Pyrazol carboxanilide and means to combat bacteria and fungi on their basis

 

(57) Abstract:

Describes pyrazol carboxanilide formula (I)

where X, Y, m and n are specified in the claims values, which can be an active ingredient to combat bacteria and fungi, a) m = 0, n = 1 and Y is 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3 - trifluoromethyl, cyano, halogen-substituted alkoxygroup or (b) m = 0, n = 2, 3, and Y represents halogen atom, alkyl group, halogen-substituted alkyl group, or C) m = 1, n = 0-2 and X is a chlorine atom, a nitro-group, alkyl group, alkoxygroup, Y means a halogen atom, a nitro-group, a cyano, alkyl group. Also describes the means to fight bacteria and fungi. The technical result consists in obtaining of compounds exhibiting high activity against some microorganisms. 2 S. and 4 C.p. f-crystals, 7 PL.

The present invention relates to the derivatives of carboxanilido possessing biological activity, more particularly to a pyrazol carboxanilides and means to combat bacteria and fungi on the basis of them.

It is already known that many carboxanilide are active against microorganisms, cha is hexylaniline 1,3-dimethyl-5-perperson-4-carboxylic acid, 2-phenylaniline 1,3-dimethylpyrazol-4-carboxylic acid and 2-(2-forfinal)anilide 1,3-dimethylpyrazol-4-carboxylic acid can be used for combating fungi. These compounds are highly efficient, however, in some cases at low rate of their properties can be improved.

Object of the invention is the expansion of the range of the pyrazole nucleus carboxanilido with activity against bacteria and fungi.

The problem is solved pyrazol-carboxanilide formula

where

a) m represents the number 0,

n means the number 1, and

Y is 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-trifluoromethyl, cyano, halogen-substituted alcobackshop with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, halogen-substituted alkylthiol group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, or

b) m represents the number 0,

n denotes the number 2 or 3 and

Y means a halogen atom, alkyl group with the number of carbon atoms from 1 to 8 halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, or

1 to 8, halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 8, halogensubstituted alkoxygroup with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5,

n means an integer from 0 to 2 and

Y means a halogen atom, a nitro-group, a cyano, an alkyl group with the number of carbon atoms from 1 to 8 halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 8, halogensubstituted alkoxygroup with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkylthiol group with carbon atoms of 1 to 8, carbalkoxy with the number of carbon atoms in the CNS, part 1 to 8.

The preferred derivative carboxanilide the above formula (I) are compounds in which

a) m represents the number 0,

n means the number 1, and

Y is 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-three-vermeil, cyano, hydroxyl, halogen-substituted alcobackshop with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, halog, what if

b) m represents the number 0,

n denotes the number 2 or 3 and

Y represents an atom of fluorine, chlorine, alkyl group with carbon atoms of 1 to 6, halogen-substituted alkyl group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, or

in) m means the number 1,

X denotes a chlorine atom, a nitro-group, alkyl group with carbon atoms of 1 to 6, halogen-substituted alkyl group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 6, halogen-substituted alkoxygroup with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5,

n means an integer from 0 to 2 and

Y represents an atom of fluorine, chlorine, bromine, a nitro-group, a cyano, alkyl group with carbon atoms of 1 to 6, halogen-substituted alkyl group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 6, halogen-substituted alkoxygroup with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkylthiol group with the number of carbon atoms from 1 to 6, carbalkoxy with the number of atoms other formulas

Pyrazol carboxanilide the above formula (I) can be obtained by reacting the acid halides of the formula

where Hal means a halogen atom,

with aniline derivatives of the formula

where X, Y, m and n have the above values,

optionally, in the presence of an acid acceptor and optionally in the presence of a diluent.

If the quality of raw materials used, the acid chloride 1,3-dimethyl-5-perperson-4-carboxylic acid and 2-(4-bromophenyl)aniline, the reaction can be represented by the following reaction scheme:

The acid halides of the formula (II) are known compounds or they can be obtained by known methods, for example in international application No. 93/11117 or on the application for European patent No. 0776889.

Derivatives of aniline of formula (III) are known or they can be obtained by known methods (application for European patent No. 0545099 and No. 0589301).

As acid acceptors can find the conventional inorganic and organic bases. Preferably for this purpose mohalla, the potassium hydroxide or ammonium hydroxide, carbonates of alkali metals, for example sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, acetates, alkali or alkaline earth metals, for example sodium acetate, potassium acetate, calcium acetate, and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclo, Diisobutylene or databaseconnect. However, work may be done, and not adding the acid acceptor or using an excess of amine component of the reaction so that it is simultaneously acted as the acid acceptor.

As a diluent it is possible to use all customary inert organic solvents. Preferably can be applied not halogenated or halogenated aliphatic, alicyclic or aromatic hydrocarbons, for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers like diethyl ether, diisopropyl ether, methyl tert-butyl ether, tert-and ITIL, propionitrile, n-butyronitrile, isobutyronitrile or benzonitrile; amides such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformamide, N is an organic or hexamethylphosphorotriamide; such esters as methyl ester of acetic acid or ethyl ester of acetic acid; such sulfoxidov as dimethyl sulfoxide, or sulfones such as sulfolane.

If the reaction temperature can vary within wide limits. In General operate in temperatures ranging from 0 to 140°C, preferably in the range from 10 to 120°C, and at atmospheric pressure. But in each case it is not excluded the possibility of carrying out the reaction under elevated or reduced pressure.

If the reaction of 1 mol of gelegenheid acid of formula (II) are added in General 1 mol or an excess of aniline derivative of the formula (III), and 1-3 mol of acid acceptor. But it does not exclude the use of reagents in different ratios. For separation of the target product using conventional techniques. In General this is done by adding to the reaction mass of water, separating the organic phase and pariva her after drying under reduced pressure. Get the example chromatographytandem or recrystallization.

Pyrazol carboxanilide the above formula (I) have strong bactericidal and fungicidal action and therefore they can be used to control pathogenic fungi and bacteria, in crop protection and for the protection of materials.

Therefore, a second object of the present invention are means to combat bacteria and fungi, which differ in the content of the pyrazole nucleus carboxanilide formula (I) p. 1 along with solvents and/or surfactants.

Fungicides can be used in plant protection for combating Plasmodiophoromycetes, Oomycetes, Chytridiomycota, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be used in plant protection for combating Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

As an example, but not limited volume of claims, you can call some pathogens of fungal and bacterial diseases, which belong to the above groups of microorganisms:

of the genus Xanthomonas, for example Xanthomonas campestris pv. oryzae;

of the genus Pseudomonas, such as Pseudomonas syringae pv. lachrymans;

of the genus Erwinia, for example, Erwinia amylovora;

of the genus Pythium, for example Pythium ultimum;

of the genus Plasmopara, for example, Plasmopara viticola;

of the genus Bremia, for example, Bremia lactucae;

of the genus Peronospora., for example, Peronospora. pisi or P. brassicae;

from the kind of Erysife, for example Erysife graminis;

of the genus Sphaerotheca, for example, Sphaerotheca fuliginea;

of the genus Podosphaera, for example, Podosphaera leucotricha;

of the genus Venturia, for example, Venturia inaequalis;

of the genus Pyrenophora, for example, Pyrenophora teres or P. graminea (form conidia Cereals, synonym Helmintosporium);

of the genus Cochliobolus, for example, Cochliobolus sativus (form conidia Cereals, synonym Helmintosporium);

of the genus Uromyces, for example, Uromyces appendiculatus;

of the genus Puccinia, for example, Puccinia recondita;

of the genus Sclerotinia, for example, Sclerotinia sclerotiorum;

of the genus Tilletia, for example, Tilletia caries;

of the genus Ustilago, for example, Ustilago nuda or Ustilago avenae;

of the genus Pellicularia, for example, Pellicularia sasakii;

of the genus Pyricularia, for example, Pyricularia orizae;

of the genus Fusarium such as Fusarium culmorum;

of the genus Botrytis, for example Botrytis cinerea;

of the genus Septoria, for example, Septoria nodorum;

of the genus Leptosphaeria, for example, Leptosphaeria nodorum;

of the genus Cercospora, for example, Cercospora canescens;

of the genus Alternaria, such as Alternaria brassicae;

of the genus Pseudocercosporella, for example, Pseudocercosporella herpotrichoides.

The pyrazole is Centrasia, which allows for the processing of ground plant parts and seed, seedlings and soil.

Especially good results are achieved when used for diseases of the vine, fruit and vegetable crops, for example against birth Venturia, Botrytis, Sclerotinia, Rhizoctonia, Uncinula, Sphaerotheca, Podosphaera, Alternaria and Colletotrichum. Good results can be achieved in the fight against disease of rice, caused by, for example, fungi of the genus Pyricularia and Pellicularia.

In the protection of materials relevant to the invention substances can be used for the protection of technical materials from decay and destruction by bacteria and fungi.

In this regard, the technical materials are non-living materials, prepared for use for technical purposes. For example, among the technical materials protected under the relevant invention the active substances from microbial damage or damage, you should call adhesives, glues, paper and cardboard, textiles, leather, wood, paints and plastics, lubricants, refrigeration equipment and other materials that can become a breeding ground for microorganisms and rsru circulation of cooling water, the functioning of which may be infringed by the reproduction of microorganisms. In the framework of the present invention to protect technical materials preferably include adhesives, glues, paper and cardboards, leather, wood, paints, lubricants for refrigeration and liquid fluids, primarily with their help protect the wood.

Depending on their physical and/or chemical properties pyrazol carboxanilide formula (I) in each case can be converted to conventional preparative forms such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, can produce finely dispersed encapsulated drugs in polymeric membranes, they can also enter into the composition of the polymer coating for seed, and formulations of ultra low volume spraying with aerosol formation and formulation forming the aerosol when heated.

These preparative forms prepared by known methods, for example by mixing the active substances with solvents, that is, liquid solvents, pressurized liquefied gases and/or solids is yousie funds and/or dispersing means, and/or blowing means. In the case of use as diluent water can be applied, for example, and organic solvents as additional solvents (solubilization). In the role of liquid solvents can be mainly aromatic compounds such as xylene, toluene or alkylnaphthalenes such chlorinated aromatics or chlorinated aliphatic hydrocarbons, as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example products of the distillation of crude oil, such alcohols, such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, and solvents with high polarity, such as dimethylformamide and dimethylsulfoxide, and water. Under liquefied gaseous diluents or substances carriers understand such liquids at normal temperature and under normal pressure are in a gaseous state, such as propellants for aerosol compositions, such as halogen-substituted hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. As solid vases is l, quartz, attapulgite, montmorillonite or infusoria earth, and ground synthetic minerals, such as finely dispersed silicic acid, alumina and silicates. As solids carriers for granular preparative forms can be, for example, crushed and fractionated natural minerals such as calcite, marble, pumice, thick, dolomite, or else synthetic granules on the basis of inorganic and organic crushed materials, and also granules of organic material such as wood flour, coconut husks, corn cobs and tobacco stalks. As emulsifying and/or foam-forming means can be, for example, nonionic and anionic emulsifiers, such as esters of fatty acids and oxides, ethers of fatty alcohols and oxides, such as ethoxylated ALKYLPHENOLS, alkyl sulphonates, alkyl sulphates, arylsulfonate, as well as protein hydrolysates. Dispersing means can be, for example, ligninase sulfite liquor and methylcellulose.

To improve the adhesion preparative forms can be applied, for example, carboxymethylcellulose, natural and synthetic as well as natural phospholipids, for example Catalina and lecithins, and synthetic phospholipids. As other additives can be mineral and vegetable oils.

Can also be used colorants such as inorganic pigments, for example iron oxide, titanium oxide, blue ferrocyanides, and organic dyes such as alizarin dyes, azo dyes and metallophthalocyanine dyes, and trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The content of active substances in the formulation in the General case may be from 0.1 to 95 wt.%, preferably from 0.5 to 90 wt.%.

Corresponding to the invention the active substance can be included in the preparative forms as the only active substance or in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to widen the spectrum of action or to prevent the development of resistance. In many cases achieved synergies, i.e. the effectiveness of the mixture is higher than the efficiency of individual components.

As components for the preparation of mixed preparer, aspropirgos, aerophilately, andapril, anilazine, azaconazole, AZOXYSTROBIN,

benalaxyl, Benadryl, benomyl, benzamycin, benzenetricarbonyl, bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, butiaba,

the calcium polysulfide, capsaicin, captafol, Captan, carbendazim, carboxin, carvon, chinomethionat, clobetasol, chlorbenzol, chloroneb, chlorpicrin, CHLOROTHALONIL, chlozolinate, clothingon, kurane, having cymoxanil, tsyprokonazolu, cyprodinil, zeroforum;

debaker, dichlorophen, diclobutrazol, dichlofluanid, declomycin, dicloran, dietphenterm, difenoconazol, dimethirimol, dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine, dipyrithione, datalists, dithianon, dodemont, Dodin, drazoxolon;

edifenphos, epoxiconazol, itaconate, ethirimol, etridiazole;

famoxadone, verapamil, fenarimol, fenbuconazole, fanforum, penetapan, fenpiclonil, fenpropidin, fenpropimorph, fenolovaya, fenoloogilised, ferbam, verison, fluazinam, flamethower, fluorone, fluquinconazole, flurried, flusilazol, glucolipid, flutolanil, flutriafol, folpet, foretelling, volatilaty, phtalic, fuberidazole, parallaxis, formate the

imazalil, kabekona, iminoctadine, iminoctadine, iminoctadine, iodosorb, ipconazole, iprobenfos (IP), iprodion, arunamarin, isoprothiolane, isovaleryl,

kasugamycin, kresoximmethyl, copper preparations such as copper hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper oxide, oxymed and Bordeaux mixture,

marcopper, MANCOZEB, MANEB, severinson, mepanipyrim, mepronil, metalaxyl, metconazole, metasurfaces, mefenoxam, metiram, matomela, metalhawk, millionizer, myclobutanil, mickleton;

the Nickel dimethyldithiocarbamate, nitratenitrogen, nuarimol,

operas, oxadixyl, oxamate, oxolinic, oxycarboxin, oxidation, paclobutrazol, peyratout, penconazole, pencycuron, forgiven, pimaricin, piperalin, polyoxin, palikari, provenzal, prochloraz, procymidone, propamocarb, propanedinitrile, propiconazol, propineb, pyrazophos, pirivenas, Pyrimethanil, pyroquilon, proxyfor,

quinceanos, quintozene (PCNB), quinoxyfen,

sulfur and preparations based on sulphur,

the tebuconazole, telital, tecnazene, tetcyclacis, tetraconazole, thiabendazol, tilian, leflunomid, thiophenemethyl, riciclata, tridemorph, triflumizole, triforine, triticonazole,

uniconazole,

validamycin And, vinclozolin, viceconsul,

Suriname, zineb, Tsira, and

dagger G,

OK-8705,

OK-8801,

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

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

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

-(5-methyl-1,3-dioxane-5-yl)--[[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-triazole-1-yl)-3-octanone,

(E)--(methoxyimino)-N-methyl-2-phenoxyphenylacetic,

isopropyl ether {2-methyl-1-[[[1-(4-were)ethyl]amino]carbonyl]propyl}-1-carbamino acid,

1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazole-1-yl)Etalon-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-methylbenzol,

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

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

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

1-the Il-1,3-thiazole-5-carboxanilide,

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

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

2,6-dichloro-N-(4-trifloromethyl)benzamid,

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

2-(2,3,3-tried-2-propenyl)-2H-tetrazol,

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

2-[[6-deoxy-4-O-(4-O-methyl-D-glycopyranosyl)--D-glyukopiranozil]amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

2 aminobutane,

2-bromo-2-(methyl bromide)pentanedinitrile,

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

2-chloro-N-(2,6-dimetilfenil)-N-(isothiocyanates)ndimethylacetamide,

2-phenylphenol (ORR),

3,4-dichloro-1-[4-(deformedarse)phenyl]-1H-pyrrole-2,5-dione,

3,5-dichloro-N-[cyan-[(1-methyl-2-PROPYNYL)oxy]methyl]benzamide,

3-(1,1-dimethylpropyl)-1-oxo-1H-inden-2-carbonitril,

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

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

4-methyltetrazole[1,5-a]hinzelin-5(4H)-he,

8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4,5]decane-2-methanamine,

8-hydroxygen later)-3-methyl-4-[(3-methylbenzoyl)oxy]-2,5-thiophencarboxylic,

CIS-1-(4-chlorophenyl)-2-(1H-1,2,4-triazole-1-yl)cycloheptanol,

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

ethyl-[(4-chlorophenyl)azo]cyanoacetate,

bicarbonate of potash,

sodium salt metanarrative,

methyl ester 1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylic acid,

methyl ester of N-(2,6-dimetilfenil)-N-(5-isoxazolidinone)-DL-alanine,

methyl ester of N-(chloroacetyl)-N-(2,6-dimetilfenil)-DL-alanine,

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

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)ndimethylacetamide,

N-(2,6-dimetilfenil)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)ndimethylacetamide,

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

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

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

N-(5-chloro-2-were)-2-methoxy-N-(2-oxo-3-oxazolidinyl)ndimethylacetamide,

N-(6-methoxy)-3-pyridinecarboxamide,

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

N-[3-chloro-4,5-bis-(2-propenyloxy)phenyl]-N'-methoxy-methanimidamide, soda is P CLASS="ptx2">O-methyl-S-phenyleneisopropylidene,

S-methyl ester of 1,2,3-benzothiadiazole-7-thiocarbonic acid,

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

Bactericides:

bronopol, dichlorophen, nitrapyrin, Nickel dimethyldithiocarbamate, kasugamycin, Actelion, francebuy acid, oxytetracycline, provenzal, streptomycin, telital, copper sulphate and other preparations based on copper.

Insecticides, acaricides, nematicides:

the abamectin, Arafat, acetamiprid, acrinathrin, alankar, aldicarb, aldoxycarb, alpha-cypermethrin, alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos And, azinphos M, azocyclotin,

Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, baculovirus, Beauveria bassiana, Beauveria tenella, bendiocarb, benfuracarb, bensultap, benoxinate, betacyfluthrin, bifenazate, bifenthrin, bioeconomical, bioprotein, VRMS, bromophos And, bofenkamp, buprofezin, butamifos, butocarboxim, butylparaben,

cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, caretakers, chlorethoxyfos, chlorfenapyr, chlorfenvinfos, chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, glavatartsi, CIS-reset is in, cyhexatin, cypermethrin, cyromazine, deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, diazinon, dichlorvos, diflubenzuron, dimethoate, dimethylene, giovanola, di-sulfate, docusinate-sodium, dienen,

althusian, emamectin, empenthrin, endosulfan, Entomopfthora spp., esfenvalerate, ethiofencarb, ation, ethoprophos, etofenprox, etoxazole, etrimfos,

fenamiphos, fenazaquin, fenbutatin, fenitrothion, fanatical, tenoxicam, fenoxycarb, fenpropathrin, feneral, generatin, fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, lubricant, flucycloxuron, flucythrinate, flufenoxuron, lotensin, fluvalinate, fonofos, tomatlan, fosthiazate, tupfenrock, furathiocarb,

granulovirus,

haloprogin, HCH, heptenophos, hexaflumuron, hexythiazox, hydroprene, Imidacloprid, isazofos, isofenphos, isoxathion, ivermectin,

nuclear predermine,

lambda cigalotrin, lufenuron,

Malathion, mecarbam, metaldehyde, metamidophos, Metharhizium anisopliae, Metharhizium flavoviride, mitigation, methiocarb, methomyl, methoxyfenozide, metolcarb, methoxamine, mevinphos, milbemectin, monocrotophos,

naled, nitenpyram, nithiazine, novaluron,

finalpos,

ribavirin

coalition, sabots, selflove, spinosad, sulfotep, sulprofos,

Tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron, Teflon-trine, temephos, timelines, terbufos, tetrachlorvinphos, tealpirate, thiamethoxam, tiopronin, tiatives, acid oxalate, thiocyclam, thiodicarb, thiofanox, thuringiensis, telocity, tralomethrin, triuralin, triazamate, triazophos, treasure, trichloride, trichlorfon, triflumuron, trimeter,

validation, unilibro, verticillium lecani,

YI 5302,

Zeta-cypermethrin, sulprofos,

(1R-CIS)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furylidene)methyl]-2,2-dimethylcyclopropanecarboxylate,

(3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate,

1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-Imin,

2-(2-chloro-6-forfinal)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydrooxazolo,

2-chloro-N-[[[4-(2,2-dichloro-1,1-diflorasone)phenyl]amino]carbonyl]benzamide,

3-methylphenylcarbinol,

4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxybenzoyl,

4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone,

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

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

Bacillus thuringiensis strain EG-2348,

2-benzoyl-1-(1,1-dimethylethyl)benzoic acid hydrazide,

3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4,5]Dec-3-EN-4-silt ether of 2,2-dimethylbutanol acid,

[3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinone]cyanamide,

dihydro-2-(nitromethylene)-2H-1,3-thiazin-3(4H)-carboxaldehyde,

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

N-(3,4,4-Cryptor-1-oxo-3-butenyl)glycine,

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

N-[(2-chloro-5-thiazolyl)methyl]-N' N-methyl-N"-nitroguanidine,

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

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

O,O-IER is active substances, for example with herbicides, or with fertilizers and growth regulators.

These active substances are used both in pure form and in the form of their formulations or forms prepared from these formulations, such as ready-to-use solutions, suspensions, dusty for spraying, pastes, wettable powders, means for powder and granulates. They are used in the usual ways, for example by pouring, sprinkling, spraying, spraying, dusting, they can be applied in the form of foams, coatings, or other methods. These active substances can also be applied in the form of compositions for ultra-low volume spraying, in addition, the active substance and formulation based on them can be injected into the soil. With their help it is possible to conduct processing of seed plant material.

In case of application of the relevant invention compounds as fungicides consumption rates, depending on the method of application can vary widely. When the processing of individual parts of plants norms of consumption of the active substance in General lie in the range from 0.1 to 10,000 g/ha, preferably from 10 to 1000 g/ha With the seed treatment norms of consumption of the active substance are tillage norms of consumption of the active substance in General comprise from 0.1 to 10,000 g/ha, preferably from 1 to 5000 g/ha

In the compositions used for the protection of technical materials, these active substances are contained in General in amounts of from 1 to 95%, preferably from 10 to 75%.

The concentration in which the relevant of the invention the active substance, dependent on species and habitats, destroy microorganisms, and on the composition of the protected material. The optimal number of substances can be determined in a series of experiments.

In General they are used in concentrations of from 0.001 to 5 wt.%, preferably from 0.05 to 1.0 wt.%, based on the weight of the protected material.

The efficacy and spectrum of biological activity which are used in accordance with the invention for the protection of materials, active substances or correspondingly produced from these funds, concentrates or in the most General sense preparative forms can be improved if their composition will be introduced other compounds with antimicrobial activity, fungicides, bactericides, herbicides, insecticides or other active ingredients to broaden the spectrum of biological activity, or to achieve special effects, for example for extra protection from nasni substances.

Getting pyrazol of carboxanilido formula (I) is illustrated by the following examples.

Example 1

To a solution of 2.5 g (0,01 mol) of 2-(4-bromophenyl)aniline in 30 ml of toluene at room temperature was added 1.0 g (0,01 mol) of triethylamine. To the resulting mixture at room temperature was added with stirring, 1.8 g (0,01 mol) of acid chloride 1,3-dimethyl-5-perperson-4-carboxylic acid. After the addition, continue stirring the mixture at room temperature for two hours and then poured it into the water. The mixture is repeatedly extracted with chloroform. The combined organic phases are dried with sodium sulfate, filtered and evaporated under reduced pressure. The resulting residue is stirred with diisopropyl ether. Drop down when this crystalline product is sucked off and dried. Thus obtained 1.6 g (41.2% of theory) of 2-(4-bromophenyl)anilide 1,3-dimethyl-5-perperson-4-carboxylic acid in the form of a solid substance with so pl. 127°C.

By analogy with the above described method are also given in table 1 pyrazol carboxanilide formula (I).

The following examples illustrate the biological activity pyrazol carboxanilido the

Solvent: 47 parts by weight of acetone.

Emulsifier: 3 part mass alkylsilanes ether polyglycol.

To obtain celebratng composition mix 1 part of weight of active substance with the specified amounts of solvent and emulsifier, and dilute the resulting concentrate with water to the desired concentration.

To study the activity of spray young plants composition prepared with the active substance when specified in the table And the rate of application of active substances. After drying the applied solution plants inoculant aqueous spore suspension of the pathogen of powdery mildew of Apple Podosphaera leucotricha. The plants installed in the greenhouse with a temperature of about 23°C and with a relative humidity of about 70%.

10 days after inoculation to assess the condition of the plants. 0% means the degree of efficiency, which corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

Active substances, consumption norms and the results of the experiments are shown in table A.

Example B

Determination of activity against Sphaerotheca on cucumbers.

Solvent: 47 parts of the mass and the appropriate ready-to-use form, the active substance is mixed one part of the mass of the active substance with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To study the activity of young plants are sprayed with preparative form of the active substance when given in table B. the rate of application of active substances. After drying of the deposited plants inoculant aqueous spore suspension Sphaerotheca fuliginea. The plants set in the greenhouse at a temperature of about 23°C at a relative humidity of about 70%.

Ten days after inoculation assess the condition of the plants. 0% corresponds to the degree of efficiency on untreated control plants, and the degree of effectiveness of 100% means that plant infection does not occur.

Active substances, consumption norms and the results of the experiments are shown in table B.

The Example In

Determination of activity against the pathogen Venturia (Apple).

Solvent: 47 parts by weight of acetone or 24.5 part of the weight of acetone and 24.5 parts of weight of dimethylacetamide.

Emulsifier: 3 part mass alkylsilanes ether polyglycol.

To obtain a suitable composition with the active substance is mixed with 1 part of weight of active substance with the specified amounts of solvent and emulsifier, and a dilute formed contentonline when specified in the table In the consumption rate of the active substance. After drying the applied solution plants inoculant with an aqueous suspension of conidia of the pathogen of Apple scab Venturia inaequalis and leave them for 1 day in an incubation cabin at a temperature of about 20°C and a relative humidity of 100%.

The plants installed in the greenhouse at a temperature of about 21°C and a relative humidity of about 90%. 12 days after inoculation to assess the condition of the plants. 0% means the degree of efficiency, which corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

The active substance, norms of consumption of active substances and the results of the experiments are shown in table C.

Example D

Determination of activity against Erysiphe on barley.

Solvent: 48.8 parts by weight of N,N-dimethylformamide.

Emulsifier: 1.2 parts by mass alkylsilanes ether polyglycol.

To obtain the appropriate ready-to-use form, the active substance is mixed one part of the mass of the active substance with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To study the activity applica G the rate of application of active substances. The day after the processing plants inoculant disputes Erysiphe graminis f. sp. hordei. The plants set in the greenhouse at a temperature of 18°C and at a relative humidity of 70%.

Seven days after inoculation to assess the condition of the plants. 0% corresponds to the degree of efficiency on untreated control plants, and the degree of effectiveness of 100% means that the infection of plants is not observed.

The active substance, norms of consumption of active substances and the results of the experiments are shown in the table,

Example D

Determination of activity against Pyrenophora teres (barley).

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

Emulsifier: 0,6 part of the mass alkylsilanes ether polyglycol.

To obtain the appropriate ready-to-use form, the active substance is mixed one part of the mass of the active substance with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To study the activity of spray young plants prepared by the composition of the active substance when given in table D. the rate of application of active substances. After drying on the ion shower at a temperature of 20°C and a relative humidity of 100%.

The plants installed in the greenhouse with a temperature of about 20°C and with a relative humidity of about 80%.

7 days after inoculation to assess the condition of the plants. 0% means the degree of efficiency, which corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

The active substance, norms of consumption of active substances and the results of the experiments are shown in table D.

Example F

Determination of activity against the pathogen Alternaria (tomatoes).

Solvent: 24,5 part of the weight of acetone,

24,5 part of the weight of dimethylacetamide.

Emulsifier: 3 part mass alkylsilanes ether polyglycol.

To obtain the appropriate composition of mix 1 part of weight of active substance with the specified amounts of solvent and emulsifier, and dilute the resulting concentrate with water to the desired concentration.

To study the activity of spray young plants composition prepared with the active substance when given in table E. the consumption rate. After drying the applied solution plants inoculant with an aqueous suspension of spores Alternaria solani. After e is P CLASS="ptx2">3 days after inoculation to assess the condition of the plants. 0% means the degree of efficiency, which corresponds to the defeat of the untreated control plants, and 100% means that the plants are not infected.

Active substances, consumption norms and the results of the experiment are shown in table E.

1. Pyrazol carboxanilide formula

where (a) m = 0;

n = 1;

Y is 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-trifluoromethyl, cyano, halogen-substituted alkoxygroup with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, halogen-substituted alkylthiol group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5,

or b) m = 0;

n = 2 or 3;

Y means a halogen atom, alkyl group with the number of carbon atoms from 1 to 8 halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number at the number of carbon atoms from 1 to 8, halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 8, halogensubstituted alkoxygroup with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5;

n = 0, 1, 2;

Y means a halogen atom, a nitro-group, a cyano, an alkyl group with the number of carbon atoms from 1 to 8 halogen-substituted alkyl group with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 8, halogensubstituted alkoxygroup with the number of carbon atoms from 1 to 6 and the number of atoms of halogen from 1 to 5, alkylthiol group with carbon atoms of 1 to 8, carbalkoxy with the number of carbon atoms in the CNS, part 1 to 8.

2. Pyrazol carboxanilide formula (I) under item 1, where (a) m = 0, n = 1 and Y is 2-chloro, 2-fluoro, 4-bromo, 2-methyl, 2-trifluoromethyl, 3-three-vermeil, cyano, hydroxyl, halogen-substituted alkoxygroup with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, halogen-substituted alkylthiol group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5;

or b) m = 0,

n = 2 IGNOU group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5;

or) m = 1, X denotes a chlorine atom, a nitro-group, alkyl group with carbon atoms of 1 to 6, halogen-substituted alkyl group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 6, halogen-substituted alkoxygroup with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, n = 0, 1, 2, and Y represents an atom of fluorine, chlorine, bromine, a nitro-group, a cyano, alkyl group with carbon atoms of 1 to 6, halogen-substituted alkyl group with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkoxygroup with the number of carbon atoms from 1 to 6, halogen-substituted alkoxygroup with 1 or 2 carbon atoms and with the number of fluorine atoms, chlorine and/or bromine from 1 to 5, alkylthiol group with the number of carbon atoms from 1 to 6, carbalkoxy with the number of carbon atoms in the CNS, part 1 to 4.

3. Pyrazol carboxanilide under item 1, representing a compound of formula

4. Pyrazol carboxanilide under item 1, representing a compound of formula

5. Pyrazol carboxanilide under item 1, representing a compound falnoga of carboxanilide formula (I) p. 1 along with solvents and/or surfactants.



 

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< / BR>
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< / BR>
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< / BR>
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FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

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