EP1003726A1

EP1003726A1 - Nitrophenyl-sulfonyl-imidazoles and use thereof for controlling vegetable and animal pests

Info

Publication number: EP1003726A1
Application number: EP98941320A
Authority: EP
Inventors: Lutz Assmann; Klaus Stenzel; Christoph Erdelen; Martin Kugler; Peter Wachtler
Original assignee: Bayer AG
Current assignee: Bayer CropScience AG
Priority date: 1997-07-24
Filing date: 1998-07-13
Publication date: 2000-05-31
Also published as: CN1264367A; US20020094936A1; PL338191A1; US6350770B1; US6262100B1; US20020022728A1; AU8974598A; US6486191B2; JP2001510828A; WO1999005116A1

Abstract

The invention relates to novel nitrophenyl-sulfonyl-imidazoles of formula (I), wherein X, R?1, R2 and R3¿ have the meanings given in the Description, to a method for producing the same, and to their use for controlling vegetable and animal pests.

Description

NITROPHENYL-SULFONYL IMIDAZOLES AND THE USE THEREOF FOR CONTROLLING PLANT AND ANIMAL PEST

The present invention relates to new nitrophenylsulfonylimidazoles, a process for their preparation and their use for controlling plant and animal pests.

It has already become known that certain phenylsulfonylimidazoles and phenylsulfonylbenzimidazoles have fungicidal properties (cf. EP-A 0 238 824 and WO 97-06 171). So l- (2-methyl-5-nitro-phenylsulfonyl) benzotriazole,

2-methyl-1- (2-methyl-5-nitro-phenylsulfonyl) imidazole and 1- (2-methyl-5-nitro-phenylsulfonyl) -2-chloro-6,6-difluoro- [1,3] - Use dioxolo- [4,5-f] -benzimidazole to fight fungi. The effectiveness of these substances is good, but leaves something to be desired in some cases at low application rates.

There have now been new nitrophenyl-sulfonyl-imidazoles of the formula

in which

a) X represents cyano,

R ^{1 represents} halogen, alkyl or phenyl,

R ^{2 represents} halogen, alkyl or phenyl or R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally substituted benzene ring or an optionally substituted heterocyclic ring,

and

R ^{3 represents} halogen, alkyl or phenyl,

or

b) X represents halogen,

R ^{1 represents} halogen, alkyl or phenyl,

R ^{2 represents} halogen, alkyl or phenyl or

R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally substituted heterocyclic ring,

or

R ¹ and R ² together for a double bonded radical of the formula

or stand

and

R ^{3 represents} halogen, alkyl or phenyl,

found. Furthermore, it has been found that nitrophenylsulfonylimidazoles of the formula (I) are obtained if imidazole derivatives of the formula

in which

R ¹ , R ² and X have the meanings given above,

with nitrobenzene sulfonyl halides of the formula

in which

R ^{3 has} the meaning given above and

Shark represents chlorine or bromine,

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

Finally, it was found that the nitrophenylsulfonylimidazoles of the formula (I) are very suitable for controlling plant and animal pests in crop protection and in the protection of materials. Surprisingly, the substances according to the invention show a better fungicidal activity than l- (2-methyl-5-nitro-phenylsulfonyl) benzotriazole and 2-methyl-l- (2-methyl-5-nitro-phenylsulfonyl) imidazole, which is constitutionally similar, are known active ingredients of the same direction.

The substances according to the invention are generally defined by the formula (I).

A preferred group of substances according to the invention are nitrophenylsulfonylimidazoles of the formula

Here, the substituents preferably have the meanings given below.

R ¹ preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.

R ² preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.

R ¹ and R ² together with the carbon atoms to which they are attached are preferably a benzene ring which can be monosubstituted to trisubstituted by identical or different substituents

Halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl; Alkyl, alkoxy, alkylthio or alkylsulfonyl each having 1 to 5 carbon atoms;

Haloalkyl, haloalkoxy, haloalkylthio or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 5 identical or different

Halogen atoms;

in each case straight-chain or branched haloalkenyl or haloalkenyloxy each having 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;

Alkylcarbonyl, alkylcarbonyloxy, alkoxy carbonyl, alkylsulfonyloxy, hydroximinoalkyl, alkoximinoalkyl or cyanimino (alkoxy) alkyl, each with 1 to 4 carbon atoms in the individual alkyl parts;

Cycloalkyl of 3 to 6 carbon atoms;

Phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio, where each of these radicals can be substituted once or twice, in the same way or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or haloalkyl 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.

R ¹ and R ² , together with the carbon atoms to which they are attached, preferably represent a benzene ring which is linked by double bonds

Alkylene with 3 or 4 carbon atoms or dioxyalkylene with 1 or 2 carbon atoms is substituted, where the alkylene or dioxyalkylene groups can be monosubstituted to tetrasubstituted, identical or different, by halogen, alkyl having 1 to 4 carbon atoms and / or haloalkyl 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms. R and R ^ together with the carbon atoms to which they are attached are preferably a 5- or 6-membered heterocyclic ring which has one, two or three identical or different heteroatoms, such as oxygen, sulfur and / or nitrogen, contains and can be mono- to triple, identical or differently substituted by halogen, cyano,

Nitro, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl with 1 to 4

Carbon atoms in the alkoxy part, cycloalkyl with 3 to 6 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkylsulfonyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino with 1 to 4 carbon atoms, hydroxyalkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl group, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl with 1 to 4 carbon atoms in the alkyl part, alkoximinoalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkylcarbonyloxy with 1 to 4 carbon atoms in the alkyl part and / or haloalkylcarbonyloxy with 1 to 4 carbon atoms in the haloalkyl group and 1 to 5 identical or different halogen atoms, but in the event that the heterocyclic ring contains more than one oxygen atom, the oxygen atoms do not ben stand next to one another.

R ³ preferably represents fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.

Another group of preferred substances according to the invention are nitrophenylsulfonylimidazoles of the formula

In this formula, the substituents preferably have the meanings given below.

Shark ¹ is preferably fluorine, chlorine or bromine.

Rl and R ^ together with the carbon atoms to which they are attached are preferably a 5- or 6-membered heterocyclic

Ring which contains one, two or three identical or different heteroatoms, such as oxygen, sulfur and / or nitrogen, and can be substituted once to three times, identically or differently, by halogen, cyano, nitro, hydroxy, amino, formyl, carboxy, carbamoyl , Thiocarbamoyl, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl with 1 up to 4 carbon atoms in the alkoxy part, cycloalkyl with 3 to 6 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino with 1 to 4 carbon atoms, Hydroxyalkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each alkyl group, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl with 1 to 4 carbon atoms in the alkyl part, alkoximinoalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkylcarbonyloxy with 1 4 carbon atoms in the alkyl part and / or haloalkylcarbonyloxy with 1 to 4 carbon atoms in the haloalkyl group and 1 to 5 identical or different halogen atoms, the oxygen atoms not being adjacent in the event that the heterocyclic ring contains more than one oxygen atom.

R ¹ and R ² also preferably together represent a double bonded radical of the formula

Compounds of the formula (Ia) in which

R ^{1 represents} fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl or phenyl,

R ^{2 represents} fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or phenyl, or

R ¹ and R ² together with the carbon atoms to which they are attached represent a benzene ring which can be substituted by up to three, the same or different Fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio , n- or i-propylthio, methylsulfonyl, ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethyloxy, trifluoromethylethyloxy, methoxycarbonyl, methoxycarbonyl, trifluoromethylethoxy, methylifoxy Ethylsulfonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, cyanimino (methoxy) methyl,

Cyclopropyl, cyclopentyl, cyclohexyl or

Phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio, where each of these radicals can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl , n-butyl, sec-butyl, iso-butyl, tert-butyl, trifluoromethyl, trichloromethyl and / or difluoromethyl, or

R ¹ and R ² together with the carbon atoms to which they are attached represent a benzene ring which is each linked by propane-l, 3-diyl,

Butane-1,4-diyl, methylenedioxy or ethylenedioxy is substituted, where the alkylene or dioxyalkylene groups can be monosubstituted to tetrasubstituted, identical or different, by fluorine, chlorine, trifluoromethyl, methyl, ethyl and / or n-propyl, or

R ¹ and R ² together with the carbon atoms to which they are attached, for a fused furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2, 3-oxadiazole, 1,2,3-thiadiazole, 1,2,3-triazole, pyridine, pyridazine, pyrazine, pyrimidine or 1,2,4-triazine ring, where these Residues can be substituted once or twice, in the same way or differently, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, Trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino,

Acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl and / or ethoxyiminoethyl and

R ^{3 represents} fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or phenyl.

Compounds of the formula (Ib) in which

Shark ^{1 represents} fluorine, chlorine or bromine,

R ¹ and R ² together with the carbon atoms to which they are attached, for a fused furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole,

Isothiazole, pyrazole, 1,2,3-oxadiazole, 1,2,3-thiadiazole, 1,2,3-triazole, pyridine, pyridazine, pyrazine, pyrimidine or 1,2,4 -Triazine ring, where these radicals can be substituted once or twice, in the same or different ways, by fluorine, chlorine, bromine, cyano, nitro, amino, hydroxy, formyl, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, Ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methylyloxy, oxyloxy, oxyloxy, oxyloxy, oxyloxy, oxyloxy, oxyloxy, oxyloxy, oxyloxy, oxyl, propylamyloxy, oxyloxy, oxyethyl, propylamyloxy, oxyloxy, oxyethyl, propylamethyl, oxyloxy, oxyethyl, propylamyloxy, methyloxy, oxyethyl, propylamethyl, oxyethyl, propylamethyl, oxyethyl, propylamethyl, oxyethyl, propylamethyl, propylamethyl, methylethyl , Hydroxyiminomethyl, Hydroxyiminoethyl, Methoxyiminomethyl, Ethoxyiminomethyl, Methoxyiminoethyl and / or Ethoxyiminoethyl,

or

R ¹ and R ² together for a double bonded radical of the formula

or stand,

and

The substituent meanings given above can be combined with one another in any manner. In addition, individual definitions can also be omitted.

Examples of substances according to the invention are the nitrophenylsulfonylimidazoles listed in the following tables. Table 1

Table 2

R ³ C ₂ H ₅ C3H7

F Cl

Table 3

in which

R ^{3 stands} for the substituents mentioned in Table 2.

Table 4

Table 5

in which R ^{3 stands} for the substituents mentioned in Table 2.

Table 6

Table 7

If 2,5-dibromo-4-methyl-1H-imidazole and 2-methyl-5-nitrobenzenesulfonic acid chloride are used as starting materials, the course of the process according to the invention can be illustrated by the following formula.

Formula (II) provides a general definition of the imidazole derivatives required as starting materials for carrying out the process according to the invention. In this formula, R ¹ , R ² and X preferably have those meanings which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

The compounds of formula (II) can exist in the following two tautomeric forms.

(Ha) (over).

Is the molecular unit

symmetrical, the tautomeric forms are identical. In the reaction according to the invention with nitrobenzenesulfonyl halides of the formula (III), only a certain end product of the formula (I) is formed, regardless of which of the two tautomeric forms reacts.

Is the molecular unit

asymmetrical, the two tautomeric forms are not identical. In the reaction according to the invention with nitrobenzene sulfonyl halides of the formula (III), end products of the formula (I) can thus form which are derived from the tautomeric forms of the formula (Ha) and / or (Ilb). If both tautomers react, end products of the formula (I) are obtained in the form of mixtures.

The imidazole derivatives of the formula (II) are known or can be prepared by known methods (cf. WO 97-06171, Chem. Ber. 85, (1952) 1012-1020), J. Med. Chem. 34 (1991) , 1110-1116 and J. Chem. Soc. 1965. 3017-3021).

Formula (III) provides a general definition of the nitrobenzenesulfonyl halides which are furthermore required as starting materials when carrying out the process according to the invention. In this formula, R ³ preferably has those meanings which have already been mentioned as preferred for this substituent in connection with the description of the substances of the formula (I) according to the invention. Shark also preferably represents chlorine or bromine.

The nitrobenzene sulfonyl halides of the formula (III) are known or can be prepared by known methods (cf. EP-A 0 238 824). Suitable acid binders for carrying out the process according to the invention are all customary inorganic or organic bases. Alkaline earth metal or alkali metal hydrides, hydroxides, amides, alcoholates, acetates, carbonates or hydrogen carbonates, such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butoxide, are preferably usable.

Sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, furthermore ammonium compounds, such as ammonium hydroxide, ammonium acetate or ammonium carbonate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylan , N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).

Suitable diluents for carrying out the process according to the invention are all inert organic solvents. Aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitrites, 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 methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones, such as sulfolane, or amines, such as pyridine.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 120 ° C. The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.

When carrying out the process according to the invention, 1 to 1.5 mol of nitrobenzenesulfonic acid halide of the formula (III) and an equivalent amount or an excess of acid binder are generally employed per mol of imidazole derivative of the formula (II) . The processing takes place according to usual methods. In general, the procedure is that water is added to the reaction mixture, the resulting mixture is extracted several times with an organic solvent which is sparingly soluble in water, and the combined organic phases are dried and concentrated. The substances obtained can, if appropriate, be purified by customary methods, such as chromatography or recrystallization.

The active compounds according to the invention are suitable for controlling plant pests and can therefore be used for controlling unwanted microorganisms, such as fungi and bacteria, in plant protection and in material protection.

Fungicides can be used in crop protection to combat Plasmodiophoromycetes,

Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes can be used.

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

Some pathogens of fungal and bacterial diseases which come under the generic names listed above may be mentioned as examples, but not by way of limitation: Xanthomonas species, such as Xanthomonas campestris pv. Oryzae;

Pseudomonas species, such as Pseudomonas syringae pv. Lachrymans; Erwinia species, such as Erwinia amylovora; Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as Plasmopara viticola;

Bremia species, such as Bremia lactucae;

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea; Podosphaera species, such as, for example, Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea

(Conidial form: Drechslera, Syn: Helminthosporium);

Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, Syn: Helminthosporium);

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Sclerotinia species, such as Sclerotinia sclerotiorum;

Tilletia species, such as Tilletia caries; Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea; Septoria species, such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

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

Pseudocercosporella species, such as Pseudocercosporella herpotrichoides. The fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

The active compounds according to the invention can be particularly successful

Combating diseases in wine, fruit and vegetable growing, such as against Venturia, Podosphaera and Plasmopara species, use. Rice diseases such as Pyricularia species are also successfully combated.

In material protection, the substances according to the invention can be used to protect technical materials against attack and destruction by undesired microorganisms.

In the present context, technical materials are to be understood as non-living materials that have been prepared for use in technology. For example, technical materials which are to be protected from microbial change or destruction by active substances according to the invention can be adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastic articles, cooling lubricants and other materials which are attacked or decomposed by microorganisms can be. As part of the to be protected

Materials are also parts of production systems, such as cooling water circuits, that can be affected by the proliferation of microorganisms. In the context of the present invention, technical materials are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer liquids, particularly preferably wood.

For example, microorganisms of the following genera may be mentioned:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora, such as Coniophora puetana, Lentinus, such as Lentinus tigrinus, Penicillium, such as Penicillium versicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride, Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonas aeruginosa, Staphylococcus, such as Staphylococcus aureus.

The active compounds according to the invention are also suitable for combating animal pests, in particular insects, arachnids and nematodes, which are useful in agriculture, in forestry, in horticulture, in the protection of stocks and materials and in the hygiene sector or in veterinary medicine, with good plant tolerance and favorable warm-blood toxicity Range occur. The substances are effective against normally sensitive and resistant species and against pests in all or individual stages of development. The animal pests mentioned above include:

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

From the order of the Diplopoda e.g. Blaniulus guttulatus.

From the order of the Chilopoda e.g. Geophilus carpophagus, Scutigera spec.

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, for example Onychiurus armatus. From the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.

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 anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga e.g. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera e.g. Hercinotbrips femoralis, Thrips tabaci.

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 e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phosophosumon - siphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiisispppp., Phyllocnistia. Phyllocnist.

Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia po- dana, Capua reticulana, Choristoneura fumiferana, Clysona ambiganana, Clysona ambiganana, Toric

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 chrysocephususpp sulcatus, Cosmopolites sordidus,

Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agribiole spp., Tenebrio molitor. Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera e.g. Aedes spp., Anopheles spp., Culex spp.,

Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp. Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

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

From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.

From the order of the Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus 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.

The substances which can be used according to the invention can be used with particularly good success

Control of plant-damaging mites, such as against the bean spider mite (Tetranychus urticae), or for controlling plant-damaging insects, such as against the caterpillars of the cabbage cockroach (Plutella maculipennis), the larvae of the horseradish leaf beetle (Phaedon cochleariae), and the green rice leafhopper (Neicephotis cinix) deploy.

The substances which can be used according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, room mites, running mites, flies (stinging and licking), parasitic fly larvae and lice ,

Hair lice, featherlings and fleas. These parasites include:

From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..

From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp. , Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp ., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida e.g. Cimex spp., Triatoma spp., Rhodnius spp.,

Panstrongylus spp.

From the order of the Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietssus spp., ., Sternostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypppectoles spp ., Psoroptes spp., Chorioptes spp.,

Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

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 fog formulations.

These formulations are prepared in a known manner, for example 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, organic solvents can, for example, 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, for example petroleum fractions, alcohols, such as butanol or glycol, and the like 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 under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. The following are suitable as solid carriers: for example, natural rock powders such as kaolins, clays, talc, chalk, quartz, artapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: 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. 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 can be used in the formulations, such as

Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and meta-uphthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc, are used.

The formulations generally contain between 0.1 and 95 percent by weight

Active ingredient, preferably between 0.5 and 90%.

Depending on their respective physical and / or chemical properties, the active compounds 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 Seed, as well as ULV cold and warm mist formulations.

As such or in their formulations, the active compounds according to the invention can also be mixed with known fungicides, bactericides, acaricides, nematicides or

Insecticides can be used, e.g. to broaden 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.

The following connections can be considered as mixed partners: Fungicides:

Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,

Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,

Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazon, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyprodinconol, cypodinconol

Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofen carb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazole-M,

Dinocap, Diphenylamine, Dipyrithione, Ditalimfos, Dithianon, Dodemorph, Dodine, Drazoxolon,

Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,

Famoxadon, Fenapanil, Fenarimol, Fenbuconazol, Fenfüram, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzon, Fluazinam, Flumetover, Fluoromid, Fluquinconazol, Flu rimidol, Flusulfonololololololololololololololusolusolazolutol, flusilazolutolutol , Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole, Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovededione,

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

Mancopper, Mancozeb, Maneb, Meferimzone, Meparjipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfiiroxam, Metiram, Metomeclam, Metsulfovax,

Mildiomycin, myclobutanil, myclozolin,

Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,

Ofürace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,

Paclobutrazol, Pefürazoat, Penconazol, Pencycuron, Phosdiphen, Pimaricin, Piperalin, Polyoxin, Polyoxorim, probenazole, Prochloraz, Procymidon, Propamocarb, Propanosine-Sodium, Propiconazole, Propineb, Pyrazophos, Pyrifen, Pyifen, Pyroyilonil

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, Tridemoφh, triflumizole, triforine, triticonazole,

Uniconazole,

Validamycin A, vinclozolin, viniconazole, Zarilamide, Zineb, Ziram and Dagger G, OK-8705, OK-8801, α- (1, 1-dimethylethyl) -ß- (2-phenoxyethyl) - IH-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-dichloro-phhenyl) -ß-methoxy-a-methyl- 1 H- 1, 2,4-triazole-1-ethanol, - (5-methyl-1,3-dioxan-5-yl) -ß - [[4- (trifluoromethyl) phenyl] methylene] - IH- 1,2,4-triazole

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

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

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

1 - (2,4-dichloφhenyl) -2- (IH- 1, 2,4-triazol-1-yl) -ethanone-O- (phenylmethyl) -oxime, l- (2-methyl-l-naphthalenyl) - lH-ρyrrol-2,5-dione,

1 - (3, 5-dichloφhenyl) -3- (2-propenyl) -2, 5-pyrrolidinedione, l - [(diiodomethyl) sulfonyl] -4-methyl-benzene,

1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1 H-imidazole,

1 - [[2- (4-chloro-phenyl) -3-phenyloxiranyl] methyl] - 1 H- 1, 2,4-triazole, 1 - [1 - [2 - [(2,4-dichloro-phenyl) methoxy]] -phenyl] -ethenyl] - 1 H-imidazole, l-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4 ^l -trj uor-methyl-l, 3-t azole-5-carboxarilide,

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

2,6-DicUor-5- (methyltMo) -4-pyrimidinyl-thiocyanate, 2,6-DicUor-N- (4-trifluoromethylbenzyl) benzamide,

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

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

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

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

2-aminobutane,

2-bromo-2- (bromomethyl) pentandinitrile, 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-1 - [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyan [(1- methyl-2-propynyl) -oxy ] -methyl] -benzamide,

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

3- [2- (4-C φhenyl) -5-ethoxy-3-isoxazominyl] 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-dymethylethyl) -N-ethyl-N-propyl-l, 4-dioxaspiro [4.5] decan-2 -methanamine,

8-hydroxyquinoline sulfate,

9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide, bis- (l-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate, ice-1 - (4-chloro-phenyl) -2- (IH-1, 2,4-triazole-1-yl) -cycloheptanol, cis-4- [3- [4- (l, l-dimethylpropyl) -phenyl- 2-methylpropyl] -2,6-dimethyl-moφholin hydrochloride,

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

Potassium hydrogen carbonate,

Methane tetrathiol 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- (cWorace1yl) -N- (2,6-dimethylphenyl) -DL-alaninate,

N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.

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-Cuor-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,

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

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 - [(c oracetyl) amino] ethyl] benzamide,

N- [3-chloro-4,5-bis- (2-propynyloxy) phenyl] -N'-methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine sodium salt,

O, O-Diethyl- [2- (dipropylarnino) -2-oxoethyl] ethylphosphoramidothioate, O-Methyl-S-phenyl-phenylpropylphosphoramidothioate, S-Methyl-1, 2,3-benzotbiadiazol-7-carbothioate, spiro [2H] -l-benzopyran-2, 1 '(3Η) -isobenzofüran] -3'-one,

Bactericides:

Bronopol, dichlorophene, nitrapyri, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam,

Copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides:

Abamectin, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz,

Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,

Bacillus thuringiensis, 4-bromo-2- (4-chloro-phenyl) - 1 - (ethoxymethyl) -5- (trifluoromethyι) - lH-pyrrole-3-carbonitrile, bendiocarb, benfüracarb, bensultap, betacyfluthrin, bifenthrin, BPMC, brofenprox, bromine A, bufencarb, buprofezin, butocarboxim, butylpyridaben,

Cadusafos, Carbaryl, Carbofüran, Carbophenothion, Carbosulfan, Cartap, Chloethocarb, Chlorethoxyfos, Chlorfenapyr, Chlorfenvinphos, Chlorfluazuron, Chlormephos, N - [(6-Chloro-3-pyridinyl) -methyl] -N-cyano-N-methyl-ethanimidamide, Chloφyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrin, Clofentezin, Cyanophos, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cyhexatin, Cypermethrin, Cyromazin,

Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, Dichlofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Diflubenzuron, Dimethoat,

Dimethylvinphos, dioxathione, disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,

Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil,

Fluazinam, Fluazuron, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,

HCH, heptenophos, hexaflumuron, hexythiazox,

Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lamda-cyhalothri, Lufenuron,

Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, Methidathione, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos,

Moxidectin,

Naled, NC 184, Nitenpyram

Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,

Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenophos, Promecarb, Propaphos, Propoxur, Prothiophos, Prothoat, Pymethrozine, Pyri-dophophion, Pyri-dlphophone Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidiferi, Pyriproxifen,

Quinalphos,

Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos,

Tebufenozide, Tebufenpyrad, Tebupirimiphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiomethon, Thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,

Vamidothione, XMC, xylylcarb, zetamethrin.

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

The active ingredients 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 can be applied. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. 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 relatively wide 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. When treating 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.

The agents used to protect industrial materials generally contain the active ingredients in an amount of 1 to 95%, preferably 10 to 75%.

The application concentrations of the active compounds according to the invention depend on the type and the occurrence of the microorganisms to be controlled and on the Composition of the material to be protected. The optimal amount can be determined by test series. In general, the application concentrations are in the range from 0.001 to 5% by weight, preferably from 0.05 to 1.0% by weight, based on the material to be protected.

The effectiveness and the spectrum of activity of the active ingredients to be used according to the invention in the protection of materials or of the agents, concentrates or very generally formulations which can be produced therefrom can be increased if further antimicrobial compounds, fungicides, bactericides, herbicides, insecticides or other active ingredients are used to enlarge the spectrum of activity or Achieving special effects such as added protection against insects. These mixtures can have a broader spectrum of activity than the compounds according to the invention.

When used against animal pests, the substances according to the invention can also be present in commercially available formulations and in the use forms prepared from these formulations as 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.

The following examples illustrate the preparation and use of substances according to the invention. Manufacturing examples

example 1

1.4 g (10 mmol) of potassium carbonate are added at room temperature to a solution of 1.7 g (7 mmol) of 2, 5-dibromo-4-methyl-1 H-imidazole in 40 ml of acetonitrile. The mixture is stirred at room temperature for 10 minutes and then 1.7 g (7 mmol) of 2-methyl-5-nitro-benzenesulfonic acid chloride are added. You stir more

20 hours at room temperature and then pour the reaction mixture onto 100 ml of water. The resulting mixture is extracted twice with 50 ml of diethyl ether. The combined organic phases are dried over sodium sulfate and then concentrated under reduced pressure. The remaining residue is chromatographed on silica gel using mobile phase methylene chloride. In this way 1.6 g (51% of theory) of l- (2-methyl-4-nitro-benzenesulfonyl) -2,4-dibromo-5-methyl-l H-imidazole are obtained in the form of a colorless solid substance of Melting point 187 to 189 ° C.

The substances listed in Table 8 below are also produced by the methods given above. Table 8

Table 8 (continued)

Examples of use

Example A

Phytophthora test (tomato) / 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, mix 1

Part by weight of active ingredient with the specified amount of solvent and emulsifier and dilute the concentrate 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

The plants are inoculated with a spray coating with an aqueous spore suspension of Phytophora infestans. The plants are then placed in an incubation cabin at approx. 20 ° C and 100% relative humidity.

Evaluation is carried out 3 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.

Active substances, application rates and test results are shown in the following table. Table A

Phytophthora test (tomato) / protective

Table A (continued)

Example B

Plasmopora 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 at about 20 ° C. and 100% relative atmospheric humidity for 1 day. 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.

Active substances, application rates and test results are shown in the following table.

Table B

Plasmopara test (vine) / protective

Example C

Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide emulsifier: 1 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.

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.

After the desired time, the mortality is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.

Table C plant-damaging insect Phaedon larva test

Example D

Plutella test

Solvent: 7 parts by weight of dimethylformamide emulsifier. 1 part by weight of alkylaryl polyglycol ether

Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and possessed by caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist

After the desired time, the death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed

Active substances, application rates and test results are shown in the following table

Table D plant-damaging insect plutella test

Table E

Material protection test

To demonstrate the activity against fungi, the minimum inhibitory concentrations (MIC values) of compounds according to the invention are determined.

Active ingredients according to the invention are added to an agar which is produced using malt extract in concentrations of 0.1 mg / 1 to 5000 mg / 1. After the agar has solidified, it is contaminated with pure cultures of test organisms. After two weeks of storage at 27 ° C and 60 to 70% relative humidity, the minimum inhibitory concentration (MIC value) is determined. The MIC value indicates the lowest concentration of active ingredient at which no growth occurs due to the microbe species used.

Active substances, test organisms and MIC values are shown in the following table.

Table E

Material protection test

Minimum inhibitory concentration (MIC value) in mg / 1

Claims

claims

1. Nitrophenyl-sulfonyl-imidazoles of the formula

in which

a) X represents cyano,

R ^{1 represents} halogen, alkyl or phenyl,

R ^{2 represents} halogen, alkyl or phenyl,

R ¹ and R ² together with the carbon atoms to which they are attached represent an optionally substituted benzene ring or an optionally substituted heterocyclic ring,

and

R ^{3 represents} halogen, alkyl or phenyl,

or

b) X represents halogen,

R ^{1 represents} halogen, alkyl or phenyl, R ^{2 represents} halogen, alkyl or phenyl,

or

R ¹ and R ² together for a double bonded radical of the formula

or stand

and

R ^{3 represents} halogen, alkyl or phenyl.

Nitrophenyl-sulfonyl-imidazoles of the formula (I) according to Claim 1, in which

X stands for cyano,

R ^{1 represents} fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl,

R ^{2 represents} fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl, or

R ¹ and R ² together with the carbon atoms to which they are attached represent a benzene ring which can be monosubstituted to triple, identical or differently substituted by Halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl;

Alkyl, alkoxy, alkyltbio or alkylsulfonyl each having 1 to 5 carbon atoms;

Haloalkyl, haloalkoxy, haloalkylthio or haloalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;

Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy,

Hydroximinoalkyl, alkoximinoalkyl or cyanimino (alkoxy) alkyl each having 1 to 4 carbon atoms in the individual alkyl parts;

Cycloalkyl of 3 to 6 carbon atoms;

Phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio, where each of these radicals can be substituted once or twice, in the same way or differently, by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 to 4 carbons - Substance atoms and 1 to 5 identical or different halogen atoms, or

R ¹ and R ² together with the carbon atoms to which they are attached represent a benzene ring which is substituted by double-linked alkylene having 3 or 4 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, the alkylene or dioxyalkylene being Groups simple to fourfold, identical or differently substituted can be halogenated, alkyl having 1 to 4 carbon atoms and / or haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, or

Rl and R ² together with the carbon atoms to which they are attached represent a 5- or 6-membered heterocyclic ring which contains one, two or three identical or different heteroatoms and can be mono- to trisubstituted, identical or differently substituted by Halogen, cyano, nitro, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms,

Alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, cycloalkyl with 3 to 6 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylamino with 1 to 4 carbon atoms, hydroxyalkylamino with 1 to 4 carbon atoms, dialkylamino with 1 up to 4 carbon atoms in each alkyl group, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl with 1 to 4 carbon atoms in the alkyl part, alkoximinoalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkylcarbonyloxy with 1 to 4 carbon atoms in the alkyl part and un d / or

Haloalkylcarbonyioxy with 1 to 4 carbon atoms in the haloalkyl group and 1 to 5 identical or different halogen atoms, where in the event that the heterocyclic ring contains more than one oxygen atom, the oxygen atoms are not adjacent,

and R ^{3 represents} fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.

3. nitrophenyl-sulfonyl-imidazoles of the formula (I) according to claim 1, in which

X represents fluorine, chlorine or bromine,

R ^{2 represents} fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl,

or

Rl and R2 together with the carbon atoms to which they are attached represent a 5- or 6-membered heterocyclic ring which contains one, two or three identical or different heteroatoms, such as oxygen, sulfur and / or nitrogen, and simply until can be triple, identical or differently substituted by halogen, cyano,

Nitro, hydroxy, amino, formyl, carboxy, carbamoyl, thiocarbamoyl, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkoxy with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl with 1 to 4 carbon atoms in the alkoxy part, cycloalkyl with 3 to 6 carbon atoms, haloalkylsulfinyl with 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, haloalkylsulfonyl with 1 to 4 carbon atoms and 1 to 5 identical or various halogen atoms, alkylamino with 1 to 4 carbon atoms, hydroxyalkylamino with 1 to 4 carbon atoms, dialkylamino with 1 to 4 carbon atoms in each Alkyl group, alkylcarbonyl with 1 to 4 carbon atoms in the alkyl part, hydroximinoalkyl with 1 to 4 carbon atoms in the alkyl part, alkoximinoalkyl with 1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl part, alkylcarbonyloxy with 1 to 4 carbon atoms in the alkyl part and / or haloalkylcarbonyloxy with 1 to 4 carbon atoms in the haloalkyl group and 1 to 5 identical or different halogen atoms, and in the event that the heterocyclic ring contains more than one oxygen atom, the oxygen atoms are not adjacent.

or

R ¹ and R ² together for a double bonded radical of the formula

and

R ^{3 represents} fluorine, chlorine, bromine, straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl.

4. A process for the preparation of nitrophenyl-sulfonyl-imidazoles of the formula (I) according to claim 1, characterized in that imidazole derivatives of the formula

in which R ¹ , R ² and X have the meanings given above,

with nitrobenzene sulfonyl halides of the formula

in which

R ^{3 has} the meaning given above and

Shark represents chlorine or bromine,

optionally in the presence of an acid binder and optionally in

In the presence of a diluent.

5. Agent for controlling plant and animal pests, characterized by a content of at least one nitrophenyl-sulfonyl-imidazole of the formula (I) according to claim 1.

6. Use of nitrophenyl-sulfonyl-imidazoles of the formula (I) according to Claim 1 for combating plant and animal pests.

7. A method for controlling plant and animal pests, characterized in that nitrophenyl-sulfonyl-imidazoles of the formula (I) according to claim 1 are applied to the pests and / or their habitat.

8. A process for the preparation of agents for controlling plant and animal pests, characterized in that nitrophenyl-sulfonyl-imidazoles of the formula (I) according to Claim 1 are mixed with extenders and / or surface-active substances.