KR20010021858A - Nitrophenyl-sulfonyl-imidazoles and use thereof for controlling vegetable and animal pests - Google Patents

Abstract

The present invention relates to a novel nitrophenyl-sulfonyl-imidazole of formula (I), a process for the preparation of the novel material, and its use for controlling plant and animal pests:

In the above formula,

X, R ¹ , R ² and R ³ have the meaning as described in the detailed description.

Description

Nitrophenyl-sulfonyl-imidazoles and their use for controlling vegetable and animal pests}

It is already known that certain phenylsulfonyl-imidazoles and phenylsulfonyl-benzimidazoles are fungicidal (see EP-A 0 238 824 and WO 97-06 171). Thus, 1- (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] -dioxolo- [4,5-f] -benzimidazole can be used to control fungi Can be. The activity of these materials is good, but in some cases a low application rate is unsatisfactory.

The present invention relates to novel nitrophenyl-sulfonyl-imidazoles, methods for their preparation, and their use for controlling plant and animal pests.

We now find a novel nitrophenyl-sulfonyl-imidazole of formula (I):

In the above formula,

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 atom to which they are attached represent an optionally substituted benzene ring, or an optionally substituted heterocycle ring,

R ³ represents halogen, alkyl or phenyl,

b) X represents halogen,

R ¹ represents halogen, alkyl or phenyl,

R ² represents halogen, alkyl or phenyl, or

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

R ¹ and R ² together formula Represents a double bonded radical of

R ³ represents halogen, alkyl or phenyl.

In addition, the nitrophenyl-sulfonyl-imidazoles of formula (I) may be prepared from the nitribenzene-sulfonyl halides of formula (III), optionally in the presence of acid acceptors and optionally in the presence of It was found that it can be obtained by reacting with:

In the above formula,

R ¹ , R ² , R ³ and X have the same meaning as described above,

Hal represents chlorine or bromine.

In the end, it has been found that nitrophenyl-sulfonyl-imidazole of formula (I) is very suitable for controlling plant and animal pests in crop protection and material protection.

Surprisingly, the substances according to the invention are already known structurally similar active substances 1- (2-methyl-5-nitro-phenylsulfonyl) -benzotriazole and 2-methyl-1- which have the same type of activity. It shows better fungicidal action than (2-methyl-5-nitro-phenylsulfonyl) -imidazole.

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

A preferred group of substances according to the invention is nitrophenyl-sulfonyl-imidazole of formula (la):

Here, the substituents preferably have the meanings described below.

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

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

In addition, R ¹ and R ² together with the carbon atom to which they are bonded, preferably

Halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl;

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

Halogenoalkyl, halogenoalkoxy, halogenoalkylthio or halogenoalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;

Halogenoalkenyl or halogenoalkenyloxy, each being straight or branched, each having 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms;

Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxideiminoalkyl, alkoximinoalkyl or cyanimino (alkoxy) alkyl each having 1 to 4 carbon atoms in each alkyl moiety;

Cycloalkyl having 3 to 6 carbon atoms;

Each radical is the same or differently made by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms Phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio which may be substituted or disubstituted

The benzene ring which may be mono- or trisubstituted same or differently by

Further, R ¹ and R ² together with the carbon atom to which they are bonded, preferably benzene, are double bonded and substituted by alkylene having 3 or 4 carbon atoms or substituted by dioxyalkylene having 1 or 2 carbon atoms Ring, wherein alkylene or dioxyalkylene is halogen, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms It may be the same or different mono- to tetra-substituted by.

In addition, R ¹ and R ² together with the carbon atoms to which they are attached preferably comprise one, two or three identical or different hetero atoms, such as oxygen, sulfur and / or nitrogen, halogen, cyano, nitro, Hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, 1 to 4 carbon atoms and 1 to 5 identical or different Halogenoalkyl having halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, 3 to 6 carbon atoms Cycloalkyl having 1 to 4 carbon atoms and halogenoalkylsulfinyl having 1 to 5 identical or different halogen atoms, 1 to 4 carbon atoms and 1 to 4 Halogenoalkylsulfonyl having 5 identical or different halogen atoms, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, di having 1 to 4 carbon atoms in each alkyl group Alkylamino, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, hydroxideiminoalkyl having 1 to 4 carbon atoms in the alkyl moiety, 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety Alkoxyiminoalkyl having a moiety, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and / or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms in the halogenoalkyl group It represents a 5- or 6-membered heterocycle ring which may be mono- or trisubstituted identically or differently by carbonyloxy. At this time, in the heterocycle ring containing one or more oxygen atoms, the oxygen atoms are not adjacent.

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

Another group of preferred substances according to the invention are nitrophenyl-sulfonyl-imidazoles of the formula (lb):

In the above formula, the substituents preferably have the meanings described below.

Hal ¹ preferably represents fluorine, chlorine or bromine.

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

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

In addition, R ¹ and R ² together with the carbon atoms to which they are attached preferably comprise one, two or three identical or different hetero atoms, such as oxygen, sulfur and / or nitrogen, halogen, cyano, nitro, Hydroxyl, amino, formyl, carboxyl, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, 1 to 4 carbon atoms and 1 to 5 identical or different halogens Halogenoalkyl with atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, having 3 to 6 carbon atoms Cycloalkyl, halogenoalkylsulfinyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, 1 to 4 carbon atoms and 1 to 5 Halogenoalkylsulfonyl having the same or different halogen atom, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkyl having 1 to 4 carbon atoms in each alkyl group Amino, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, hydroxyliminoalkyl having 1 to 4 carbon atoms in the alkyl moiety, 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety Alkoxyiminoalkyl having, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and / or halogenoalkyl carbo having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms in the halogenoalkyl group 5- or 6-membered heterocycle ring which may be mono- or tri-substituted identically or differently by nyloxy. At this time, in the heterocycle ring containing one or more oxygen atoms, the oxygen atoms are not adjacent.

In addition, R ¹ and R ² together, preferably, Represents a double bonded radical.

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

Especially preferred is

R ¹ represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, 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,

R ¹ and R ² together with the carbon atoms to which they are attached,

Fluorine, chlorine, bromine, cyano, nitro, formyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-pro Foxy, methylthio, ethylthio, n- or i-propylthio, methylsulfonyl, ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy , Trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfonyl, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, Butoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroxideiminomethyl, hydroxideiminoethyl, methoximinomethyl, ethoximinomethyl, methoximinomethyl, ethoximinoethyl, cyanimino,

Cyclopropyl, cyclopentyl, cyclohexyl or

Each radical is fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl, trifluoromethyl, trichloromethyl And / or phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio which may be mono- or di-substituted identically or differently by difluoromethyl.

Or a benzene ring which may be the same or differently mono- to trisubstituted by

R ¹ and R ² together with the carbon atom to which they are attached represent a benzene ring each substituted by double bonds propane-1,3-diyl, butane-1,4-diyl, methylenedioxy or ethylenedioxy Wherein, alkylene or dioxyalkylene may be mono- or tetrasubstituted identically or differently by fluorine, chlorine, fluoromethyl, methyl, ethyl and / or n-propyl, or

R ¹ and R ² together with the carbon atoms to which they are attached are fused furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-oxadia Sol, 1,2,3-thiadiazole, 1,2,3-triazole, pyridine, pyridazine, pyrazine, pyrimidine or 1,2,4-triazine ring, wherein these radicals represent fluorine, Chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbomil, 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, di Fluoromethoxy, trifluoromethoxy, difluoromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, methylamino, ethylamino, n- or i -Propylamino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroxyiminomethyl, hydroxyiminoethyl, methy Mono- or di-substituted identically or differently with methoxyiminomethyl, ethoxyiminomethyl, methoxyiminoethyl and / or ethoxyiminoethyl,

R ³ is a compound of formula la which represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or phenyl.

Also particularly preferred

Hal ¹ represents fluorine, chlorine or bromine,

R ¹ represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, 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,

R ¹ and R ² together with the carbon atoms to which they are attached are fused furan, thiophene, pyrrole, oxazole, thiazole, imidazole, isoxazole, isothiazole, pyrazole, 1,2,3-oxadia Sol, 1,2,3-thiadiazole, 1,2,3-triazole, pyridine, pyridazine, pyrazine, pyrimidine or 1,2,4-triazine ring; these radicals represent fluorine, chlorine, bromine , Cyano, nitro, amino, hydroxyl, formyl, carboxyl, 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-propyl Mino, dimethylamino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyloxy, ethylsulfonyloxy, hydroxyiminomethyl, hydroxyiminoethyl, methoxyimino Mono- or di-substituted identically or differently with methyl, ethoxyiminomethyl, methoxyiminoethyl and / or ethoxyiminoethyl, or

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

R ³ is a compound of formula Ib which represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or phenyl.

The meanings of the substituents described above may be combined with each other in any desired manner. In addition, the respective definitions may also be omitted.

The nitrophenyl-sulfonylimidazoles shown in the following tables may be mentioned as examples of materials according to the invention.

Table 1

TABLE 2

TABLE 3

From here,

R ³ represents a substituent mentioned in Table 2.

Table 4

Table 5

From here,

R ³ represents a substituent mentioned in Table 2.

Table 6

TABLE 7

If 2,5-dibromo-4-methyl-1H-imidazole and 2-methyl-5-nitrobenzenesulfonyl chloride are used as starting materials, the course of the process according to the invention will be described by the following scheme Can be.

Imidazole derivatives required as starting materials for carrying out the process according to the invention are generally defined by formula (II). In this formula, R ¹ , R ² and X preferably have the meanings already mentioned as preferred for these substituents in connection with the description of the substances of formula (I) according to the invention.

Compounds of formula (II) may exist in two tautomeric forms.

Molecular unit If is symmetric, the tautomeric forms are the same. Thus, in the reaction according to the invention using nitrobenzenesulfonyl halides of formula (III), in each case only one specific desired product of formula (I) is formed, in which two tautomeric forms react It is formed regardless of.

Molecular unit If is asymmetric, the tautomeric forms are not the same. Thus, in the reaction according to the invention using nitrobenzene-sulfonyl halides of formula (III), the desired product of formula (I) derived from the tautomeric forms of formula (IIa) and / or (IIb) forms. Can be. When the two tautomers react, the desired product of formula (I) is obtained in the form of a mixture.

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

Nitrobenzene-sulfonyl halides, which are also necessary as starting materials for carrying out the process according to the invention, are generally defined by formula (III). In this formula, R ³ preferably has the meaning as already mentioned as preferred for these substituents in connection with the description of the substances of formula (I) according to the invention. Hal also preferably represents chlorine or bromine.

Nitrobenzene-sulfonyl halides of formula (III) are known or can be prepared by known methods (see EP-A 0 238 824).

All conventional inorganic or organic bases are suitable as acid acceptors for carrying out the process according to the invention. Hydrides, hydroxides, amides, alcoholates, acetates, carbonates or bicarbonates of alkaline earth metals or alkali metals, for example sodium hydride, sodium amide, sodium methylate, sodium ethylate, potassium tert-butyl Latex, sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate or sodium bicarbonate, also ammonium compounds, for example ammonium hydroxide, ammonium acetate Or ammonium carbonate, and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N- Methylmorpholine, N, N-dimethylaminopyridine, diazobicyclooctane (DABCO), diazabi Nonene (DBN) or diazabicyclo a cycle bicyclo-undecene (DBU) are preferably used.

All inert organic solvents are suitable as diluents for carrying out the process according to the invention. Aliphatic, alicyclic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; Halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetrachloromethane, 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; 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 hexamethylphosphorotriamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Sulfones such as sulfolane, or amines such as pyridine can be preferably used.

When carrying out the process according to the invention, the reaction temperature can be varied within a relatively wide range. In general, the temperature is used between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out at atmospheric pressure. However, it may also be carried out under pressure or reduced pressure.

When carrying out the process according to the invention, 1 to 1.5 mol of nitrobenzene-sulfonyl halides of formula (III) and equivalent or excess acid acceptors are used per mole of imidazole derivative of formula (II) do. Post-treatment is achieved by conventional methods. Generally, water is added to the reaction mixture, and the resulting mixture is extracted several times with a slightly water soluble organic solvent, and then the combined organic phases are dried and then evaporated. The material obtained can be optionally purified by conventional methods such as chromatography or recrystallization.

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

Fungicides include Plasmodiophoromycetes, Oomycetes, Chitridiomycetes, Zygomycetes, Ascomycetes in crop protection. ), Basidiomycetes and Deuteromycetes and the like can be used to rescue.

A bactericidal agent is used to rescue Pseudomonadaceae, Rhizobiaceae, enterobacteriaceae, Corynebacteriaceae, and Streptomycetaceae in crop protection. Can be used.

Several pathogens of fungal and bacterial diseases included under the above generic names may be mentioned as examples by way of example and without limitation.

Xanthomonas species, for example Xanthomonas campestris fib. Orizae (campestris pv. Oryzae);

Pseudomonas species, for example Pseudomonas shiringa fib. Lachrymans (syringae pv. Lachrymans);

Erwinia species, for example Erwinia amylovora;

Pythium species, for example Pythium ultimum;

Phytophthora species, for example Phytophthora infestans;

Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;

Plasmopara species, for example Plasmopara viticola;

Bremia species, for example Bremia lactucae

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

Erysiphe species, such as, for example, Erysiphe graminis;

Sphaerotheca species, for example spaerotheca fuliginea;

Podosphaera species, such as, for example, leucotricha;

Venturia species, for example Venturia ininaquialis;

Pyrenophora species, for example Pyrenophora teres or Pyrenophora graminea (conidia form: Drechslera, isoform: Helminthosporium ));

Cocciliobolus species, for example Cocciliobolus sativus (conidia form: Dresslera, isoform: Helmintosporium);

Uromyces species, for example uromyces appendiculatus;

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

Sclerotinia species, for example Sclerotinia sclerotiorum;

Tilletia species, for example Tilletia caries;

Ustilago species, for example Ustilago nuda or Ustilago avenae;

Pellicularia species, such as, for example, Pelicularia sasaki;

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

Fusarium species, for example Fusarium culmorum;

Botrytis species, for example Botrytis cinerea;

Septoria species, for example Septoria nodorum;

Leptosphaeria species, for example Leptosperia nodorum;

Cercospora species, for example Cercospora canescens;

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

Pseudocercosporella species, for example Pseudocercosporella herpotrichoides.

Since the plant tolerates the active substance at the concentration necessary to control plant disease, the plant's tops, breeding stems and seeds, and soil can be treated with the active substance.

The active substances according to the invention can be used particularly successfully for the control of diseases in grape cultivation or fruit and vegetable production, for example for Venturi, grapes spaera, and Plasmopara species. They are also successfully used to control, for example, rice disease caused by pyricuria species.

In the protection of materials, the materials according to the invention can be used to protect industrial materials from being infected by unwanted microorganisms and destroyed by unwanted microorganisms.

Industrial materials in this application are understood to mean inanimate objects prepared for industrial use. Industrial materials intended to protect against changes or destruction by microorganisms using the active substances according to the invention are destroyed by adhesives, glue, paper and planks, textiles, leather, wood, coating materials and plastics, cold lubricants and microorganisms. It may be another substance that can be infected or infected. In plant production, for example, cooling water circulation, which may be damaged by the growth of microorganisms, may also be mentioned within the range of substances to be protected. Industrial materials which may be mentioned within the scope of the invention are preferably adhesives, glue, paper and planks, leather, wood, coating materials, cold lubricants and heat transfer liquids, particularly preferably wood.

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

Alternaria, for example Alternaria tenuis,

Aspergillus, for example Aspergillus niger,

Chaetomium, for example Chaetomium globosum,

Coniophora, for example Coniohora puetana,

Lentinus, for example Lentinus tigrinus,

Penicillium, for example Penicillium versicolor,

Aureobasidium, for example Aureobasidium pullulans,

Sclerophoma, for example Sclerophoma pityophila,

Trichoderma, for example Trichoderma viride,

Escherichia, for example Escherichia coli,

Pseudomonas, for example Pseudomonas aeruginosa,

Staphylococcus, for example Staphylococcus aureus.

The active substances according to the invention are also suitable for the control of animal pests, especially insects, arachnids and nematodes, which appear in the fields of agriculture, forestry, horticulture, stored products and substances, and in the field of hygiene or veterinary medicine, with excellent plant resistance and warm blooded animals. Has favorable toxicity to The material acts on pest species with moderate sensitivity and resistance, and on all or part of the stage of development of the pest. Animal pests mentioned above include:

Isopoda neck, for example Oniscus asellus, Armadillidium vulgare and Porcellio scaber.

From the order of Diloplopoda, for example Blaniulus guttulatus.

From the neck of Chilopoda, for example, Geophilus carpophagus and Scutigera spec.

From the order of the symphyla, for example Scutigerella immaculata.

From the order of Thysanura, for example, Lepisma saccharina.

The neck of Collembola, for example Onychiurus armatus.

From the order of Orthoptera, for example, Blata orientalis, Periplaneta americana, Leucophaea maderae, Blatella germanica, Ah Keta Domestikus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis and Systoser Schistocerca gregaria.

From the order of the dermaptera, for example Porficula auricularia.

Termite Isoptera, for example Reticulitermes spp.

Anoplura, for example Pediculus humanus corporis, Haematopinus spp. And Linognathus spp.

Allophaga, for example Trichodectes spp. And Damalinea spp.

From the order of the Thysanoptera, for example, Hercinothrips femoralis and Tripps tabaci.

From the order of the Heteroptera, for example Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rodney Rhodnius prolixus and Triatoma spp.

The cicada (Homoptera), for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Apis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Apis fabae, Apis pomi, Eriosoma lanigerum, hyaloptherus arun Hyniopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humulli humuli, Rhopalosiphum padi, Empoasca spp., Eucelis bilobatus, Nephotettix cincticeps, Lecanium corni ), Saisetia oleea (Sais) setia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudo Pseudococcus spp. And Psylla spp.

The order of the Lepidoptera, such as Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euprotis chrysorrhoea, Lymantria spp. , Buculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Et al. Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodorfte Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo species ( Chilo spp.), Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tynea pelionella Tinea pellionella, Hofmannophila pseudospretella, Cacoacia podana, Capua reticulana, Choristoneura fumiferana, Clichy am herma Clysia ambiguella, Homona magnanima, and Tortrix viridana.

The order of the Coleoptera, for example, Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus , Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp. .), Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antoninomus species (Anthonomus spp.), Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Cethorrinkus assimilus s assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Antrenus spp., Atenagen spp. ., Lyctus spp., Meligethes aeneus, Pintin spp., Niptus hololeucus, Gibbium psylloides ), Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melonta melolontha, Amphimalon solstitialis and Costelitra zealandica.

Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis and Vespa species ( Vespa spp.).

Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca species ( Musca spp.), Pannia spp., Califora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp. ), Gastrophilus spp., Hippobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp. , Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomina hyoskomi (Pegomyia hyoscyami), Ceratitis capitata, Dacus oleae and Tipula paludosa.

From the tree of Siphonaptera, for example Xenopsylla cheopis and Ceratophyllus spp.

Arachnida, for example Scorpio maurus and Latrodectus mactans.

The order of the ticks Acarina, for example, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriopies libis (Eriophyes ribis), Phyllocoptruta oleivora, Bophillus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp. ., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp. ), Bryobia praetiosa, Panonychus spp. And Tetranychus spp.

Plant-parasitic nematodes include Pratylenkus spp., Radopholus similis, Ditylenchus dipsaci, Tylenkulus semipenetrans, and heterodera species. (Heterodera spp.), Globoderra spp., Melodogyne spp., Apelenchoides spp., Longidorus spp., And xinepine species (Xiphinema spp.) And Trichodorus spp.

Materials that can be used according to the invention are for the control of plant-damaging mites, for example bean spider mite (Tetranychus urticae), or for plant-damaging insects, for example For example, caterpillars of diamond-back moth (Plutella maculipennis), larvae of horseradish leaf beetle (Phaedon cochleariae), and green It can be used particularly successfully for the control of green rice cicada (Nephotettix cincticeps).

Materials that can be used according to the invention are also not only pests of plants, hygiene and stored products, but also animal parasites (external parasites) in the field of veterinary medicine, for example, scale ioxodid ticks, princess mites It is active against argasidae, mange mite, trombiidae, flies (spit or vampire), parasitic fly larvae, teeth, stinging teeth, avian teeth and fleas. These parasites include:

Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phetirus spp. And Solenopo Solenopotes spp.

Molophagida and Amoklycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton species spp.), Bovicola spp., Weneckiella spp., Lepikentron spp., Damalina spp., Trichodextes spp. ) And Felicola spp.

Pseudomonas and Amok nematocerina and Brachyycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium species ( Simulium spp.), Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops species spp.), Hibomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philippimia spp. , Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morelia Morellia spp., Pannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp. ), Allpatia species ( Wohlfahrtia spp.), Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca species (Hyppobosca) spp.), Lipoptena spp. and Melophagus spp.

Fleas, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp. And Ceratophyllus spp.

From the order Heteroopterida, for example Cimex spp., Triatoma spp., Rhodnius spp. And Panstrongylus spp.

Neck of the Battarida, for example Blata orientalis, Periplaneta americana, Blatela germanica, and Supella spp.

Acarida subclass and the tree of Meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp. ), Ixodes spp., Amblyomma spp., Bophillus spp., Dermacentor spp., Haemaphysalis spp., Hyalomma spp., Ripicephalus spp., Dermanyssus spp., Rileytia spp., Pneumonyssus spp., Sturk Sternostoma spp. And Varroa spp.

Actinedida (Prostigmata) and Acaridida (Astigmata), such as, for example, Acarapis spp., Cheiletiella spp. spp.), Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp. ), Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. ), Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp. ), Notoedres spp., Knemidocoptes spp., Cytodites spp., And Laminosioptes spp.

The active substances according to the invention are also suitable for increasing the harvest yield. In addition, they are less toxic and have good plant resistance.

Depending on their respective physical and / or chemical properties, the active substances may be prepared in solution, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in coating compositions for polymers and seeds, and ULV antifoams. And conventional preparations such as warming agents.

These formulations are known methods, for example using surfactants, ie emulsifiers and / or dispersants and / or foam-forming agents, to extend the active substance with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers. Prepare by mixing. When water is used as the extender, for example an organic solvent can also be used as cosolvent. As the liquid solvent, mainly aromatic compounds such as xylene, toluene or alkylnaphthalene; Chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride; Aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions; Alcohols such as butanol or glycols and their ethers and esters; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; Strong polar solvents such as dimethylformamide and dimethylsulfoxide, or water are suitable. Liquefied gas extender or carrier means a liquid that is gaseous at standard temperature and atmospheric pressure, for example, halogenated hydrocarbons or aerosol propellants such as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Suitable granular carriers for granules are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husks, corn cobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam-forming agents are for example polyoxyethylene fatty acid esters, such as polyoxyethylene fatty acid alcohol ethers such as alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysis products Nonionic and anionic emulsifiers. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate can be used in the formulations, natural and synthetic polymers in the form of granules or emulsions, or natural and synthetic phospholipids such as cephalin and lecithin. have. As other additives, mineral oil and vegetable oil may be used.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc; You can also use the same micronutrients.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active substance.

Depending on their respective physical and / or chemical properties, the active substances may be prepared in solution, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules in coating compositions for polymers and seeds, and ULV antifoams. And conventional preparations such as warming agents.

The active substances according to the invention can be prepared by themselves or in their formulations, for example, to use known fungicides, bactericides, acaricides, nematicides or pesticides in order to broaden the spectrum of action or to prevent resistance from developing. It can be mixed and used. In many cases a synergistic effect is observed. In other words, the activity of the mixture exceeds the activity of the individual components.

Examples of suitable components in the mixture include the following compounds.

Fungicides:

Aldimorph, Ampropyl Force, Ampropyl Force Potassium, Andoprim, Anilazine, Azaconazole, Azoxystrobin,

Benalacyl, Benodanil, Benomyl, Benzamacryl, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Vitertanol, Plasticin-S, Bromuconazole, Buptrimate, Part Thioate,

Calcium Polysulfide, Capsaicin, Captapol, Captan, Carbendazim, Carboxin, Carbon, Kinomethionate (Quinomethionate), Clobenthiazone, Chlorfenazole, Chloronev, Chloropicrine, Chlorotalonyl, Chlo Zolinate, clozilacon, cupranev, cymoxanyl, cyproconazole, cyprodinyl, cypropuram,

Debaccarb, dichlorophene, diclobutrazole, diclofloanid, diclomezin, dichloran, dietofencarb, difenokonazole, dimethymolol, dimethomorph, dinicoazole, dinicoazole- M, dinocap, diphenylamine, dipyrithione, dietalifoss, dithianon, dodemorph, dodine, drazoxolone,

Edifene Force, Epoxyconazole, Etaconazole, Ethirimol, Etridiazole,

Sofasadon, phenafanil, phenarimol, fenbuconazole, fenfuram, phenytropane, fenpiclonyl, phenpropidine, fenpropormorph, fentin acetate, fentin hydroxide, ferbam, perimzone, flua Gina, flumetober, fluoromid, fluquinonezol, fluprimidol, flusilazole, flusulfamid, flutoranil, flutriafol, polpet, pocetyl-aluminum, pocetyl-sodium, phthalide, Fuberidazole, furalacyl, furamemetr, furcarbonyl, furconazole, furconazole-cis, purmecyclox,

Guazatin,

Hexachlorobenzene, hexaconazole, hymexazole,

Imazalyl, imibenconazole, iminottadine, iminottadine albesylate, iminottadine triacetate, iodocarb, ifconazole, iprobenfos (IBP), iprodione, irumamycin, isoprothiolane, iso Ballet,

Kasugamycin, cresoxime-methyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, auxin-copper and Bordeaux mixtures,

Mancoper, Mancozeb, Manev, Meperimzone, Mepanipyrim, Mepronyl, Metallaccil, Metconazole, Metasulfocarb, Metfuroxam, Methiram, Metomeclam, Metsulfobox, Mildiomycin , Michaelrobutanyl, michaelrozoline,

Nickel dimethyldithiocarbamate, nitrotal-isopropyl, noarimol,

Opuras, oxadixyl, oxamocarb, oxolinic acid, oxycarboxime, oxypentyin,

Paclobutrazole, pepurazoate, fenconazole, pensicuron, phosphodiphene, fimaricin, piperaline, polyoxine, polyoxolim, probenazole, prochloraz, procmidone, propamocarb, Propanosine-sodium, propiconazole, propineb, pyrazophos, pyriphenox, pyrimethanyl, pyroquilon, pyroxifer,

Quinconazole, quintozen (PCNB),

Sulfur and sulfur preparations,

Tebuconazole, Teclophthalam, Tecnazen, Tecyclcyclase, Tetraconazole, Thiabendazole, Tiothiophene, Trifluzamide, Thiophanate-methyl, Tiram, Thioxymide, Tollclofos-methyl, Tolylufluoride, triadimefon, triadimenol, triazbutyl, triazoxide, triclamid, tricyclazole, tridemorph, trifluzazole, tripolin, triticazole,

Uniconazole,

Validamycin A, vinclozoline, viniconazole,

Zarylamide, geneb, ziram

Dagger G,

OK-8705,

OK-8801,

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

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

α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,

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

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

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

1-isopropyl {2-methyl-1-[[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamate,

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

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

1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,

1-[(diiodomethyl) sulfonyl] -4-methylbenzene,

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

1-[[2- (4-chlorophenyl) -3-phenyloxyranyl] methyl] -1 H-1,2,4-triazole,

1- [1- [2-[(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1 H-imidazole,

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

2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide,

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

2,6-dichloro-5- (methylthio) -4-pyrimidinylthiocyanate,

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) pentanedinitrile,

2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-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- [cyano-[(1-methyl-2-propynyl) oxy] methyl] benzamide,

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

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

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

4-methyltetrazolo [1,5-a] quinazolin-5 (4H) -one,

8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-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-thiophendicarboxylate,

Cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) -cycloheptanol,

Cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,

Ethyl [(4-chlorophenyl) azo] cyanoacetate,

Potassium bicarbonate,

Methane tetrathiol sodium salt,

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

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

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

N- (2,3-dichloro-4-hydroxyphenyl) -1-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-nitrobenzolsulfonamide,

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'-methoxymethaneimidoamide,

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

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

O-methyl S-phenyl phenylpropylphosphoramidothioate,

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

Spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran-3'-one.

Salbacterase:

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octylinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, teclophthalam, copper sulfate and other copper agents.

Pesticides / Acaricides / Nematicides:

Abamectin, acephate, acrinatrin, alanicab, aldicarb, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinfos A, azinfos M, azocyclotin,

Bacillus thuringiensis, 4-bromo-2- (4-chlorophenyl) -1- (ethoxymethyl) -5- (trifluoromethyl) -1H-pyrrole-3-carbonitrile, bendiocarb, ben Furacarb, bensultap, beta cyptrin, bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, butocacarsim, butylpyridaben,

Kadusafos, cabaril, carbofuran, carbophenothione, carbosulphan, cartope, chloretocarb, chlorethoxy force, chlorfenapyr, chlorfenbinfos, chlorfluazuron, chloromephos, N-[( 6-Chloro-3-pyridinyl) -methyl] -N'-cyano-N-methyl-ethanimidoamide, chloropyrifos, chlorpyrifos M, cis-resmethrin, clocitrin, clofentezin, Cyanoforce, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,

Deltamethrin, Demethone-M, Demethone-S, Demethone-S-methyl, Diapentiouron, Diazinon, Diclopention, Dichlorbos, Diclifoss, Dicrotophos, Diethion, Difluben Juron, Dimethoate,

Dimethylvinforce, dioxation, disulfotone,

Edifene force, emamectin, esfen valerate, thiophencarb, ethion, etofenprox, etoprofos, erythropose,

Phenamifos, phenaquinone, fenbutatin oxide, phenythrothione, phenobcarb, phenothiocarb, phenoxycarb, phenpropatrine, fenpyrad, fenpyroximate, pention, fenvalrate, fipro Neil, Fluazinam, Fluazuron, Flucycloxonon, Flucytinate, Flufenoxuron, Flufenprox, Fluvalinate, Phonophos, Formomones, Phosthiazate, Pufenfenx, Fura Thiocarb,

HCH, heptenophos, hexaflumuron, hexthiaxans,

Imidacloprid, ifprobenfoss, isazofoss, isofenfoss, isoprocarb, isoxation, ibemectin,

Lambda-cyhalothrin, lufenuron,

Malathion, Mecarbam, Mevinforce, Mesulfenfos, Metaldehyde, Metacryphos, Metamidophos, Metidathione, Methiocarb, Methomil, Mettolcarb, Milvemectin, Monoclotophosphate, Moxidecine,

Nalred, NC 184, nitenpiram,

Ometoate, oxamyl, oxydemethone M, oxydepropos,

Parathion A, Parathion M, Permethrin, Pentoate, Forate, Posalon, Phosmet, Phosphomidone, Bombardment, Pyrimicarb, Pyrimiphos M, Pyrimiphos A, Propenophos, Promecab, Propa Phos, propoxur, prothiophos, protoate, pymetrozine, pyraclophos, pyridapention, pyresmethrin, pyrethrum, pyridaben, pyrimidipene, pyriproxyfen,

Quinal Force,

Salitione, cebufoss, silafluorene, sulfotep, sulfpropos,

Tebufenozide, Tebufenpyrad, Tebupyrimphos, Teflubenzuron, Tefluthrin, Temephos, Terbham, Terbufos, Tetrachlorbinfos, Thiaphenox, Thiodicarb, Thiophanox, Thiomethone, thiazineazine, turingiencin, tralomethrin, triarathene, triazofoss, triazuron, trichlorphone, triflumuron, trimetacarb,

Tamidothione, XMC, xylylcarb, zetamethrin.

It is also possible to mix with other known active substances such as herbicides, fertilizers and growth regulators.

The active substances can be used on their own or in the form of their preparations, or in the forms of use prepared from them, such as ready-to-use solutions, suspensions, hydrating powders, pastes, soluble powders, powders and granules. It is used by conventional methods such as watering, spraying, spraying, misting, spraying, foaming, brushing and the like. In addition, the active substance may be applied by the microvolume method, or the active substance preparation or the active substance itself may be injected into the soil. It is also possible to treat seed of plants.

When the active substance which can be used according to the invention is used as a fungicide, the application rate may vary within a relatively wide range depending on the application method. When treating a part of the plant, the application rate of the active substance is generally 0.1 to 10,000 g / dL, preferably 10 to 1,000 g / dL. When treating seeds, the application rate of the active substance is generally from 0.001 to 50 g, preferably from 0.01 to 10 g per kg of seed. When treating the soil, an active substance application ratio of generally 0.1 to 10,000 g / dl, preferably 1 to 5,000 g / dl is used.

Compositions used for the protection of industrial materials generally contain from 1 to 95%, preferably from 10 to 75% of active material.

The concentration of use of the active substance according to the invention depends on the generation and species of the microorganism to be controlled and on the composition of the substance to be protected. Optimal usage can be determined by a series of tests. In general, the use concentration is in the range of 0.001 to 5% by weight, preferably 0.05 to 1.0% by weight, based on the material to be protected.

The activity and spectrum of action of the active substances, compositions, concentrates or very general preparations which can be prepared from them according to the invention may optionally further comprise substances with antimicrobial activity, fungicides, It can be increased by adding pesticides, herbicides, pesticides or other active substances that broaden the spectrum of action or other active substances to achieve a particular effect, for example to provide additional protection against insects. . These mixtures may have a broader spectrum of action than the compounds according to the invention.

In addition, when used against animal pests, the substances according to the invention may be present as mixtures with synergists in commercial formulations and in the forms of use prepared from these formulations. Synergists are compounds that increase the activity of an active substance without the need for the synergist added to exhibit activity on its own.

The content of active substance in the use form produced from commercial formulations can vary within wide ranges. The active substance concentration in the use form can be 0.0000001 to 95% by weight, preferably 0.0001 to 1% by weight.

Application is carried out in a conventional manner suitable for the form of use.

The preparation and use of the material according to the invention is illustrated by the following examples.

Manufacturing Example

Example 1

1.4 g (10 mmol) of potassium carbonate is added to a solution of 1.7 g (7 mmol) of 2,5-dibromo-4-methyl-1H-imidazole in 40 ml of acetonitrile at room temperature. The mixture is stirred for 10 minutes at room temperature, then 1.7 g (7 mmol) of 2-methyl-5-nitro-benzenesulfonyl chloride are added. After stirring for an additional 20 hours at room temperature, the reaction mixture is poured onto 100 ml of water. The resulting mixture is extracted twice with 50 ml of diethyl ether each. The combined organic layer is dried over sodium sulfate and then evaporated under reduced pressure. The remaining residue is chromatographed on silica gel using methylchloride as mobile phase. In this way 1.6 g of 1- (2-methyl-4-nitro-benzenesulfonyl) -2,4-dibromo-5-methyl-1H-imidazole in the form of a colorless solid substance having a melting point of 187-189 ° C. (theoretical value) 51%) is obtained.

The materials shown in Table 8 below are also prepared by the methods described above.

Table 8

Use Example

Example A

Phytophthora test (tomato) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To prepare a suitable formulation of the active substance, 1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and then the concentrate is diluted with water to the desired concentration.

For the protection test, young plants are sprayed with the preparation of the active substance at the above mentioned application rates. After the spray coating has dried, the plant is inoculated with an aqueous spore suspension of phytophthora infestans. The plant is then placed in a culture chamber with a relative humidity of 100% and a temperature of about 20 ° C.

Three days after the inoculation, the evaluation is performed. 0% means potency corresponding to the untreated control, while 100% potency means no infection is observed.

The active substances, application rates and test results are shown in the table below.

Table A

Phytophthora test (tomato) / protective

Example B

Plasmopora test (vines) / protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To prepare a suitable formulation of the active substance, 1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and then the concentrate is diluted with water to the desired concentration.

For the protection test, young plants are sprayed with the preparation of the active substance at the above mentioned application rates. After the spray coating has dried, the aqueous spore suspension of Plasmopara viticola is inoculated with the plant, and then the plant is placed in a culture chamber having a relative humidity of 100% and a temperature of about 20 ° C. for 1 day. The plant is then placed for 5 days in a plastic house with a relative humidity of about 90% and a temperature of about 21 ° C. The plant is then moistened and placed in the incubator for 1 day.

Six days after the inoculation, the evaluation is performed. 0% means potency corresponding to the untreated control, while 100% potency means no infection is observed.

The active substances, application rates and test results are shown in the table below.

TABLE B

Plasmopara test (vines) / protective

Example C

Phaedon Larva Test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 weight part of alkylaryl polyglycol ethers

To prepare a suitable formulation of the active substance, 1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and then the concentrate is diluted with water to the desired concentration.

After dipping the cabbage leaves (brassica oleracea) in the preparation of the active substance of the desired concentration, the larvae of horseradish beetle (Phaedon cochleariae) while the leaves are moistened. Infect.

After the target time, the percent rescued is measured. 100% means that all the beetle larvae have been killed; 0% means that the beetle larva is not killed at all.

The active substances, application rates and test results are shown in the table below.

Table C

Plants-Damaged Insects

Phaedon Larva Test

Example D

Flutella test

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: 1 weight part of alkylaryl polyglycol ethers

To prepare a suitable formulation of the active substance, 1 part by weight of the active substance is mixed with the aforementioned amounts of solvent and emulsifier and then the concentrate is diluted with water to the desired concentration.

Cabbage leaves (brassica oleracea) are soaked in a preparation of the active substance of the desired concentration, and then infected with a caterpillar of the diamondback moth (Plutella xylostella) while the leaves are moist. .

After the target time, the percent rescued is measured. 100% means that all caterpillars have been killed; 0% means that the caterpillar has not been killed at all.

The active substances, application rates and test results are shown in the table below.

Table D

Plants-Damaged Insects

Flutella test

Example E

Substance protection test

To demonstrate activity against fungi, the minimum inhibitory concentration (MIC value) of the substance according to the invention is measured.

The active substance according to the invention at a concentration of 0.1 mg / l to 5000 mg / l is added to agar medium prepared using malt tablets. After condensation of the agar medium, it is contaminated with pure cultures of the test organism. After storage for 2 weeks at 27 ° C. and 60-70% relative humidity, the minimum inhibitory concentration (MIC value) is measured. MIC values represent the lowest concentration of active substance in which growth of all microbial species used is inhibited.

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

Table E

Substance protection test

Minimum inhibitory concentration (MIC value) (mg / l)

Test organism Active substance number according to the example 2 5 Penicillium brevicaule 100 100 Caetomium globosum 100 100 Aspergillus niger 200 200

Claims (8)

Nitrophenyl-sulfonyl-imidazole of formula (I): In the above formula, 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 atom to which they are attached represent an optionally substituted benzene ring, or an optionally substituted heterocycle ring, R ³ represents halogen, alkyl or phenyl, b) X represents halogen, R ¹ represents halogen, alkyl or phenyl, R ² represents halogen, alkyl or phenyl, or R ¹ and R ² represent an optionally substituted heterocycle ring together with the carbon atom to which they are attached, R ¹ and R ² together formula Represents a double bonded radical of R ³ represents halogen, alkyl or phenyl. The method of claim 1, X represents cyano, R ¹ represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms, R ² represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms, or R ¹ and R ² together with the carbon atoms to which they are attached, Halogen, cyano, nitro, formyl, carbamoyl, thiocarbamoyl; Alkyl, alkoxy, alkylthio or alkylsulfonyl having 1 to 5 carbon atoms each; Halogenoalkyl, halogenoalkoxy, halogenoalkylthio or halogenoalkylsulfonyl each having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms; Halogenoalkenyl or halogenoalkenyloxy, each being straight or branched, each having 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms; Alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulfonyloxy, hydroxideiminoalkyl, alkoximinoalkyl or cyanimino (alkoxy) alkyl each having 1 to 4 carbon atoms in each alkyl moiety; Cycloalkyl having 3 to 6 carbon atoms; Each radical is the same or differently made by halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms Phenyl, phenoxy, phenylthio, pyridyl, pyridyloxy and / or pyridylthio which may be substituted or disubstituted Or a benzene ring which may be the same or differently mono- to trisubstituted by R ¹ and R ² together with the carbon atom to which they are attached represent a benzene ring which is double bonded and substituted by alkylene having 3 or 4 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, Wherein alkylene or dioxyalkylene is the same or differently by halogen, alkyl having 1 to 4 carbon atoms and / or halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms Mono- or tetra-substituted, R ¹ and R ² together with one or two or three identical or different hetero atoms, together with the carbon atoms to which they are attached, include halogen, cyano, nitro, hydroxyl, amino, formyl, carboxyl, carbamoyl, Thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, 1 to 4 carbon atoms And halogenoalkoxy having 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, 1 to 4 carbon atoms and 1 to 5 Halogenoalkylsulfinyl having 4 identical or different halogen atoms, halogen having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms Genoalkylsulfonyl, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, 1 to 4 in the alkyl moiety Alkylaminoalkyl having 1 to 4 carbon atoms in the alkoxy moiety, 1-4 carbon atoms in the alkoxy moiety, and 1-4 carbon atoms in the alkyl moiety, alkyl moiety in the alkyl moiety Same or differently by halogenoalkylcarbonyloxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms to the alkylcarbonyloxy and / or halogenoalkyl group having 1 to 4 carbon atoms It represents a 5- or 6-membered heterocycle ring which may be substituted to tri-substituted, wherein the hetero yarn containing one or more oxygen atoms In keulhwan oxygen atoms are not adjacent, R ³ is nitrophenyl-sulfonyl-imidazole of formula (I) which represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms. The method of claim 1, X represents fluorine, chlorine or bromine, R ¹ represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms, R ² represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms, or R ¹ and R ² together with the carbon atoms to which they are attached comprise one, two or three identical or different hetero atoms, such as oxygen, sulfur and / or nitrogen, halogen, cyano, nitro, hydroxyl, amino, Formyl, carboxyl, carbamoyl, thiocarbamoyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogeno having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms Alkyl, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety, cycloalkyl having 3 to 6 carbon atoms, 1 to Halogenoalkylsulfinyl having 4 carbon atoms and 1 to 5 identical or different halogen atoms, 1 to 4 carbon atoms and 1 to 5 identical or phases Halogenoalkylsulfonyl having one halogen atom, alkylamino having 1 to 4 carbon atoms, hydroxyalkylamino having 1 to 4 carbon atoms, dialkylamino having 1 to 4 carbon atoms in each alkyl group, alkyl Alkyl carbonyl having 1 to 4 carbon atoms in the moiety, Hydroxyminoalkyl having 1 to 4 carbon atoms in the alkyl moiety, Alkoxy having 1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety Minoalkyl, alkylcarbonyloxy having 1 to 4 carbon atoms in the alkyl moiety and / or halogenoalkylcarbonyloxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms in the halogenoalkyl group To a 5- or 6-membered heterocycle ring, which may be identically or differently mono- to trisubstituted, wherein at least one oxygen In a heterocycle containing atoms, the oxygen atom is not adjacent, R ¹ and R ² together, Represents a double bonded radical of R ³ is nitrophenyl-sulfonyl-imidazole of formula (I) which represents fluorine, chlorine, bromine, straight or branched chain alkyl or phenyl having 1 to 6 carbon atoms. The imidazole derivative of formula (II) is reacted with the nitrobenzene-sulfonyl halide of formula (III), optionally in the presence of an acid acceptor and optionally in the presence of a diluent, Process for preparing nitrophenyl-sulfonyl-imidazole: In the above formula, R ¹ , R ² , R ³ and X have the meaning as described in claim 1, Hal represents chlorine or bromine. A composition for controlling plant and animal pests, characterized by containing at least one nitrophenyl-sulfonyl-imidazole of formula (I) according to claim 1. Use of the nitrophenyl-sulfonyl-imidazole of formula (I) according to claim 1 for controlling plant and animal pests. A method for controlling plant and animal pests, characterized in that the nitrophenyl-sulfonyl-imidazole of formula (I) according to claim 1 is applied to pests and / or habitats thereof. A process for preparing a composition for controlling plant and animal pests, characterized in that the nitrophenyl-sulfonyl-imidazole of formula (I) according to claim 1 is mixed with an extender and / or a surfactant.