymethyl) phenyl] acetic acid amide melting point 68-69 ° C.  

Example 3

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

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

Analogous to Examples 1 to 3 and in accordance with the general description of the manufacturing method according to the invention, for example, the in of the compounds listed in Table 1 below:  

Table 1

Examples of use Example A Erysiphe test (wheat) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part 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 one Concentration.

To test for curative effectiveness, young plants with spores from Erysiphe graminis f.sp. tritici pollinated. 48 hours after inoculation the plants with the active ingredient preparation in the application rate indicated sprayed.

The plants are grown in a greenhouse at a temperature of approx. 20 ° C and set up at a relative humidity of approx. 70% to achieve the Favor development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. B. the connection according to production example (6) in a exemplary active ingredient application rate of 250 g / ha an efficiency of 100%.  

Example B Erysiphe test (wheat) / protectiv

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part 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 one Concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate.

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

The plants are grown in a greenhouse at a temperature of approx. 20 ° C and set up at a relative humidity of approx. 80% to achieve the Favor development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. B. the compounds according to preparation examples (2), (6), (10) and (11) with an exemplary active ingredient application rate of 250 g / ha an efficiency of 100%.  

Example C Erysiphe test (barley) / curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part 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 one Concentration.

To test for curative effectiveness, young plants with spores from Erysiphe graminis f.sp. hordei pollinated. 48 hours after inoculation the plants with the active ingredient preparation in the application rate indicated sprayed.

The plants are grown in a greenhouse at a temperature of approx. 20 ° C and set up at a relative humidity of approx. 80% to achieve the Favor development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. B. the connection according to production example (6) in a exemplary active ingredient application rate of 250 g / ha an efficiency of 100%.  

Example D Erysiphe test (barley) / protectiv

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part 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 one Concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate.

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

The plants are grown in a greenhouse at a temperature of approx. 20 ° C and set up at a relative humidity of approx. 80% to achieve the Favor development of mildew pustules.

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. B. the connection according to preparation example (10) an effective amount of active ingredient of 250 g / ha of 100%.  

Example E Podosphaera test (apple) / protectiv

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part 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 one Concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants are pollinated with conidia of the powdery mildew pathogen Podosphaera leucotricha inoculated.

The plants are grown in a greenhouse at 23 ° C and at a relative Humidity of approx. 70% set up.

Evaluation is carried out 10 days after the inoculation.

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

Claims (12)

1. Carboxamides of the general formula (I) in which
A¹ represents hydrogen or alkyl.
A² represents hydrogen or alkyl.
A³ represents hydrogen, alkyl or cyano.
Ar¹ stands for optionally substituted arylene or heteroarylene.
Ar² stands for optionally substituted aryl or heteroaryl.
E represents a 1-alkene-1,1-diyl grouping which contains a radical R 1 in the 2-position, or represents a 2-aza-1-alkene-1,1-diyl grouping which is in 2- Position contains a radical R², or represents an optionally substituted imino group ("Azamethylene", N-R³), or represents a 3-aza-1-propene-2,3-diyl grouping, which is in the 1-position contains a radical R⁴ and in the 3-position a radical R⁵, or stands for a 3-oza-1-propene-2,3-diyl grouping which contains a radical, R⁴ in the 1-position, or for a 3-thia -1-propen-2,3-diyl grouping which contains a radical R 1 in the 1-position, or stands for a 1-aza-1-propene-2,3-diyl grouping which has a 1-position Radical R⁶ and in the 3-position contains a radical R⁵, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R⁴ in the 1- position and a radical R⁵ in the 3-position, or represents a 1,3-diaza-1-propene-2,3-diyl grouping which has a radical R 1 in the 1-position d in the 3-position contains a radical R⁵, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R⁶ in the 1-position, or represents a 1-aza -3-thia-1-propen- 2,3-diyl grouping, which contains a radical R⁶ in the 1-position, wherein
R¹ represents hydrogen, halogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R² stands for hydrogen, amino, cyano or for optionally optionally substituted alkyl, alkoxy, alkylamino or di alkylamino, and
R³ represents hydrogen, cyano or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,
R⁴ represents hydrogen, halogen, cyano or optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
R⁵ represents alkyl,
R⁶ stands for hydrogen, amino, cyano or for optionally substituted alkyl, alkoxy, alkylamino or dialkyl amino.
G for a single bond, for oxygen, sulfur or for alkanediyl, alkenediyl, alkynediyl or one of the following groups, each optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl
-Q-CQ-, -CQ-Q-, -CH₂-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 (R⁷) = NO-, -C (R7) = NO-CH₂-, -N (R⁸) -, -CQ-N (R⁸) -,
-N (R⁸) -CQ-, -Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO-CH₂- or -N (R⁸) -C (R⁷) = NO-CH₂, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
R⁸ represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl,
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
A¹ represents hydrogen or alkyl having 1 to 6 carbon atoms,
A² represents hydrogen or alkyl having 1 to 6 carbon atoms,
A³ represents hydrogen, alkyl having 1 to 6 carbon atoms or cyano,
Ar¹ 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 from the list below are selected:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, 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, 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, in each case optionally egg n times or more, identical or different, 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 bonded alkylene or dioxyal kylene each having 1 to 6 carbon atoms,
Ar² is phenyl, naphthyl or heteroaryl 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 are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, 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;
each 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;
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 singly or multiply, 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 each having 1 to 6 carbon atoms;
Cycloalkyl of 3 to 6 carbon atoms;
Heterocyclyl or heterocyclyl-methyl with 3 to 7 rings each, 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 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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or 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, each substituted twice linked alkylene or dioxyalkylene each having 1 to 6 carbon atoms, substituted phenyl, phenoxy, phenylthio, benzyl, benzyloxy, phenylethyl or phenylethyloxy.
E represents one of the groupings below: wherein
R¹ 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 C₁-C₄alkoxy,
R² represents hydrogen, amino, cyano or alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C₁-C₄alkoxy, and
R³ for hydrogen, cyano or for alkyl, alkenyl or alkynyl each optionally substituted by halogen, cyano or C₁-C₄alkoxy, each having up to 6 carbon atoms or for in each case optionally halogen, cyano, carboxy, C₁-C₄alkyl or C₁- C₄-alkoxy-carbonyl substituted cycloalkyl or cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl and optionally 1 to 4 carbon atoms in the alkyl part,
R⁴ 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 C₁-C₄alkoxy,
R⁵ represents alkyl having 1 to 6 carbon atoms,
R⁶ represents hydrogen, amino, cyano or alkyl, alkoxy, alkylamino or dialkylamino, each of which has 1 to 6 carbon atoms in the alkyl radicals and is optionally substituted by halogen, cyano or C₁-C₄alkoxy, and
G for a single bond, for oxygen, sulfur or for in each case optionally substituted by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₃-C₆-cycloalkyl, alkanediyl, Al kendiyl, alkynediyl each having up to 4 carbon atoms or one of the groupings below
-Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-,
-Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O) _n -, -CH₂S (O) _n -, -CQ-,
-S (O) _n -CH₂-, C (R⁷) = NO-, -C (R⁷) = NO-CH₂-, -N (R⁸) -, -CQ-N (R⁸) -,
-N (R⁸) -CQ-, -Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO-CH₂
or -N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ for hydrogen, cyano, optionally substituted by halogen, cyano or C₁-C₄-alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for each GE optionally by halogen, cyano, carboxy, C₁ -C₄-alkyl or C₁-C₄-alkoxy-carbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and
R⁸ for hydrogen, hydroxy, cyano or for optionally substituted by halogen, cyano or C₁-C₄-alkoxy alkyl having 1 to 6 carbon atoms or for optionally by halogen, cyano, carboxy, C₁-C₄-alkyl or C₁-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, the same or different, by halogen, cyano, hydroxy, amino, C₁-C₄alkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl or C₁-C₄alkylsulfonyl (each of which may optionally be substituted by halogen may) substituted alkyl of 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 is optionally substituted by halogen, cyano, C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy or C₁-C₄-haloalkoxy is), C₁-C₄-alkyl or C₁-C₄-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 are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;
each straight-chain or branched alkyl, alkoxy, alkyl thio, 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;
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;
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;
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 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, pyridyl or thienyl part, one or more times, identically or differently
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 having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
and / or 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 linked 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
A¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
A² represents hydrogen-methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
A³ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or cyano,
Ar¹ for optionally substituted ortho-, meta- or para-phenylene, for furandiyl, thiophendiyl, pyrroldiyl, pyrazole diyl, triazole diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, oxadiazole diyl, thiadiazole diyl, pyridinediyl (especially pyridinediyl) (especially pyridinediyl) Pyrimidinediyl, pyridazinediyl, 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,
Ar² for each optionally mono- 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, the possible substituents preferably being derived from the following count 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, trifluorethoxy, difluoromethylthioiflifluorifluorifluoromifluoromifluoromifluoromifluoromifluoromifluoromethyl, trifluoromethylthioifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromifluoromethylfifluoromethyl Ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, 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 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 substituted one or more times, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl substituted, in each case substituted methyl or ethylenedioxy, substituted phenyl, phenoxy, phenylthio, benzyl or benzyloxy,
E represents one of the groupings below wherein
R1 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,
R² 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,
R³ for hydrogen, cyano or for methyl, ethyl n- or i-propyl, n-, i- or s-butyl, optionally substituted by fluorine, cyano, methoxy or ethoxy, 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,
R⁴ represents hydrogen, fluorine, chlorine, bromine, cyano or methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylithio, methylamino, ethylamino or dimethylamino, each optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy,
R⁵ represents methyl, ethyl n- or i-propyl, n-, i- or s-butyl,
R⁶ represents 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 methylene, dimethylene (ethane-1.) Which is optionally substituted by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl , 2-diyl), ethene-1,2-diyl, ethyne-1,2-diyl or one of the groupings below
-Q-CQ-, -CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-,
-Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O) _n -, -CH₂S (O) _n -, -CQ-,
-S (O) _n -CH₂, -C (R⁷) = NO-, C (R⁷) = NO-CH₂-, -N (R⁸) -,
-CQ-N (R⁸) -, -N (R⁸) -CQ-, -Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-,
-CH₂-ON = C (R⁷) -, -N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-,
-N (R⁸) -CQ-Q-CH₂-, -QC (R⁷) = NO-CH₂ or
-N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ for hydrogen, cyano, optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, butoxy, methyl thio, ethylthio, propylthio, butylthio, methylamino, ethylamino, propylamino, dimethylamino or diethylamino or for cyclopropyl which is optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclobutyl, cyclopentyl or cyclohexyl, and
R⁸ for hydrogen, hydroxy, cyano or for each ge optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for optionally by Fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxy-carbonyl or ethoxycarbonyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,
m represents the numbers 0, 1 or 2 and
Z for methyl which is monosubstituted to fluorine, chlorine, bromine, cyano, hydroxy, amino, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine) , 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 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, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy), 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, tetrahydro furyl, perhydropyranyl, pyrrolidinyl, piperidinyl or Morpholinyl is available, the possible substituents being preferably selected from the list below:
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, methyl sulphinyl, ethylsulphinyl methoxy, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoro, difluorochloromethoxy, trifluoroethoxy, methylthio difluoro, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl , Methyl amino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxy carbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyl oxy, hydroximinomethyl, hydroximinoethyl, methoximino 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, 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, difluorochloromethylthio, trifluoromethylthio, or in each case G or the same or differently, by one or more times 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. 4. Compounds of formula (I) according to claim 1, in which
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, optionally monosubstituted to trisubstituted in the same or different manner, Pyrimidinyl, pyridazinyl, pyrazinyl, 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethyl, ethoxifoxymethyloxyethyloxyethyloxymethyloxyethyloxyethyloxymethyloxymethyloxyethyloxymethyloxymethyloxymethyloxyoxymethyloxyoxoxymethyloxyoxymethyloxymethyloxoxymethyloxy
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 ge optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E represents one of the groupings below wherein
R¹ and R² each represent methoxy,
G for oxygen, sulfur or for in each case optionally substituted by fluorine, chlorine or bromine, dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or one of the following groups
-CQ-Q-, -CH₂-Q-; -Q-CH₂-, -CQ-Q-CH₂-, -Q-CQ-Q-CH₂-, -N = N-,
-S (O) _n -CH₂-, -C (R⁷) = NO-, -C (R⁷) = NO-CH₂-, -N (R⁸) -CQ-,
-Q-CQ-N (R⁸) -, -N = C (R⁷) -Q-CH2-, -CH₂-ON = C (R⁷) -,
-N (R⁸) -CQ-Q-, -CQ-N (R⁸) -CQ-Q-, -N (R⁸) -CQ-Q-CH₂-,
-QC (R⁷) = NO-CH₂ or -N (R⁸) -C (R⁷) = NO-CH₂-, where
n represents the numbers 0, 1 or 2,
Q represents oxygen or sulfur,
R⁷ represents hydrogen, cyano, methyl, ethyl or cyclopropyl and
R⁸ represents hydrogen, methyl, ethyl or cyclopropyl,
m represents 0, 1 or 2 and,
Z for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thia diazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimidinyl which are each mono- to trisubstituted in the same or different ways , 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, ethoxy methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro, difluoromethylthio, trifluoromethylthio, difluorochloromethyl thio, 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, 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 one or more times, the same or different by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each substituted twice linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio. 5. Compounds of the general formula (Ia), in which
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, optionally monosubstituted to trisubstituted in the same or different manner, Pyrimidinyl, pyridazinyl, pyrazinyl, 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethyl, ethoxifoxymethyloxyethyloxyethyloxymethyloxyethyloxyethyloxymethyloxymethyloxyethyloxymethyloxymethyloxymethyloxyoxymethyloxyoxoxymethyloxyoxymethyloxymethyloxoxymethyloxy
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 ge optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E for stands
m represents 0, 1 or 2 and,
Z¹ is phenyl which is optionally 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, trifluoromethyloxyethyl, ethyl, ethoxifoxymethyloxyethyloxyethyloxymethyloxyethyloxyethyloxymethyloxymethyloxyethyloxymethyloxymethyloxymethyloxyoxymethyloxyoxoxymethyloxyoxymethyloxymethyloxoxymethyloxy
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
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar 1 represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, optionally monosubstituted to trisubstituted in the same or different manner, Pyrimidinyl, pyridazinyl, pyrazinyl, 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethyl, ethoxifoxymethyloxyethyloxyethyloxymethyloxyethyloxyethyloxymethyloxymethyloxyethyloxymethyloxymethyloxymethyloxyoxymethyloxyoxoxymethyloxyoxymethyloxymethyloxoxymethyloxy
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 ge optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E for stands
m represents 0, 1 or 2 and,
Z² represents phenyl, pyridyl or pyrimidyl which may be monosubstituted to trisubstituted identically or differently, 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, ethoxy methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoro, difluoromethylthio, trifluoromethylthio, Difluorchlor methylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, Ethox iminomethyl, 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, 7. Compounds of the general formula (Ic), in which
A¹ represents hydrogen or methyl,
A² represents hydrogen, methyl or ethyl,
A³ represents hydrogen, methyl, ethyl or cyano,
Ar² for phenyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, optionally monosubstituted to trisubstituted in the same or different manner, Pyrimidinyl, pyridazinyl, pyrazinyl, 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethyloxyethyl, ethyl, ethoxifoxymethyloxyethyloxyethyloxymethyloxyethyloxyethyloxymethyloxymethyloxyethyloxymethyloxymethyloxymethyloxyoxymethyloxyoxoxymethyloxyoxymethyloxymethyloxoxymethyloxy
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 ge optionally mono- or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, phenoxy , Phenylthio, benzyl or benzyloxy,
E represents one of the groupings below wherein
R¹ and R² each represent methoxy,
m represents 0, 1 or 2 and,
Z³ for 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyrimidinyl, or 1,3, each substituted once or twice, identically or differently , 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, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylifluoromethyl, trifluoromethyl
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 one or more times, the same or different by fluorine, chlorine, methyl, trifluoromethyl or ethyl, each substituted twice linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl, thienyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio. 8. Pesticides, characterized by a content of at least one compound of formula (I) according to claim 1. 9. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 on pests and / or let their living space take effect. 10. Use of compounds of formula (I) according to claims 1 to 7 for pest control. 11. Process for the preparation of pesticides, thereby characterized in that compounds of the formula (I) according to the Claims 1 to 7 with extenders and / or surface-active agents mixed. 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
Ar¹, 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
A¹, A², A³, Ar² 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.