Derivatives of pyrazole, how to use them, herbicide composition and method of struggle

 

(57) Abstract:

Describes new pyrazole derivatives of the formula I, where the values of R1- R4specified in paragraph 1 of the claims, which may find application in controlling undesirable plants. Describes the method of obtaining the above-mentioned compounds, herbicide composition and method of dealing with connections famuly I. 7 C. and 31 C. p. F.-ly, 8 PL.

The technical field

The present invention relates to herbicide compounds, in General generic in title of the invention, containing formulations (compositions) and methods of producing these compounds.

Background of the invention

In the literature there are known various compounds derivatives of substituted 3-aryl - and 5-arylpyrazole. Such compounds have a variety of useful, for example, are used as chemical intermediates, pharmaceuticals and herbicides.

Among the substituted 3-aryl-5-(halogen)ALKYLPHENOLS and 5-aryl-3-(halogen)ALKYLPHENOLS in the art known compounds having different substituents are radicals in ariline and/or pyrazol fragments compounds, for example alkyl, CT is itagroup etc. For example, the known compounds of this type, in which the aryl part is a substituted or unsubstituted phenyl radical, where the substituents are alkyl, cycloalkyl, trifluoromethyl, etc. and the pyrazole radical substituted in different positions of the nitrogen atoms or carbon alkyl, halogen, alkoxyl, heterocycles, S(O)nR-groups, in which n is 0-2, and R may be different radicals, such as radicals, substituted in the aryl or pyrazol part.

Compounds of the above type having utility as herbicides, usually require consumption norms in 5 or 10 or more kilograms per hectare to achieve adequate results in weed control. In accordance with the present invention is the proposal of a new class of compounds of type arylpyrazole with unique high unit fetotoksicheskoe activity against a spectrum of weeds, including uzkolistnyi and broadleaf weeds, with a high degree of security for many types of crops, especially fine-grain loaves of bread and/or row crops such as wheat, barley, maize, soya beans, groundnuts, etc.

The described 1-(halo)alkyl-3-(substituted)aryl-4-halo-5-gogenie of the invention

The present invention relates to herbicide active compounds, to compositions containing these compounds, methods of producing these compounds and methods of their application as herbicides.

Herbicide compounds according to the present invention include compounds characterized by the structure of formula I

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and their agricultural-acceptable salts and hydrates, in which

R1represents independently C1-8-alkyl, C3-8-cycloalkyl, cycloalkenyl, cycloalkenyl or cycloalkenyl; C2-8alkenyl or quinil, benzyl, in which the above-mentioned members may be arbitrarily substituted with halogen, amino, nitro, cyano, hydroxy, alkoxy, alkylthio,

CYR8, -CR9, YR10or NR11R12,

R2represents a C1-5-haloalkyl,

R3represents a halogen

R4is an R1member, thioalkyl, alkoxyalkyl or polyalkoxyalkyl, carbamyl, halogen, amino, nitro, cyano, hydroxy, C1-10-heterocycle containing 1-4 O, S(O)mand/or NR18-heteroatoms, C6-12aryl aralkyl or alkaryl, YR15or NR16R17-group. Any two of R4groups can be combined pobraniem cyclic ring, with up to 9 members in the ring, and which may be substituted by any of R4member,

X is O, S(O)m, NR19or CR20R21,

Y is O, S(O)mor NR22,

R8-22represents hydrogen or one of R4member

m is 0-2 and

n is 1-5.

A preferred subclass substituted arylpyrazole compounds in the present invention are compounds corresponding to the formula II:

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and their agricultural-acceptable salts and hydrates, in which:

R1represents a C1-15-alkyl, alkylthio, alkoxyalkyl, C2-4alkenyl, benzyl, which may be substituted with halogen, amino, nitro, cyano, hydroxy or

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R2, R3X, Y, and R8have the meanings specified for formula I,

R5represents a halogen or hydrogen,

R6and R7have the meanings indicated for R4member in the formula I.

Particularly preferred compounds of the present invention are compounds according to formula III:

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and their agricultural-acceptable salts and hydrates, in which:

R1represents a C1-5-alkyl

R2, R3and R5matter, kasandora or R4member and

R6and R7United through saturated and/or unsaturated carbon, -(C= X)- and/or hetero O, S(O)mand/or NR18-due to the formation of a cyclic ring having up to 9 ring members, and which may be substituted by any of R4member, provided that when the link contains

the specified cyclic ring has at least six ring members, and

X, Y, R18and m have the above significance.

Even more preferred compounds in accordance with formula III and their agricultural-acceptable salts and hydrates, in which:

R1represents methyl,

R2is a CF3, CF2Cl or CF2H,

R3represents chlorine or bromine,

R5represents fluorine,

R6represents chlorine,

R7represents propargyloxy, allyloxy, polyalkoxy, OCH(R23)COR24where R23is hydrogen, methyl or ethyl, and R24is YR10or NR11R12,

R6and R7United through-OCH2(C=O)N(R18) is due to the formation of condensed six-membered rings and

Y, R10-R12and R18are vanam include the following:

4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5- (trifluoromethyl)-1H-pyrazole,

2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-pertenece)propanoic acid, ethyl ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4 - pertenece)acetic acid, 1-metaliteracy ester,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-pertenece)acetic acid, 1,1-dimethylethylene ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 3-pertenece)acetic acid,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-Formentera acid, 2-ethoxy-1-methyl-2-oksietilnye ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-Formentera acid, 2-methoxy-1-methyl-2-oksietilnye ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-Formentera acid, ethyl ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-Formentera acid, 1-metaliteracy ether and

6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro - 4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-he.

Some of the compounds according to the present invention may have more than one possible stereoisomer, and these stereoisomers can fill in their herbicide effectiveness. The shown structure is shown with the intention to include all possible stereoisomers.

The above compounds varying the mode of their application, for example pre-emergence and/or post-harvest processing, surface coating, pre-implementation, etc.

Another aspect of the present invention relates to methods of preparing compounds according to formulas I - III and their precursors, intermediate and/or source with whom I refer to herbicide compositions, containing the compounds of formula I - III and to methods of using these compositions as a means to destroy unwanted weeds.

Further, to the field of the present invention is that substituted arylpyrazole compounds according to formulas I - III can be included in the formulation of compositions containing other herbicide compounds as serviceof, such as acetamide, especially acetanilide, THIOCARBAMATE, urea, sulfonylurea, sulfonamide, imidazolinone, benzoic acid and its derivatives, diphenyl ethers, salts glifosato etc.

In such herbicide formulations may include other additives as desired and appropriate, such as antidotes (additives that increase security) for herbicides, drugs for the prevention of plant diseases, such as fungicides, insecticides, nematicides, other pesticides.

Used herein, the terms "alkyl", "alkenyl", "quinil", taken alone or in compound form, such as haloalkyl, haloalkyl, alkoxy, alkoxyalkyl etc. cover both linear and compounds with branched chain. Preferred representatives of Akilov is lower alkali having from 1 to 4 carbon atoms, and predpochtitelney haloalkyl (haloalkyl) is used to denote alkyl radicals, substituted by one or more than one halogen atom (chlorine, bromine, iodine or fluorine), the preferred members of this class are those compounds which have from 1 to 4 carbon atoms, in particular kaleidotile radicals such as trifluoromethyl. In polygaloides the Halogens may be the same or mixed.

Not an exhaustive list of representatives alkyl, alkenyl, etkinlik, cycloalkyl, cycloalkenyl, cycloalkenyl and cycloalkenyl radicals includes:

methyl, ethyl, isomeric propylene, butyl, Penteli, exile, reptile, octile, lonely, decile and so on; vinyl, allyl, crotyl, methallyl, isomeric butenyl, pentenyl, hexenyl, heptenyl, octenyl; tinily, isomeric propinyl, butinyl, pentenyl, hexenyl and so on; alkoxy, polyalkoxy, alkoxyalkyl and polyalkoxyalkyl analogues of the above alkyl groups, for example methoxy, ethoxy, propoxy, butoxy, peroxyl and exactily and appropriate polyalkoxy and alkoxyalkyl, for example, methoxyethoxy, ethoxyethoxy, ethoxyethoxy, ethoxyethoxy, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, propoxymethyl, isopropoxyphenyl, butoxymethyl, isobutoxy, tert.-butoxide propeller, cyclobutylmethyl, cyclopentylmethyl and so on; isomeric cyclopentene, cyclohexene and cycloheptene with mono - or di-unsaturation; representatives aryl, kalkilya and alkalinic groups include phenyl, isomeric Tolly and kilili, benzyl, naphthyl, etc.

Representatives of mono-, di - and tri-haloalkyl include chloromethyl, chloroethyl, methyl bromide, bromacil, iodomethyl, iodates, chloropropyl, bromopropyl, improper, 1,1-dichloromethyl, 1,1-dibromoethyl, 1,1-dichloropropyl, 1,2-dibromopropyl, 2,3-dibromopropyl, 1-chloro-2-bromacil, 2-chloro-3-bromopropyl, trifluoromethyl, trichloromethyl, etc.

Representatives of the heterocyclic compounds include: alkylthiomethyl, piperidyl, piperidinyl, DIOXOLANYL, thiazolyl, alkylaryl, benzothiazolyl, halogenoacetyl, furyl, alkyl substituted furyl, shrilly, pyridyl, alkylpyridine, alkyloxyaryl, tetrahydrofuranyl, 3-cantieni, tanisaki, alkyl substituted thienyl, 4,5-polyalkylene-thienyl, piperidinyl, alkylpiperidines, pyridyl, di - or tetrahydropyridine, alliteratively, alkylsulfonyl, azabicycloalkanes, diisobutylamine, benzoylchloride, oxazolidinyl, perhydroanthracene, alkyloxyalkyl, verilocation, taylorisation, acylaminoalkyl, alkylidene, pyrrolidinyl, piperidinyl, peligrosamente, perhydroanthracene, pyrazolyl, dihydropyrazolo, piperazinil, perhydro-1,4-diazepine, chinoline, ethenolysis, di-, Tetra - and perhydroxyl or ethanolic, indolyl and di - and peridontal and these heterocyclic members, substituted radicals, such as radicals, as defined in formulas I - III.

Under "agricultural-acceptable salts" of the compounds defined by the above formulas, we mean salt or salts, which are easily ionized in aqueous medium, forming a cation or anion of these compounds and the corresponding salt of the anion and the cation, and salt reduce herbicide properties of this herbicide and allow you to prepare various mixtures, for example herbicide-antidote compositions without unnecessary problems mixing, suspension, stability, application equipment, coating, packaging, etc.

Under "herbicide effective" refers to the amount of herbicide required for significant damage or destruction of a significant part of the processed unwanted plants or weeds. Although it is not a hard rule, but from a commercial point of view, it is desirable unichtozhayuthie and at much lower levels, in particular with some very harmful, persistent herbicides to the plants.

Detailed description of the invention

The following describes the connection in accordance with the present invention, obtained in a number of ways.

In a broad aspect of a preferred General method of preparing compounds of formulas I - III may best be considered on an individual stages of the method required to obtain the desired intermediate products, immediate predecessors and the final products of the above formula. Products "the way I are intermediates needed for methods II - XVI. Products in accordance with formulas I - III are obtained by any one method "II - XVI, or any combination of methods II - XVI. It should be clearly understood that discusses the various modifications obvious to a person skilled in this field. Specific options are described below in the examples 1 to 42.

In the sequence of the process steps described below, various symbols defining the radical substituents, such as R1- R24X, Y, etc. have the same meaning as in the compounds of formulas I - III, unless otherwise indicated.

Method I.

This method describes Prague formulas I - III.

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The method of obtaining the compounds of formula B comes from compounds of formula A. the compounds of formula A are prepared by known means from substituted acetophenones, which is also known from the prior art. Have in mind that the structure represented by formula A, embodies all possible tautomeric forms or mixtures her. The compounds of formula A can be prepared in any anhydrous solvent or mixture of solvents; the preferred solvents are the ether alcohols, dimethylsulfoxide, toluene, benzene, and so on, the reaction of a substituted acetophenone in the presence of the ester with a strong base such as an alkali metal alkoxide, alkali metal amide or hydride of an alkali metal, preferably an alkali metal alkoxides such as sodium methoxide. The reaction temperature is in the range from -100oC to 200oC, preferably from -78oC to 50oC. the reaction Period may be chosen in the range from several minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction, the compound of the formula A are diluting the reaction mixture with water, possibly with subsequent acidification of the aqueous layer or, alternatively, ri solvent extraction. If necessary, the product is purified by standard methods. Cyclization of this intermediate compound with formation of compounds of formula B can be provided in any suitable solvent by the action of hydrazine or substituted hydrazines, preferably by acylhydrazone. The reaction temperature in the range from -78oC to 200oC, preferably between 10oC to 120oC. the reaction Period may be chosen in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

In the case of adding hydrazine to compounds of the formula A resulting pyrazole of the formula C can be treated with an alkylating agent to produce compounds of formula B. In this case, the products of formula B can be obtained by processing the above-mentioned compounds, alkylating agent, such as methyliodide, allylbromide, dimethylsulfate etc., the Preferred solvents are toluene, dimethylsulfoxide, acetone, dimethylformamide, di is the change carbonates of alkali metal or of metal such as sodium carbonate or sodium hydroxide. The reaction temperature ranges from -78oC to 200oC, preferably 10oC - 120oC. the reaction Time can be selected in the range from few minutes to several weeks depending on the amounts of reactants, reaction temperature and so on, the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

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Compounds represented by formula C can exist in two possible tautomeric forms or as 5-allpyral or as a 3-arylpyrazole. Have in mind that 5-arylpyrazole represented by formula C, includes both the possible tautomeric forms. Table 1 shows typical examples of the compounds of formula C.

In all tables in this description of the boiling point and the melting point measured in degrees Celsius (oC) and, unless otherwise stated, the refractive indices refer to the 25oC.

2-fluoro-4-chloro-5-methoxyacetophenone used for connection NN 3, 4 and 9 by the above method, was obtained from 2-chloro-4-fortisalberta 2-chloro-4-fernicola titanium tetrachloride and dichlorodiammineplatinum at room temperature gives 2-fluoro-4-chloro-5-methoxybenzaldehyde. 2-fluoro-4-chloro-5-methoxybenzaldehyde was converted into 2-fluoro-4-chloro-5-methoxyacetophenone treatment stands Grignard reagent, followed by oxidation using standard methods known from the prior art.

The above 2-fluoro-4-chloro-5-methoxyacetophenone and its analogue predecessor 2-fluoro-4-chloro-5-methoxybenzaldehyde and methods of obtaining them are the subject of the invention other persons (the Beam C. Hamper and Kendrick L. Lesinski), which is used here by the assignee.

Tables 2 and 3 show typical examples of the compounds obtained by the method 1.

Method II

In this way one class of products in accordance with formula I, in which R3represents halogen, received halogenoalkanes the corresponding compounds of formula B. In this way R1may have the above meaning and to include hydrogen.

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Any inert solvent can be used in this reaction, which is not significantly impedes the course of the reaction or the reaction can be carried out without solvent. Such solvents include, but are not limited to, organic acids, inorganic acids, hydrocarbons, halogenated hydrocarbons, aromessence reactions include bromine, chlorine, N-bromosuccinimide, N-chlorosuccinimide, sulfurylchloride, etc. With some of halogenation agents, it is preferable to use an organic peroxide or light as the catalyst. The amount of halogenation agent can vary from less than one molar equivalent to the excess. The reaction temperature is in the range from -100oC to 200oC, preferably between 10oC to 100oC. the reaction Time can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction product produce by diluting the reaction mixture with water and then the product produce by the method of crystallization or solvent extraction. If necessary, the product was then purified by standard methods.

Method III

This section describes the method of obtaining the compounds in accordance with formula D (a compound of the formula I in which one of R4-residues is a nitro-group) on the basis of compounds of formula I.

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Nitrouse agents, such as concentrated nitric acid, fuming sulfuric acid, alternately and acetonitrite suitable for this reaction. Can be used solvents, as is anchored and water or a mixture of these solvents. Niteroi agent may be used in equimolar amounts or in excess, the reaction Temperature is in the range from -100oC to 200oC, preferably from -10oC to 100oC. the reaction Time can be selected in the range from few minutes to several days depending on the number of reagents, reaction temperature, etc. At the end of the reaction product produce by diluting the reaction mixture with water and the product produce by methods such as crystallization or solvent extraction. If necessary, the product was then purified by standard methods.

Method IV

In the description of this method in one class of products in accordance with the formula F (a variation of the compounds of formula (II) was obtained by replacement of the Z-radical corresponding compounds of formula E, where Z is any suitable leaving group above R4members.

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The formation of the products of formula E can be achieved by treatment of compounds of formula D alkoxide, toolboxitem, amine, etc. or alcohol, mercaptan, amine, etc., in the presence of a base in any suitable solvent or mixture of solvents. The preferred solvent is dimethyl sulfoxide, acetone, dimethylformamid is another organic solvent). The base can be an organic base (such as trialkylamine or other organic amine or an inorganic base (carbonate of an alkali metal, such as potassium carbonate or sodium or an alkali metal hydroxide such as sodium hydroxide). In the case of two immiscible liquid phases, it is desirable to add the catalyst phase transfer, such as halide benzyltrialkylammonium or other ammonium salt. The reaction temperature is in the range from -100oC to 200oC, preferably from -10oC to 100oC. the reaction Time can be selected in the range from few minutes to several weeks depending on the amounts of reactants, reaction temperature and so on, the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

Method V

When describing this method, the compounds of formula I are obtained from compounds of the formula G (compounds of formula I in which one of R4member is nitroaldol).

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A. In the first stage of this two-stage method of connection in accordance with the forms is an amino group. Reducing agents usable in the acidic environment include, but are not limited to, metals such as iron, zinc or tin. The solvent for the reaction may include any organic or inorganic acid, such as acetic acid or hydrochloric acid, and can be used in the form of concentrated solutions of acids or dilute aqueous solutions. The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 120oC. the reaction Time can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc.

Upon completion of the reaction product produce by diluting the reaction mixture with water and the product produce by methods such as crystallization or solvent extraction. If necessary, the product was then purified by standard methods.

Alternative compounds of formula G can be recovered by catalytic hydrogenation. For catalytic hydrogenation, which can be conducted at atmospheric or elevated pressure, suitable catalysts include Raney Nickel, palladium carbon, palladium black, palladium on any suitable media, Akito does not inhibit the reaction, including alcohols, ethers, etc., the Product emit filtration and concentration of the reaction mixture. If necessary, the product is purified by standard methods, such as extraction, crystallization, column chromatography, etc.

B. Amine radical of the product of stage And can be turned into a number of functional groups, for example halogen (preferably), cyano, hydroxyl, etc., In the case of conversion of the amine radical in the halogen solution or suspension of the product of stage And processed copper salts, including chlorides of copper (II) halides, copper (I) or other copper salts, and mixtures thereof, and alkyllithium or organic nitrate such as t-butylnitrite. In this reaction can be applied to any suitable solvent, although the preferred anhydrous solvent such as anhydrous acetonitrile. The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 100oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reactants, reaction temperature and so on, the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If you sell the S="ptx2">

Operations alternative way to make radikalen in various functional groups, including those mentioned in the previous paragraph, include the use of various conventional procedures, for example the reaction of Sandmeyer, Meerwein and so on, which are used as intermediate products of diazonium salts.

Method VI

In the description of this method of connection according to the formula I, in which one of R4member is YH, prepared from compounds of the formula I in which one of R4member represents YR15and R15is not hydrogen.

The reaction may be carried out in solution or suspension in any suitable solvent or without solvent. Can be used Lewis acid, such as (but not limited to) BBr3, AlCl3etc., or inorganic or organic acids, such as hydrochloric, sulfuric, Hydrobromic, acetic acid, etc. Alternative can be used nucleophilic reagents dealkylation, including trimethylsilylmethyl, cyanide salts, mercaptide salts, halides of alkali metals and so on, the reaction Temperature is in the range from 0oC to 200oC, preferably from the fir weeks depending on the amounts of reactants, the reaction temperature and so on, the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

Method VII

When describing this method, compounds in accordance with formula I which include compounds of formulas II and III), in which one of R4member represents YR15and R15is not hydrogen, are prepared from compounds in accordance with formula I, in which one of R4member represents YH or NR16R17.

In representative embodiments of this method the formation of the above products can be made by processing raw materials alkylating agent, such as alkylhalides or alkylsulfonate, such as methyliodide, allylbromide, propylbromide, methyl ester vinylsulfonic acid, etc. or allermuir agent. The reaction can be conducted in any suitable solvent or mixture of solvents, with catalyst or without it, in the presence or absence of a base. Preferred solvents are dimethyl sulfoxide, acetone, dimethylformamide, the organic solvent). In the case of two immiscible liquid phases, it is desirable to add the catalyst phase transfer, such as benzyltrialkylammonium or other ammonium salt. The base can be an organic base (such as trialkylamine or other organic amine or an inorganic base (carbonate of alkali metal or alkali metal such as sodium carbonate or potassium or sodium hydroxide). The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 100oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reactants, reaction temperature and so on, the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

Method VIII

This method describes how to obtain compounds of the formula K (formula II, in which R7represents YCH2-p(R25)p-COYR27from the corresponding compounds of formulas. In the radicals R25-27members of the R4have the above meaning; Y are members independently is this two-stage method, the compounds of formula H is transformed into the compounds of formula J by hydrolysis of the radical YR26. The reaction may be conducted in any suitable solvent or mixture of solvents, with catalyst or without catalyst, in the presence of base or acid. Preferred solvents are water, alcohols, dioxane, dimethylsulfoxide, acetic acid, acetone, dimethylformamide, etc., In the case of alkaline hydrolysis preferred inorganic bases such as hydroxides of alkali metals. In the case of acid hydrolysis can be used inorganic acids such as concentrated hydrochloric acid or sulfuric acid, organic acid or mixture of such acids. The reaction temperature is in the range from about 0oC to 200oC, preferably between 10oC to 100oC. the reaction Period may be chosen from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction product produce by diluting the reaction mixture with water and/or treatment of a solution of acid (in the case of alkaline hydrolysis) and the product then allocate this method, as crystallization or extraction. If necessary, the product was then purified by standard methods.

B. the Last stage of this method includes preholocene derivatives of carboxylic acids. This stage of the process is the esterification or reaction of formation of the amide. The etherification can be carried out using an excess of alcohol in accordance with the target air in the presence of a mineral acid (e.g. sulfuric acid). Derivative amide can be obtained by treating compounds of formula K desirable aminoethanol without solvent or in a suitable solvent. The esterification reaction or amidopolyamine can also be carried out in the presence of an inert solvent and dehydrating agent.

Alternative product stage And can be turned into galoyanized or anhydride acid and treated with an alcohol or amine. Cooking galodamadruga acid is carried out in the presence of a halogenation agent such as thionyl chloride, Piatigorsky phosphorus, oxalicacid etc (this list is not exhaustive) with solvents or without solvent. Can be used any inert solvent that does not reacts. To accelerate this reaction may be added a catalytic amount of amine base, such as triethylamine, pyridine or dimethylformamide, and so on, the reaction Temperature should be within -20oC deov depending on the quantities of reagents used and the reaction temperature. Upon completion of the reaction the excess of halogenation agent and solvent (solvents) are removed from the reaction product by evaporation or distillation. The resulting galoyanized acid can be subjected to the action of the amine or alcohol directly or purified by conventional means.

Galoyanized acid is treated with an alcohol or amine, receiving compound of the formula K. the Reaction can be carried out in the absence of solvent, in the presence of an inert solvent or mixtures of solvents, including two-phase mixture (such as water and methylene chloride or other organic solvent). To accelerate this reaction may be added a base, such as triethylamine, pyridine, alkali metal hydroxide and/or a catalytic amount of the catalyst phase transfer, such as the chloride benzyltrialkylammonium or other ammonium salt. The reaction temperature ranges from -20oC to the boiling point of the employed solvent. The duration of the reaction varies from several minutes to 48 hours depending on the quantities of the reagents and the reaction temperature. The product emit after the reaction by filtration and/or concentration of the reaction mixture. Protography etc.

The compounds, required as starting materials for methods IX-XI, obtained by the above methods II-VIII.

Method IX

In the description of this method of connection in accordance with the formula N are obtained from compounds in accordance with formula M (compounds of formula II, where R6represents YCH2-q(R28)qCOOR29, R7-the nitro radical, Y has the above value, q is an integer from 0 to 2, and the radicals R28-30defined above for the specified R4member, as described below.

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A. In the first stage of this two-stage process connection in accordance with the formula L is transformed into the compounds of formula M restoration of the nitro moiety in the amine radical and subsequent cyclization. The choice of reaction conditions can be obtained either nettlesbey amine (compounds of formula L where microradian substituted amine radical), or cyklinowanie product. Generally, reaction conditions are selected so that cyklinowanie product was obtained directly. Alternative nettlesbey amine can be isolated by the standard method and cycletour with obtaining the compounds of formula M in separate stages using standard conditions shall let, zinc or tin. The solvent used in the reaction may include organic or inorganic acid, such as acetic or hydrochloric acid, and can be used either as a concentrated acid solution or a diluted aqueous solutions. The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 120oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc.

Upon completion of the reaction product produce by diluting the reaction mixture with water and produce by this method, as the crystallization and solvent extraction. If necessary, the product was then purified by standard methods.

Alternative compounds of formula L can be recovered by catalytic hydrogenation. Catalysts suitable for catalytic hydrogenation, which can be carried out at normal or elevated pressure, include Raney Nickel, palladium on charcoal, palladium black, palladium on any suitable media, etc. Solutions include any inert solvent which does not appreciably hinder the reaction, including Spirou nitro radical substituted aminoven radical), or cyklinowanie product. Generally, reaction conditions are chosen such that directly worked cyklinowanie product. On the other hand, nettlesbey amine may be isolated by standard methods and cycletour obtaining compounds of formula M in separate stages using standard conditions. The product after the reaction allocate filtration and concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, chromatography on columns, etc.

B. In this stage, the product from step A is transformed into the compounds of formula N. the formation of the products defined above, can be carried out by treating compounds of formula M alkylating agent, such as alkylhalides or alkylsulfonate, such as methyliodide, allylbromide, propylbromide, methyl ester vinylsulfonate and so on, or allermuir agent. The reaction can be carried out in a suitable solvent or mixture of solvents, with catalyst or without catalyst, in the presence or absence of a base. Preferred solvents are dimethyl sulfoxide, acetone, dimethylformamide, dioxane, etc. or mixture of solvents, vklyuchivshihsya liquid phases, it is desirable to add the catalyst phase transfer, such as benzyltrialkylammonium or other ammonium salt. The base can be an organic base (such as trialkylamine or other organic amine or an inorganic base such as a carbonate or hydroxide of potassium or sodium. The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 120oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. of the Product after the reaction allocate filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, chromatography on columns, etc.

Method X

In the description of this method of connection in accordance with the formula Q in which R33is not hydrogen, are obtained from compounds according to the formula O (compounds of formula II in which R6represents a nitro radical, R7YCH2-r(R31)r)-COOR32Y has the above meaning, r is an integer from 0 to 2, and the radicals R31-33previously defined for R4members.

< / BR>
the Oia formula P recovery of nitroreductase in the amine radical and subsequent cyclization. The choice of reaction conditions can be obtained either nettlesbey amine (compound of formula H in which microradian substituted aminoven radical), or cyklinowanie product. Generally, reaction conditions are selected so as to obtain directly cyklinowanie product. However, nettlesbey amine may be isolated by standard methods and cycletour obtaining compounds of formula P in a separate step using standard conditions. Reducing agents suitable in the acidic environment, include (not limited to this list) metals such as iron, zinc or tin. The solvent used in the reaction may include any organic or inorganic acid, such as acetic or hydrochloric acid, and can be applied in the form of a concentrated acidic solutions or dilute aqueous solutions. The reaction temperature is in the range from 0oC to 200oC, preferably between 10oC to 120oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc.

Upon completion of the reaction product is separated by diluting the reaction mixture with water and then allocate time methods.

Alternative compounds of formula O can be recovered by catalytic hydrogenation. Catalysts suitable for catalytic hydrogenation, which can be carried out at normal or elevated pressure, include Raney Nickel, palladium carbon, palladium black, palladium on any suitable media, palladium oxide, platinum, platinum black, etc. Solvents include any inert solvent that does not appreciably impede the reaction, including alcohols, ethers, etc. Choice of reaction conditions can be obtained either nettlesbey amine (compound of the formula O, in which microradian substituted aminoven radical) or cyklinowanie product. Generally, reaction conditions are selected so as to directly receive cyklinowanie product. However, nettlesbey amine may be isolated by standard methods and cycletour using standard conditions. The product isolated after the reaction by filtration or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, chromatography on columns, etc.

B. At this stage the product from step A is transformed into the compounds of formula Q, where RoC to 200oC, preferably between 10oC to 120oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, chromatography on columns, etc.

Method XI.

This section describes the method of obtaining compounds of the radical, R7represents YC(R34)SCCR35Y has the above value, s is an integer from 0 to 2, and the radicals R34-36are previously defined R4-members).

< / BR>
Method of producing compounds of the formula S comes from compounds of the formula R. In this reaction may be any suitable solvent, although the preferred anhydrous solvents, such as acetonitrile. The solution or suspension of the compounds of formula R treated with copper salts, including chlorides of copper (II) halides, copper (I), a mixture of halides of copper (II and I) and other copper salts, and mixtures thereof, and alkylnitrates or organic nitrite such as t-butylnitrite. The reaction temperature is in the range from 0oC to 200oC, preferably 10oC to 100oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. the Product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

Method XII.

This method is about what represents an alkyl, substituted alkyl, haloalkyl, carboxaldehyde, carboxylic acid or carboxylic acid derivative, such as CXYR8or CXR9from compounds of formula T. the Radicals R37and R38have the same value that was previously defined for R4member, and X1and X2are halogen-free. A process diagram is shown below.

< / BR>
< / BR>
< / BR>
< / BR>
In the first stage of this process, the compounds of formula T turn either in the compounds of formula U, or W, or a mixture of these products. Any inert solvent can be used in this reaction, which does not impede significantly the course of the reaction. Such solvents include, but are not an exhaustive list, organic acids, inorganic acids, hydrocarbons, halogenated hydrocarbons, aromatic hydrocarbons, ethers, sulfoxidov or sulfones. Halogenation agents suitable for the above reactions include bromine, chlorine, N-bromosuccinimide, N-chlorosuccinimide, sulfurylchloride, etc. With some of halogenation agents, it is desirable to use an organic peroxide or light as the catalyst. The amount of halogenation agent can vary from less than one mole to excess. Temperature alnost reaction can be selected from few minutes to several weeks depending on the amounts of reactants, the reaction temperature, etc. At the end of the reaction product or products emit, diluting the reaction mixture with water and separating the product (s) by this method, as crystallization or solvent extraction. If necessary, the product (s) is cleaned by standard methods.

The compounds of formula U can be transformed into compounds of formula V substitution of halogen radical X1a suitable nucleophile. The formation of the products of formula C may occur in the processing of compounds of formula U alkoxide anion, dialkoxy, cyanide, amine, alkyl or aryl, etc. or alcohol, mercaptan, amine, etc., in the presence of a base in any suitable solvent or mixture of solvents. Preferred solvents are dimethyl-sulfoxide, acetone, dimethylformamide, dioxane, water, etc. or a mixture of solvents, including two-phase mixture (such as water and methylene chloride or other organic solvent). The base can be an organic base (such as trialkylamine or other organic amine or an inorganic base (carbonate of an alkali metal such as potassium carbonate or sodium carbonate or hydroxide of an alkali metal such as sodium hydroxide). In dialkylaminoalkyl or other ammonium salt. The reaction temperature ranges from -78oC to 200oC, preferably between 10oC to 120oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature and so on, the Product is separated after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

The formation of the products of formula X may occur as a result of acid hydrolysis of compounds of formula W. For the implementation of the acid hydrolysis of the compounds of formula W is subjected to the action of an excess of mineral acid, such as hydrochloric or sulfuric acid, preferably an excess of sulfuric acid. The reaction temperature is in the range from 0oC to the boiling point of the inert solvent, preferably from 10oC to 100oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction product or products are separated by dilution of reactions is IMO, product (s) is cleaned by standard methods.

The compounds of formula Y are obtained by oxidation of compounds of formula X. this reaction can be used any inert solvent including hydrocarbons, aromatic hydrocarbons, pyridine and its derivatives, water, etc. Used oxidants include, but are not limited to this list, potassium permanganate or potassium dichromate. The reaction temperature is in the range from -50oC to the boiling point of the inert solvent, preferably from 10oC to 100oC. the duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction product or products separated by diluting the reaction mixture with water and the provision of such a method, as crystallization or solvent extraction. If necessary, the product (s) is cleaned by standard methods.

The last stage of this process involves the conversion of compounds of formula Y in the compounds of formula Z by any of a wide variety of standard methods of obtaining derivatives of carboxylic acids. This stage of the process is the esterification or reaction AMICAALL the compounds of formula Y. The esterification can be performed using an excess of the alcohol corresponding to the target air in the presence of a mineral acid (e.g. sulfuric acid). Derivative amide can be obtained by treating compounds of formula Y desired aminoethanol without solvent or in passing the solvent. The esterification reaction or amidopolyamine can also be carried out in the presence of an inert solvent and dehydrating agent.

Alternative compounds of formula Y can be transformed into galoyanized or anhydride acid and treated with an alcohol or amine. Cooking galodamadruga acid is carried out in the presence of a halogenation agent such as thionyl chloride, Piatigorsky phosphorus, oxalicacid etc (this list is not exhaustive) in the presence of an inert solvent or without solvent. Can be used any inert solvent which does not inhibit the reaction. Can be added a catalytic amount of amine base, such as triethylamine, pyridine or dimethylformamide, or the like, to accelerate this reaction. The reaction temperature ranges from -20oC to the boiling point of the used solvent. Prodolzhitelnost and the reaction temperature. Upon completion of the reaction the excess of halogenation agent and solvent (solvents) are removed from the reaction product by evaporation or distillation. Galoyanized acid is treated with an alcohol or amine, receiving compound of formula Z. the Reaction can be carried out in the absence of solvent, in the presence of an inert solvent or mixture of solvents, including two-phase mixture (such as water and methylene chloride or other organic solvent). To accelerate this reaction may be added a base, such as triethylamine, pyridine, alkali metal and/or a catalytic amount of the catalyst phase transfer, such as benzyltrialkylammonium or other ammonium salt. The reaction temperature ranges from -20oC to the boiling point of the employed solvent. The duration of reaction is from several minutes to 48 hours depending on the quantities of the reagents and the reaction temperature. The product emit after the reaction by filtration and/or concentration of the reaction mixture. If necessary, the product was then purified by standard methods, such as extraction, crystallization, column chromatography, etc.

The way XIII

This RA who is a thiol group (formula (AA), on the basis of compounds in accordance with formula I.

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In this way the desired products are obtained by preparing a derivative haloalkaliphilic and subsequent recovery of obtaining compounds AA. Can be used any solvent which does not impede the flow of the reaction, such as halogenated hydrocarbons, ethers, alternately, mineral acids, etc., For a derivation chlorosulfonyl preferred excess chlorosulfonic acid as a reagent and as a solvent. The reaction temperature is in the range from 25oC to the boiling point of the employed solvent. The duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. After completion of the reaction product or products are separated by diluting the reaction mixture with water, and the products are then highlighted by such method as crystallization or solvent extraction. If necessary, the product (s) are purified by standard methods.

Restore derived haloalkaliphilic can be carried out in organic or inorganic acids, such as vinegar is teli, suitable acidic environment include, but are not limited to this list, metals such as iron, zinc or tin. The reaction temperature is in the range from 0oC to 150oC, preferably between 10oC to 150oC. the Duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc.

After the reaction product is separated by diluting the reaction mixture with water and the product is then allocate this method such as crystallization or solvent extraction. If necessary, the product was then purified by standard methods.

Method XIV.

This section describes the method of preparing compounds according to formula I, in which one of R4residues represents a cyclic (thio)kotelny or (thio)acutally radical (formula CC), based on the compounds in accordance with formula BB.

< / BR>
R39represents hydrogen or a previously defined R4member, A and B are independently O or S, and n is an integer from 0 to 2. In this way the desired compounds of formula CC are prepared from compounds of formula BB transformation karbonilnoj group in the cyclic (thio)ACET is, what itiola or hydroxytrol. Can be used any solvent which does not impede the progress of the reaction, such as halogenated hydrocarbons, aromatic hydrocarbons, ethers, alternately, mineral acids, etc. Alternative reaction can be carried out in the absence of solvent. Typically, the reaction may be conducted in the presence of acids, such as mineral acids, organic acids and so on, the reaction Temperature is in the range from 25oC to the boiling point of the employed solvent. The duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. After completion of the reaction product or products are concentrating the reaction mixture and purified by this method, as crystallization or solvent extraction. If necessary, the product (s) is subjected to further purification by standard methods.

The way XV.

This section describes the method of obtaining the compounds according to the formula DD, based on the compounds according to the formula BB.

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R39-41represent the above defined R4-members. The compounds of formula DD polute carried out by treatment of compounds of formula BB reagent type reagent Wittig, such as alkalinebattery, the ylides derived from phosphonium salts or esters of phosphonium, alcaligenaceae etc. Suitable solvents include, but are not limited to this list, aromatic hydrocarbons, alcohols, alkanes, ethers, halogenated hydrocarbons, etc. the reaction Temperature is in the range from -50oC to the boiling point of the employed solvent. The duration of the reaction may be selected from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. After completion of the reaction product or products produce by concentrating the reaction mixture and the product (s), then purified by means of crystallization or solvent extraction. If necessary, the product (s) is subjected to further purification by standard methods.

Method XVI.

This section describes the method of obtaining the compounds in accordance with formula EE, based on the compounds according to the formula BB.

< / BR>
R39and R42represent the above defined R4-members. In this stage of the process the compounds of formula EE, which have oxinny Deputy as one of the phenyl radicals derived from compounds formulados. The original aldehyde or ketone of formula BB can be processed O-substituted oxime with getting oxime of formula EE. From this compound can be obtained derived by standard methods known to the expert. Examples of this approach include, but are not limited to, treatment of the aldehyde or ketone (aminooxy) acetic acid or other 2-(aminooxy)carboxylic acid and conversion of the resulting carboxylic acid in any of a number of derivatives of carboxylic acids, such as amides, esters, complex thioethers, etc. Alternative oxime can be obtained by treating compounds of formula BB hydroxylamine or gidroksilaminami salts. The resulting oxime can be alkylated with obtaining derivatives by treatment with an alkylating agent such as haloalkyl, alkyl sulphonates, etc. Suitable for the above reactions include, but are not limited to this list, aromatic hydrocarbons, alkanes, ethers, alcohols, halogenated hydrocarbons, etc. the reaction Temperature is in the range from -50oC to the boiling point of the employed solvent. The reaction can be carried out with base or without base. In cases where the base may be acetate natricis sodium. The duration of the reaction can be selected in the range from few minutes to several weeks depending on the amounts of reagents, reaction temperature, etc. At the end of the reaction product or products are concentrating the reaction mixture, and the product (s) is cleaned by methods such as crystallization or solvent extraction. If necessary, the product (s) is subjected to further purification.

The following examples 1 to 42 describe specific embodiments of the method of obtaining the representatives of the compounds in accordance with the present invention.

Examples 1 to 4 describe a specific embodiment of method I.

Example 1.

This example describes how to obtain 3-(2,5-differenl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole (compound No. 40) and 5-(2,5 - differenl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole (compound No. 20).

A. 28.5 g of 2,5-defloration and 26 g of ethyl ether triperoxonane acid was stirred in 400 ml of anhydrous ether and cooled in an ice bath. Then was added over 5 minutes 42 ml of 25% (wt.) solution of sodium methoxide in methanol. After stirring for 1 hour at room temperature the reaction mixture was extracted with odion.

B. to 34.5 g of 1-(2,5-differenl)-3-trifluoromethyl)-propane-1,3-dione was dissolved in 250 ml of acetic acid was slowly added to a solution of 9.5 ml of methylhydrazine. The mixture was heated at 100oC for 5 minutes, then cooled and diluted with water. The ether solution was washed with water and potassium carbonate solution, then dried with magnesium sulfate, filtered and concentrated. The residue was chromatographically getting 9.5 g of 3-(2,5-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole.

The analysis.

calculated for C11H7N2F5: C 50,39%, H 2,69%, N IS 10.68%

found: C 50,48%, H 2,72%, N at 10.64%.

and 21,11 g of 5-(2,5-differenl)-1-(methyl-3-(trifluoromethyl)-1H - pyrazole (i.e. square 38 - 39oC).

The analysis.

calculated for C11H7N2F5: C 50,39%, H 2,69%, N 10.68%, FOR

found: C 50,63%, H 2,65%, N the 10.40%.

Example 2.

This example describes how to obtain 5-(2,4-differenl)-3-(trifluoromethyl)-1H-pyrazole (compound No. 6).

A. To a solution of 40.0 g (0,256 mole) of 2',4'-defloration (commercially available) in 400 ml of diethyl ether at 0oC was added (0,405 mole) of ethyl ether triperoxonane acid. When 5oC was added over 15 minutes, 80 ml of 25% (wt.) solution of sodium methoxide in methanol is obavljale of 21.3 ml of 0.37 mole) of acetic acid. The organic layer was twice washed with water, dried over anhydrous MgSO4and concentrated in vacuum, obtaining 62,85 g (97%) of 4-(2,4-differenl)-1,1,1-Cryptor-4-hydroxy-3-butene-2-it is in the form of a yellow oil.1H-NMR (CDCl3) ppm: is 6.61 (s, 1H), 6.87 in (m, 1H), 6,97 (m, 1H), 7,97 (m, 1H).

The analysis.

calculated for C10H5F5O2: C 47,64%, H 2,00%

found: C 47,70, H 1,96%.

B. When the 24oC 15.0 g (0,06 mole) of the product of stage A was dissolved in 50 ml of glacial acetic acid and treated with 2 ml (0,064 mole) of anhydrous hydrazine added over 5 minutes. The reaction mixture was heated to 95oC for 30 minutes. The reaction mixture was cooled and poured into 300 ml of ice water. The suspension was filtered, and the filter cake was washed with water and dried by air, getting 13,86 g (94%) of 5-(2,4-differenl)-3-(trifluoromethyl)-1H-pyrazole in the form of a solid white color, so pl. 157 - 158oC.

The analysis.

calculated for C10H5F5N2: C 48,40, H 2,03, N 11,29

found: C, 48.38 per, H 2,03, N 11,32.

Example 3.

This example describes how to obtain 3-(2,4-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound No. 42) and 5-(2,4-differenl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole (link is of ladida in 150 ml of acetone was stirred overnight at 25oC. the Solution was diluted with 300 milliliters of cold water and was extracted three times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatography using 5% ethyl acetate in hexane as the eluent, getting to 78.3 g (58%) of 3-(2,4-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in the form of a solid white color, so pl. 51oC.

The analysis.

calculated for C11H7F5N2: C 50,39, H 2,69, N IS 10.68

found: C 50,36, H 2,70, N 10,70.

Using chromatography, as described in the above preparation method, was awarded a second fraction, which was collected, concentrated and the residue was led, obtaining 4.0 g (28% yield) of 5-(2,4-differenl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole in the form of a solid white color, so pl. 37 - 38oC.

The analysis. calculated for C11H7F5N2: C 50,39, H 2,69, N IS 10.68

found: C 50,40, H to 2.67, N 10,67.

Example 4.

This example describes the preparation of 3-(2,5-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound No. 40).

A solution of 8.5 g (34 mmole) of dry 5-(2,5-differenl)-1H-3- (trifluoromethyl)-1H-pyrazole in 100 ml of anhydrous that is methyl sulfate. The mixture was heated under reflux for 5 hours, allowed to cool and washed with 10% (wt./about.) aqueous NaOH. The organic phase was dried MgSO4and focused, getting 7,74 g (86.2 per cent) transparent, almost colorless oil, nD 1,4925 (25oC).

The analysis.

calculated for C11H7N2F5: C 50,39, H 2,69, N IS 10.68%

found: C 50,48, H 2,72, N at 10.64%.

Examples 5 to 7 describe a specific embodiment of the method 11.

Example 5.

This example describes the preparation of 4-chloro-5-(2,5-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound 361 N).

At 25oC of 5.24 g (0,02 mol) of 3-(2,5-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole was dissolved in 40 ml of glacial acetic acid and for more than 1 hour was barbotirovany 2.1 g (0,03) mole of hargasha. The reaction mixture was stirred for 2 hours. The reaction solution was poured into 200 ml of ice water and was extracted with ethyl acetate. The organic layer was washed with water, saturated solution of NaHCO3, brine and dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatography using 3% solution of ethyl acetate in hexane as the eluent, getting by 5.87 g (99%) 4-chloro-5-(2,5-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole centuries>Cl1F5N2: C 44,56, H 2,04, N 9,44%, Cl 11,95.

found: C 44,53, H 2,00, N 9,44, Cl 11,94%.

Example 6.

This example describes how to obtain 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole (compound N 389).

To of 5.00 g of 3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole dissolved in 50 ml of acetic acid was added 15 ml of sulfurylchloride. The mixture was gently irrigated with 2 ml portions of sulfurylchloride added every 15 minutes. After 6 hours the mixture was cooled, then diluted with water and was extracted with ether. The ether was washed three times with water, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was chromatographically, getting quantitative yield 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H - pyrazole.

Analytically calculated for C11H5N3O2Cl1F5: C 38,67, H 1,48, N 12,30%

found: C 38,73, H 1,48, N 12,34%.

Example 7.

This example describes how to obtain 4-chloro-3-(4-chloro-2-fluoro-5 - methoxyphenyl)-1-(1-methylethyl)-5-(trifluoromethyl)-1H-pyrazole (compound N 489).

To a solution of 1.6 g of 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-(1 - methylethyl)-5-(trifluoromethyl)-1H-pyrazole in 20 ml of dimethylformamide was added 2.0 g of N-chloracne was extracted three times with methylene chloride, the combined organic extracts were washed with water, dried MgSO4and concentrated give crude oil. The oil was purified by chromatography and distilled from a flask into the flask, getting 1.54 g of 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-(1-methylethyl)-5- (trifluoromethyl)-1H-pyrazole as a yellow oil, nD 1,5192 (24oC).

Analytically calculated for C14H12N2O1F4Cl1: C 45,31, H 3,26, N 7.55 PER CENT

found: C 45,19, H is 3.27, N 7,49%.

Examples 8 to 10 describe a specific embodiment of method III.

Example 8.

This method describes how to obtain 3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound N 388).

It chilled with ice to a solution of 50 ml of fuming nitric acid (90%) was slowly added 8,29 g of 3-(2,5-differenl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole. After the addition the mixture was allowed to warm to room temperature and then gently heated to 52oC. were Heated for 2.5 hours, then cooled and poured into ice. The resulting mixture was extracted with ether which was then washed twice with water, dried with anhydrous magnesium sulfate, filtered and the solvent was removed by concentration under vacuum. The residue was purified using a combination of chromatogra is.

Analytically calculated for C11H6N3O2F5: C 43,01, H 1,97, N 13,68%

found: C 42,99, H 1,97, N 13,68%.

Example 9.

This example describes how to obtain 4-bromo-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound N 396).

15oC 9.5 g (0,03 mole) 4-bromo-3-(2,5-differenl)-1 - methyl-5-(trifluoromethyl)-1H-pyrazole was slowly added to 100 ml of fuming nitric acid. The reaction was heated to 28oC for a period of 20 minutes. The reaction mixture was stirred at 30oC for 4 hours. The mixture was poured into 500 ml of ice. After stirring for 1 hour the suspension was extracted three times with methylene chloride. Methylenechloride extracts were washed with water, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using a 10% solution of ethyl acetate in hexane as the eluent, and received of 5.84 g (55%) of 4-bromo-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H - pyrazole as a white solid, so pl. 45,5oC.

Analytically calculated for C11H5Br1F5N3O2: C 34,22, H 1,31, N 10,88%

found: C 34,25, H 1,38, N 10,76%/

Example 10.

This example describes how to obtain 4-chloro-3-(2,5-debtor-4-niutil-5-(trifluoromethyl)-1H-pyrazole in 6 ml of concentrated H2SO4was cooled to 15oC and exposed dropwise of a solution of 1.8 g of 70% HNO3in 2 ml of concentrated H2SO4. The reaction mixture was stirred at 30oC for 5 hours and then was treated with additional 1.8 g of 70% HNO3. After stirring over night at room temperature the mixture was poured into 250 ml of ice water and was extracted with methylene chloride. Methylenechloride extracts washed three times with saturated aqueous NaHCO3twice with water, dried MgSO4and concentrated in vacuum. The resulting material was chromatographically through silicic anhydride, using a 10% solution of ethyl acetate in hexane as the eluent, getting 3,93 g (58%) of 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole.

Analytically calculated for C11H5N3O2Cl1F5: C 38,67, H 1,48, N 12,30%

found: C 38,73, H 1,48, N 12,34%.

Examples 11-15 describe a specific embodiment of method IV.

Example 11.

This example describes the preparation of 4-chloro-3-(2-fluoro-5-methoxy - 4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1-pyrazole (compound N 390).

5,04 g of 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole was dissolved sodium in methanol. After the addition the ice bath was removed and the mixture was stirred for 30 minutes at room temperature. Then the solution was extracted 4 times with water, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was chromatographically getting 4,63 g of 4-chloro-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole, so pl. 115 - 116oC.

Analytically calculated for C12H8N3O3Cl1F4: C 40,75, H 2,28, N 11,88%

found: C 40,84, H 2,24, N 11,88%.

Example 12.

This example describes how to obtain 4-chloro-3-(2-fluoro-4-methoxy-5 - nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound N 387).

When 35oC of 13.7 g (of 0.04 mole) 4-chloro-3-(2,4-debtor-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H - pyrazole, 5.5 g (0,04 mol) K2CO3and 100 ml of methanol was stirred for 1 hour. The reaction mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatographically using a 25% solution of ethyl acetate in hexane as the eluent, getting 13,0 g (90%) 4-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifa C12H8Cl1F4N3O3: C 40,75, H 2,28, N 11,88%

found: C 40,74, H 2,34, N 11,90%.

Example 13.

This example describes how to obtain (5-(4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro-2-nitrophenyl)teoksessa acid, ethyl ester (compound N 393).

At 25oC 1.5 g (4.5 mmole) of 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H - pyrazole, 0,69 g (5.0 mmole) K2CO3, 0,55 ml (5.0 mmole) of ethyl ether mercaptohexanol acid and 0.05 g (0.5 mmole) CuF2were suspended in 15 ml of 1-methyl-2-pyrrolidinone. The reaction mixture was stirred at 28oC for 24 hours. The mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatography, using a 10% solution of diethyl ether and 15% aqueous solution of methylene chloride in hexane as the eluent, getting 0,86 g(43%) (5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H - pyrazole-3-yl)-4-fluoro-2-nitrophenyl)teoksessa acid, ethyl ester in the form of a solid yellow color, so pl. 79oC.

Analytically calculated for C15H12Cl1F4N3

This example describes the preparation of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro-N - methyl-2-nitro-N-propylbenzamide (compound No. 402).

At 25oC 6,83 g (0,02 mol) 4-chloro-3-(2,5-debtor-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H - pyrazole, 4.1 g (0,03 mole) K2CO3and 3.1 ml (0,03 mole) N-methyl-N-Propylamine and a catalytic amount CuF2suspended in 50 ml of 1-methyl-2-pyrrolidinone. The reaction mixture was stirred at 35oC for 2 hours. The mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatographically using a 15% solution of ethyl acetate in hexane as the eluent, obtaining 6.8 g (86%) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro-N - methyl-2-nitro-N-propylbenzamide in the form of an orange oil, n2D51,5534.

Analytically calculated for C15H15Cl1F4N4O2: C 45,64, H 3,83, N 14,19

found: C 45,52, H a 3.87, N 14,32%.

Example 15.

This example describes the preparation of (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2 - nitrophenoxy)acetic sour is riformati)-1H - pyrazole and 1.4 ml (to 0.011 mol) butylglycol in 25 ml anhydrous THF was cooled to 0oC. Maintaining the temperature below 5oC, portions was added 0.33 g (of 0.11 mol) NaH. Once the addition was complete, the reaction mixture was allowed to warm to 25oC. After 3 hours the mixture was carefully tempered with water and was extracted with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically 20% ethyl acetate/hexane, receiving 3.25 g(72%) (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2 - nitrophenoxy)acetic acid, butyl ester as light yellow oil, so pl. 65oC.

Analytically calculated for C17H16Cl1F4N3O5:

C 45,00, H 3,55, N 9,26%

found: C 44,97, H of 3.56, N 9,29%

Examples 16-19 describe a specific embodiment of the method V

Example 16.

This example describes how to obtain 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole (compound N 312).

A. To a solution of 4.05 g of 4-chloro-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole in 50 ml of acetic acid was added 1.39 g (0,0249 mole) of iron powder. The reaction mixture was heated close to the irrigation within 2 hours, treated of 1.39 grams of iron Poros g of 4-chloro-3-(4-amino-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole.

B. 3,064 g of 4-chloro-3-(4-amino-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole was dissolved in 50 ml of anhydrous acetonitrile was added 1.90 g of anhydrous copper chloride (II). Then was added dropwise within 10 minutes of 1.93 ml t-butylnitrite (technical. 90%), dissolved in 10 ml of anhydrous acetonitrile, another 20 minutes was stirred and then concentrated. The residue was collected in ethyl acetate, was extracted three times 10% hydrochloric acid, dried with anhydrous magnesium sulfate, filtered, concentrated and chromatographically getting 2,10 g of 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, so pl. 70-71oC.

Analytically calculated for C12H8N2O1Cl1F4:

C 42,01, H 2,35, N 8,16%

found: C 42,15, H 2,34, N 8,18%.

Example 17.

This example describes how to obtain 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro - N-methyl-N-propylbenzamide (compound N 166).

A. a Solution of 5.2 g (0,013 mol) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro - N-methyl-2-nitro-N-propylbenzamide in 100 ml of acetic acid was heated to 80oC in nitrogen atmosphere. The heat and the nitrogen was removed and added over 5 minutes with three portions of 2.2 g (0,039 mole) of iron powder. Dissolve the water and was extracted three times with ethyl acetate. An ethyl acetate extracts were washed with saturated solution of NaHCO3, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using a 30% solution of ethyl acetate in hexane as the eluent, obtaining of 3.85 g (80%) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro - N-methyl-N-propyl-1,2-benzenediamine in the form of light yellow oil, n2D51,5352.

Analytically calculated for C15H17Cl1F4N4:

C 49,39, H 4,70, N 15,36%.

found: C 49,40, with 4.64 H, N 15,16%

B. All equipment was flame dried under nitrogen atmosphere. The solution to 3.35 g (9,2 mole) of the product of stage A in 60 ml of acetonitrile at 25oC was exposed 0.9 g (9.2 mmole) of CuCl and 1.8 g (13.3 mmole) CuCl2. Within 5 minutes was added a solution of 2.2 ml (18,4 mmole) of 90% t-butylnitrite. After 2 hours the mixture was desirerable in the 28oC in vacuum. The residue from the reaction was collected in ethyl acetate and washed three times 10% HCl solution, twice with brine and dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using 20% solution of ethyl acetate in hexane as the eluent, obtaining of 2.45 g (70%) of 2-chloro-5-(4-chorus-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-f the tx2">

Analytically calculated for C15H15Cl2F4N3:

C 46,89, H 3,94, N 10,94%

found: C 46,84, H 3,83, N of 10.93%.

Example 18.

This example describes the preparation of 4-bromo-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound 313 N).

A. a Solution of 3.16 g (of 7.9 mmole) of 4-bromo-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 59 ml of acetic acid was heated to 80oC in nitrogen atmosphere. The heat and the nitrogen was removed and added over 5 minutes with three portions of 1.76 g (of 31.6 mmole) of iron powder. The solution was stirred at 80oC for a further 30 minutes the Solution was cooled and filtered through Celite. The filtrate was diluted with 100 ml water and was extracted three times with diethyl ether. The ether extracts were washed with brine, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using a 40% solution of ethyl acetate in hexane as the eluent, obtaining 2.4 g (83%) of 4-(4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2 - methoxy-benzenamine in a solid white color, so pl. 85 - 86oC.

Analytically calculated for C12H10Br1F4N3O1:

C 39,15, H is 2.74, N 11,41(0,0179 mole) of the product of stage A in 100 ml of Acrylonitrile was cooled to 5oC. was Added 1.8 g (0,018 mol) CuCl and 3.7 g (0,027 mol) CuCl2when 5oC. was Added a solution of 4.8 ml (being 0.036 mole) of 90% t-butylnitrite in 15 ml of acetonitrile for 15 minutes and then was allowed to warm up to the 28oC. After 2 hours at 28oC the reaction mixture was desirerable under vacuum. The residue from the reaction was collected in diethyl ether and washed three times 10% HCl solution, twice with brine and dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using 20% solution of ethyl acetate in hexane as the eluent, obtaining 6.3 g (91%) of 4-bromo-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole in the form of a solid white body, so pl. 85-86oC.

Analytically calculated for C12H8Br1Cl1F4N2O1:

C 37,19, H 2,08, N OF 7.23%

found: C 37,23, H 2,08, N 7,24%.

Example 19.

This example describes the preparation of 4-chloro-3-(5-chloro-2,4-differenl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound N 354).

A. a Solution of 3.4 g (0,01 mol) of 4-chloro-3-(2,4-differenl-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 50 ml of acetic acid was heated to 80oC in nitrogen atmosphere. The heat and the nitrogen was removed and was added within 5 min trailerable through Celite. The filtrate was diluted with 100 ml water and was extracted three times with ethyl acetate. An ethyl acetate extracts were washed with saturated solution of NaHCO3, dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatography using 35% ethyl acetate in hexane as the eluent, obtaining of 2.46 g (79%) of 5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-2,4 - differentley in the form of a white solid, so pl. 82oC.

Analytically calculated for C11H7Cl1F5N3:

C 42,40, H AND 2.26, N 13,48%

found: C 42,40, H and 2.26, N 13,49%.

B. All equipment was flame dried under nitrogen atmosphere. A solution of 2.0 g (6.4 mmole) of the product of stage A in 50 ml of acetonitrile at 25oC were treated to 0.63 g (6.4 mmole) of CuCl and 1.2 g (9.4 mmole) CuCl2. Within 5 minutes was added a solution of 1.74 ml (5.0 mmole) of 90% t-butylnitrite. After 4 hours at 28oC the reaction mixture was desirerable in vacuum. The residue from the reaction was collected in ethyl acetate and washed three times 10% HCl solution, twice with brine and dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatography using 10% solution of ethyl acetate in hexane as the eluent, getting 1.63 g (78%) 4 the

Analytically calculated for C11H5Cl2F5N2:

C 39,91, H 1,52, N 8,46%

found: C 39,89, H 1,52, N 8,39%.

Examples 20-21 describe a specific embodiment of the method VI.

Example 20.

This method describes the preparation of 4-chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-(hydroxyphenyl)- 1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound N 325).

1.39 g of 4-chloro-3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole was dissolved in 80 ml of anhydrous methylene chloride and then cooled on a dry ice/acetone bath and added to 0.14 ml tribromide boron. After she was allowed to warm to room temperature, the mixture was added to 0.28 ml tribromide boron. Added 1.0 ml of tribromide boron and stirred at room temperature for 6 hours. After stirring was added 30-50 ml of chilled ice water and the mixture was stirred for 10 minutes. The organic phase was extracted with water, dried with anhydrous magnesium sulfate, filtered and concentrated, obtaining the amount of 1, 258 g of 4-chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-(trifluoromethyl)- 1H-pyrazole, so pl. 123,0 - 126,0oC.

Analytically calculated for C11H6N2O1Cl2F4:
< / the 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2-NITROPHENOL (compound N 429).

A solution of 1.4 g (4 mmole) of 4-chloro-3-(2-fluoro-4-methoxy-5-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 20 ml of methylene chloride was cooled to 0oC. and Then slowly for 10 minutes was added to 5.0 ml of a 1M solution of BBr3(4.9 mmole) in methylene chloride. The solution was stirred over night at room temperature. The solution was washed twice with water, dried over anhydrous MgSO4and concentrated in vacuum. The residue was recrystallized from hexane, gaining 0.7 g (54%) of 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2 - NITROPHENOL in a solid beige color, so pl. 89-90oC. the Analytically expected for C11H6Cl1F4N3O3:

C 38,90, H 1,78, N 12,37%

Found: C 38,93, H 1,78, N 12,16%

Examples 22-24 describe a specific embodiment of method VII.

Example 22.

This example describes the preparation of 4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H - pyrazole (compound N 261).

1.01 g of 4-chloro-3-(4-chloro-2-fluoro-5-getcompany)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, of 0.44 g of anhydrous potassium carbonate and 0.5 ml of propargylamine (80% by weight in toluene) was dissolved in 20-30 ml of anhydrous DMF. The mixture was heated at 65oC for 90 minutes. After cooling, the mixture R is left the house taking anhydrous magnesium sulfate, filtered, concentrated and chromatographically, receiving of 1.05 g of 4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, so pl. 89,5-91,0oC.

Analytically calculated for C14H8N2O1Cl2F4:

C 45,80, H 2,20, N 7,63%

found: C 45,93, H 2,21, N to 7.61%.

Example 23.

This example describes the preparation of (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2-nitrophenoxy) acetic acid ethyl ester (compound 386 N).

At 25oC 6.11 g (0,018 mole) of 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2-NITROPHENOL, 2,5 g is 0.019 mol) K2CO3and 2.0 ml is 0.019 mole) of ethyl ether bromoxynil acid suspended in 100 ml of acetone. The reaction mixture was stirred at 40oC for 4 hours. The mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was recrystallized from methylcyclohexane, getting 7.5 g (99%) of 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2-nitrophenoxy) acetic acid, ethyl ester, in the form of light yellow oil, so pl. 95-96oC.

Analytic, H 2,83, N 9,85%

Example 24.

This example describes how to obtain (2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece) acetic acid ethyl ester (compound N 290).

At 25oC 13,16 g (of 0.04 mole) 4-chloro-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole, 6,1 g (of 0.44 mol) K2CO3and 4.8 ml of 0.44 mol) of ethyl ether bromoxynil acid suspended in 25 ml of acetone. The reaction mixture was stirred at 25oC for 16 hours. The reaction solution was poured into 150 ml of ice water, filtered, washed with water and dried with air. The residue was recrystallized from hexane, receiving 16.6 g (100%) (2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)-acetic acid ethyl ester in the form of a solid white color, so pl. 130-131oC.

Analytically calculated for C15H12Cl2F4N2O3:

C 43,40, H 2.91 IN, N 6.75% PER

found: C 43,54, H 2.91 in, N 6,77%.

Examples 25 and 26 describe a specific embodiment of the method VIII.

Example 25.

This example describes obtaining 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4 - pertenece)-N-methyl-propanamide (compound N 237).

A. To a suspension of 1.4 g (3.3 mm in the ml of water and 30 ml of 1,4-dioxane was added 1.3 ml (3.3 mmole) in 10% aqueous NaOH solution. After 30 minutes the solution was cooled and set the pH to 3 with concentrated HCl. The reaction mixture was extracted with diethyl ether. The ether solution was washed with water, dried over anhydrous MgSO4and concentrated in vacuum. The residue was recrystallized from methylcyclohexane, receiving 1.3 g (100%) 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)- propanoic acid in a solid white color, so pl. 150-151oC.

Analytically calculated for C14H10Cl2F4N2O3:

C 41,92, H OF 2.51, N 6,98%

found: C 41,96, H 2,48, N 7,00%.

B. To a solution of 0.8 g (2.0 mmole) of the product of stage a in 100 ml of methylene chloride was added 0.5 ml (6.0 mmole) of oxalicacid for 5 minutes, causing the evolution of gas. When the evolution of gas has ended, was added one drop of DMF and the solution was stirred until then, until gas evolution ceased. The solution was desirbale to dryness in vacuum. The residue was dissolved in 10 ml of THF and added to a solution of 5 ml of 40% aqueous methylamine and 10 ml of THF at 0oC for 5 minutes. The reaction mixture was stirred for 30 minutes at room temperature. The solution was diluted with 100 ml of cold water, was extracted with ethyl acetate. This is crystallizable from methylcyclohexane, getting 0,83 g (99%) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece) -N-methylpropanamide in a solid white color, so pl. 134,5 - 135,5oC.

Analytically calculated for C15H13Cl2F4N3O2:

C 43,50, H, AND 3.16, N 10,16%

found: C 43,70, H, and 3.16, N 10,20%.

Example 26.

This example describes how to obtain 2-(2-chloro-5-(4-chloro - 1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)propanoic acid, 3-methylbutanol ester (compound N 288).

To a solution of 1.9 g (5.0 mmole) of 2-(chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)- propanoic acid in 50 ml of methylene chloride was added 1.3 ml (15,0 mmole) of oxalicacid for 5 minutes, causing the evolution of gas. When gas evolution ceased, was added one drop of DMF and the solution was stirred until then, until gas evolution ceased. The solution was desirbale to dryness in vacuum. The acid chloride of the acid was dissolved in 40 ml of 3-methyl-1-butanol and heated to form phlegmy within one hour. The reaction mixture was cooled, diluted with 100 ml of cold water and was extracted with ethyl acetate. The ethyl acetate was washed with brine, dried over anhydrous MgSO4and concentrated in vacuum. Ostolaza 2.17 g (95%) of 2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4 - pertenece)-propanoic acid, 3 methylbutanol ether, in the form of a solid white color, so pl. 128oC.

Analytically calculated for C18H18Cl2F4N2O3:

C 47,28, H 3,97, N 6,13%

found: C 47,32, H 3,95, N 6.17 per cent.

Example 27.

This example describes how to obtain 2H-1,4-benzoxazin-3 (4H)-it, 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3 (4H)-she (compound 446 N) and is a specific embodiment of the method IX.

A. a Solution of 4.5 g (0,0106 mol) (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-5-fluoro-2-nitrophenoxy)- acetic acid ethyl ester in 75 ml of acetic acid was heated to 80oC in nitrogen atmosphere. The heat and the nitrogen was removed and added over 5 minutes with three portions of 1.8 g (0,033 mole) of iron powder. The solution was stirred at 80oC for another 3 hours. The solution was cooled and filtered through Celite. The filtrate was diluted with 100 ml water and was extracted three times with ethyl acetate. An ethyl acetate extracts were washed with saturated solution of NaHCO3, dried over anhydrous MgSO4and concentrated in vacuum. The residue was recrystallized from methylcyclohexane/ethyl acetate, getting 2,95 g (80%) 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-2H-1,4-benzo what I C13H8Cl1F4N3O2:

C 44,65 H 2,31 N 12,02%

found: C 44,66, H 2,31, N of $ 11.97.

B. When 25oC 3.0 g (8.6 mmole) of the product of stage A, 1.22 g (6.0 mmole) K2CO3and 0.79 ml (8.8 mmole) 80% propylbromide suspended in 50 ml of acetone. The reaction mixture was stirred PI 40oC for 6 hours. The reaction was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was recrystallized from methylcyclohexane, receiving of 2.97 g (89%) 2H-1,4-benzoxazin-3(4H)-it, 6-(4-chloro - 1-methyl-5-(trifluoromethyl)1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3(4H)-it is in the form of a solid beige color, so pl. 142-143oC.

Analytically calculated for C16H10Cl1F4N3O2:

C 49,57, H 2,60, N 10,84%

found: C 49,58, H 2,62, N 10,85%

Example 28.

This example describes obtain 7-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-6-fluoro-4-(2-PROPYNYL)- 2H-1,4-benzoxazin-3(4H)-she (compound N 479) and is a specific embodiment of the method X.

A. a Solution of 2.3 g (5.4 mmole) of (5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fluoro-2-nitrophen is about and the nitrogen was removed and within 5 minutes three portions were added 0.9 g (16.2 mmole) of iron powder. The solution was stirred at 80oC for another 50 minutes. The solution was cooled and filtered through Celite. The filtrate was diluted with 100 ml water and was extracted three times with ethyl acetate. An ethyl acetate extracts were washed with saturated solution of NaHCO3, dried over anhydrous MgSO4and concentrated in vacuum. The residue was recrystallized from methylcyclohexane/ethyl acetate, getting 0.96 g (50%) 7-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-6-fluoro-2H-1,4-benzoxazin - 3(4H)-it is in the form of a white solid substance, so pl. 242oC.

Analytically calculated for C13H8Cl1F4N3O2:

C 44,65, H 2,31, N 12,02%

found C 44,61, H 2,27, N 11,99%.

B. When 25oC 2.7 g (7.7 mmole) of the product of stage A, 1.1 g (8.0 mmole) K2CO3and 0.9 ml (8.0 mmole) 80% propylbromide suspended in 25 ml of DMSO. The mixture was stirred at 45oC for 10 hours. The mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatography using methylene chloride as eluent, obtaining 2.7 g (90%) of 7-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole - 3-yl)-6-caps calculated for C16H10Cl1F4N3O2:

C 49,57, H 2,60, N 10,84%

found: C 49,48, H 2,56, N 10,95%.

Example 29.

This example describes the production of CIS - and TRANS-4-chloro-3- (3-chlormethine)-5-fluoro-2,3-dihydro-6-benzofuranyl)-2-methyl-5- (trifluoromethyl)-1H-pyrazole (compound NN 481 and 482) and is a specific embodiment of the method XI.

All the equipment was flame dried under nitrogen. A solution of 2.0 g (of 5.75 mmole) of 4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole - 3-yl)-5-fluoro-2-(2-propyloxy)benzoylamino in 100 ml of acetonitrile at 25oC was treated with 0.6 g (of 5.75 mmole) CuCl and 0.8 g (of 5.75 mmole) CuCl2. Within 5 minutes was added 1.1 ml (8.6 mmole) of 90% t-butylnitrite. After 6 hours at 28oC the reaction mixture was desirerable in vacuum. The residue from the reaction was collected in ethyl acetate and washed three times 10% Hcl solution, twice with brine and dried over anhydrous MgSO4and concentrated in vacuum. The residue was purified chromatographically using 20% solution of ethyl acetate in hexane as the eluent, getting 0.73 g (35%) of CIS-4-chloro-3-(3-(chloro - methylene)-5-fluoro-2,3-dihydro-6-benzofuranyl)-1-methyl-5- (trifluoromethyl)-1H-pyrazole in the form of a white solid substance, so to 140.5 square - 142,5oC.

Analytically calculated for C14H8oC.

Analytically calculated for C14H8Cl2F4N2O1:

C 45,80, H 2,20, N 7,63, Cl 19,31%

found: C 45,71, H 2,23, N 7,63, Cl 19,28%.

Examples 30 to 37 describe a specific embodiment of the method XII.

Example 30.

This example describes how to obtain 3-[5-(methyl bromide)-4-chloro-2 - forfinal]-4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound 108 N).

A suspension of 3-[5-methyl-4-chloro-2-forfinal]-4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole (25 g, 76,4 mmole) and N-bromosuccinimide (13,6 g, 76,4 mmole) in 100 ml of carbon tetrachloride in 500-ml round-bottom flask with magnetic stir bar, was treated with catalytic amount of benzoyl. The temperature was raised to education phlegmy within one hour. The reaction mixture was cooled to room temperature, filtered and concentrated, getting to 31.5 g of a white solid. Materials double-paracrystal is in the form of a white solid, so pl. 112 - 114oC.

Analytically calculated for C12H7N2F4Cl2Br1:

C 35,50, H 1,74, N 6,90%

found: C 35,57, H 1,76, N 6,88%.

Example 31.

This example describes how to obtain (((2-chloro-5-(4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-forproper)methyl)thio)acetic acid, ethyl ester (compound N 123).

A mixture of 1.62 g (4.0 mmole) of 3-[5-(methyl bromide)-4-chloro-2-forfinal]- 4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole, of 0.44 ml of ethyl ether mercaptohexanol acid and 0.55 g K2CO3suspended in 25 ml of acetone. The reaction mixture was left to mix overnight at room temperature. After dilution with 100 ml of cold water the mixture was extracted with ethyl acetate, the organic extracts were washed with water, dried MgSO4and concentrated in vacuum. The residue was purified chromatographically, receiving 1.7 g (96%) (((2-chloro-5-(4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl)-4-forfinal)methyl)thio)acetic acid, ethyl ester in the form of a solid white color, so pl. 63oC.

Analytically calculated for C16H14Cl2F4N2O2S1:

C 43,16, H 3,17, N 6,29%

found: C 43,16, H, and 3.16, N 6,27%.

Example 32.

Etoa N 122).

To a solution of 7.1 g (0,0175 mmole) of 3-[5-(methyl bromide)-4-chloro - 2-forfinal]-4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 20 ml of DMF was added 1.5 g (0,018 mmole) of sodium acetate. The mixture was poured into 100 ml of cold water and the solid filtered substance was dried. The product was recrystallized from ethanol/water and was obtained 6.0 g (90%) of 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4 - ferbinteanu, acetate (ester), so pl. 90oC. the Acetate was dissolved in 10 ml of 1,4-dioxane and 10 ml of water was added 6.3 ml (0,0158 mole) of a 10% NaOH solution. After 30 minutes the solution was neutralized with concentrated HCl, filtered and the solid was dried. The solid is recrystallized from ethanol/water, getting to 5.4 g (99%) of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl] -4 - ferbinteanu in a solid white color, so pl. 103oC.

Analytically calculated for C12H8N2O1F4Cl2:

C 42,01, H 2,35, N 8,16%

found: C 41,88, H 2,34, N 8,09%.

Example 33.

This example describes how to obtain ((2-chloro-5-(4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-forfinal)methoxy)-acetic acid, 1-methylethylamine (compound No. 119).

At 25oC 1.7 g (5.0 mmole) of 2-chloro-5-[4-chloro-1-methyl - 5-(trifluoromethyl)-1H-Pirai acid suspended in 15 ml DMSO. The mixture was stirred overnight at 45oC. the Mixture was cooled, diluted with 100 ml of cold water and was extracted four times with ethyl acetate. An ethyl acetate extracts were washed with brine, dried over anhydrous MgSO4and desirerable in vacuum. The residue was purified chromatography using 10% solution of ethyl acetate in hexane as the eluent, obtaining 0.9 g (41%) ((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole - 3-yl)-4-forfinal)methoxy)acetic acid, 1-mutilative ether in a solid white color, so pl. 55oC.

Analytically calculated for C17H16Cl2F4N2O3:

C 46,07, H OF 3.64, N 6,32%

found: C 46,21, H 3,69, N 6,11%.

Example 34.

This example describes how to obtain 4-chloro-3-[4-chloro-5- (dibromomethyl)-2-forfinal]-1-methyl-5-(trifluoromethyl)-1H-pyrazole (compound No. 132).

In a 250 ml round bottom flask with magnetic stir bar, was preparing a suspension of 3-[5-methyl-4-chloro-2-forfinal] -4 - chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole (8,18 g, 25 mmole) and N-bromosuccinimide (8,9 g, 50.0 mmole) in 50 ml of carbon tetrachloride. Was added a catalytic amount of benzoyl peroxide and raised the temperature to education phlegmy and supported Eaton was purified chromatographically, getting 10.6 g (85%) 4-chloro-3-[4-chloro-5- (dibromomethyl)-2-forfinal] -1-methyl-5-(trifluoromethyl)-1H-pyrazole in the form of a solid white color, so pl. 89 - 92oC.

Analytically calculated for C12H6N2F4Cl2Br2:

C 29,72, H 1,25, N 5,78%

found: C 29,72, H 1,25, N 5.78 percent.

Example 35.

This example describes how to obtain 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-forventelige (compound N 133).

In a 100 ml round bottom flask with magnetic stir bar, 4-chloro-3-[4-chloro-5-(dibromomethyl)-2-forfinal] -1-methyl-5- (trifluoromethyl)-1H-pyrazole (5.0 g, 10.0 mmole) was stirred for 30 minutes in 20 ml of sulfuric acid. The resulting clear yellow solution was left to stand at room temperature for 10 days, was stirred for a short time to remove the color and then poured into 200 ml of ice/water. The aqueous mixture was extracted with ether and the organic layer was dried MgSO4was filtered and concentrated, obtaining of 3.15 g of white solid, which was recrystallized from cold hexanol, receiving 2.5 g (71%) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl] -4-forventelige in a solid white color, so pl. 70 - 72oC.

Eno: C 42,22, H 1,78, N 8,24%.

Example 36.

This example describes how to obtain 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-fermenting acid (compound N 149).

To a solution of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole - 3-yl] -4-forventelige (4.5 g, 13.2 mmole) in 14 ml of acetone was added 13 ml (26 mmole) of Jones reagent. The solution was stirred at ambient temperature for 2 hours and poured into 400 ml of water. The resulting solid was filtered and dried in the air, receiving 4.5 g (96%) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-perbenzoic acid in a solid white color. A sample for analysis was recrystallized from ether/hexanol, so pl. 179 - 181oC.

Analytically calculated for C13H6N2O2F4Cl2:

C 40,36, H 1,69, N 7,84%

found: C 40,49, H 1,74, N to 7.77%.

Example 37.

This example describes how to obtain 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl] -4-fermenting acid, 1-mutilative ester (compound N 135).

To a solution of 4.3 g (0,012 mol) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl] -4-fermenting acid in 50 ml of methylene chloride was added 3.1 ml (being 0.036 mole) oxalicacid until there is no further gas evolution. The solution was concentrated in vacuo and the resulting residue was dissolved in 25 ml of isopropanol and heated to 60oC for 1 hour. The solution was cooled, poured into 200 ml of cold water and the solid was filtered and dried. The product was recrystallized from ethanol/water, getting 1,69 g (70%) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl] -4-fermenting acid, 1-mutilative ether, in the form of a solid white color, so pl. 69oC.

Analytically calculated for C15H12Cl2F4N2O2:

C 45,13, H 3,03, N 7,02%

found: C 45,14, H 3.04 from, N 7,03%.

Examples 38 and 39 describe a specific embodiment of the method XIII.

Example 38.

This example describes how to obtain 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl] -4-forbindelsesfaneblad (compound N 346).

A solution of 4-chloro-3-(4-chloro-2-forfinal)-1-methyl-5- (trifluoromethyl)-1H-pyrazole in 20 ml of chlorosulfonic acid was heated at 120oC in an oil bath for four hours and allowed to cool to room temperature. Added methylene chloride and the solution was added dropwise to a stirred mixture of ice and water (be careful, very reactive). The layers were separated, the aqueous layer was prom is causesa the solid residue was washed very small quantity of ether and recrystallized from hexanol, receiving of 1.65 g (63%) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-forbindelsesfaneblad in a solid white color, so pl. 116 - 117oC.

Analytically calculated for C11H5N2O2S1F4Cl3:

C 32,10, H 1,22, for 6.81 N, Cl 25,84%

found: C 32,15, H 1,17, N 6,76, Cl 25,77%.

Example 39.

This example describes how to obtain 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-portifino (compound N 343).

To a solution of 12.8 g (0,031 mole) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-forbindelsesfaneblad in 100 ml of acetic acid are added 40,7 g (of 0.62 mol) of zinc powder. The suspension was stirred at 80oC for 4 hours, allowed it to cool and filtered through Celite. The filtrate was poured into 1.0 l of water, the solid was filtered and dried. The solid is recrystallized from ethanol/water, getting 10.2 g (95%) of 2-chloro-5-[4-chloro-1-methyl-5-(trifluoromethyl)- 1H-pyrazole-3-yl]-4-portifino in a solid white color, so pl. 56 - 58oC.

Analytically calculated for C11H6N2S1F4Cl2:

C 38,28, H 1,75, N 8,12%

found: C 38,29, H 2,02, N 8,12%.

Example 40.

In the apparatus, equipped with a trap Dean-stark for azeotropic removal of water, was heated 2.4 g (7.0 mmole) of 2-chloro-5-[4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole-3-yl] -4-forventelige, 0.4 ml (7.7 mmole) of ethylene glycol and a catalytic amount of p-toluensulfonate acid in 50 ml of toluene to form phlegmy within 24 hours. The resulting mixture was concentrated and the residue was dried chromatographic receiving of 1.65 g (61%) of 4-chloro-3-(4-chloro-5-(1,3-dioxolane-2-yl)-2-forfinal)-1-methyl-5-(trifluoromethyl)-1H - pyrazole in the form of a clear colorless oil, n2D51,5348.

Analytically calculated for C14H10Cl2F4N2O2:

C 43,66, H 2,62, N 7,27%

found: C 43,67, H 2,59, N 7,24%.

Example 41

This example describes how to obtain 3-(2-chloro-5-(4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-forfinal)propanoic acid, methyl ester (compound N 128) and is a specific embodiment of the method XV.

To a solution of 2.3 g (6.8 mmole) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl] -4-forventelige in 25 ml of methanol was added, and 2.27 g (6.8 mmole) of methyl(triphenylphosphonium)acetate, keeping the temperature below 35oC. the Reaction mixture was left to mix for 15 minutes and is atok was purified chromatographically using 20% solution of ethyl acetate in hexane as the eluent, obtaining 2.0 g (74%) of 3-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-forfinal)propanoic acid, methyl ester in the form of a solid white color, so pl. 117oC.

Analytically calculated for C15H10Cl2F4N2O2:

C 45,36, H 2,54, N 7,05%

found: C 45,41, H 2,59, N 7,03%.

Example 42.

This example describes how to obtain((((2-chloro-5-(4-chloro-1-methyl - 5-(trifluoromethyl)-1H-pyrazole-3-yl] -4-forfinal)methylene)amino) oxy)acetic acid (compound N 130) and is a specific embodiment of the method XVI.

A mixture of 3.4 g (0,01 mol) of 2-chloro-5-[4-chloro-1-methyl-5- (trifluoromethyl)-1H-pyrazole-3-yl]-4-forventelige, 2,73 g (of 0.0125 mole) of polyhydroxylated of carboxymethylamino and 1.03 g (of 0.0125 mole) of sodium acetate in 50 ml of ethanol was heated to education phlegmy within 2 hours. The reaction mixture was left cooled, and treated with 150 ml water, the precipitate was collected and dried. The product was recrystallized from methylcyclohexane with a minimal amount of ethyl acetate, receiving at 3.35 g(81%) ((((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)- 4-forfinal)methylene)amino)oxy)acetic acid in a solid white color, so pl. 170oC.

Analytically, expect the CLASS="ptx2">

Tables 4 to 6 show examples of the compounds obtained in accordance with methods II - XVI. Table 4 lists examples of 1-methyl-5-arylpyrazole compounds. Table 5 shows examples of 1-methyl-3-arylpyrazole. Table 6 contains a variety of compounds, most of which include compounds in which R6and R7cyklinowanie, forming a condensed heterocyclic structure.

Table 6 presents various compounds in accordance with formula I, patterns are difficult to specify in tables 4 and 5.

Preschedule trials of herbicide.

As noted above, the compounds according to the present invention were unexpectedly effective as herbicides.

Tests redshadow herbicide activity was carried out as follows:

the top layer of soil was placed in an aluminum tray and condensed to a depth of 0.95 - 1.27 cm from the top of the tray. Then the soil was sown specified number of seeds of each species of various monocotyledonous and dicotyledonous annuals and/or vegetative shoots of various species of perennial plants. Then directly on the bed with seeds inflicted known as an active ingredient, raitala, and the bed is then covered with a layer of untreated soil, filling the tray flush with its edges. After processing, the trays were placed on a bench in the greenhouse, where they were watered from below as needed to ensure adequate moisture for germination and growth.

Approximately 10 to 14 days (usually 11 days) after sowing and treatment trays were examined and the results (% inhibition) was recorded.

Tables 7 and 7A contain the results of the tests predsjedava herbicide activity on weeds compounds according to the present invention. Herbicide evaluation shown in these tables represents the percentage inhibition of each plant species. Species of plants considered weeds, which was used in one series of tests, the details of which are shown in the tables identified by the letter headings over graphs in accordance with the following

Yens - Yellow nutsedge (yellow sedge)

Anbg - annual bluegrass (Annual bluegrass)

Sejg - sapling jonssonova grass (Guma) - Seedling johnsongrass

Dobr - fire roofing - Dawny Brome

Bygr - millet plushie - Barnyardgrass

Modl - bindweed purple (ipomea) - Morningglory

Cobu - brusnik - Coklebur

Vele - canetic Theophrastus - Velvetleaf

Inmu - mustard Indian - India00% destruction of weeds, and the symbol "N" indicates that the corresponding species were sown, but for whatever reason the data is not received.

Post-harvest testing of herbicide

Post-harvest herbicide activity of some of the various compounds according to the present invention was demonstrated by testing in the greenhouse in the following way. The top layer of soil was placed in an aluminum tray that has holes in the bottom, and condensed to a depth of 0.95 - 1.27 cm from the top of the tray. The soil has made a specified number of seeds of each of the different types of annual dicotyledonous and monocotyledonous plants and/or vegetative shoots of perennial plant species and pressed them into the soil surface. Seeds and/or vegetative shoots are covered with soil and leveled. The trays were then placed on a bench in the greenhouse and watered from below as needed. After plants have reached the desired age (two or three weeks), each tray individually moved into the irrigation chamber and watered using a spray gun operating at a pressure spray 170,3 kPa (10 psig) when the expenditure norms. The solution is to spray contained a certain amount of the mixture of emulsifying agent, such that the content of the emulsifier in respelt a sufficient amount of the test chemical, to obtain the rates of consumption of the active ingredient corresponding to those in tables 8 and 8A, when using the total quantity of solution or suspension, equivalent to 1870 l/ha (200 Gal/acre). The trays were returned to the greenhouse and watered as before, and after approximately 10 to 14 days (usually 11 days) was observed damaged plants compared with controls, and in some cases was observed again after 24 - 28 days (usually 25 days) after irrigation. Post-harvest herbicide activity shown in these tables represents the percentage inhibition of each plant species.

Herbicide compositions according to the present invention, including concentrates which require dilution prior to application, may contain at least one active ingredient and additive in liquid or solid form. The compositions are prepared by mixing the active ingredient with the additive, including diluents, extenders, carriers and modifying agents to obtain compositions in the form of finely pulverized solid particles, granules, beads, solutions, dispersions and emulsions. Thus, it is assumed that the active ingredient could be used with additives such as finely dispersed solids, liquids organicheskikh the Suitable wetting agents include the alkyl benzene and alkylnaphthalene, sulfated fatty alcohols, amines or acid amides, long chain acid esters of isethionate sodium esters of sulfosuccinate sodium sulfonated esters or from sulphonated fatty acids, sulfonates of petroleum, from sulphonated vegetable oils, decret-acetylene glycols, polyoxyethylene derivatives of ALKYLPHENOLS (particularly isooctylphenol and Nonylphenol) and polyoxyethylene derivatives of mono-higher fatty acid esters of mexicanvalium (for example, sorbitan). Preferred dispersing agents are methyl cellulose, polyvinyl alcohol, ligninsulfonate sodium, naphthalenesulfonate sodium, polymer alkylnaphthalene, naphthalenesulfonate sodium and polymethylene-naphthalenesulfonate. Wetting the powders are water-dispersible compositions containing one or more active ingredients, inert solid filler-extender and one or more wetting and dispersing agents. Inert solid fillers-expanders are usually of mineral origin, such as natural clays, diatomaceous earth and synthetic minerals, derivatives of silica, etc. are Examples of such extenders include kaolinites, attapulgite clay and sin is 0.5 to 60 parts, preferably from 5 to 20 parts) of the active ingredient, from 0.25 to 25 parts (preferably from 1 to 15 parts) of wetting agent, from 0.25 to 25 parts (preferably from 1.0 to 15 parts) of dispersant and from 5 to 95 parts (preferably 5 - 50 parts) inert solid filler-extender, all parts of the essence of the weight of the total composition. Where required, from about 1.0 to 2.0 parts of inert solid extender, can be replaced by a corrosion inhibitor or protivovspenivayushchie agent, or both.

Other recipes include Gustavia concentrates containing from 0.1 to 60% by weight of active ingredient in a suitable extender; these dusty can be diluted for use in concentrations ranging from 0.1 to 10% by weight.

Aqueous suspension or emulsion can be obtained by mixing the non-aqueous solution of water-insoluble active ingredient and an emulsifier with water until a homogeneous state and subsequent homogenization of obtaining stable emulsions are very finely distributed particles. The resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that after dilution and dispersion is achieved very uniform coating. Suitable concentrations of these formulations is aetsa limit of solubility of the active ingredient in the solvent. Concentrates are usually solutions of active ingredient in water-immiscible or partially water-immiscible solvents together with surface-active substance. Suitable solvents for the active ingredient according to the present invention include dimethylformamide, dimethyl sulfoxide, organic, hydrocarbons and is not miscible with water, ethers, esters or ketones. However, there may be prepared other liquid concentrates high castle by dissolving the active ingredient in a solvent with further dilution, such as kerosene, to the concentration of the spray.

The compositions of the concentrates described here, usually contain from 0.1 to 95 parts (preferably 5 to 60 parts) of the active ingredient, from 0.25 to 50 parts, preferably from 1 to 25 parts) surface-active substances and, where required, from 5 to 94 parts solvent, all parts of the essence of the weight of the total weight of the emulsified oil.

Granules are physically stable dispersion compositions containing the active ingredient, coupled with the main matrix of inert finely dispersed filler-extender or distributed through it. To facilitate the leaching of the act the main substance. Natural clay, pyrophyllite, illite and vermiculite are examples of applicable classes of dispersed mineral extenders. The preferred extenders are porous adsorbing preshaped particles, such as pre-granulated and sifted attapulgite or thermally enhanced dispersion and fine vermiculite clays, such as kaolin clay, hydrated attapulgite or bentonite compounds, preventing clay. These dilators are sprayed on the active ingredient or mixed with it for education herbicide granules.

Granular compositions according to the present invention may contain from 0.1 to about 30 parts by weight of active ingredient per 100 parts by weight of clay and 0 to 5 parts by weight of surfactant per 100 parts of the dispersed clay.

The compositions according to the present invention may also contain other additives, such as fertilizers, other herbicides, other pesticides, additives that improve the safety of the applied compositions, etc., used as such or in combination with the above-described additives. Chemicals that can be used in combination with the active ingredients of the present sobreprotegi acetic acid or phenol, THIOCARBAMATE, triazole, azolopyrimidine, benzoic acid and its derivatives, NITRILES, biphenylene esters, nitrobenzol etc., such as:

Heterocyclic derivatives of nitrogen/sulfur

2-chloro-4-ethylamino-6-isopropylamino-S-triazine

2-chloro-4,6-bis(isopropylamino)-S-triazine

2-chloro-4,6-bis(ethylamino)-S-triazine

3-isopropyl-1H-2,1,3-benzothiadiazin-4-(3H)-2,2-dioxide

3-amino-1,2,4-triazole

6,7-dihydropyrido (1,2-2',1'-c)-peridiniella salt

5-bromo-3-isopropyl-6-methyluracil

1,1'-dimethyl-4,4'-bipyridine

2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-3 - quinoline-carboxylic acid

Isopropylamine salt of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid

Methyl ester of 6-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2 - yl)-m-Holloway acid and methyl ester of 2-(4-isopropyl-4-methyl-5 - oxo-2-imidazolin-2-yl)-p-Holloway acid

Urea/sulfobetaine

N-(4-chlorophenoxy)phenyl-N,N-dimethylation

N,N-dimethyl-N'-(3-chloro-4-were)urea

3-(3,4-dichlorophenyl)-1,1-dimethyloxetane

1,3-dimethyl-3-(2-benzothiazolyl)urea

3-(p-chlorophenyl)-1,1-dimethyloxetane

1-butyl-3-(3,4-dichlorophenyl)-1-metalmachine

2-chloro-N/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl

Methyl ester 2 -((((( a 4.3-dimethyl-2-pyrimidinyl)amino)carbonyl) amino)sulfonyl)benzoic acid

Ethyl ester 1-/methyl-2-(((((4,6-dimethyl-2-pyrimidinyl) amino)carbonyl)amino)sulfonyl)/benzoic acid

Methyl-2 ((4,6-dimethoxy-pyrimidine-2-yl)aminocarbonyl)amino - sulfanilyl)benzoic acid

Methyl ester 2 -((((( 4-methoxy-6-methyl-1,3,5-triazine - 2-yl)-amino)carbonyl)amino)sulfonyl)benzoic acid

Carbamates/THIOCARBAMATE

2-korallovy ether pttc acid

S-(4-Chlorobenzyl)N,N-diethylthiocarbamate

Isopropyl ester N-(3-chlorophenyl)carbamino acid

S-2,3-dichloropropyl ether N,N-diisopropylethylamine acid

S-N,N-dipropylthiocarbamate

S-propyl ester N,N-dipropylthiocarbamate acid

S-2,3,3-trichloroallyl-N,N-diisopropylethylamine

Acetamide/acetanilide/anilines/amides

2-chloro-N,N-deallocated

N,N-dimethyl-2,2-diphenylacetamide

N-(2,4-dietitian-3-yl)-N-(1-methoxypropan-2-yl)-2-chloracetamide

N-(1H-pyrazole-1-ylmethyl-N-(2,4-dimethylthiazol-3-yl)-2-chloracetamide

N-(1-pyrazole-1-ylmethyl)-N-(4,6-dimethoxypyrimidine-5-yl)-2-chloracetamide

N-(2,4-dimethyl-5-///Trifluoromethyl)sulfonyl/amino/phenyl/-ndimethylacetamide

N-isopropyl)-2-chloroacetanilide

2',6'- diethyl-N-(2-n-propoxyethyl)-2-chloroacetanilide

2',6'-dimethyl-N-(1-pyrazole-1-ylmethyl)-2-chloroacetanilide

2',6'-diethyl-N-methoxymethyl-2-chloroacetanilide

2'-methyl-6'-ethyl-N-(2-methoxypropan-2-yl)-2-chloroacetanilide

2'-methyl-6'-ethyl-N-(ethoxymethyl)-2-chloroacetanilide

,,, trifter-2,6-dinitro-N,N-dipropyl-p-toluidine

N-(1,1-dimethylpropyl)-3,5-dichlorobenzamide

Acid/esters/alcohols

2,2-dichloropropionic acid

2-methyl-4-chlorophenoxyacetate acid

2,4-dichlorophenoxyacetic acid

Methyl-2-/4-(2,4-dichlorphenoxy)phenoxy/propionate

3-amino-2,5-dichlorobenzene acid

2-methoxy-3,6-dichlorobenzene acid

2,3,6-trichlorophenylacetic acid

N-1-naftemporiki phthalic acid

5-/2-chloro-4-(trifluoromethyl)phenoxy/-2-nitrobenzoate sodium

4,6-dinitro-o-sec.-the butylphenol

N-(phosphonomethyl)glycine and its salts

Butyl ether (R)-2-/4-/(5-trifluoromethyl)-2-pyridinyl/hydroxy/ phenoxy/propanoic acid

Ethers,

2,4-dichlorphenol-4-nitrophenyloctyl ether

2-chloro -,,- Cryptor-p-tolyl-3-ethoxy-4-nitrodiphenyl ether

5-(2-chloro-4-triptoreline)-N-methylsulphonyl-2-nitrobenzamide

1'-(carboethoxy)ethyl ester 5-/2-chloro-4-(trifluoromethyl)-precisely

Sodium salt metamellomai acid

2-(2-chlorophenyl)methyl-4-, 4-dimethyl-3-isoxazolidinone

7-oxabicyclo-(2.2.1)-heptane, 1-methyl-4-(1-methylethyl)-2-(2 - methylphenylene)-, Exo-glyphosate and its salts.

Fertilizers that can be used in combination with the active ingredients include, for example, ammonium nitrate, urea, potash, and superphosphate. Other useful additives include materials in which take root and grow vegetable organisms, such as compost, manure, humus, sand, etc.

Herbicide formulations described above, considered as being in the scope of the present invention, shown here in several illustrative examples.

1. Emulsifiable concentrates is the Weight percent of

A. Connection 308 N - 11,00

The free acid of complex organic phosphate or the aromatic or aliphatic hydrophobic bases (e.g., GAFAC RE-610, registered trademark of GAF Corp. - 5,59

The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH, registered trademark of Union Carbide Corp.) - 1,11

Phenol - 5,34

Monochlorbenzene - 76,96 - 100,00

B. Connection N 261 - 25,0

The free acid integrated the
The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH) - 1,60

Cyclohexanone - 4,75

Monochlorbenzene - 63,65 - 100,0

C. the Compound N 291 TO 12.0

The free acid of complex organic phosphate or the aromatic or aliphatic hydrophobic base (e.g., GAFAC RE-610, registered trademark of GAF Corp.) - 6,00

The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH, registered trademark of Union Carbide Corp.) - 1,5

Cyclohexanone - 5,5

Monochlorbenzene - 75,0 - 100,0

, Connection N 229 - 20,0

The free acid of complex organic phosphate aromatic or aliphatic hydrophobic bases (e.g., GAFAC RE-610) - 5,00

The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH) - 2,0

Cyclohexanone - 5,0

Monochlorbenzene - 68,0 - 100,0

D. Connection 312 N - 11,0

The free acid of complex organic phosphate or the aromatic or aliphatic hydrophobic base (e.g., GAFAC RE-610, registered trademark of GAF Corp.) - 5,59

The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH, registered trade is/BR> The free acid of complex organic phosphate aromatic or aliphatic hydrophobic bases (e.g., GAFAC RE-610) - 5,00

The block copolymer of polyoxyethylene/polyoxypropylene with butanol (e.g., tergitol XH) - 1,60

Cyclohexanone - 4,75

Monochlorbenzene - 63,65 - 100,0

II. Fluid recipes - Weight percent

A. Connection N 261 - 25,0

Methylcellulose - 0,3

The aerogel silica - 1,5

Sodium lignosulphonate is 3.5

N-methyl-N-eleitoral sodium - 1,0

Water - 67,7 - 100,00

B. Connection 270 N - 45,0

Methylcellulose - 0,3

The aerogel silica - 1,5

Sodium lignosulphonate is 3.5

N-methyl-N-eleitoral sodium - 1,0

Water - 47,7 - 100,00

C. the Compound N 294 - 30,0

Methylcellulose - 0,3

The aerogel silica - 1,5

Sodium lignosulphonate is 3.5

N-methyl-N-eleitoral sodium - 3,0

Water - 62,0 - 100,00

, Connection N 135 - 23,0

Methylcellulose - 0,5

The aerogel silica - 2,0

Sodium lignosulphonate is 3.5

N-methyl-N-eleitoral sodium - 2,0

Water - 69,00 - 100,00

D. Connection N 148 - 45,0

Methylcellulose - 0,3

The aerogel silica - 1,3

Sodium lignosulphonate is 3.5

N-methyl-N-eleitoral sodium - 1,0

Water - 47,7 - 100,00

III Smailer-taurate sodium - 1,0

Amorphous silica (synthetic) - 71,0

B. Connection 312 N - 45,0

Dioctylsulfosuccinate sodium - 1,25

The calcium lignosulfonate is 1.75

Amorphous silica (synthetic) - 52,0 - 100,00

C. the Compound N 237 - 10,0

Sodium lignosulphonate - 3,0

N-methyl-N-oleyl-taurate sodium - 1,0

Kalinicheva clay - 86,0 - 100,00

, Connection N 463 - 30,0

Sodium lignosulphonate - 3,0

N-methyl-N-oleyl-taurate sodium - 1,0

Kaolin - 56,0

Amorphous silica (synthetic) - 10,0 - 100,0

D. Connection N 446 - 75,0

Dioctylsulfosuccinate sodium - 1,25

The calcium lignosulfonate is 1.75

Kaolin - 12,0

Amorphous synthetic silica - 10,0 - 100,00

That is, the Compound N 482 - 15,0

Sodium lignosulphonate - 3,0

N-methyl-N-oleyl-taurate sodium - 1,0

Amorphous silica, synthetic - 10,0

Kalinicheva clay - 71,0 - 100,00

IV. Granules

A. Connection N 74 - 15,0

Dipropyleneglycol - 5,0

Pelletized attapulgite (20/40 mesh) - 80,0 - 100,00

B. Connection N 390 - 15,0

Dipropyleneglycol - 5,0

Diatomaceous earth (20/40) - 80,0 - 100,00

C. the Compound N 399 - 1,0

The glycol - 5,0

Methylene blue - 0,1

Pyrophyllite - 93,9 - 100,00

, Connection N 393 - 5,0

Etilenglikolya attapulgite (20/40 mesh) - 80,00 - 100,00

That is, the Compound N 324 - 25,00

Diatomaceous earth (20/40 mesh) - 75,00 - 100,00

J. the Compound N 261 - 5,0

The glycol - 5,0

Methylene blue - 0,5

Pyrophyllite - 94,5 - 100,0

H. the Compound N 262 - 10,0

Propylene glycol - 5,0

Pyrophyllite (20/40) - 85,0 - 100,0

V. Suspension concentrates Weight percent

A. Connection N 262 - 16,0

Nonylphenolethoxylate of 9.5 mol of EO Steaks NJ EN-Jay - 13,8

Sodium lignosulphonate (reax V) - 12,2

Water - 58,0 - 100,0

B. Connection N 446 - 32,5

Potassium salt of a condensate of naphthalenesulfonate with formaldehyde (DAXAD IIKLS) - 9,0

Nonylphenolethoxylate 10 mol EO (Igepal si-cu-660) - 9,0

Water - 49,5 - 100,0

C. the Compound N 76 - 10,0

Dioctylsulfosuccinate sodium, aerosol RE - 11,0

Castor oil +36 ethylene oxide (Flomo 3 g) - 11,00

Water - 70,0 - 100,0

That is, the Compound N 261 - 15,0

Nonylphenolethoxylate of 9.5 mol of EO Steaks EN-Jay

that 0

Sodium lignosulphonate (Reax V) - 5,0

Water - 79,00 - 100,00

D. Connection N 290 - 30,0

Potassium salt of a condensate of naphthalenesulfonate with formaldehyde (DAXAD II KLS) - 4,0

Nonylphenolethoxylate 10 moles EO (Igepal si-cu-660) - 2,0

Water - 64,0 - 100,0

That is, the Compound N 135 - 18,0

Nonylphenolethoxylate of 9.5 mol of EO Sterculia salt of a condensate of naphthalenesulfonate with formaldehyde (DAXAD aag) - 8,0

Nonylphenolethoxylate 10 mol of EO (Igepal si-cu-660) - 10,0

Water - 48,0 - 100,0

H. the Compound N 482 - 14,0

Dioctylsulfosuccinate sodium, aerosol RE - 3,0

Castor oil + 36 ethylene oxide (Flomo 3 g) - 3,0

Water - 80,0 - 100,0

VI. Liquid concentrates - Weight percent

A. Connection N 76 - 20,0

Xylene - 80,0 - 100,0

B. Connection N 229 - 10,0

Xylene - 90,0 - 100,0

C. the Compound N 217 - 25,0

Xylene - 75,0 - 100,0

, Connection N 482 - 15,0

Xylene - 85,0

100,0

VII. Microcapsules - the Weight percent of

A. Connection N 135, encapsulated in a shell of polyurea - 4,5

Reeks C-21 - 1,5

NaCl - 5,0

Water - 89,0 - 100,0

B. Connection N 137, encapsulated in a shell of polyurea - 20,0

Reeks V - 2,0

NaNO3- 10,0

Xylene - 30,0

Water - 38,0 - 100,0

C. the Compound N 138, encapsulated in a shell of polyurea - 4,8

Reeks W - 1,2

NaNO3- 5,0

Kerosene - 20,0

Water - 69,0 - 100,0

, Connection N 148, encapsulated in the urea-formaldehyde polymer membrane - 50,0

Reeks C-21 - 1,5

NaCl - 8,5

Petroleum oil (aromatic 200) - 20,0

Water - 20,0 - 100,0

That is, the Compound N 229, encapsulated in tiomochevina-formaldehyde polymer balanoe in the polyurea shell - 7,5

Reeks V - 1,5

NaCl - 8,0

Aromatic 200 - 30,0

Water - 53,0 - 100,0

H. the Compound N 308, encapsulated in a shell of a melamine-formaldehyde copolymer - 9,0

Reax 88B - 2,0

NaNO3- 10,0

Kerosene - 40,0

Water - 39,0 - 100,0

I. the Compound N 446, encapsulated in polymeric urea-formaldehyde shell - 15,0

Reax 88B - 10,0

NaNO3- 8,0

Xylene - 42,0

Water - 25,0 - 100,0

K. the Compound N 312, encapsulated in a polyurea shell - 22,0

Reax 88B - 2,0

NaCl - 8,0

Xylene - 35,0

Water - 33,0 - 100,0

When carrying out the present invention the effective amount of the compounds according to the present invention applied to the soil containing seeds or vegetative shoots, or implement them in whatever way is appropriate. The introduction of liquid or solid dispersed compounds to the soil can be carried out by conventional means, for example by mechanical afiliates, Lancet and hand sprayers and aerosol dispensers. The compositions may also be made from airplanes as a dust or aerosol due to their effectiveness at low doses. The exact amount of active ingredient that is applied depends on various factors, including the x specific compounds. When selective pre-emergence application or applying to the soil dosage is usually from 0.02 to 11.2 kg/ha, preferably from 0.1 to 5.60 kg/ha In some cases may require a higher and a lower consumption rates. The specialist can easily determine from this specification, including the examples above, the optimal level of consumption in each individual case.

The term "soil" is used in its most broad sense, including all the usual "soil" as defined in Webster's New International Dictionary, second edition, unabridged (1961). Thus, the term refers to any substance or any environment in which vegetation may take root and grow, and includes not only the earth but also compost, manure, litter, humus, loam, silt, mud, clay, sand, etc., adapted to support plant growth.

Although the present invention is described with specific examples, the details of these embodiments may not be considered as limitations. Various equivalents, changes and modifications can be made without going beyond the nature and scope of the present invention, and such equivalent embodiments are understood as part of the present invention.

B>1
-C1-3-alkyl, kaleidotile, or (C1-C3-alkoxycarbonylmethyl;

R2-C1-C3-haloalkyl;

R3- halogen;

R4- independently from each other represent1-3-alkyl, (C2-4alkenyl)-R19, (C1-3)alkoxy(C1-3)alkyl, (C1-3)alkoxy (C1-3)alkoxy(C1-3)alkyl, C1-3-haloalkyl, halogen, the nitro-group, cyano, cyclic substituents, such as dihydrooxazolo, morpholinyl, DIOXOLANYL, dithiolane, oxathiolane, isoindole-3-dione, which can be unsubstituted or optionally substituted by the substituents R15and R16,

< / BR>
YR10, NR11R12, (C1-3-alkyl)-R19, -C(CH3)=NOCH2R19or two groups R4associated with the formation of rings, which in combination with the phenyl ring gives a substituted or unsubstituted bicyclic group which is selected from 1,4-benzoxadiazole, benzoxazinone, benzofuranyl, imidazobenzodiazepine, benzoxazine, benzoxazinone, benzimidazole or khinoksalinona, each of which may be substituted in the heterocyclic ring with one or two groups R22;

X - nezavisna O or S;

Y is O or S(O)m;

m is 0-2;

n the sludge, (C1-4-alkyl)-R19or (C1-4-haloalkyl)-R19;

R9is hydrogen, C1-6-alkyl or NR17R18or NHOR20;

R10is hydrogen, halogen, C1-10-alkyl, C1-4-haloalkyl,2-4alkenyl,2-4-quinil, (C1-5-alkyl)-R19, (C1-4-haloalkyl)-R19, (C=O)-R16, pyrazolyl, NR11R12or phenyl, optionally substituted by one or two substituents R15and R16< / BR>
R11and R12independently represent hydrogen, C1-4-alkyl, C2-4alkenyl,2-4-quinil, -(C=X)-YR13-(C=X)-R14, RHO(R14)2, (C1-3-alkyl)-R19, YR20;

R13- H1-3-alkyl, C1-3-haloalkyl,1-3-CNS group, WITH2-4-alkoxyalkyl,1-3-alkoxycarbonylmethyl;

R14- H, C1-3-alkyl, C1-3-haloalkyl,1-3-CNS group, WITH2-4-alkoxyalkyl,1-3-alkoxycarbonylmethyl;

R15and R16independently represent hydrogen, halogen, a nitro-group, WITH1-3-alkyl, C1-3-haloalkyl,2-4-alkoxyalkyl;

R17and R18independently represent hydrogen, C1-4-alkyl, C1-4-haloalkyl,1-yl)NOCH2R231,3-dioxolane-2-yl, 2-pyridyl, 2-chlorothiophene, (C1-3alkyl)-dihydrooxazolo, (C1-3alkyl)-oxiranyl, (C1-3alkyl)-tetrahydro-2H-pyranyl, (C1-3alkyl)-DIOXOLANYL;

R20- C1-5-alkyl, C1-4-galidakis,2-8-alkoxyalkyl,1-4-hydroxyalkyl,3-6-cycloalkyl,1-3-alkoxycarbonylmethyl,1-3-alkoxycarbonylmethyl, N(CH3)2, SO2CH3;

R22- C1-4-alkyl, (C1-4-alkyl) - R23WITH2-4-alkoxyalkyl,3-8-cycloalkenyl,2-5alkenyl,3-5-quinil, pyridinylmethyl, phenyl;

R23- COOH, N2, NH(C1-3-alkyl), COO(C1-3-alkyl), tetrahydrofuranyl, 1,3-dioxane or 1,3-DIOXOLANYL.

2. Connection on p. 1 of formula II

< / BR>
and their agricultural-acceptable salts and hydrates, where

R1, R2and R3defined for formula I;

R5is halogen or hydrogen;

R6and R7have the meanings defined for R4formula I.

3. Connection on p. 2 of the formula III

< / BR>
and acceptable in agriculture salts and hydrates, where

R1- C1-3-alkyl,

R2, R3and R5matter, ODA
R8defined in paragraph 1;

Y is 0.

4. The compounds, salts and hydrates under item 3, where R1is methyl, R2-CF3, CF2Cl or CF2H; R3is chlorine or bromine; R5- fluorine, R6- chlorine; R7- COOR8; R8- C1-5-alkyl.

5. Connection on p. 1, selected from the group consisting of

4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

2-(2-chloro-5-(4-chloro-1-methyl-5(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)propanoic acid, ethyl ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1-mutilative ester,

4-chloro-3(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

(2-chloro-5-(4-chloro-1-methyl-5(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1,1-dimethylethylene ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 2-ethoxy-1-methyl-2-xoetrope ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting cantinas acid, ethyl ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 1-mutilative ether and

6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-it.

6. Connection on p. 1, a 4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole.

7. Connection on p. 1, representing 1-metaliteracy ether, (2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid.

8. Connection on p. 1 representing 2-methoxy-1-methyl-2-oksietilnye ester 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-2-yl)-4-fermenting acid.

9. Connection on p. 1, representing 1-metaliteracy ester 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid.

10. Connection on p. 1, representing 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-he.

11. Herbicide composition containing a pyrazole derivative as an active ingredient and an additive, characterized in that the active ingredient it contains herbicide-effective amount of compounds of formula 2 as an active ingredient.

13. Herbicide composition according to p. 12, characterized in that it contains a compound of the formula III under item 3 as an active ingredient.

14. The composition according to p. 13, where the group R1-R8in the formula III have the meanings given in paragraph 4.

15. The composition according to p. 11, in which the active ingredient is a compound selected from the group

4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)propionic acid, ethyl ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1-mutilative ester,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1,1-dimethylethylene ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 2-ethoxy-1-methyl-2-xoetrope ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-FSol-3-yl)-4-fermenting acid, ethyl ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 1-mutilative ether and

6-(4-chloro-1-methyl-5-(trifluoromethyl)-2H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-it.

16. The composition according to p. 11 containing herbicide-effective amount of 4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole.

17. The composition according to p. 11 containing herbicide-effective amount of 1-mutilative ether (2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid.

18. The composition according to p. 11 containing herbicide-effective amount of 2-methoxy-1-methyl-2-xoetrope ether, 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid.

19. The composition according to p. 11 containing herbicide-effective amount of 1-mutilative ether 2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid.

20. The composition according to p. 11 containing herbicide-effective amount of 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-it.

21. The method of combating unwanted plants in crops, comprising applying to the place is the Association of the formula I in herbicide-effective amount.

22. The method according to p. 21, characterized in that the said compound is selected from the group of compounds of formula II under item 2.

23. The method according to p. 22, characterized in that the said compound is selected from the group of compounds of formula III under item 3.

24. The method according to p. 23, characterized in that the compound I is selected from the group of compounds of formula III under item 4.

25. The method according to p. 21, in which the indicated compound I selected from the group consisting of

4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

2-(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)propanoic acid, ethyl ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1-mutilative ester,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

4-chloro-3-(4-chloro-2-fluoro-5-(methoxyethoxy)phenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid, 1,1-dimethylethylene ester,

(2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-pertenece)acetic acid,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 2-atok is the notes, 2-methoxy-1-methyl-2-xoetrope ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, ethyl ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 1-mutilative ether and

6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-it.

26. The method according to p. 21, in which the indicated compound according to formula III selected from the group consisting of

4-chloro-3-(4-chloro-2-fluoro-5-propargyloxy)-1-methyl-5-(trifluoromethyl)-1H-pyrazole,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fervency acetic acid, 1-mutilative ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 2-methoxy-1-methyl-2-xoetrope ester,

2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-4-fermenting acid, 1-mutilative ether and

6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl)-7-fluoro-4-(2-PROPYNYL)-2H-1,4-benzoxazin-3-(4H)-it.

27. The method of obtaining derivatives of pyrazole of the General formula I on p. 1, characterized in that conduct interaction derived 1-phenylpropane-1,3-dione of formula a or its tautomeric forms

< / BR>
where R2, R4and n determine the>defined in paragraph 1, to obtain the compounds of formula In the case of the substituted hydrazine:

< / BR>
or compounds of formula in the case of unsubstituted hydrazine, provided that the compound obtained of the formula

< / BR>
where R2, R4and n are defined in paragraph 1,

subjected to interaction with an alkylating agent to obtain a connection, which is then further treated halogenation agent to obtain compounds of formula I.

28. The method of obtaining the compounds of formula

< / BR>
characterized in that interact compounds of formulas AND

< / BR>
with a substituted or unsubstituted hydrazine, provided that when hydrazine is not substituted, the resulting compound of the formula

< / BR>
subjected to interaction with the alkylating agent and in which in the above formulas, R1, R2, R4and n have the previously specified value.

29. The method according to p. 23, characterized in that the compound of formula get essentially in the form of regioisomer, the corresponding 1-alkyl-3-aryl-5-galoiduglyerodov.

30. The method according to p. 29, characterized in that the alkylation reaction is carried out in the absence of base.

31. The method according to p. 30, wherein SUB> - previously defined.

32. The method according to p. 30, characterized in that the compound of the formula In which R4)nindependently represents a halogen, a nitro-group, YR10or1-3-alkyl, where R10previously defined and n is an integer from 1 to 3.

33. Method of producing compounds of the formula I, which comprises carrying out the reaction of compounds of formula In with a halogenation agent, where R1-R4and h defined in paragraph 1

< / BR>
34. The method according to p. 33, wherein receiving the above compounds of formula I are compounds of formula III under item 3, where R1-R7defined in paragraph 1, provided that R6can also be hydrogen.

35. The method according to p. 33, in which R1is methyl, R2- CF3, CF2Cl or CF2H, R3is chlorine or bromine, R5is fluorine and R6and R7defined in paragraph 1.

36. The method of obtaining derivatives of pyrazole, corresponding to the formula Z

< / BR>
where R1-3, R5, R6defined in the PP. 1 and 2, and R38represents NR17R18, YR8, characterized in that the pyrazole derivatives of the formula V

< / BR>
in which R1-3, R5and R6have the specified values are subject Asteri is B>.

37. The method according to p. 36, where in the formula Z R38represents OC1-5alkyl or(C1-4-alkyl)-R19where R19defined in paragraph 1.

38. The method according to p. 37, where R38represents OCH(CH3)2or och(CH3)CO2CH3.

Priority points:

18.10.90 - PP.1-37;

25.09.91 - PP.1-37 (varieties radicals).

 

Same patents:

The invention relates to pyrazole derivative of the General formula I

< / BR>
in which R1is phenyl, substituted cyclo(lower)alkyl, hydroxy(lower)alkyl, cyano, lower alkylenedioxy, carboxy, (lower alkoxy)carbonyl group, a lower alkanoyl, lower alkanoyloxy, lower alkoxy, phenoxy or carbamoyl, optionally substituted lower alkyl;

R2is halogen, halo(lower)alkyl, cyano, carboxy, (lower alkoxy)carbonyl group, carbamoyl, optionally substituted by alkyl;

R3is phenyl, substituted lower alkylthio, lower alkylsulfonyl, or lower alkylsulfonyl, provided that when R1is phenyl, substituted lower alkoxy, then R2represents halogen or halo(lower)alkyl,

or their pharmaceutically acceptable salts

The invention relates to a method for producing 1-phenyl-2,3-dimethyl-4 iteration-5 (yodanthipirina) with antipyretic antineuralgic action, part antiemeticski drugs such as Felsol, Vastylu and also shown high activity against tick-borne encephalitis

The invention relates to new derivatives of 3-phenylpyrazole, to methods for their preparation, to compositions containing them and to a method of protecting plants from fungal diseases

The invention relates to new 1-aryl-5-(substituted)alkylidene the pyrazoles, methods for their preparation, to compositions containing these compounds, to methods of their use for combating arthropods, nematodes, helminths or protozoa pests

The invention relates to new derivatives of 3-phenylpyrazole, to methods for their preparation, to compositions containing them and to a method of protecting plants from fungal diseases

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

FIELD: organic chemistry, agriculture, fungicide compositions.

SUBSTANCE: invention relates to compounds of formula I

, wherein R1 and R2 are hydrogen or C1-C4-alkyl; X is C3-C8-cycloalkyl, phenyl or styryl, as well as method for production thereof and fungicide composition containing the same. Compounds of present invention have fungicide activity and are useful in effective controlling of deleterious fungi.

EFFECT: compounds and fungicide composition with improved effectiveness.

3 cl, 2 tbl, 4 ex

FIELD: organic chemistry, insecticides, chemical technology.

SUBSTANCE: invention describes derivative of 1-aryl-3-cyano-5-heteroarylalkylaminopyrazole of the general formula (1): wherein A means: (A-1) , (A-2) , (A-3) and (A-4) and wherein X represents C-halogen; R1 represents (C1-C4)-alkyl group or halogen-(C1-C4)-alkyl group; A represents any group among (A-1) - (A-4) wherein R4 represents hydrogen atom or (C1-C4)-alkyl group; n = 0, 1 or 2 under condition that R1 represents halogen-(C1-C4)-alkyl group with exception for perhalogenalkyl group when A represents (A-1) and n = 0, and that n doesn't equal 0 when A represents (A-4). Also, invention describes derivative of pyrazole of the formula (2): wherein A means: (A-1) and Y means: (Y-1) , (Y-2) and (Y-3) wherein X, R2, R3 and R4 have values given above; R5 represents hydrogen atom; A represents (A-1); Y means any group among (Y-1) - (Y-3); Z represents halogen atom that are intermediate compounds used for synthesis of the compound (1). Invention describes methods for preparing compounds of the formula (1) and (2) and insecticide comprising compound of the formula (1) as an active component. Insecticide shows high systemic activity, high safety and reduced harmful effect on environment in vicinity areas of its applying.

EFFECT: improved methods for preparing, valuable insecticide properties of compound.

11 cl, 9 tbl, 19 ex

FIELD: organic chemistry, fungicides, agriculture.

SUBSTANCE: invention describes pyrazolcarboxamide of the formula (I) wherein if X means oxygen atom (O) then R1 represents (C1-C3)-alkoxy-(C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means fluorine (F), chlorine (Cl) or bromine atom (Br), and if X means sulfur atom (S) then R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means halogen atom. Also, invention describes a method for preparing compounds of the formula (I), a composition for control of microorganisms and prevention for their attack and damage of plants, and a method for control of phytopathogen organisms, and compound of the formula (V) wherein X means sulfur atom (S); R1 means (C1-C3)-alkyl; R2 means (C1-C3)-halogenalkyl; R3 means chlorine, bromide or iodine atom. Invention provides control and prevention in infection of plants with phytopathogenic microorganisms - fungi in agriculture and horticulture.

EFFECT: valuable agricultural properties of compounds.

9 cl, 4 tbl, 12 ex

FIELD: agriculture, in particular method for controlling of specific insect pests.

SUBSTANCE: invention relates to method for controlling of lepidopterous, homopterous, hemipterans, coleopterous, and physopods by contacting of said pests or environment thereof with effective amount of compound of formula I SSS1, N-oxide or agriculturally acceptable salt thereof being effective against abovementioned insects, wherein A and B are independently O or S; R1, R2 represent H, C1-C6-alkyl; R3 represents H, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or C3-C6-cycloalkyl; R4 represents H, C1-C6-alkyl, C2-C6-alkinyl, C1-C6-haloalkyl, CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, NO2;. R5 represents H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-hydroxyalkyl, CO2R11R12, halogen or C1-C4-alkoxy; R6 represents H, C1-C6-alkyl, C1-C6-haloalkyl; R7 represents H, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, phenyl ring, benzyl ring, or 5-6-membered heteroaromatic rind, naphthyl ring system, or 8-10-membered condensed heterodicyclic system. Also claimed are compound of formula I and benzoxazine derivative of formula 10 .

EFFECT: compounds effective against agriculture spineless depredators.

22 cl, 13 tbl, 1 dwg, 24 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes insecticide composition comprising the active amount of one pyridine compound of the formula (I)

or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

wherein X represents oxygen atom; R1 and R2 represent independently hydrogen atom, alkyl group comprising from 1 to 6 carbon atoms and substituted with cyan-group, and one insecticide taken among carbofuran, carbosulfan, cipermethrin, bifentrin, acetamiprid, chlorfauazuron, fluphenoxuron, piriproxiphen, spinosad, emamectine benzoate, avermectin, buprophezin and fipronil taken in the weight ratio of compound of the formula (I) and other insecticide = from 1:2 to 100:1. The composition provides stable and strong effect and eradicates insects.

EFFECT: strong insecticide effect of composition.

4 cl, 11 tbl, 5 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

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