DE19510297A1 - Substituted heterocycloalkenes - Google Patents

Abstract

Compounds of formula (I) in which A is possibly substituted alkylene, Ar is possibly substituted arylene or heteroarylene, E is preferably one of the grouping (a), (b), (c), (d), (e), Y<1> is oxygen, sulphur or a possibly alkyl-substituted imino grouping ("azamethylene", NH, N-alkyl), Y<2> is oxygen or a possibly alkyl-substituted imino grouping ("azamethylene", NH, N-alkyl), Y<1> and Y<2> not simultaneously standing for oxygen, and Z-G stands for various constituents, and the use of said compounds as fungicides.

Description

The invention relates to new substituted heterocycloalkenes, several processes their production and use as fungicides and new intermediates and several methods of making them.

It is known that certain substituted heterocyclic compounds are fungicidal Have properties (see, for example, WO-A 9422844). The effect of this However, especially in the case of low application rates, connections are not common Areas of application completely satisfactory.

The new substituted heterocycloalkenes of the general formula (I) found,

in which
A represents optionally substituted alkylene.
Ar represents optionally substituted arylene or heteroarylene.
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 R¹ and in the 3-position a radical R³, or represents a 3-oza-1-propene-2,3-diyl grouping which contains a radical R¹ in the 1-position, or represents a 3-thia- 1-propen-2,3-diyl grouping which contains a R 1 radical in the 1-position, or represents a 1-aza-1-propene-2,3-diyl grouping which has a radical in the 1-position R² and in the 3-position contains a radical R³, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R¹ in the 1-position and a radical R³ in the 3-position, or stands for a 1,3-diaza-1-propene-2,3-diyl grouping which has a radical R² in the 1-position and in 3-P osition contains a radical R³, or for a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R² in the 1-position, or for a 1-aza-3-thia -1-propen-2,3-diyl grouping which contains a radical R² in the 1-position, where

• R¹ for hydrogen, halogen, cyano or for each optionally substituted ized alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
• R² for hydrogen, amino, hydroxy, cyano or for each optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and
• R³ for hydrogen, cyano, hydroxy or for each optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

G for a single bond, for oxygen, sulfur or for any given if substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl tes alkanediyl, alkenediyl, 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 (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂- ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹- or -T-Ar¹-Q-, where

• Ar¹ for optionally substituted arylene, heteroarylene, cycloalkylene or Heterocycloalkylene (i.e. a doubly linked aliphatic ring, in which one or more carbon atoms by heteroatoms, d. H. from Carbon different atoms are replaced),
• n represents the numbers 0, 1 or 2,
• Q represents oxygen or sulfur,
• R⁴ represents hydrogen, cyano or in each case optionally substituted alkyl, Alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
• R⁵ for hydrogen, hydroxy, cyano or in each case optionally substituted ized alkyl, alkoxy or cycloalkyl and
• T for a single bond, for oxygen, sulfur, -CH₂-O-, -CH₂-S- or represents optionally substituted alkanediyl,

Y¹ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl),
Y² represents oxygen, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl),
where Y¹ and Y² are not simultaneously oxygen and
Z represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl.

Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, such as. B. Phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.  

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped Compounds in which at least one ring member has a heteroatom, i.e. H. one of Carbon is different atom. If the ring contains several heteroatoms, you can these be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If necessary, the ring-shaped connections form with others carbocyclic or heterocyclic, fused or bridged rings together a polycyclic ring system. Mono- or bicyclic are preferred Ring systems, especially mono- or bicyclic, aromatic ring systems.

Furthermore, it was found that the new substituted heterocycloalkenes general formula (I) obtained when one

• a) Hydroxy compounds of the general formula (II) in which
  A, Ar, E, G and Z have the meaning given above, where
  Y³ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl) and
  Y⁴ represents oxygen, or an imino group optionally substituted by alkyl ("azamethylene", NH, N-alkyl),
  with a sulfurization reagent and / or a condensing agent, optionally in the presence of a diluent, or if
• b) nitrogen-containing carboxylic acid derivatives of the general formula (III) in which
  A, Ar, E, G, Y¹, Y² and Z have the meaning given above and
  X¹ represents halogen, arylsulfonyl or alkylsulfonyl,
  with an acid acceptor, optionally in the presence of a diluent.

Finally, it was found that the new substituted heterocycloalkenes of all 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 isomers, but optionally also of tautomers are present. It will both the E and the Z isomers, any mixtures of these isomers, and the possible tautomeric forms claimed.

The invention preferably relates to compounds of the formula (I) in which
A represents alkylene with 1 to 4 carbon atoms,
Ar for each optionally substituted phenylene or naphthylene, for mono- or bicyclic heteroarylene each having 5 or 6 ring members or for benzo-fused heteroarylene having 5 or 6 ring members, of which at least one each represents oxygen, sulfur or nitrogen and, if appropriate, one or two more represents nitrogen, where the possible substituents are preferably selected from the list below:
Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thio carbamoyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, in each case ge 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 haloalkyl sulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched halogen alkenyl or haloalkenyloxy each having 2 to 6 Carbon atoms and 1 to 11 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxy carbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, in each case 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, in each case doubly linked alkylene or Dioxyalkylene with 1 to 6 carbon atoms each,
E represents one of the groupings below:

wherein

• R¹ for hydrogen, halogen, cyano or for each optionally by Halogen, cyano or C₁-C₄ alkoxy substituted alkyl, alkoxy, alkyl thio, alkylamino or dialkylamino each having 1 to 6 carbon atoms is in the alkyl residues,  
• R² for hydrogen, amino, hydroxy, cyano or for each optionally alkyl, alkoxy substituted by halogen, cyano or C₁-C₄alkoxy, Alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl radicals,
• R³ for hydrogen, cyano, hydroxy or for each optionally by Halogen or cyano substituted alkyl, alkoxy, alkoxyalkyl, alkenyl or alkynyl each having up to 6 carbon atoms or for each optionally by halogen, cyano, C₁-C₄-alkyl or C₁-C₄-alkoxy- substituted cycloalkyl or cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl parts and optionally 1 to 4 carbon atoms in the alkyl part,

G for a single bond, for oxygen, sulfur or for any given if by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-haloalkyl or C₃-C₆- Cycloalkyl-substituted alkanediyl, alkenediyl, alkindiyl each with 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 (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂- ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹- or -T-Ar¹-Q-, where

• n represents the numbers 0, 1 or 2,
• Q represents oxygen or sulfur,
• R⁴ for hydrogen, cyano, each optionally by halogen, cyano or C₁-C₄ alkoxy substituted alkyl, alkoxy, alkylthio, alkylamino 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 with 3 is up to 6 carbon atoms, and
• R⁵ represents hydrogen, hydroxy, cyano or, if appropriate, 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 with 3 to 6 Carbon atoms stands and
• Ar¹ is phenylene, naphthylene, cycloalkylene or heteroarylene or heterocycloalkylene with 3 to 7 ring members, each of which is 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, 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 11 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, and;
  Cycloalkyl with 3 to 6 carbon atoms and
• T for a single bond, for oxygen, sulfur, -CH₂-O-, -CH₂-S- or represents alkanediyl having 1 to 3 carbon atoms,

Y¹ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl having 1 to 3 carbon atoms ("azamethylene", NH, N- C₁-C₃-alkyl),
Y² for oxygen, or one optionally by alkyl with 1 to 3
Imino group substituted by carbon atoms ("azamethylene", NH, N- C₁-C₃-alkyl),
where Y¹ and Y² are not simultaneously oxygen 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 having 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, identical or different, 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 mono- or polysubstituted in the same or different ways, at least one of which is oxygen, sulfur or nitrogen and, if appropriate, one or two more are nitrogen, where 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 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 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximinoalkyl each having 1 to 6 carbon atoms in the individual alkyl parts;
each optionally 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 halogeno alkyl 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;
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.

In the definitions are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms, as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched.

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
A for methylene, 1,1-ethylene, 1,2-ethylene 1,1-, 1,2-, 1,3- or 2,2-propylene, 1,1-, 1,2-, 1,3- , 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 1,3-i-butylene,
Ar 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 (especially pyridinediyl) (especially , 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, cyclopropyl, trifluoromethyl, methoxy, ethoxy, methylthio, methylsulfinyl or methylsulfonyl,
E represents one of the groupings below:

wherein

• R1 is hydrogen, fluorine, chlorine, bromine, cyano or any given if substituted by fluorine, chlorine, cyano, methoxy or ethoxy Methyl, ethyl, propyl, methoxy, ethoxy, methylthio, ethylthio, methyl amino, ethylamino or dimethylamino,
• R² for hydrogen, amino, hydroxy, cyano or for each optionally methyl substituted by fluorine, chlorine, cyano, methoxy or ethoxy, Ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino stands,
• R³ for hydrogen, cyano or for each optionally by fluorine, chlorine or cyano, substituted methyl, ethyl, n- or i-propyl, n-, i- or s- Butyl, methoxy, ethoxy or methoxymethyl, for allyl or propargyl or for each optionally by fluorine, chlorine, cyano, methyl, ethyl, n- or i-propyl, methoxy or ethoxy-substituted cyclopropyl, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutyl is methyl, cyclopentylmethyl or cyclohexylmethyl,

G for a single bond, for oxygen, sulfur or for any given if by fluorine, chlorine, bromine, hydroxy, methyl, ethyl, n- or i-propyl, Trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl substit methylene, dimethylene (ethane-1,2-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 -, -CH₂-S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂- ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹- or -T-Ar¹-Q-, where

• n represents the numbers 0, 1 or 2,  
• Q represents oxygen or sulfur,
• R⁴ for hydrogen, cyano, each optionally 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, propyl amino, dimethylamino or diethylamino or for each optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, Methoxycarbonyl or ethoxycarbonyl substituted cyclopropyl, Cyclobutyl, cyclopentyl or cyclohexyl, and
• R⁵ for hydrogen, hydroxy, cyano or for each optionally by Fluorine, chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or for each optionally by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, Methoxy-carbonyl or ethoxy-carbonyl-substituted cyclopropyl, Cyclobutyl, cyclopentyl or cyclohexyl,
• Ar¹ for phenylene, naphthylene, furandiyl, thiophene diyl, oxazole diyl, isoxazole diyl, thiazole diyl, isothiazole diyl, 1,2,4-oxadiazole diyl, 1,3,4-oxadiazole diyl, 1,2,4-thiadiazole diyl, 3,4-thiadiazole diyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl, 1,3,5-triazinediyl, oxiranediyl, oxetanediyl, tetrahydrofuranediyl, perhydro pyranediyl or pyrrolidinediyl the possible substituents are 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, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoromethyl, difluoromethylfluifluoromethyl, diflifluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl, difluoromethyl , Propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroximino methyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl or cyclopropyl and
• T for a single bond, for oxygen, sulfur, -CH₂-O-, CH₂-S-, Methylene, ethylene or propylene stands and

Y¹ represents oxygen, sulfur, -NH-, -N (CH₃) - or -N (C₂H₅) -,
Y² represents oxygen, -NH-, -N (CH₃) - or -N (C₂H₅) -,
where Y¹ and Y² are not simultaneously oxygen 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, each 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 stands, whereby the possible substituents are preferably selected from the list below:
Fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carb amoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy , n- or i-propoxy, methylthio, ethylthio, n- or i-propyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoro methyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulphinyl or trifluoromethylsulphonyl , Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethyl sulfonyloxy, 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.

Compounds of the general formula (I) are very particularly preferred,
in which
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,
Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
E represents one of the groupings below

wherein

• R¹ and R² each represent methoxy and
• R³ for hydrogen, cyano, methyl, ethyl, n- or i-propyl, methoxy or Ethoxy stands,

G for oxygen or for each optionally by fluorine, chlorine or bromine substituted dimethylene (ethane-1,2-diyl), ethene-1,2-diyl or one of the following standing 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 (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂- ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹ - or -T-Ar¹ -Q-, where

• n represents the numbers 0, 1 or 2,
• Q represents oxygen or sulfur,
• R⁴ represents hydrogen, cyano, methyl, ethyl or cyclopropyl and
• R⁵ represents hydrogen, methyl, ethyl or cyclopropyl,
• Ar¹ for each optionally monosubstituted to trisubstituted, identically or differently substituted, phenylene or pyridinediyl, for each optionally substituted monosubstituted pyrimidinediyl, pyridazinediyl, pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl or 1,3,5-triazinediyl or stands for 1,2,4-thiadiazole diyl, 1,3,4-thiadiazole diyl, 1,2,4-oxadiazole diyl, 1,3,4-oxadiazole diyl, the possible substituents preferably being selected from the list below:
  Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, cyclopropyl, 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 trifluoromethyl sulfonyl and
• T for a single bond, for oxygen, sulfur, -CH₂-O-, CH₂-S-, Methylene, ethylene or propylene stands and

Y¹ represents oxygen, sulfur, -NH- or -N (CH₃) -,
Y² represents oxygen, -NH- or -N (CH₃) -,
where Y¹ and Y² are not simultaneously oxygen 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, optionally substituted once to three times, identically or differently , 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, chloromethoxy methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluoro, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, chloromethylthio difluoro, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, Methox iminoethyl, 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.

A particularly preferred group of compounds according to the invention are those compounds of the formula (I)
in which
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,
Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
E represents one of the groupings below,

wherein
R¹ and R² each represent methoxy and
G represents -O-CH₂ and
Y¹ represents oxygen, sulfur, -NH- or -N (CH₃) -,
Y² represents oxygen, -NH- or -N (CH₃) -,
where Y¹ and Y² are not simultaneously oxygen and
Z represents phenyl which is monosubstituted to trisubstituted identically or differently in each case, 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, ethifyl, trifluoromethyloxyethyl, ethoxifoxyloxymethyloxoxy, methylifoxyloxymethyloxoxy, methylifoxyloxymethyloxoxy,
each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy or ethylenedioxy.

Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
in which
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,
Ar represents ortho-phenylene, pyridine-2,3-diyl or thiophene-2,3-diyl,
E represents one of the groupings below,

wherein
R¹ and R² each represent methoxy and
G represents -C (R⁴) = NO-CH₂-, wherein
R⁴ represents hydrogen, cyano, methyl, ethyl or cyclopropyl,
Y¹ represents oxygen, sulfur, -NH- or -N (CH₃) -,
Y² represents oxygen, -NH- or -N (CH₃) -,
where Y¹ and Y² are not simultaneously oxygen and
Z represents phenyl, pyridyl or pyrimidyl which is optionally 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, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, Difluorchlor methoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, in each case optionally up to four times, the same or different fluorine, chlorine, methyl, trifluoromethyl or ethyl, each linked twice methylenedioxy or ethylenedioxy.

Another particularly preferred group of compounds according to the invention are those compounds of the formula (I)
in which
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene,
Ar represents ortho-phenylene,
E represents one of the groupings below:

wherein
R¹ and R² each represent methoxy,
G represents -T-Ar¹-Q-, wherein

• Q represents oxygen or sulfur,
• Ar¹ for 1,2,4-thiadiazole diyl, 1,3,4-thiadiazole diyl, 1,2,4-oxadiazole diyl, 1,3,4- Oxadiazole diyl or for each optionally single or double, identical or different by fluorine, chlorine, cyano, methyl, cyclopropyl, Methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy,  Difluorochloromethoxy substituted, pyridinediyl, pyrimidinediyl or 1,3,5- Triazinediyl stands,
• T for a single bond, for oxygen, sulfur, -CH₂-O-, CH₂-S-, Methylene, ethylene or propylene stands and

Y¹ represents oxygen, sulfur, -NH- or -N (CH₃) -,
Y² represents oxygen, -NH- or -N (CH₃) -,
where Y¹ and Y² are not simultaneously oxygen and
Z for each, if appropriate, single to triple, identical or different, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy, difluorochloromethoxy, trifluoroethoxy, trifluoromethoxy or, if appropriate, monosubstituted or polysubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl, in each case doubly linked methylenedioxy or ethylenedioxy, substituted phenyl, pyridyl or thienyl stands.

The general or priority areas listed above Definitions apply both to the end products of formula (I) and accordingly to the raw materials or intermediate products required for the production.

These residual definitions can be among themselves, that is, between the specified Areas of preferred connections, can be combined as desired.

Examples of the compounds according to the invention are in Tables 1 to 8 listed:  

Table 1

Table 2

Table 3

Table 4

Table 5

Table 6

Table 7

Table 8

The be to carry out the method a) as starting materials Required hydroxy compounds are generally defined by the formula (II). In A, Ar, E, G and Z of this formula (II) preferably or in particular have that Meaning already in connection with the description of the invention ß compounds of formula (I) as preferred or as particularly preferred for A, Ar, E, G and Z was specified. Y³ stands for oxygen, sulfur, or one optionally substituted by alkyl, preferably methyl, ethyl, n- or i-propyl Imino grouping and Y⁴ stands for oxygen, or one optionally by alkyl, preferably methyl, ethyl, n- or i-propyl substituted imino grouping.

The hydroxy compounds of formula (II) are not yet known; stand in the Formula (II) Y³ and Y⁴ simultaneously for oxygen, but they are the subject of a own earlier application (see DE-A 43 26 908 from August 11, 1993). Are Y³ and Y⁴ not simultaneously for oxygen, they are the subject of the present application.

It has furthermore been found that the hydroxy compounds of the general formula (II) also show a very strong fungicidal effect.

The hydroxy compounds of formula (II) are obtained (method a-1)) if carboxylic acid derivatives of the general formula (IV),

in which
Ar, E, G, Y³ and Z have the meaning given above and
X² represents halogen or alkoxy,
with a hydroxyalkyl compound of the formula (V),

in which
A and Y⁴ have the meaning given above,
optionally in the presence of a diluent such as toluene, pyridine, dichloromethane or tetrahydrofuran and optionally in the presence of an acid acceptor such as triethylamine, pyridine, dimethylaminopyridine, sodium hydroxide or potassium carbonate, at temperatures from -20 to 100 ° C, preferably 0 to 80 ° C , implements.

Those for carrying out the process a-1) according to the invention for producing the Hydroxy compounds of the general formula (II) are required as starting materials Carboxylic acid derivatives are generally defined by the formula (IV). In this formula (IV) Ar, E, G, Y³ and Z preferably or in particular have the meaning the already in connection with the description of the Ver Bonds of formula (I), or the hydroxy compounds of formula (II), as before added or was specified as particularly preferred for Ar, E, G, Y³ and Z. X² stands for halogen, preferably chlorine, or for alkoxy, preferably ethoxy or Methoxy.

The carboxylic acid derivatives of the formula (IV) are known and / or 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, EP-A 528 681).

The continue to carry out the method a-1) according to the invention Preparation of the hydroxy compounds of the general formula (II) as starting materials Required hydroxyalkyl compounds are generally defined by the formula (V). In this formula (V) A and Y⁴ preferably or in particular that Be interpretation already in connection with the description of the invention Compounds of formula (I), or the hydroxy compounds of formula (II), as was preferred or indicated as particularly preferred for A and Y⁴.  

The hydroxyalkyl compounds of formula (V) are known and / or can according to known processes can be prepared (see, for example, J. Chem. Soc., Chem. Com. 1986, 903 or J. Med. Chem. 1968, 504).

As a sulfurization reagent for carrying out process a) according to the invention all reagents are possible that are capable of oxygen in a molecule exchange for sulfur, such as B. hydrogen sulfide, phosphorus pentasulfide, Lawesson's reagent.

Process a) according to the invention is optionally carried out in the presence of a suitable diluent. As a diluent for Carrying out the process a) according to the invention comes from all inert organic Solvent. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, Cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated Hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, Chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetra hydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones like Acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethyl form amide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexa methylphosphoric triamide; Esters such as methyl acetate or ethyl acetate ester; Sulfoxides such as dimethyl sulfoxide; or sufones, such as sulfolane.

Process a) according to the invention is optionally carried out in the presence of a suitable condensing agent. As such, all the usual ones come Reagents that are capable of releasing water from a molecule. Acid halide formers such as phosgene, phosphorus tribromide, Phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride; Anhydride formers such as ethyl chloroformate, methyl chloroformate, Isopropyl chloroformate, isobutyl chloroformate or Methanesulfonyl chloride; Carbodiimides such as N, N'-dicyclohexylcarbodiimide (DCC) or  other common condensing agents, such as phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride.

The reaction temperatures can be carried out when carrying out the process according to the invention Process a) can be varied over a wide range. Generally you work at temperatures between 0 ° C and + 200 ° C, preferably at temperatures between between 10 ° C and 140 ° C.

To carry out the method a) for the production of the verb Solutions of formula (I) are used per mole of hydroxy compound of formula (II) in all 0.1 to 10 mol, preferably 0.1 to 5 mol of sulfurization reagent.

The be to carry out process b) according to the invention as starting materials Required nitrogen-containing carboxylic acid derivatives are general by the formula (III) Are defined. In this formula (III), A, Ar, E, G, Y¹, Y² and Z preferably or in particular the meaning already in connection with the description Exercise of the compounds of formula (I) according to the invention as preferred or ins particularly preferred for A, Ar, E, G, Y¹, Y². X¹ stands for Halogen, arylsulfonyl or alkylsulfonyl, preferably for chlorine, methylsulfonyl or 4-tolylsulfonyl.

The nitrogen-containing carboxylic acid derivatives of the formula (III) are not yet known; as new substances, they are the subject of the present application.

It was also found that the nitrogen-containing carboxylic acid derivatives of the formula (III) also show a very strong fungicidal activity.

The nitrogen-containing carboxylic acid derivatives of the formula (III) are obtained (Method b-1)) if one considers the above in connection with the Preparation of the compounds of the formula (I) according to the invention by process a) described hydroxy compounds of formula (II), with a Halogenierungsmit tel, such as B. thionyl chloride, optionally in the presence of a diluent, such as toluene, xylene or chlorobenzene, optionally in the presence of a  Reaction aids such as dimethylformamide or pyridine Temperatures from -20 to 120 ° C, preferably 0 to 100 ° C, or with a Sulfonic acid halide, such as. B. methanesulfonic acid chloride or 4- Toluenesulfonic acid chloride, optionally in the presence of a diluent, such as for example toluene, pyridine, dichloromethane or tetrahydrofuran and given if in the presence of an acid acceptor, such as triethylamine, pyridine, Dimethylaminopyridine, sodium hydroxide or potassium carbonate, at temperatures of -20 to 120 ° C, preferably 0 to 100 ° C, implemented.

The continue to carry out the method b-1) according to the invention Preparation of the nitrogen-containing carboxylic acid derivatives of the general formula (II) as Halogenating agents or sulfonic acid halides required as starting materials are well-known reagents in organic chemistry.

As further required to carry out method b) according to the invention Acid acceptors come with all the usual inorganic or organic bases in question. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates, such as for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, Potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, Sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, Potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammoni umcarbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N- Methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabi cyclonones (DBN) or diazabicycloundecene (DBU).

As a diluent for carrying out process b) according to the invention all inert organic solvents. These preferably include aliphatic, alicyclic or aromatic hydrocarbons, such as Pe trol ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or Decalin; halogenated hydrocarbons, such as chlorobenzene, dichloro benzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or  Trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or Anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Ni triles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides like N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sufones such as Sulfolan; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, Ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol mono methyl 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 b) can be varied over a wide range. Generally you work at temperatures between -20 ° C and + 130 ° C, preferably at temperatures between between 0 ° C and 100 ° C.

To carry out the process b) according to the invention for producing the verbin The formula (I) is used per mole of nitrogen-containing carboxylic acid derivative Formula (II) generally 0.8 to 15 moles, preferably 0.8 to 8 moles of Acid acceptor.

Processes a) and b) according to the invention are generally below normal printing done. However, it is also possible to increase or decrease it Pressure - generally between 0.1 bar and 10 bar - to work.

He carried out the reaction, working up and isolating the reaction products follows according to known methods (see also the production examples).

The active compounds according to the invention have a strong microbicidal action and are used in practice to combat unwanted microorganisms. The active ingredients are for use as pesticides, especially as Suitable for fungicides.  

Fungicides in crop protection are used to combat plasmo diophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basi diomycetes, 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 Pseu doperonospora 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: Drechs lera, synonym: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.

The good plant tolerance of the active ingredients in the control of plants concentrations necessary for diseases, allows treatment above ground Plant parts, as well as a treatment of planting and seeds and the soil.

The active compounds according to the invention are particularly successful control of cereal diseases, such as against Erysiphe species or of diseases in wine, fruit and vegetable growing, such as against Venturia, Podospherea and Sphaerotheca species used. With good success Rice diseases such as for example, Pyricularia species fought.

The active ingredients are dependent on their respective physical and / or chemical properties optionally converted into conventional formulations, such as e.g. B. solutions, emulsions, suspensions, powders, foams, pastes, granules, Aerosols, very fine encapsulations in polymeric substances and in coating materials for seeds, as well as ULV cold and warm fog formulations.  

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with diluents, i.e. liquid solvents, are under pressure Liquefied gases and / or solid carriers, optionally under Use of surface-active agents, i.e. emulsifiers and / or dispersers yawing and / or foaming agents. In case of using water as an extender z. B. also organic solvents as auxiliary solvents be used. The following are essentially suitable as liquid solvents: Aro mat, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. 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 such liquids meant which are gaseous at normal temperature and pressure, e.g. B. aerosol propellants, such as halogenated hydrocarbons and 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; come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made of 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. Ligninsulfitablaugen and methyl cellulose.

Adhesives such as Carboxymethyl cellulose, natural and synthetic, powdery, granular or  latex-shaped polymers such. B. gum arabic, polyvinyl alcohol, Polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins and synthetic phospholipids. Other possible additives are 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 phthalocyanine dyes and trace nutrients such as salts of iron, manganese, Boron, copper, cobalt, molybdenum and zinc added.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention are used as such or in their formulations also in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides are used, e.g. B. to broaden the spectrum of activity or To prevent the development of resistance.

In many cases, synergistic effects are observed.

For the mixtures, for example:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thizole-5-carboxanilide; 2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -otolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,
Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate,
Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb,
Cymoxanil, cyproconazole, cyprofuram,
Dichlorophen, diclobutrazole, diclofluanide, 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, flutolanil, futriafol, futriafol , 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, Nuarimol,
Ofurace, oxadixyl, oxamocarb, oxycarboxin,
Pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon,
Quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, 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, Teclof talam, 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, Chloethocarb, Chlorethoxyfos, Chloretoxyfos, Chlorfenvinphos,
Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin,
Clocythrin, clofentezin, cyanophos, cycloprothrin, cyfluthrin, 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, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
Fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, fenthion, fenvalerate,
Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluv alinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivemectin,
Lamda-cyhalothrin, Lufenuron,
Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
Methamidophos, methidathione, methiocarb, methomyl, metolcarb, milbemectin,
Monocrotophos, moxidectin,
Naled, NC 184, NI 25, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
Phosphamdon, Phoxim, Pirimicarb, Pirimiphos M, Primiphos A, Profenofos,
Profenophos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothiophos, Prothoat,
Pymetrozine, Pyrachlophos, Pyraclofos, Pyraclophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen,
Quinalphos,
RH 5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,
Tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralomethrononium, Triaromenontronium, Triaromenhroniaz, Triaratheniazin, Triaratheniazon
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

If appropriate, the active compounds according to the invention are also used with others Known active ingredients, such as herbicides or with fertilizers and Growth regulators mixed.

The active substances are taken as such, in the form of their formulations or from them prepared application forms, such as ready-to-use solutions, suspensions, Spray powder, pastes, soluble powders, dusts and granules are used. The Application happens in the usual way, e.g. B. by pouring, spraying, spraying, Scattering, dusting, foaming, brushing, etc. If necessary, the  Active ingredients applied according to the ultra-low-volume process or Active substance preparation or the active substance itself is injected into the soil. If necessary, the seeds of the plants are also treated.

In the treatment of parts of plants, the drug concentrations in the Application forms can be varied in a larger area: They are generally mean 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, is required at the site of action.

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, is required at the site of action.  

Manufacturing examples Example (I-1) (Method b))

0.4 g (1.067 mmol) 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) -O- (2- chloroethyl) acetamidoxime are dissolved in 10 ml of N-methylpyrrolidone and slowly 35 mg of sodium hydride (1.17 mmol; 80% in paraffin) were added. Stir for 16 hours 100 ° C, pour on water, extract several times with ethyl acetate, wash again with water, the organic phase dries with magnesium sulfate and distills it Solvent in a vacuum. The residue is then over silica gel chromatographed (eluent toluene: acetone = 15: 1). 0.23 g (64% of theory Theory) 3- {1- [2- (2-methylphenoxymethyl) phenyl] -1- (methoximino) methyl} -5,6- dihydro-4H-1,2,4-oxadiazine. MS: 89, 116, 143, 170, 201, 232, 308, 339 M⁺.  

Example (I-2) Procedure a)

4 g (11.2 mmol) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) -N- (2- hydroxyethoxy) acetamide are dissolved in 40 ml of toluene and then with 2.4 g (11.2 mmol) of phosphorus pentasulfide. The mixture is heated to reflux for 10 minutes and cooled quickly, pour on water, extract with ethyl acetate, wash again with Water, dry over magnesium sulfate and distill the solvent in vacuo from. The residue is chromatographed on silica gel (mobile phase Toluene: acetone = 15: 1). Then it is in ethyl acetate with activated carbon boiled, filtered and concentrated. 0.9 g (22% of theory Theory) 3- {1- [2- (2-methylphenoxymethyl) phenyl] -1- (methoximino) methyl} -5,6- dihydro-4H-1,4,2-oxathiazine. 1 H-NMR (CDCl₃ 2.2, 3.2, 4.0, 4.1, 5.0, 6.8-7.6 ppm).  

Example (I-3) (Method b))

1.0 g (2.5 mmol) of N '- (2-chloroethyl) -N'-methyl-2-methoximino-2- [2- (2-methylphen oxymethyl) phenyl] acethydrazide is placed in 20 ml of anhydrous toluene and with 0.35 g (3.1 mmol) of potassium tert-butoxide. The mixture will last 15 minutes heated to boiling under reflux and, after cooling, successively with water, dilute hydrochloric acid and washed again with water. The organic phase will Dried over sodium sulfate and concentrated in vacuo. The arrears with Petroleum ether / ethyl acetate (4: 1) chromatographed on silica gel. 0.39 g (45% theory 2- {1-methoximino-1- [2- (2-methylphenoxymethyl) phenyl] methyl} -4- methyl-5.6-dihydro-4H-1.3.4-oxadiazine. logP = 3.54

Analogous to Examples (I-1) and (I-3), and in accordance with the general Description of the manufacturing process according to the invention can also be obtained in of the compounds of the invention listed below in Table 9 Formula (I):

Preparation of the starting product Example (II-1) Procedure a-1)

10 g (0.032 mol) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) acetic acid Acid methyl ester are dissolved in 100 ml of methanol and then with 5 g (0.064 mol) of 2- Hydroxyethylhydroxylamine added. Then 12.6 g are added dropwise at 10 ° C. Sodium methoxide (0.064 mol; 30% in methanol) to the reaction mixture. After that the mixture is stirred for 6 h at 30 ° C., poured onto water, acidified with hydrochloric acid, extracted with Ethyl acetate, washed again with water, dried over magnesium sulfate and the solvent is distilled off in vacuo. The residue is over silica gel chromatographed (mobile phase cyclohexane: ethyl acetate first 1: 1, then 1: 2). 7 g (61% of theory) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- are obtained. (methoximino) -N- (2-hydroxyethoxy) acetamide. 1 H-NMR (CDCl₃ / TMS): δ = 4.08 (s, 3H) ppm.  

Preparation of the starting product Example (II-2) Procedure a-1)

0.5 g (1.6 mmol) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) acetimide ethyl acetate, 0.25 g (3.21 mmol) 2-hydroxyethyl hydroxylamine and 10 mg (0.19 mmol) of ammonium chloride are suspended in 5 ml of ethanol and 16 hours at 40 ° C. heated. Then pour the reaction mixture onto 100 ml of water, acidify with 1N hydrochloric acid to pH 2 to 3, extracted three times with 100 ml of ethyl acetate, combines the organic phases and dries over magnesium sulfate. To The residue is distilled off under reduced pressure Chromatographed on silica gel (mobile phase cyclohexane: ethyl acetate = 3: 1). 0.43 g (69% of theory) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- is obtained. (methoximino) -O- (2-hydroxyethylethyl) acetamidoxime. 1 H-NMR: (CDCl₃) 1.58, 2.27, 2.77, 3.73, 3.93, 4.0, 5.0, 5.1, 7.1-7.6 ppm.  

Preparation of the starting product Example (II-3) Procedure a-1)

A mixture of 0.23 g (3 mmol) of 2- (N-methylhydrazino) ethanol and 0.42 ml (3 mmol) of triethylamine in 30 ml of dichloromethane is added dropwise at 20 ° C. at 20 ° C. 0.95 g (3 mmol) of 2-methoximino-2- [2- (2-methylphenoxymethyl) phenyl] acetic acid chloride and stirred at 20 ° C. for 18 hours. The mixture is poured onto water and washed first with sodium hydrogen carbonate solution and then with water. The organic phase is dried over sodium sulfate, filtered and concentrated again. The residue is chromatographed on silica gel using petroleum ether / ethyl acetate (5: 1).
0.3 g (27% of theory) of N '- (2-hydroxyethyl) -N'-methyl-2-methoximino- 2- [2- (2-methylphenoxymethyl) phenyl] acethydrazide of melting point 68-69 is obtained ° C.

Analogous to Examples (II-1) to (II-3), and in accordance with the general Description of the manufacturing process according to the invention can also be obtained in of the compounds of the invention listed below in Table 10 Formula (II):

Preparation of the starting product example (III-1) Procedure b-1)

0.5 g (1.29 mmol) 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) -O- (2- hydroxyethyl) acetamidoxime are dissolved in 5 ml of chloroform and slowly 1.5 g (12.94 mmol) thionyl chloride was added dropwise. The mixture is stirred at 20 ° C. for 16 h, then poured Reaction mixture on water, extracted with ethyl acetate, washed again with Water, dry the organic phase with sodium sulfate and distill it Solvent in a water jet vacuum. 0.45 g (94% of theory) of 2- [2- (2-methylphenoxymethyl) phenyl] -2- (methoximino) -O- (2-chloroethyl) acetoamide oxime. MS: 116.158, 188, 237, 268, 344, 375 M⁺.  

Preparation of the starting product Example (III-2) Procedure b-1)

To a solution of 1.0 (2.7 mmol) N '- (2-hydroxyethyl) -N'-methyl-2-methoximino- 2- [2- (2-methylphenoxymethyl) phenyl] acethydrazide in 20 ml dichloromethane 0.4 ml (5.4 mmol) of thienyl chloride are added dropwise. The mixture is allowed to stir at 20 ° C. for 4 hours and the solvent is distilled off. The residue is dissolved in dichloromethane, washed successively with water, sodium hydrogen carbonate solution and again with water. The organic phase is dried over sodium sulfate and concentrated in vacuo. 1.1 g (100% of theory) of N '- (2-chloroethyl) -N'- methyl-2-methoximino-2- [2- (2-methylphenoxymethyl) phenyl] acethydrazide are obtained as an oil, that continues to be used raw.
1 H-NMR (CDCl₃ / TMS): δ = 4.08 (s, 3H) ppm.

Analogous to Examples (III-1) and (III-2), and in accordance with the general Description of the manufacturing process according to the invention can also be obtained in of the compounds of the invention listed below in Table 11 Formula (III):

Example A Venturia test (apple) / protective

Solvent: 12.5 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 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 with an aqueous conidia suspension of the Venturia apple scab pathogen inaegualis and then remain for 1 day at 20 ° C and 100% relative humidity activity in an incubation cabin.

The plants are then grown in a greenhouse at 20 ° C and a relative Humidity of approx. 70% set up.

Evaluation is carried out 12 days after the inoculation.

In this test, e.g. B. the following compounds (I-1) and (I-2) in one Active ingredient concentration of 500 ppm an efficiency of 100%.  

Example B Erysiphe test (barley) / protective

Solvent: 12.5 parts by weight of N-methyl-pyrrolidone
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 concentration.

To test for protective effectiveness, young plants are sprayed with the active ingredient substance preparation in the specified application rate. After the Plants are sprinkled with Erysiphe graminis f.sp.hordei spores.

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

Evaluation is carried out 7 days after the inoculation.

In this test, e.g. B. the following compounds (I-1) and (I-2) in one Active ingredient concentration of 500 ppm an efficiency of 90%.  

Example C Podosphaera test (apple) / protective

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 concentration.

To test for protective effectiveness, young plants are sprayed with the active ingredient fabric preparation to dripping wet. After the spray coating has dried on, the Plant by dusting with conidia of the apple scab pathogen Podosphaera leucotricha inoculated.

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

Evaluation is carried out 10 days after the inoculation.

In this test, e.g. B. the following compound (I-2) in an active ingredient concentration of 100 ppm an efficiency of 90%.  

Example D Sphaerotheca test (cucumber) / protective

Solvent: parts by weight
Emulsifier: parts by weight

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation to dripping wet. After the spray coating has dried on the plants are dusted with conidia of the fungus Sphaerotheca fuliginea.

The plants are then at 23 to 24 ° C and at a relative Air humidity of approx. 75% set up in the greenhouse.

Evaluation is carried out 10 days after the inoculation.

In this test, e.g. B. the compound (I-2) at an active ingredient concentration of 100 ppm an efficiency of 96%.

Claims (12)

1. Compounds of formula (I) in which
A represents optionally substituted alkylene.
Ar represents optionally substituted arylene or heteroarylene.
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 1- Position contains a radical R¹ and in the 3-position a radical R³, or represents a 3-oza-1-propen-2,3-diyl grouping which contains a radical R¹ in the 1-position, or a 3-thia -1-propen-2,3-diyl grouping which contains a radical R¹ in the 1-position, or represents a 1-aza-1-propene-2,3-diyl grouping which has a 1-position Radical R² and in the 3-position contains a radical R³, or represents a 1-aza-1-propene-2,3-diyl grouping which contains a radical R¹ in the 1-position and a radical R³ in the 3-position, or for a 1,3-diaza-1-propene-2,3-diyl grouping which has a radical R² in the 1-position and in 3-positi contains a radical R³, or represents a 1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R² in the 1-position, or represents a 1-aza-3-thia -1-propen-2,3-diyl grouping, which contains a radical R² in the 1-position, where

• R¹ represents hydrogen, halogen, cyano or any optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkyl amino,
• R² stands for hydrogen, amino, hydroxy, cyano or for optionally optionally substituted alkyl, alkoxy, alkylamino or dialkyl amino, and
• R³ represents hydrogen, cyano, hydroxy or optionally substituted alkyl, alkoxy, alkoxyalkyl, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

G for a single bond, for oxygen, sulfur or for alkanediyl, alkenediyl, alkynediyl or one of the following groupings -Q-CQ-, -CQ-Q-, -CH₂-Q, each optionally substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl -; -Q-CH₂-, -CQ-Q-CH₂-, -CH₂-Q-CQ-, -Q-CQ-CH₂-, -Q-CQ-Q-CH₂-, -N = N-, -S (O ) _n -, -CH ₂ -S (O) _n -, -CQ-, -S (O) _n -CH₂-, -C (R⁴) = NO-, -C (R⁴) = NO-CH₂-, - N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂ -ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹- or -T-Ar¹-Q-, where

• Ar 1 represents optionally substituted arylene, heteroarylene, cycloalkylene or heterocycloalkylene (ie a double-linked aliphatic ring in which one or more carbon atoms have been replaced by heteroatoms, ie atoms other than carbon),
• n represents the numbers 0, 1 or 2,
• Q represents oxygen or sulfur,
• R⁴ represents hydrogen, cyano or in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and
• R⁵ represents hydrogen, hydroxy, cyano or in each case optionally substituted alkyl, alkoxy or cycloalkyl and
• T represents a single bond, oxygen, sulfur, -CH₂-O-, -CH₂-S- or optionally substituted alkanediyl,

Y¹ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl),
Y² represents oxygen, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl),
where Y¹ and Y² are not simultaneously oxygen and
Z represents optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heterocyclyl. 2. Compounds of formula (I), according to claim 1, in which
A represents alkylene with 1 to 4 carbon atoms,
Ar stands for optionally substituted phenylene or naphthylene, for mono- or bicyclic heteroarylene with 5 or 6 ring members each or for benzo-fused heteroarylene with 5 or 6 ring members, at least one of which represents oxygen, sulfur or nitrogen and optionally one or two more Are nitrogen, where 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, 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 11 identical or different halogen atoms, each straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroximinoalkyl or alkoximino alkyl, each with 1 to 6 carbon atoms in the individual alkyl parts, in each case optionally simple ch or multiply, identically or differently, 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 1 to 6 carbon atoms each,
E represents one of the groupings below: wherein

• R¹ represents hydrogen, halogen, cyano or alkyl, alkoxy, alkyl thio, 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 stands for hydrogen, amino, hydroxy, cyano or for alkyl, alkoxy, alkylamino or dialkylamino each optionally substituted by halogen, cyano or C₁-C gegebenenfallsalkoxy, each having 1 to 6 carbon atoms in the alkyl radicals,
• R³ for hydrogen, cyano, hydroxy or for alkyl, alkoxy, alkoxyalkyl, alkenyl or alkynyl each optionally substituted by halogen or cyano, each having up to 6 carbon atoms or for each optionally halogen, cyano, C₁-C₄-alkyl or C₁-C₄- Alkoxy-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,

G for a single bond, for oxygen, sulfur or for alkane diyl, alkenediyl, alkynediyl, each with up to 4 carbon atoms or one, optionally substituted by halogen, hydroxy, C₁-C₄-alkyl, C₁-C₄-halogeno alkyl or C₃-C₆-cycloalkyl the following groupings -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 (R⁴) = NO-, -C (R⁴) = NO-CH₂-, -N (R⁵) -, -CQ-N (R⁵) -, -N (R⁵) -CQ-, -Q-CQ-N (R⁵) -, -N = C (R⁴) -Q-CH₂-, -CH₂- ON = C (R⁴) -, -N (R⁵) -CQ-Q-, -CQ-N (R⁵) -CQ-Q-, -N (R⁵) -CQ-Q-CH₂-, -QC (R⁴) = NO-CH₂-, -N (R⁵) -C (R⁴) = NO-CH₂-, -O-CH₂-C (R⁴) = NO-CH₂-, -N = NC (R⁴) = NO-CH₂-, -T-Ar¹- or -T-Ar¹-Q-, where

• n represents the numbers 0, 1 or 2,
• Q represents oxygen or sulfur,
• R⁴ for hydrogen, cyano, for alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, each optionally substituted by halogen, cyano or C₁-C₄alkoxy, 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
• R⁵ 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 and
• Ar¹ is phenylene, naphthylene, cycloalkylene or heteroarylene or heterocycloalkylene with 3 to 7 ring members, each of which is 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 11 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, and cycloalkyl having 3 to 6 carbon atoms and
• T represents a single bond, oxygen, sulfur, -CH₂-O-, -CH₂- S- or alkanediyl having 1 to 3 carbon atoms,

Y¹ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl having 1 to 3 carbon atoms ("azamethylene", NH, N-C₁-C₃-alkyl),
Y² represents oxygen, or an imino group ("azamethylene", NH, N-C₁-C₃-alkyl) which is optionally substituted by alkyl having 1 to 3 carbon atoms,
where Y¹ and Y² are not simultaneously oxygen and
Z for optionally single or multiple, identical or different, by halogen, cyano, hydroxy, amino, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl (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;
for each optionally mono- or polysubstituted, identically or differently substituted phenyl, naphthyl or for heterocyclyl with 3 to 7 rings, at least one of which is oxygen, sulfur or nitrogen and optionally one or two more are nitrogen, the possible ones 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 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 11 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. 3. A process for the preparation of compounds of formula (I), according to claim 1, characterized in that

• a) Hydroxy compounds of the general formula (II) in which
  A, Ar, E, G and Z have the meaning given above, where
  Y³ represents oxygen, sulfur, or an imino group which is optionally substituted by alkyl (“azamethylene”, NH, N-alkyl) and
  Y⁴ represents oxygen, or an imino group optionally substituted by alkyl ("azamethylene", NH, N-alkyl),
  with a sulfurization reagent and / or a condensing agent, optionally in the presence of a diluent,
  or if you
• b) nitrogen-containing carboxylic acid derivatives of the general formula (III) in which
  A, Ar, E, G, Y¹, Y² and Z have the meaning given above and
  X¹ X¹ represents halogen, arylsulfonyl or alkylsulfonyl,

with an acid acceptor, optionally in the presence of a dilution means, implements. 4. pesticides, characterized by a content of minde at least one compound of formula (I) according to claim 1. 5. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 for pests and / or lets their living space take effect. 6. Use of compounds of formula (I) according to claims 1 to 3 for Pest control. 7. Process for the production of pesticides, characterized characterized in that compounds of the formula (I) according to Claims 1 to 3 mixed with extenders and / or surfactants.