WO2001000574A1 - Pyrrole derivatives - Google Patents

Abstract

The invention relates to novel pyrrole derivatives, to a number of methods for the production thereof, and to their use for controlling harmful organisms. The invention also relates to novel intermediate products and to the use thereof for producing pyrrole derivatives.

Description

pyrrole

The invention relates to new pyrrole derivatives, several processes for their preparation and their use for controlling harmful organisms.

It has already been known that certain compounds which are constitutionally similar to those described below have fungicidal properties (see e.g. EP-A 532127 or EP-A 273572). The action of these compounds against plant pests, however, leaves something to be desired, particularly when the application rates are low.

The new pyrrole derivatives of the general formula (I) have now been found

in welcher

in which

A stands for oxygen or -NH-,

E represents nitrogen or = CH-, where

L ¹ , L ² and L ^{3 are the} same or different and each independently represents hydrogen, halogen, cyano, nitro, in each case unsubstituted or halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, G for oxygen or for alkynediyl which is in each case unsubstituted or substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl or one of the following groups in which the left side in each case is bonded to Z: -O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C (R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH-

-C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) = NO-CH ₂ -, -O-CH ₂ - C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^{! 1} ) -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^{1 1} ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^{1 1} ) -C (R ⁸ ) = NN = CH-

stands, where

Q represents oxygen or sulfur,

R ^{8 represents} hydrogen, cyano or in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or

Cycloalkyl stands,

R ^{9 represents} cyano or unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl,

R ^{10 represents} hydrogen, hydroxy, cyano or in each case unsubstituted or substituted alkyl, alkoxy or cycloalkyl,

R ^{11 represents} hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, unsubstituted or substituted arylalkyl and

Z for unsubstituted or substituted alkyl, alkenyl, alkynyl,

Cycloalkyl, aryl or heterocyclyl, or

stands for -CH ₂ -ON = CH- with the left side bound to Z, and Z stands for unsubstituted or substituted cycloalkyl or heterocyclyl or for substituted aryl.

In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, are in each case straight-chain or branched, also in combination with heteroatoms, such as, for example, in alkoxy or alkylthio. Unless otherwise stated, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.

Haloalkyl stands for partially or completely halogenated alkyl. In the case of polyhalogenated haloalkyl, the halogen atoms can be the same or different. Preferred halogen atoms are fluorine and chlorine and especially fluorine. If the haloalkyl carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.

Aryl stands for aromatic, mono or polycyclic hydrocarbon rings, e.g. Phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl, which can optionally also be condensed with further aliphatic or heterocyclic rings.

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped compounds in which at least one ring member is a hetero atom, ie an atom other than carbon. If the ring contains several heteroatoms, these can be the same or different. Heteroatoms are preferably oxygen, nitrogen or sulfur. If the ring contains several oxygen atoms, they are not adjacent. If appropriate, the ring-shaped compounds together with further carbocyclic or heterocyclic, fused or bridged rings together form a polycyclic ring system. A polycyclic ring system can be linked via the heterocyclic ring or a fused carbocyclic ring. The heterocyclyl described in this way can also be mono- or polysubstituted, preferably by methyl, ethyl, halogen or chlorine. Mono- or bicyclic ring systems are preferred, in particular mono- or bicyclic aromatic ring systems.

Haloalkoxy stands for partially or completely halogenated alkoxy. In the case of polyhalogenated haloalkoxy, the halogen atoms can be the same or different. Preferred halogen atoms are fluorine and especially chlorine. If the haloalkoxy carries further substituents, the maximum possible number of halogen atoms is reduced to the remaining free valences.

Furthermore, it was found that the new pyrrole derivatives of the general formula (I) can be obtained if

(Process a) pyrrole acetic ester of the formula (II),

in welcher

in which

A, G, L ¹ , L ² , L ³ and Z have the meanings given above,

with a formic acid ester, optionally in the presence of a diluent such as dimethylformamide or toluene and optionally in the presence of a base such as sodium hydride, and the crude product is then worked up with a methylating agent, such as for example iodomethane or dimethyl sulfate, if appropriate in the presence of a diluent, such as, for example, dimethylformamide, and if appropriate in the presence of a base, for example potassium carbonate,

or if (process b), enamines of the formula (III),

in welcher

in which

A, G, L ¹ , L ² , L ³ and Z have the meanings given above,

hydrolyzed with an aqueous mineral acid, such as hydrochloric acid, if appropriate in the presence of a diluent, such as, for example, an alcohol, and the crude product is then worked up with a methylating agent, such as iodomethane or dimethyl sulfate, if appropriate in the presence of a diluent, such as dimethylformamide , and optionally in the presence of a base, such as potassium carbonate,

or if (process c), aldehydes of the formula (IV),

in welcher

in which

A, E, L ¹ , L ² and L ^{3 have} the meanings given above,

with a nitrogen compound of the general formula (V),

ZG ¹ -NH ₂ (V) in which

G ¹ for a grouping -CH (R ⁹ ) -O-, -C (R ⁸ ) = N-, -C (= NOR ^π ) -C (R ⁸ ) -O- or

-C (= NOR ^{1 1} ) -C (R ⁸ ) = N-, in which the respective left side is bound to Z, in which

R ⁸ , R ⁹ and R ^{1 1 have} the meanings given above, and

Z has the meaning given above,

if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst and if appropriate in the presence of a dehydrating agent,

or if (process d) methylpyrroles of the formula (VI),

in welcher A, E, L¹, L² und L³ die oben angegebenen Bedeutungen haben und

in which A, E, L ¹ , L ² and L ^{3 have} the meanings given above and

X ^{1 represents} halogen or trialkylammonium, including an anion,

with an oxygen compound of the general formula (VII),

ZG ² -OH (VII) in which

G ² for a single bond or a grouping

-C (R ⁸ ) = N-, -QC (R ⁸ ) = N-, -N (R ¹⁰ ) -C (R ⁸ ) = N-, -O-CH ₂ -C (R ⁸ ) = N- , or -C (= NOR ^{1: 1)} -C (R ⁸⁾ = N-, in which each left hand side is bound to Z, is wherein

Q, R ⁸ , R ¹⁰ and R ¹ * have the meanings given above, and

Z has the meaning given above,

or a sulfur compound of the general formula (VIII),

ZN = C (R ⁸ ) -SH (VIII) in which

R ⁸ and Z have the meanings given above,

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

Finally, it was found that the new pyrrole derivatives of the general formula (I) show a very strong activity against harmful organisms. In addition, the compounds of the formula (I) are important intermediates, in particular for the production of pesticides.

The compounds according to the invention can optionally be in the form of mixtures of various possible isomeric forms, in particular stereoisomers, such as e.g. E and Z, or optical isomers are present. Both the E and the Z isomers, the individual enantiomers, the racemates and any mixtures of these isomers are claimed.

The present application preferably relates to new pyrrole derivatives of the formula (I) in which

A stands for oxygen or -NH-,

E stands for nitrogen or = CH-,

L ¹ , L ² and L ^{3 are the} same or different and are each independently

Hydrogen, halogen, cyano, nitro, in each case unsubstituted or substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or

Alkylsulfonyl each having 1 to 6 carbon atoms, and especially for

Are hydrogen or methyl,

G represents oxygen or alkynediyl which is in each case unsubstituted or substituted by halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl or one of the following groups, in which the left side is in each case bound to Z:

-O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C (R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH-,

-C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) = NO-CH ₂ -, -O-CH ₂ - C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^π ) -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ⁿ ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^π ) -C (R ⁸ ) = NN = CH-, where

Q represents oxygen or sulfur,

R ^{8 represents} hydrogen, cyano, each unsubstituted or substituted by halogen, cyano or C ₁ -C ₄ alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for unsubstituted or halogen, Cyano, carboxy, C ₁ -C ₄ alkyl or C _j -C ₄ alkoxycarbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and

R ⁹ for cyano, for in each case unsubstituted or substituted by halogen, cyano or C _j - C alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each having 1 to 6 carbon atoms in the alkyl groups or for each unsubstituted or halogen, cyano , Carboxy, C1-C4-alkyl or -CC ₄ -alkoxycarbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and

R ¹⁰ for hydrogen, hydroxy, cyano or for each unsubstituted or through

Halogen, cyano or C _j -C ₄ alkoxy substituted alkyl having 1 to 6 carbon atoms or for each unsubstituted or substituted by halogen, cyano, carboxy, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy carbonyl substituted cycloalkyl having 3 to 6 carbon atoms,

R ^{1 1} for hydrogen, C _r C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C _r C ₄ haloalkyl, C ₂ -C ₄ haloalkenyl or unsubstituted or by halogen , Cyano, alkyl or alkoxy each having 1 to 6 carbon atoms, haloalkyl or haloalkoxy each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms substituted phenylalkyl each having 1 to 4 carbon atoms in the alkyl part, and optionally mono- or polysubstituted by identical or different halogen, cyano, hydroxy, amino, _C1 -C4- alkoxy, C ₁ -C ₄ - alkylthio, C1-C ₄ - alkylsulfinyl or C _j -C ₄ alkylsulfonyl (each of which optionally substituted by halogen) 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, identically or differently, by halogen, cyano, carboxy, phenyl (which is optionally substituted by halogen, cyano, C1-C4-alkyl, -C-C4-haloalkyl, C _r C - alkoxy or -C4-haloalkoxy ), C1-C ₄ - alkyl or -C-C4-alkoxy-carbonyl-substituted cycloalkyl with 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 preferably being from selected from the list below:

Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl;

in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms;

each straight-chain or branched alkenyl or alkenyloxy each with

2 to 6 carbon atoms; in each case straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfmyl or haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy 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 or alkylsulfonyloxy, each having 1 to 6 carbon atoms in the individual alkyl parts;

each by single or multiple, the same 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, substituted and 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 -

A¹ für Alkyl mit 1 bis 4 Kohlenstoffatomen oder Cycloalkyl mit 1 bis 6 Kohlenstoffatomen steht undor a group in which

A ^{1 represents} alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and

A ² for alkyl optionally substituted by cyano, alkoxy, alkylthio, alkylamino, dialkylamino, benzyl or phenyl with 1 to 4

Carbon atoms, alkenyl or alkynyl each having 2 to 4 carbon atoms, or

G stands for -CH ₂ -ON = CH-, the left side being bound to Z, and

Z represents unsubstituted or substituted cycloalkyl or heterocyclyl or substituted aryl, the preferred substituents being the same as those already mentioned above as substituents for Z.

The present application relates in particular to methoximinophenylacetic acid amides of the formula (I) in which

A stands for oxygen or -NH-,

E stands for nitrogen or = CH-,

L ¹ , L ² and L ^{3 are the} same or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case optionally by 1 to 5

Halogen atoms substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or

Alkylsulfonyl each having 1 to 6 carbon atoms, especially for

Are hydrogen or methyl,

G for unsubstituted or halogen, hydroxy, alkyl,

Haloalkyl or cycloalkyl substituted alkynediyl or for oxygen or one of the following groups, in which the left side is bound to Z:

-O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C (R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH-,

-C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) = NO-CH ₂ -,

-O-CH ₂ -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^{1 1} ) -C (R ⁸ ) = NO-CH ₂ -,

-C (= NOR ⁿ ) -C (R ⁸ ) -ON = CH-, or -C (= NOR ⁿ ) -C (R ⁸ ) = NN = CH-, where

Q represents oxygen or sulfur,

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

R ^{9 represents} cyano, methyl, ethyl or cyclopropyl and

R ^{10 represents} hydrogen, methyl, ethyl or cyclopropyl,

R ^{1 1} for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-butenyl, 3-methyl-2-butenyl, propargyl, or for optionally by Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,

Trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy or trifluoroethoxy substituted benzyl or phenylethyl,

Z represents phenyl, pyridine, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1, 2,4-oxadiazolyl, 1,3,4-oxadiazolyl, ^" pyridinyl, optionally substituted once to three times, identically or differently , Pyrimidyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl or 1,3,5-triazinyl, where the possible substituents are preferably selected from the list below: Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, di-fluoromethyloxy, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, difluoromethyl

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

A or a grouping .2 κι, where

^{A s} o

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

for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl,

But-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylfhiomethyl, ethylthio-methyl, methylthioethyl, ethylfhioethyl, dimethylaminomethyl, dimethylaminoethyl, Methylaminomethyl, methylaminoethyl or benzyl, or

stands for -CH ₂ -ON = CH-, the left side being bound to Z, and

stands in each case for unsubstituted or substituted cycloalkyl or heterocyclyl or for substituted aryl, the preferred substituents being the same as those already mentioned above as substituents for Z. Irrespective of the definitions given above, A also very particularly preferably stands for oxygen.

Irrespective of the definitions mentioned above, L ¹ and L ² also very particularly preferably represent hydrogen.

Irrespective of the definitions mentioned above, L ³ also very particularly preferably represents hydrogen or methyl.

Irrespective of the definitions given above, E also very particularly preferably stands for = CH-.

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

A stands for oxygen or -NH-,

E stands for = CH-,

L ¹ , L ² , and L ^{3 represent} hydrogen,

G represents -CH (CH ₃ ) -ON = CH-, -C (CH ₃ ) = NN = CH- or -CH = NN = CH-, and

Z 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 ethylsulfonyl,

Trifluoromethyl, difluoromefhoxy, trifluoromethoxy, di fluorochloromethoxy, tri- fluoroethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl,

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 or a grouping _Δ 2, wherein

O ^

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

A ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl,

Propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylfhiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, Methylaminomethyl, methylaminoethyl or benzyl.

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

A stands for oxygen,

E stands for = CH-,

L ¹ , L ² , and L ^{3 represent} hydrogen,

G stands for -CH ₂ -ON = CH- and Z for single to triple, identical or differently substituted phenyl or

Pyridine is, 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, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio,

Trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl,

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 or a grouping _Δ 2, wherein

O ^

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

A ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl,

Propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl,

Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl,

Methylaminoethyl or benzyl.

Another particularly preferred group of compounds according to the invention are those compounds of the formula (I) in which A stands for oxygen or -NH-,

stands for = CH-,

L ¹ , L ² and L ^{3 represent} hydrogen,

G stands for -C (= NOR ^π ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^π ) -C (R ⁸ ) = NN = CH-, where

R ^{8 represents} cyclopropyl or methyl, in particular methyl,

R ¹ * for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,

Allyl, 2-butenyl, 3-methyl-2-butenyl, propargyl, or, if appropriate, by fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromefhoxy, trifluoromethoxy, difluorochloromefhoxy or trifluoroethoxy substituted benzyl or phenylethyl,

Z for each, if necessary, single to triple, identical or different

Fluorine, chlorine, bromine, cyano, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl or phenyl.

The general or residual definitions given above or in the preferred ranges apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. The radical definitions given for the radicals in the respective combinations or preferred combinations of radicals are replaced independently of the radical combination of the radicals given, as desired, by radical definitions of others.

Formula (II) provides a general definition of the pyrrole acetic esters required as starting materials for carrying out process a) according to the invention for the preparation of the compounds of the formula (I). In this formula (II), A, G, L ¹ , L ² , L ³ and Z preferably or in particular have those meanings which have already been mentioned as preferred above in connection with the description of the compounds of the formula (I) according to the invention, or as particularly preferred for A, G, L ¹ , L ² , L ³ , and Z were mentioned.

The starting materials of formula (II) are not yet known. They are new substances and are also the subject of this application.

They are obtained if (process e) pyrrolaldehydes of the general formula (IX),

in welcher

in which

A, L ¹ , L ² and L ^{3 have} the meanings given above,

with a nitrogen compound of the general formula (V),

ZG ¹ -NH ₂ (V) in which

G ¹ and Z have the meanings given above,

optionally in the presence of a diluent and optionally in

In the presence of a catalyst and optionally in the presence of a dehydrating agent,

or if (process f) pyrroloximes of the general formula (X),

in welcher

in which

A, L ¹ , L ² and L ^{3 have} the meanings given above,

with a halogen compound of the general formula (XI),

in welcher

in which

Z and R ^{8 have} the meanings given above and

X ^{2 represents} halogen, if appropriate in the presence of a diluent, such as, for example, dimethylformamide and, if appropriate, in the presence of an acid acceptor, such as, for example, sodium hydride,

or if (process g) pyrrolesulfonic acid ester of the formula (XII),

in welcher

in which

A, lΛ L ² and L ^{3 have} the meanings given above and

R ^{12 represents} alkyl or optionally substituted aryl,

with an oxygen compound of the general formula (VII),

ZG ² -OH (VII) in which

G ² for a single bond or a grouping

-C (R ⁸ ) = N-, -QC (R ⁸ ) = N-, -N (R ¹⁰ ) -C (R ⁸ ) = N-, -O-CH ₂ -C (R ⁸ ) = N- , or -C (= NOR ^{1: 1)} -C (R ⁸⁾ = N-, in which each left hand side is bound to Z, is wherein

Q, R ⁸ , R ¹⁰ and R ¹ 'have the meanings given above, and Z has the meaning given above,

or a sulfur compound of the general formula (VIII),

ZN = C (R ⁸ ) -SH (VIII) in which

R ⁸ and Z have the meanings given above,

optionally in the presence of a diluent such as dimethylformamide and optionally in the presence of an acid acceptor such as sodium hydride or potassium carbonate.

Formula (IX) provides a general definition of the pyrrolaldehydes required as starting materials for carrying out process e) according to the invention for the preparation of the compounds of the formula (II). In this formula (IX) A, L ¹ , L ² and L ³ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for A. , L ¹ , L ² and L ³ were mentioned.

The pyrrolaldehydes of the formula (IX) are known and can be prepared by known processes (compare, for example, EP-A 532126 or EP-A 532127).

Formula (V) provides a general definition of the nitrogen compounds required to carry out process e) according to the invention for the preparation of the compounds of the formula (II) as starting materials. In this formula (V) G ¹ stands for a grouping -CH (R ⁹ ) -O-, -C (R ⁸ ) = N-, -C (= NOR ⁿ ) -C (R ⁸ ) -O- or - C (= NOR ^π ) -C (R ⁸ ) = N-, in which the left side in each case is bound to Z, in which R ⁸ , R ⁹ and R ^{1 1 are} preferably or in particular those meanings which are already related above with the loading the compounds of the formula (I) according to the invention were mentioned as preferred, or as particularly preferred for R ⁸ , R ⁹ and R ¹¹ . Z also preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for Z.

The nitrogen compounds of the formula (V) are known and can be prepared by known processes (see, for example, Tetrahedron, 1995, 11473-11488 or DE-A 9745375).

Formula (X) provides a general definition of the pyrroloximes required as starting materials for carrying out process f) according to the invention for the preparation of the compounds of the formula (II). In this formula (X) A, L ¹ , L ² and L ³ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the invention

Formula (I) was mentioned as preferred, or as particularly preferred for A, L ¹ , L ² and L ³ .

The pyrroloximes of the formula (X) are known and can be prepared by known processes (compare, for example, EP-A 532126).

Formula (XI) provides a general definition of the halogen compounds required as starting materials for carrying out process f) according to the invention for the preparation of the compounds of the formula (II). In this formula (XI), Z and R ⁸ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for Z and R ⁸ . X ² represents halogen, preferably chlorine or bromine. The halogen compounds of the formula (XI) are known and can be prepared by known processes (see, for example, J. Org. Chem., 51, 1, 1986, 109-111; J. Chem. Soc. Perkin Trans. 2, 1986, 593 -598 or WO 98-17653).

The to carry out the method g) for the production of the

Compounds of the formula (II) pyrrolesulfonic acid esters required as starting materials are generally defined by the formula (XII). In this formula (XII), A, L ¹ , L ² and L ³ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for A. .

L ¹ , L ² and L ³ were mentioned. R ¹² represents alkyl, preferably methyl or optionally substituted aryl, preferably 4-tolyl.

The pyrrole sulfonic acid esters of the formula (XII) are not yet known. They are new substances and are also the subject of this application.

They are obtained if (process h) hydroxymethylpyrroles of the formula (XIII),

in welcher

in which

A, L ¹ , L ² and L ^{3 have} the meanings given above,

with a sulfonic acid halide of the formula (XIV) R ¹² -SO ₂ -X ³ (XIV) in which

R ^{12 has} the meaning given above,

optionally in the presence of a diluent, such as dichloromethane and optionally in the presence of an acid acceptor, such as triefhylamine.

Those for carrying out the process h) for the production of the

Compounds of the formula (XII) hydroxymethylpyrroles required as starting materials are generally defined by the formula (XIII). In this formula (XIII) A, L ¹ , L ² and L ³ preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for A. .

L ¹ , L ² and L ³ were mentioned.

The hydroxymethylpyrroles of the formula (XIII) are not yet known. They are new substances and are also the subject of this application.

They are obtained when (process i) pyrrolaldehydes of the general formula (IX) are reacted with a reducing agent, such as sodium borohydride, optionally in the presence of a diluent, such as methanol.

The pyrrolaldehydes of the formula (IX) required as starting materials for carrying out the process i) for the preparation of the hydroxymethylpyrroles of the formula (XIII) have already been described above in connection with the description of the process e) according to the invention. Formula (XIV) generally defines the sulfonic acid halides of formula (XIV) required as starting materials for carrying out process h) according to the invention for the preparation of the compounds of formula (XII). In this formula (XIV), R ¹² preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (XII) according to the invention as preferred or as particularly preferred for R ¹² . X ³ represents halogen, preferably chlorine.

The sulfonic acid halides of the formula (XIV) are known synthetic chemicals.

Formula (VII) provides a general definition of the oxygen compounds required to carry out process g) according to the invention for the preparation of the compounds of the formula (II) as starting materials. In this formula (VII), Z preferably or in particular has the meaning which was mentioned above as preferred or as particularly preferred for Z in connection with the description of the compounds of the formula (I) according to the invention. G ² represents a single bond or a group -C (R ⁸ ) = N-, -QC (R ⁸ ) = N-, -N (R ¹⁰ ) -C (R ⁸ ) = N-, -O-CH ₂ -C (R ⁸⁾ = N-, or -C (= NOR ^{1: 1)} -C (R ⁸⁾ = N-, in which each left side is attached to Z, wherein

R ⁸ , R ¹⁰ and R ^{1 1} preferably or in particular have those meanings which are already preferred above in connection with the description of the compounds of the formula (I) according to the invention, or as particularly preferred for R ⁸ , R ¹⁰ and R ^{1 !} were called.

The oxygen compounds of the formula (VII) are known synthetic chemicals or can be prepared by known methods (see, for example, WO 96-32373 and WO 97-06133).

Those which are furthermore alternatively required as starting materials for carrying out the process g) according to the invention for preparing the compounds of the formula (II) Sulfur compounds are generally defined by formula (VIII). In this formula (VIII), R ⁸ and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention as preferred or as particularly preferred for R ⁸ and Z. ,

The sulfur compounds of the formula (VIII) are known and can be prepared by known processes (compare, for example, JP 09012551, CA: 126: 171587; EP-A 243971; EP-A 243970; JP 09059110, CA: 126: 277279) ,

The formic acid esters which are further required as starting materials for carrying out the process a) according to the invention for the preparation of the compounds of the formula (I) are generally known synthetic chemicals.

The to carry out the method b) for the production of the

Compounds of the formula (I) enamines required as starting materials are generally defined by the formula (III). In this formula (III) A, G, L ¹ , L ² , L ³ and Z preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred, or as were particularly preferred for A, G, L ¹ , L ² , L ³ and Z.

The enamines of the formula (III) are not yet known. They are new substances and are also the subject of this application.

They are obtained if (process j) pyrrole acetic ester of the formula (II),

with bis- (dimethylamino) -rnethoxymethane or bis- (dimethylamino) -t-butoxymethane

optionally in the presence of a diluent, such as toluene or xylene. Formula (II) provides a general definition of the pyrrole acetic esters required as starting materials for carrying out process j) according to the invention for the preparation of the enamines of the formula (III). In this formula (II), A, G, L ¹ , L ² , L ³ and Z preferably or in particular have those meanings which have already been mentioned above as preferred or in connection with the description of the compounds of the formula (I) according to the invention were particularly preferred for A, G, L ¹ , L ² , L ³ and Z.

The to carry out the method j) for producing the

Enamines of the formula (III) required as starting materials pyrrole acetic esters of the formula (III) have already been described above in connection with the description of the process a) according to the invention.

The substances bis- (dimethylamino) -methoxymethane or bis- (dimethylamino) -t-butoxymethane, which are further required as starting materials for carrying out process j) for the preparation of the enamines of the formula (III), are known synthetic chemicals.

Iodomethane or dimethyl sulfate are preferably also suitable as methylating agents required as starting materials for carrying out process b) according to the invention for the preparation of the compounds of formula (I). Iodomethane and dimethyl sulfate are known synthetic chemicals.

The to carry out the method c) for producing the

Compounds of formula (I) required as starting materials aldehydes are generally defined by formula (IV). In this formula (IV), A, E, L ¹ , L ² and L ³ preferably or in particular have those meanings which are already preferred above or in particular preferred in connection with the description of the compounds of the formula (I) according to the invention for A, E, L ¹ , L ² and L ³ . The starting materials of the formula (IV) are known and can be obtained by known methods (compare, for example, EP 532127 or EP 273572).

The nitrogen compounds of the formula (V) which are furthermore required to carry out the process c) according to the invention for preparing the compounds of the formula (I) as starting materials have already been described above in connection with the description of the process e) according to the invention.

The to carry out the method d) for producing the

Compounds of the formula (I) methylpyrroles required as starting materials are generally defined by the formula (VI). In this formula (VI), A, E, L ¹ , L ² and L ³ preferably or in particular have those meanings which are already preferred above or in connection with the description of the compounds of the formula (I) according to the invention particularly preferred for A, E, L ¹ ,

L ² and L ^{3 were} named. X ¹ represents halogen, preferably chlorine or bromine, or X ¹ represents trialkylammonium, preferably trimethylammonium, including an anion, preferably chloride, bromide or iodide.

The starting materials of formula (VI) are known and can be known

Methods are obtained (compare e.g. EP-A 273572).

The oxygen compounds of the formula (VII) which are furthermore required as starting materials for carrying out the process d) according to the invention for the preparation of the compounds of the formula (I), or the sulfur compounds of the

Formula (VIII) have already been described above in connection with the description of process g) according to the invention.

Suitable diluents for carrying out process c) according to the invention are all inert organic solvents. These include, for example and preferably, aliphatic, alicyclic or aromatic hydrocarbons. substances 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, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as, for example, methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane; Alcohols, such as, for example, methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.

Process c) according to the invention is optionally carried out in the presence of a water-binding agent. As such, preferably water-binding salts, such as sodium sulfate or magnesium sulfate, or molecular sieves come into question.

The reaction temperatures can be varied within a substantial range when carrying out process c) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 50 ° C to 120 ° C.

To carry out process c) according to the invention for the preparation of the compounds of the formula (I), 1 to 5 mol, preferably 1 to 3 mol, of nitrogen compound of the formula (V) are generally employed per mol of the aldehyde of the formula (IV). Suitable diluents for carrying out process d) according to the invention are all inert organic solvents. These include, for example and preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as, for example, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as, for example, 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; Nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as, for example, methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane.

Process d) according to the invention is optionally carried out in the presence of a suitable acid acceptor. All conventional inorganic or organic bases are suitable as such. These include, for example and preferably, alkaline earth metal or alkali metal hydrides, carbonates or hydrogen carbonates, such as sodium hydride, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, and tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclonecene (DBU).

The reaction temperatures can be varied within a substantial range when carrying out process d) according to the invention. In general, temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C. To carry out process d) according to the invention for the preparation of the compounds of the formula (I), 1 to 5 mol, preferably 1 to 3 mol, of oxygen compound of the general formula (VII) are generally employed per mole of the methylpyrrole of the formula (VI).

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.

The substances according to the invention have a strong microbicidal action and can be used to control unwanted microorganisms, such as fungi and bacteria, in crop protection and in material protection.

Fungicides can be used to control Plasmodiophoromycetes,

Use Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in crop protection to combat Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

Some pathogens of fungal and bacterial are exemplary but not limiting

Diseases that fall under the generic names listed above:

Xanthomonas species, such as, for example, Xanfhomonas campestris pv. Oryzae;

Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;

Erwinia species, such as, for example, Erwinia amylovora;

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 cubensis;

Plasmopara species, such as, for example, Plasmopara viticola;

Bremia species, such as, for example, Bremia lactucae;

Peronospora species, such as, for example, Peronospora pisi or P. 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, Venruria inaequalis;

Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as, for example, Cochliobolus sativus

(Conidial form: Drechslera, Syn: Helminthosporium);

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

Puccinia species, such as, for example, Puccinia recondita; Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;

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 heφotrichoides.

The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil. According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or cult pot plants (including naturally occurring culinary plants). Cult plant plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plant cultivars. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well

Roots, tubers and thizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of plants and parts of plants according to the invention with the

Active substances take place directly or by influencing their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation materials, in particular in the case of seeds, furthermore by coating in one or more layers.

The active compounds according to the invention can be used with particularly good success in combating cereal diseases, for example against Erysiphe or Puccinia species, for diseases in wine, fruit and vegetable cultivation, for example against Venturia or Plasmopara species, or of Use rice diseases, such as against Pyricularia species.

The active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance. Depending on their respective physical and / or chemical properties, the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in coating compositions for seeds, and ULV -Cold and warm mist formulations.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water. Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. Possible solid carriers are: e.g. natural rock meals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and silicates. The following are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as 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 emulsifiers and / or foaming agents come in

Question: eg non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates. Possible dispersants are, for example, lignin sulfite liquor and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

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

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

In addition, the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad spectrum of antimycotic effects, especially against dermatophytes and shoots, mold and diphasic fungi (e.g. against Candida species such as Candida albicans,

Candida glabrata) such as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii. The list of these mushrooms is in no way a limitation of the detectable mycotic spectrum, but has only an explanatory character. The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the customary manner, for example by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible for the

Applying active ingredients according to the ultra-low-volume method or injecting the active ingredient preparation or the active ingredient itself into the soil. The seeds of the plants can also be treated.

When the active compounds according to the invention are used as fungicides, the application rates can be varied within a substantial range, depending on the type of application. In the treatment of parts of plants, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and

10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The pests mentioned above include:

From the order of the Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus. From the order of the Chilopoda, for example Geophilus caφophagus, Scutigera spp.

From the order of the Symphyla e.g. Scutigerella immaculata.

From the order of the Thysanura e.g. Lepisma saccharina.

From the order of the Collembola e.g. Onychiurus armatus.

From the order of the Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera e.g. Forficula auricularia.

From the order of the Isoptera e.g. Reticulitermes spp ..

From the order of the Phthiraptera e.g. Pediculus humanus coφoris, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..

From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of the Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of the Homoptera, for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatatausidumonidium, aphidata lidium aphidata, aphidata, aphidata, pseudophilia stratata, pseudophyllum aphid stratiformes, pelphid stratiformes, pelphid stratiformes, pelphid stratiformes, pelphid stratiformes, pelphid stratiformes, pelphid stratiformes, pelphid stratiformes, sap ., Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppppi, Fitrella, Phyllocnist spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Caφocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionellaiaellaellaellaanaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella pellaella pellaella, Hofmann , Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp ..

From the order of the Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Orilamaria varispp.

Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meliginusus seneus. Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca ., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata,

Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..

From the order of the Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp ..

From the class of the Arachnida e.g. Scoφio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalommodes spp., I. Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp ..

Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaph.

They can be used with particularly good success to control plant-damaging mites, such as, for example, bean spider mite (Tetranychus urticae), or to control plant-damaging insects, such as, for example, the larvae of the horseradish beetle (Phaedon cochleariae) and green peach aphid (Myzus persicae).

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, impregnated with active ingredients

Natural and synthetic substances as well as very fine encapsulation in polymeric substances. These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-producing agents

Means.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar

Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:

e.g. Ammonium salts and natural rock flours, such as kaolins, clays,

Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic Granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose. Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt,

Molybdenum and zinc can be used.

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

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to spread the spectrum of activity or to prevent the development of resistance. In many cases, synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.

Particularly cheap mixing partners are e.g. the following:

fungicides:

Aldimoφh, Ampropylfos, Ampropylfos Potassium, Andoprim, Anilazine, - Azaconazole, Azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,

Binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate, Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol

Debacarb, dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomoφh, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianonodolone, dithianonodol, dithianonodol, dithianonodol, dithianonodol,

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimoφh, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon,

Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Fluφrimidol, Flusilazol, Flusulfamid, Flutolanil, Flutriafol, Folpet, Fosetyl-Alminium, Fosetyl-Sodium, Fthalid, Fuberidazol, Furalaxyl, Furametpyr, Furcarbonil, Fazazoloxolox, Furconazoloxol, Furconazoxoxolox

guazatine,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalil, imibenconazole, iminoctadine, iminoctadineal besilate, iminoctadine triacetate,

Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,

Kasugamycin, Kresoxim-methyl, copper preparations such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxy-copper and

Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphene, pimaricin, piperalin,

Polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur,

Quinconazole, Quintozen (PCNB), Quinoyfen,

Sulfur and sulfur preparations,

Tebuconazole, Tecloftalam, Tecnazen, Tetcyclacis, Tetraconazole, Thiabendazole, Thicyofen, Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,

Tolylfluanid, Triadimefon, Triadimenol, Triazbutil, Triazoxid, Trichlamid, Tricyclazol, Tridemoφh, Triflumizol, Triforin, Triticonazol,

uniconazole

Validamycin A, vinclozolin, viniconazole,

Zarilamid, Zineb, Ziram as well

Dagger G, OK 8705,

OK 8801,

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

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

α- (2,4-dichloφhenyl) -ß-methoxy-a-methyl-1 H-1, 2,4-triazole-1-ethanol,

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

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

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

{2-Methyl-l - [[[1 - (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester

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

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

l- (3,5-Dichlθφhenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

l - [(diiodomethyl) sulphonyl] -4-methylbenzene,

l - [[2- (2,4-Dichloφhenyl) -l, 3-dioxolan-2-yl] methyl] -lH-imidazole,

1 - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] - 1 H-1, 2,4-triazole, l- [l- [2 - [(2,4-Dichlθφhenyl) methoxy] phenyl] ethenyl] -lH-imidazole,

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

2 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-l, 3-thiazole-5-carboxarilide,

2,2-dichloro-N- [1 - (4-chloro-phenyl) -ethyl] - 1-ethyl-3-methyl-cyclopropanecarboxamide,

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

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

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

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

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

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

2-aminobutane,

2-bromo-2- (bromomethyl) -pentandinitril,

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

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

2-phenylphenol (OPP), 3,4-dichloro-l- [4- (difluoromethoxy) phenyl] -lH-pyrrole-2,5-dione,

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

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

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

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

4-methyl-tetrazolo [l, 5-a] quinazolin-5 (4H) -one,

8- (l, l-dimethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decane-2-methanamine,

8-hydroxyquinoline sulfate,

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

bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate,

ice 1 - (4-chloro-phenyl) -2- (1 H-1, 2,4-triazol-1-yl) -cycloheptanol,

cis-4- [3- [4- (l, 1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,

Ethyl - [(4-chloφhenyl) azo] cyanoacetate,

potassium bicarbonate,

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

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

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

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

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

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

N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,

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

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

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

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

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

N- [3-chloro-4,5-bis- (2-propynyloxy) -phenyl] -N'-methoxy-methanimidamid,

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

O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioat, O-methyl-S-phenyl-phenylpropylphosphoramidothioate,

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

spiro [2H] -l-benzopyran-2, (3Η) -isobenzofüran] -3'-one,

bactericides:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, teclofalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,

Alpha-cypermefhrin, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azamethiphos, Azinphos A, Azinphos M, Azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb,

Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomethrin, Biopermethrin, BPMC, Bromophos A, Bufencarb, Buprofezin, Butathiofos, Butocarboxim, Butylpyridaben,

Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap,

Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chloφyrifos, Chloφyrifos M, Chlovaporthrin, Cis-Resmethrin, Cispermethrin, Clocythrin, Cloethocarb, Clofentezine, Cyanophoputhrin, Cycloprin, Cyprin, Cyprin, Cyprin Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlorvos, Diflubenzuron, Dimethoat, Dimethylvmphos, Diofenolan, Disulfoton, Docusat-sodium, Dofenapyn,

Eflusilanate, Emamectin, Empenfhrin, Endosulfan, Entomopfthora spp.,

Esfenvalerate, Ethiofencarb, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,

Fenamiphos, Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flucythrin

Flufenoxuron, Flutenzine, Fluvalinate, Fonophos, Fosmethilan, Fosthiazate, Fubfenprox, Furathiocarb,

granulosis

Halofenozide, HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,

Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nucleopolyhedroviruses

Lambda cyhalothrin, lufenuron

Malathion, mecarbam, metaldehyde, methamidophos, metharhilic anisopliae, metharhilic flavoviride, methidathione, methiocarb, methomyl, methoxyfenozide,

Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos,

Naled, Nitenpyram, Nithiazine, Novaluron

Omethoate, Oxamyl, Oxydemethon M Paecilomyces fumosoroseus, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pyromhrhridosine, Pymmethrofinos, Pymmethrofinos , Pyridathione, pyrimidifen, pyriproxyfen,

quinalphos,

ribavirin

Salithion, Sebufos, Silafluofen, Spinosad, Sulfotep, Sulprofos,

Tau fluvalinate, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Temivinphos, Terbufos, Tetrachlorvinphos, Theta-cyper-methrin, Thiamethoxam, Thiapronil, Thiatripham hydrogen, Thiapronil

Thiodicarb, Thiofanox, Thuringiensin, Tralocythrin, Tralomethrin, Triarathene, Triazamate, Triazophos, Triazuron, Trichlophenidine, Trichlorfon, Triflumuron, Trimethacarb,

Vamidothion, Vaniliprole, Verticillium lecanii

Yl 5302

Zeta-cypermethrin, zolaprofos

(IR-cis) - [5- (phenylmethyl) -3-furanyl] methyl-3 - [(dihydro-2-oxo-3 (2H) -furanylidene) methyl] -2,2-dimethylcyclopropane carboxylate

(3-phenoxyphenyl) methyl-2,2,3,3-tetramethylcyclopropanecarboxylat l - [(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5-dimethyl-N-nitro-l, 3,5-triazin-2 (1H) - imine

2- (2-chloro-6-fluoφhenyl) -4- [4- (l, l-dimethylethyl) phenyl] -4,5-dihydro-oxazol

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

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

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

3-methylphenyl propyl carbamate

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

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

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

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

Bacillus thuringiensis strain EG-2348

Benzoic acid [2-benzoy 1- 1 - (1, 1-dimethylethyl) hydrazide

Butanoic acid 2,2-dimethyl-3- (2,4-dichloφhenyl) -2-oxo-l-oxaspiro [4.5] dec-3-en-4-yl ester

[3 - [(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene] -cyanamide Dihydro-2- (nitromethylene) -2H- 1,3-thiazine-3 (4H) -carboxaldehyde

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

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

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

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

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

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

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

A mixture with other known active ingredients, such as herbicides or with fertilizers and growth regulators, is also possible.

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. The application takes place in a customary manner adapted to the application forms.

When used against hygiene and storage pests, the stands out

Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

The following examples serve to explain the invention. However, the invention is not limited to the examples.

Preparation Examples

example 1

3-Methoxy-2- {2 - [(- 2 - {- l- [3- (trifluoromethyl) phenyl] ethylidene} hydrazono) methyl] - 1 H-pyrrole-1 -yl} -2-propenoic acid methyl ester.

Procedure c)

0.87 g (0.0043 mol) of l- [3- (trifluoromethyl) phenyl] -l-ethanone hydrazone and 0.85 g

(0.0040 mol) (Z) -2- (2-formyl-1 H-pyrrole-1-yl) -3-methoxy-2-propenoic acid methyl ester, and 2.5 g of molecular sieve are placed in 40 ml of methylene chloride at room temperature and heated under reflux overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo. 1.54 g (98% of theory) of 3-methoxy-2- {2 - [(- 2 - {- l- [3- (trifluoromethyl) phenyl] ethylidene} hydrazono) methyl] -l H- pyrrole-1-yl} -2-propenoic acid methyl ester. HPLC: logP = 3.86

^! H-NMR: 2.45 (s), 3.71 (s), 3.89 (s)

Example 2: 3-methoxy-2- (2- {[(1-phenylethoxy) imino] methyl} - 1 H-pyrrole-1-yl) -2-propenoic acid methyl ester

Procedure c)

0.43 g (0.00315 mol) O- (l-phenylethyl) hydroxylamine, 0.63 g (0.00300 mol) 2- (2-formyl-1 H-pyrrole-l-yl) -3-methoxy- Methyl 2-propenate, 0.27 ml (0.0033 mol)

Pyridine and 2.5 g molecular sieve are refluxed in 40 ml dichloromethane overnight. The reaction mixture is filtered and the filtrate is concentrated in vacuo. 0.87 g (88.3% of theory) of 3-methoxy-2- (2 - {[(l-phenylethoxy) imino] methyl} -l H-pyrrole-1-yl) -2-propenoic acid methyl ester is obtained as a mixture of stereoisomers , HPLC: isomer A: log P = 3.24

Isomer B: log P = 3.32

GC / MS: m / e = 328

Analogously to Examples 1 and 2, and in accordance with the general description of the preparation processes according to the invention for the preparation of the compounds of the formula (I), the following compounds of the formula (I) according to the invention which are mentioned in Table 1 and in which L ¹ , L ² and L ^{3 represents} hydrogen.

Table 1

'' The logP values were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid)

Example A

Erysiphe test (barley) / protective

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

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

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

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

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

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

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the substances according to the invention listed in Examples (1), (2), (3), (12), (13) and (15) show an efficiency of 95% or more at an application rate of 250 g / ha. Example B

Puccinia test (wheat) / protective

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

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with the conidia suspension of Puccinia recondita. The plants remain in an incubation cabin at 20 ° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at a temperature of approximately 20.degree. C. and a relative atmospheric humidity of 80% in order to promote the development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the substances according to the invention listed in Examples (3), (4), (5), (6), (7), (8), (9), (10), (13) and (14) show with an application rate of 250 g / ha, an efficiency of 95% or more. Example C

Plasmopara test (vine) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Plasmopara viticola and then remain in an incubation cabin for 1 day at approx.

20 ° C and 100% relative humidity. The plants are then placed in a greenhouse at about 21 ° C. and about 90% relative atmospheric humidity for 5 days. The plants are then moistened and placed in an incubation cabin for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the examples (1), (3), (4), (5), (6), (8), (9), (12), (13), (14), (15 ), (16), (17) and (18) listed substances according to the invention in a

Application rate of 100 g / ha an efficiency of 97% or more. Example D

Venturia test (apple) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

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

To test for protective activity, young plants are sprayed with the active compound preparation in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the apple scab pathogen Venturia inaequalis and then remain in an incubation cabin at about 20 ° C. and 100% relative atmospheric humidity for 1 day.

The plants are then placed in the greenhouse at approx. 21 ° C. and a relative humidity of approx. 90%.

Evaluation is carried out 12 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the examples (1), (3), (4), (5), (6), (7), (8), (9), (15),

(16), (17) and (18) listed substances according to the invention at an application rate of 1 Og / ha an efficiency of 90% or more. Example E

Pyricularia test (rice) / protective

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

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

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

To test for protective activity, young rice plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Pyricularia oryzae and then remain at 100% rel. Humidity and 26 ° C.

The plants are then in a greenhouse at 80% rel. Humidity and 26 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infection is observed.

In this test, the substances according to the invention listed in Examples (1), (3), (5), (9) and (13) show an efficiency of 90% or more at an application rate of 125 g / ha. Example F

Myzus Test

Solvent: 6 parts by weight of dimethylformamide

67 parts by weight of methanol emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Broad bean seedlings (Vicia faba), which are infested with the green peach aphid (Myzus persicae), are added to the active ingredient preparation of the desired

Concentration dipped and placed in a plastic can.

After the desired time, the kill is determined in percent. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, for example, the compound of preparation example (5) with an exemplary active ingredient concentration of 0.05% causes a kill of 100% after 6 days. Example G

Phaedon larvae test

Solvent: 6 parts by weight of dimethylformamide

67 parts by weight of methanol emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Cabbage leaves (Brassica oleracea) are treated with the active ingredient preparation of the desired concentration. A treated leaf is placed in a plastic can and filled with larvae (L2) of the horseradish leaf beetle (Phaedon cochleariae). After 2 days, an untreated sheet is used for the replenishment. After the desired time, the kill is determined in%. 100% means that all animals have been killed; 0% means that no animals have been killed.

In this test, for example, the compound of preparation example (3), with an exemplary active ingredient concentration of 0.01%, kills 100% after 6 days.

Example H

Tetranychus test (OP-resistant / immersion treatment)

Solvent: 6 parts by weight of dimethylformamide

67 parts by weight of methanol emulsifier: 2 parts by weight of alkylaryl polyglycol ether

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

Bean plants (Phaseolus vulgaris), which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.

After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0%> means that no spider mites have been killed.

In this test, e.g. the compounds of the preparation examples (3), (7), (8) and (9) at an exemplary active ingredient concentration of 0.05%> after 7 days a kill of 90% and more.

Claims

claims 1. pyrrole derivatives of the general formula (I),

in which A stands for oxygen or -NH-, E represents nitrogen or = CH-, where L ¹ , L ² and L ^{3 are} identical or different and each independently represents hydrogen, halogen, cyano, nitro, in each case unsubstituted or halogen-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl, G for oxygen or for alkynediyl which is in each case unsubstituted or substituted by halogen, hydroxyl, alkyl, haloalkyl or cycloalkyl or one of the following groups in which the respective left side is bonded to Z: -O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C (R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH- -C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) -NO-CH ₂ -, -O-CH ₂ -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^H ) -C (R ⁸ ) = NO-CH ₂ -, -C (= N- OR ^{1 1} ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^{1 1} ) -C (R ⁸ ) = NN = CH-, where Q represents oxygen or sulfur, R ^{8 represents} hydrogen, cyano or in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, R ^{9 represents} cyano or unsubstituted or substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, R ^{10 represents} hydrogen, hydroxy, cyano or in each case unsubstituted or substituted alkyl, alkoxy or cycloalkyl, R ^{1 1 represents} hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, unsubstituted or substituted arylalkyl and Z for unsubstituted or substituted alkyl, alkenyl, Alkynyl, cycloalkyl, aryl or heterocyclyl, or G stands for -CH ₂ -ON = CH- with the left side bound to Z, and Z represents unsubstituted or substituted cycloalkyl or heterocyclicl or substituted aryl. 2. Compounds of formula (I), according to claim 1, in which A stands for oxygen or -NH-, represents nitrogen or = CH-, L ¹ , L ² and L ^{3 are the} same or different and are each independently hydrogen, halogen, cyano, nitro, each unsubstituted or substituted by 1 to 5 halogen atoms, alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 Carbon atoms, and in particular hydrogen or methyl, G for oxygen or for each unsubstituted or substituted by halogen, hydroxy, alkyl, haloalkyl or cycloalkyl Alkindiyl or one of the following groups, in which the left side is bound to Z: -O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C (R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH-, -C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) = NO-CH ₂ -, -O-CH ₂ - C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^π ) -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ⁿ ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^π ) -C (R ⁸ ) = N- N = CH-, where Q represents oxygen or sulfur, R ⁸ for hydrogen, cyano, for each unsubstituted or through Halogen, cyano or C ₁ -C ₄ alkoxy-substituted alkyl, Alkoxy, alkylthio, alkylamino or dialkylamino with each 1 to 6 carbon atoms in the alkyl groups or for each unsubstituted or by halogen, cyano, carboxy, -C-C ₄ alkyl or CC ^ alkoxycarbonyl substituted cycloalkyl having 3 to 6 carbon atoms, and R ^{9 represents} cyano, each unsubstituted or substituted by halogen, cyano or C _j -C alkoxy alkyl, alkoxy, alkylthio, alkylamino or dialkylamino each with 1 to 6 Carbon atoms in the alkyl groups or represents in each case unsubstituted or substituted by halogen, cyano, carboxy, C1-C ₄ - represents alkyl or Cι-C ₄ -alkoxycarbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and R ¹⁰ for hydrogen, hydroxy, cyano or for in each case unsubstituted or substituted by halogen, cyano or C1-C ₄ - alkoxy alkyl having 1 to 6 carbon atoms or for each unsubstituted or by halogen, cyano, carboxy, C1-C ₄ - alkyl or

substituted Cycloalkyl having 3 to 6 carbon atoms, R ^{1 1} for hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, -C-C ₄ haloalkyl, C ₂ -C4 haloalkenyl or unsubstituted or by halogen , Cyano, alkyl or alkoxy each having 1 to 6 carbon atoms, haloalkyl or haloalkoxy each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms substituted phenylalkyl each having 1 to 4 carbon atoms in the alkyl part, and for optionally single or multiple, identical or different by halogen, cyano, hydroxy, amino, Cj-C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C1-C ₄ -alkylsulfinyl or -C ₄ - alkylsulfonyl (which in each case optionally by Halogen can be substituted) 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, identically or differently, by halogen, cyano, carboxy, phenyl (which, if appropriate, by halogen, cyano, C1-C4-alkyl, C ₁ -C4 -haloalkyl, C1-C ₄ -alkoxy or -CC ₄ -Halogenalkoxy is substituted), C ₁ -C4 alkyl or -C-C4-alkoxy-carbonyl substituted cycloalkyl with 3 to 6 carbon atoms; for phenyl, naphthyl or heterocyclyl with 3 to 7 ring members, each of which is mono- or polysubstituted by identical or different substituents, at least one of which is for oxygen, Sulfur or nitrogen and optionally one or two more are nitrogen, the possible substituents preferably being selected from the list below: Halogen, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl; in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms; each straight-chain or branched alkenyl or alkenyloxy each having 2 to 6 carbon atoms; each straight-chain or branched haloalkyl, haloalkoxy, Haloalkylthio, haloalkylsulfmyl 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 or alkylsulfonyloxy, each having 1 to 6 carbon atoms in the individual alkyl parts; each optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms and / or straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each linked 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 - A ¹ - or a grouping _Δ 2 _N , wherein A ^{1 represents} alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and A ^{2 represents} optionally substituted by cyano, alkoxy, alkylthio, alkylamino, dialkylamino, benzyl or phenyl alkyl having 1 to 4 carbon atoms, alkenyl or alkynyl each having 2 to 4 carbon atoms, or G stands for -CH ₂ -ON = CH-, the left side being bound to Z, and Z represents unsubstituted or substituted cycloalkyl or heterocyclyl or substituted aryl, the preferred substituents being the same as those already mentioned above as substituents for Z. 3. Compounds of formula (I) according to claim 1, in which A stands for oxygen or -NH-, E stands for nitrogen or = CH-, L ¹ , L ² and L ^{3 are} identical or different and are each independently of one another hydrogen, halogen, cyano, nitro, in each case alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 6 carbon atoms, in each case optionally substituted by 1 to 5 halogen atoms, in particular represents hydrogen or methyl, G for unsubstituted or halogen, hydroxy, alkyl, Haloalkyl or cycloalkyl-substituted alkynediyl or for oxygen or one of the following groups, in each of which the left side is bonded to Z: -O-CH ₂ -, -C (R ⁸ ) = NO-CH ₂ -, -N = C ( R ⁸ ) -Q-CH ₂ -, -CH (R ⁹ ) -ON = CH-, -C (R ⁸ ) = NN = CH-, -QC (R ⁸ ) = NO-CH ₂ -, -N (R ¹⁰ ) -C (R ⁸ ) = NO-CH ₂ -, -O-CH ₂ -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^{! 1} ) -C (R ⁸ ) = NO-CH ₂ -, -C (= NOR ^π ) -C (R ⁸ ) -ON = CH-, or -C (= NOR ⁿ ) -C (R ⁸ ) = NN = CH-, where Q represents oxygen or sulfur, R ^{8 represents} hydrogen, cyano, methyl, ethyl or cyclopropyl and R ^{9 represents} cyano, methyl, ethyl or cyclopropyl and R ^{10 represents} hydrogen, methyl, ethyl or cyclopropyl, R ^1! for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-butenyl, 3-methyl-2-butenyl, propargyl, or for optionally by fluorine, chlorine , Bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromefhoxy, trifluoromethoxy, difluorochloromethoxy or Trifluoroethoxy substituted benzyl or phenylethyl, for phenyl, pyridine, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, pyridinyl, pyrimi which are each mono- to trisubstituted in the same or different ways - dyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2, 4-triazinyl or 1,3,5- Triazinyl is, 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, methyl sulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluorethoxy, difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl, trifluoromethylcarbonyl each optionally monosubstituted to tetrasubstituted, identically or differently, by fluorine, chlorine, methyl, trifluoromethyl or ethyl and in each case doubly linked methylenedioxy, ethylenedioxy, A or a grouping _Ä 2 _N , wherein A ^{1 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, Propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, Methylaminomethyl, methylaminoethyl or benzyl, or G stands for -CH ₂ -ON = CH- with the left side bound to Z, and Z stands for unsubstituted or substituted cycloalkyl or heterocyclyl or for substituted aryl, the preferred substituents being the same as those already mentioned above as substituents for Z. Compounds of formula (I) according to claim 1, in which A stands for oxygen or -NH-, E stands for = CH-, L ¹ , L ² , and L ^{3 represent} hydrogen, G represents -CH (CH ₃ ) -ON = CH-, -C (CH ₃ ) = NN = CH- or -CH = NN = CH-, and Z represents phenyl which is in each case monosubstituted to trisubstituted by identical or different substituents, the possible substituents preferably being selected from the list below: Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n - or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, Trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, 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 or a grouping .2 _N , where A ^{1 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-ene -3-yl, Cyanmethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl, dimethylaminomethyl, dimethylaminoethyl, methylaminomethyl, methylaminoethyl or benzyl. 5. Compounds of formula (I), according to claim 1, in which represents oxygen, stands for = CH-, L ¹ , L ² , and L ^{3 represent} hydrogen, G stands for -CH ₂ -ON = CH- and represents mono- to trisubstituted, identical or differently substituted phenyl or pyridine, 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, di fluorochloromethoxy, trifluoroethoxy, difluoromethylthio, Trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, 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 ¹ or a grouping »2, in which ^A ^ O ^" A ^{1 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl or cyclobutyl and A ² for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Allyl, propargyl, but-2-en-l-yl, 2-methyl-prop-l-en-3-yl, Cyanomethyl, methoxymethyl, ethoxymethyl, methoxyethyl, Ethoxyethyl, Mefhylfhiomethyl, Ethylthiomethyl, Methylthio-ethyl, Ethylthioethyl, Dimethylaminomethyl, Dimethylaminoethyl, Methylaminomethyl, Methylaminoethyl or Benzyl ^* stands. 6. Compounds of formula (I) according to claim 1, in which A stands for oxygen or -NH-, stands for = CH-, L ¹ , L ² and L ^{3 represent} hydrogen, G for -C (= NOR ^u ) -C (R ⁸ ) -ON = CH- or -C (= NOR ^u ) -C (R ⁸ ) = N- N = CH-, where R ^{8 represents} cyclopropyl or methyl, in particular methyl, R ^{1 l} for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, 2-butenyl, 3-methyl-2-butenyl, propargyl, or for optionally by Fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromefhoxy , Difluorochloromethoxy or trifluoroethoxy substituted benzyl or phenylethyl, Z for in each case optionally up to triple, identical or different, fluorine, chlorine, bromine, cyano, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl or phenyl. 7. Compounds of the formula (II),

in which A, G, L ¹ , L ² , L ³ and Z have the meanings given in claim 1. 8. Compounds of the formula (XII),

in which A, L ¹ , L ² and L ^{3 have} the meanings given in claim 1 and R ^{12 represents} alkyl or optionally substituted aryl. 9. Compounds of the formula (XIII),

in which A, L ¹ , L ² and L ^{3 have} the meanings given in Claim 1. 10. Compounds of the formula (III),

in which A, G, L ¹ , L ² , L ³ and Z have the meanings given in claim 1. 11. agent containing extenders and / or carriers and optionally surface-active substances, characterized by a content of at least one compound as defined in claims 1 to 6. 12. A method for controlling pests, characterized in that compounds as defined in claims 1 to 6 or agents as defined in claim 11 are allowed to act on pests and / or their habitat. 13. A process for the preparation of pesticides, characterized in that compounds of the formula (I) according to Claims 1 to 6 are mixed with extenders and / or surface-active agents. 14. Use of compounds as defined in claims 1 to 6 or in agents as defined in claim 11 for controlling pests. 15. A process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that (Process a) pyrrole acetic ester of the formula (II),

in which A, G, L ¹ , L ² , L ³ and Z have the meanings given above, with a formic acid ester, if appropriate in the presence of a diluent and if appropriate in the presence of a base, and the crude product is then reacted without working up with a methylating agent, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or (process b), enamines of the formula (III),

in which A, G, L ¹ , L ² , L ³ and Z have the meanings given above, hydrolyzed with an aqueous mineral acid, if appropriate in the presence of a diluent, and the crude product is then reacted without working up with a methylating agent, if appropriate in the presence of a diluent and if appropriate in the presence of a base, or (process c), aldehydes of the formula (IV),

in which A, E, L ¹ , L ² and L ^{3 have} the meanings given above, with a nitrogen compound of the general formula (V), ZG ¹ -NH ₂ (V) in which G ¹ for a grouping -CH (R ⁹ ) -O-, -C (R ⁸ ) = N-, -C (= NOR ^π ) -C (R ⁸ ) - O- or -C (= NOR ⁿ ) - C (R ⁸ ) = N-, in which the left side in each case Z is bound in what R ⁸ , R ⁹ and R ^{u have} the meanings given above, and Z has the meaning given above, if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst and if appropriate in the presence of a dehydrating agent, or (process d) methylpyrroles of the formula (VI),

in which A, E, L ¹ , L ² and L ^{3 have} the meanings given above and X ^{1 represents} halogen or trialkylammonium, including an anion, with an oxygen compound of the general formula (VII), ZG ² -OH (VII) in which G ² for a single bond or a grouping -C (R ⁸ ) = N-, -QC (R ⁸ ) = N-, -N (R ¹⁰ ) -C (R ⁸ ) = N-, -O-CH ₂ -C (R ⁸ ) = N- , or -C (= NOR ^u ) -C (R ⁸ ) = N-, in which the respective left side is bound to Z, in which Q, R ⁸ , R ¹⁰ and R ¹ 'have the meanings given above, and Z has the meaning given above, or a sulfur compound of the general formula (VIII), ZN = C (R ⁸ ) -SH (VIII) in which R ⁸ and Z have the meanings given above, if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.