Herbicide composition

 

(57) Abstract:

Usage: agriculture, chemical plant protection products. The inventive herbicide composition comprises a derivative of 1,2,4-triazolo-[1,5-c] pyrimidine-2-sulfonamida f-ly I, where X-C1-C2-Alexi: methyl, Y1-C2-alkoxy, hydrogen, methyl, trifluoromethyl, chlorine, bromine or fluorine, Z is methoxy, hydrogen, methyl, trifluoromethyl, chlorine, bromine or fluorine, And fluorine, chlorine, bromine, CO2(C1-C3)-alkyl, CON(CH3)2, CF3or NO2, Is hydrogen, fluorine, chlorine, bromine, methyl, methoxy, D is hydrogen or CH3provided that at least one of X and Y means och3or OC2H5the number of 6-12%. target Supplement the rest. Connection structure 1:

3 C.p. f-crystals, 3 tables.

The present invention relates to the use of new alkoxy-substituted 1,2,4 triazolo [1,5-C] pyrimidine-2-sulfonamidnuyu of herbicide compounds in compositions for the control of undesirable vegetation.

The controlling undesirable vegetation by chemical means, i.e., herbicides, is an important aspect of modern agriculture and farming. Although there are currently many is to be placed, with higher General or specific to certain plant species activity, are less toxic to cultivated crops are safe for humans and the environment, less expensive to use or possess other valuable benefits.

It is known that some 1,2,4-triazolo [1,5-a] pyrimidine-2-sulfonamides possess herbicide activity (European patent application 0142152, published may 22, 1985). These compounds are effective when used against weeds in the pockets of their distribution by pre-emergence or post-harvest processing.

The known N-(2,6-differenl)-5,7-dimethyl-1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide with herbicide activity.

It was found that alkoxy-substituted-1,2,4-triazolo[1,5-C] pyrimidine-2-sulfonamides of the formula 1

< / BR>
where X OCH3OS2H5or CH3;

THE CO3OC2H5N, CH3, C1, Br, F, or CF3;

Z CO3N, CH3, CF3, CL, Br or F;

And F, C1, Br CO2(C1-C3-alkyl), SOP (CH3)2CF or NO2;

In H, F, C1, Br, CH3or och3;

D N or CH3;

J and V each is B> have activity against unwanted vegetation and can be used in the fight against undesirable vegetation in the presence of forage crops and soybean crops. The compounds of formula I, used usually in the form of herbicide compositions containing the above compounds in combination with agronomically acceptable adjuvant or carrier, are herbicide properties when applied directly to the lesions spread of undesirable vegetation or by pre-emergence or post-harvest processing.

The compounds of formula I include alkoxy-substituted 1,2 4 triazolo-[1,5 - C] pyrimidine-2-sulfonamides, where a, b, D, J, V, X, Y and Z are defined above. Each of these compounds contains at least one alkoxy-substituents on the pyrimidine ring and the electron has a substituent in one or two 2 - and 6-positions of aniline rings.

Although each of 1,2,4-triazolo [1,5-C] pyrimidin-sulfonamidnuyu compounds described by formula I, is included in the scope of the present invention, the degree of their herbicide activity and a range of weeds against which these compounds can be applied varies depending on present deputies and sledovat is inane formula I, in which at least one of X and Y is methoxy or sort. The compounds of formula I in which X is methoxy or sort of particularly preferred. Also can sometimes be preferred compounds in which both X and Y are methoxy or ethoxy. In addition, compounds in which Y and/or Z are hydrogen, chlorine, bromine, or florigraphy may sometimes be preferred. The compounds of formula I having at least one electron-withdrawing Deputy selected from the substituents listed for a and b (see above) in the ortho-position of the aniline ring, also included in the scope of the present invention. Compounds in which a is fluorine, chlorine, bromine, nitro, CO2WITH1-C3-alkyl, SOP (CH3)2or trifloromethyl are usually preferred.

The compounds of formula I, where V is hydrogen, can generally be obtained by a reaction between 1,2,4 triazolo [1,5-C] pyrimidine - 2 - sulfanilamide formula II with the correspondingly substituted N - trialkylsilyl formula III in the presence of pyridine amine compounds, tertiary bus or dimethylsulfoxide catalyst. Excess amine can be used to interact with halogenated such as they were defined above for formula I. substituent R1formula III is a1WITH4the alkyl or benzyl, and preferably the stands.

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The process of obtaining, usually carried out by placing 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfanilamide formula II, N-trialkylsilyl formula III, catalyst and any solvent used in a vessel and heat for the reaction. After the formation of significant amounts of compounds of formula I or after using up a significant amount of sulfanilamide formula II, the reaction mixture is cooled and subjected to contact with an aqueous reagent, i.e., water or a solution containing water in combination with other components such as solvents, acids or bases, which do not cause decomposition of the compounds of formula I. by-products of amine halogen salt formed by using as catalysts amine bases, sometimes precipitate and can be removed by filtration before adding reagent water. In other cases, the solvents and other volatile components are removed by evaporation under reduced pressure, and the by-products from the data thus can be purified by standard methods such as liquid chromatography, chromatography on paper, solvent extraction, and crystallization from solvents.

Typically use approximately equimolar amounts of the compounds of formulas II and III, although it may be used or excess of one or other connection. It is often better to use an excessive amount trialkylsilanes.

Most tertiary amine bases, such as trialkylamine meridiachlamydia, and pyridine bases, such as pyridine, pikolines and lutidine are valuable catalysts for the reaction. Preferred is pyridine. Amine bases can be used in approximately equimolar amounts of compounds of the formula II or in excess. Sometimes it is preferable to use them in considerable excess. The most preferred catalyst is dimethyl sulfoxide, however, as a rule, it is used in amount less equimolar amount. Quantities of more than about 0.5 molar equivalent, have a deleterious effect on the reaction. Optionally, there may be used a solvent which is not soluble reaction. Suitable solvents are acetonitrile, dimethylformamide, toluene, etc., the Preferred solvent is acetonitrile.

For the implementation of the reaction the reaction mixture is heated at a sufficiently high temperature and for a sufficient period of time. Usually, the temperature is from 10 to 150oC. are Preferred room temperature and the temperature from 30 to 100oC. the Period of time, usually up to 72 hours, and preferably from 12 to 48 hours. In addition, the above reaction is preferably carried out with stirring in a vessel equipped with appropriate devices for removing moisture from the system.

Often, it is convenient to obtain the desired N-trialkylsilyl formula III from the appropriate aniline and trialkylsilanes and that their product is directly used in the reaction. Usually, to a suspension of sodium iodide in acetonitrile add excess trialkylsilanes corresponding aniline and triethylamine, and after stirring for several hours to add a simple ether. The mixture is then filtered, and volatile components are removed by evaporation under reduced pressure, leaving in OCTA is tion can be obtained in a simple way by using the reaction between sulfanilamide formula II with the correspondingly substituted aniline in pyridine solution at a moderate temperature. However, the yield in this reaction is often unsatisfactory.

The compounds of formula I, where X and/or Y are OCH3OC2H5can be obtained from the corresponding compounds of formula I, where X and/or Y are CL, by treatment with an appropriate nucleophilic reagent, such as sodium methoxide in methanol. Reaction conditions are generally the same as those performed when the exchange reactions of 2 - and 4-chloropyrimidine. It is preferable to conduct the reaction in an anhydrous environment. Selective substitution of chlorine in the X-position can be easily achieved, because the chlorine is much more reactive than chlorine in the Y - position.

1,2,4-triazolo [1,5-C] pyrimidine-2-sulfanilamide formula II can be obtained by treating compounds of formula IV where R is hydrogen, benzyl, or C2-C4the alkyl and X, Y and Z are as defined above for formula I, except that X may be chlorine water chloroform or aqueous acetic acid. This technique is well known in the art and have been applied to certain compounds related to the compounds of formula II, but with different substituents (see, for example, patent UK N as intermediates in obtaining the compounds of formula II, are well known in the art, as are methods for their preparation. For example, it is known that many 4 - hydrazinopyridazine, optionally substituted in 2-, 5 - and 6-positions, interact with carbon disulfide and an alkali metal hydroxide in an alcohol solvent to form compounds of formula IV, where R" is hydrogen. The methodology described in Australian Journal of Chemistry 32, 2713 2726 (1979) and in other works. Instead of the alkali metal alkoxide is often used trialkylamine. This reaction involves an unusual rearrangement, and position of substituents in the resulting compound of formula IV can be predicted by comparing the substituents of formula V with substituents the same letter symbols in the formula IV.

< / BR>
The compounds of formula IV, where R" is benzyl or C2-C4-alkyl, can be obtained from the corresponding compounds where R" is hydrogen by alkylation with a suitable alkylating agent, such as benzylchloride, ethylbromide, propylaminosulfonyl, etc. This reaction is usually carried out under standard conditions, usually used in the alkylation of mercaptans. Mostly used base such as alkoxide of an alkali metal or tertiary and is obtained by the method described above without highlighting.

4 Hydrazinopyridazine having alkoxy-substituent in 2-position, however, does not provide a 5-alkoxy substituted compounds of formula IV (X is alkoxy) in the way specified above; instead, the formation of 5-hydroxy-compounds. For the 5-alkoxy-compounds of formula IV can be converted to 5-hydroxy-link 5-chloro-compounds by treatment with phosphoric chloroacetyl, then get the 5-alkoxy-compounds by processing the obtained 5-loratadinee a sodium alkoxide in the same spirit.

If trialkylamine, such as triethylamine, to use as a base in the reaction of compounds of formula V with carbon disulphide and benzylchloride, unusual rearrangement described above, occurs more slowly and, as a rule, you can select neperekodirovano 1,2,4-triazolo a 4.3 with a pyrimidine compound of the formula VI as product.

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Often get a mixture of compounds of formula IV and formula VI. The compounds of formula VI can be converted into compounds of formula IV by treatment with alkali metal alkoxide. Usually the reaction is carried out in an alcohol solvent, and the mixture is typically heated. The compounds of formula IV and VI can be distinguished by their UV spectra in the range of 200 to 280, sformula VI also have a relatively short retention time in reversed phase liquid chromatography with high blood pressure.

It is also possible, and in some cases preferable, to obtain the compounds of formula IV, where X is OCH3OC2H5and R" is a valid group other than hydrogen, by first obtaining the compounds of formula IV or formula VI, where X is a C1-C4-alkylthio and preferably methylthio, from compounds of formula V where X is a C1-C4-alkylthio, and then sharing alkylthio to OR is part of, and in the case of compounds of formula VI, rearrangement of the heterocycle. The desired reaction can be carried out by treating the compounds of formula IV and VI, where X is a C1-C4-alkylthio, alkoxide with1-C3alkali metal in a medium containing the corresponding alcohol, in the presence of a carbonyl or CYANOGEN-substituted vinyl compounds which is reactive with respect to C1-C4-alcantera. The last of these reagents, which can be one of these compounds, as diallylmalonate, and methyl vinyl ketone are acronitrile, present as pobocha product to interact with the received Alcantara, and then removed from the solution.

This creates conditions conducive to carrying out the desired reaction. Source is siteline, in equimolar amounts. On the other hand, the alkoxide of an alkali metal, generally used in catalytic amounts in the range from 5 to 30 M from the starting compounds of formula IV and VI. Preferably, if the reaction proceeds at temperatures from 0oC to the boiling point of the alcohol solvent and in the period of time from 10 minutes to 4 hours. The target product of the formula IV, where X is OCH3OC2H5can be isolated by neutralizing the acid catalyst, such as acetic acid, followed by removing the solvent and any volatile substances by evaporation or by addition of water and collection of nerastvorimogo substances. Further purification can be carried out by standard methods, such as dissolving in methylene chloride or other water-immiscible solvent, extraction with water and removing the solvent by evaporation. The final products are solids, which are often paracrystalline from solvents such as hexane and ethanol.

The compounds of formula IV, where R" is benzyl or2-C4-alkyl, X is OCH2OS2H5and and are independently OCH3OS2H5

N - trialkylsilyl formula III are known compounds.

Substituted 6-(or 4-) hydrazine-pyrimidine used as starting compounds or suitable methods of obtaining these compounds and the necessary raw materials for these methods are known in the art. Basically, hydrazinopyridazine obtained by a reaction between 6-(or 4-) halogenopyrimidines with an excess of hydrazine or approximately equimolar amounts of hydrazine and a base such as potassium carbonate or sodium bicarbonate. The reaction is similar to a related reaction, amination, which is well known in the art. These methods are systematized in the monograph "the Pyrimidines" The Cyrimidines, D. J. Brown from the series the Chemistry of heterocyclic compounds, The Chemistry of Heferocyclic Compounds published Wessberger emd Taylor.

1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamides of the formula I can be used directly as herbicides, however, it is preferable to use them in mixtures containing herbicide effective amount of the compounds in combination, at least one agronomically pickup is livepim cultures substances, especially, in the concentrations used in the preparation of compositions intended for use in a selective effect on the weeds in the presence of crops; these adjuvants or carriers should not enter into chemical reaction with compounds of the formula I or other ingredients of the composition. These mixtures can be designed to be applied directly to the weeds or to the centers of their distribution, or may be concentrates or preparations that before use, usually diluted with additional media or adjuvantly. They can be solids, such as powders, granules, dispersible in water, granules, or wettable powders or liquid substances, such as emulsion concentrates, solutions, emulsions or suspensions.

Appropriate agronomically acceptable adjuvants and carriers, which are typically used in the manufacture of herbicide mixtures, well-known to experts.

As liquid carriers can be used water, toluene, xylene, naphtha, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, manometers, ethylene glycol, propylene glycol, glycerin, etc., For diluting concentrates mainly use water.

Suitable solid carriers can serve as talc, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, mullerova earth, husk, cotton seeds, wheat flour, soybean flour, pumice, wood flour, flour from the husk of the nut, lignin, etc.

In the composition of the present invention, it is often preferable to enter one or more surfactants. Such surfactants are preferably used in solid and liquid compositions, particularly those which are intended for dilution with a carrier before use. Surfactants can be anionic, cationogenic or nonionic in their properties and can be used as emulsifying agents, wetting agents, suspendida agents, or for other purposes. Typical surfactants are salts of alkyl sulphates, such as lauryl of gitanemane; alkylarylsulfonate salt, such as dodecylbenzenesulfonate calcium; alcalde additive products such as, tridecylalcohol C16-ethoxylate; Soaps, such as sodium stearate alkyldiethanolamine salts such as dibutylaminoethanol sodium; salt dialkylamino esters of succinic acid, such as di (2-ethylhexyl) sulfosuccinate sodium; sorbitol esters, such as sorbifolia; Quaternary amines, such as lauryldimethylamine; esters of polyethylene glycol fatty acids, such as polietilenglikolmonostearat; block copolymers of ethylene oxide and of propylene oxide; and salts of mono - and dialkylated esters of phosphoric acid.

Examples of other adjuvants normally used in pronomina compositions can serve protivovspenivayushchie substances; substances that improve compatibility; substances that contribute to isolation; neutralizing agents and buffers; inhibitory corrosion; colorants; fragrances; auxiliary additives that improve infiltration; substances that increase the wetting ability; binding agents; dispersing agents; thickeners; substances, lowering the freezing point; antimicrobial agents; etc. Compositions of the present invention can also contain other compatible componet in compositions together with solid or liquid fertilizers, the particulate fillers fertilizers, such as ammonium nitrate, urea, etc.

The concentration of the active ingredients of the formula I, members of the herbicide compositions, mostly ranges from 0.001 to 98 mass. Commonly used concentrations from 0.01 to 90 wt. In compositions intended for use as concentrates, the active ingredient is present in an amount of 5 to 98 mass. and preferably from 10 to 90 mass. These compositions before use, usually diluted with an inert medium such as water. The diluted composition intended for direct processing of weeds or foci of their distribution, mainly the weeds or foci of their distribution, mainly contain 0.001 to 5 mass. the active ingredient, and preferably 0.01 to 0.5 wt.

The compounds of formula I are valuable predchodcami and post-harvest herbicides. Some of the compounds of formula I possess valuable properties as selective herbicides against broad-leaved weeds and against sociopathic weeds in cereals, such as corn, wheat, barley and rice, and especially as selective herbicides against broad-leaved weeds, praise is s, growing in soybean. Examples of such broadleaf weeds can serve various types of breast barbed, purple Finch, cocklebur, dope ordinary, canetic Theophrastus, quinoa, white, and black nightshade. These compounds can also be used against grassy weeds as weed and Alopecurus. However, as is known to any specialist, not all compounds can be applied against all these weeds and not all of them are selective for all of these cultivated crops.

The term "herbicide", as used in this description means an active ingredient that suppresses, or has an adverse effect on plant growth. Herbicide effective or overwhelming vegetation quantity is the amount of active ingredient that causes adverse effects on the natural growth of plants, including its destruction, dehydration, slow growth, etc., the Terms "plant" and "vegetation" means germinated seeds, seedlings and rooted plant.

Compounds of the present invention exhibit herbicide activity when applied directly to the plant or to the center of its distribution in Svedeniya and size of the sprayed droplets, the particle size of the solid components, the environmental conditions during the application of the compounds, particularly compounds used, the type used adjuvants and carriers, soil type, etc., as well as the number of used chemicals. The above and other factors, can be tailored by experts to stimulate selective herbicide action. For maximum effect when applied to broadleaf weeds, mainly, it is preferable to use compounds of the present invention in the post-harvest period to relatively immature plants. It is preferable to use these compounds in conditions where broadleaf weeds are destroyed in the presence of wheat culture.

Applied doses in post-harvest processing mainly consists of 0.001 to 10 kg/ha, and when predsjedava processing these doses are primarily 0.01 to 10 kg/ha.

Below are examples illustrating various embodiments of the present invention.

EXAMPLES

NMR spectra and IR spectra of the compounds obtained showed that the structures of these compounds prospective structures of these compounds Conn, nc. equipped with a C-18 column ( BondlapacTN) with elution with a mixture of water and acetonitrile (60:40) containing 0.5 acetic acid. The content was monitored by UV detector at 254 n.a. Gas chromatography (GC) was performed using a chromatograph 5830 (Hewlett PackardTH) equipped with a conductivity detector and a glass column filled with 5 DC 410 on Gaschrem Q diameter 175 250 μm. The melting point was determined using capillary devices for determining the melting point Themas Hoover.

EXAMPLE 1

Obtaining 4,5-sodium dichloro-6-methoxy-2-methylpyrimidine

The solution containing 38 g (0.17 M) of 2-methyl-4,5,6 of trichloropyridine in 200 ml of methanol was cooled in an ice bath to 10 15oC and slowly added sodium methoxide in the form of a 25 solution in methanol, while stirring, until then, until the original pyrimidine no longer be detected by GC. Then added water and the resulting mixture was extracted with methylene chloride. After removal from the extract solvent and other volatiles by evaporation under reduced pressure was obtained target compound as a white powder with a melting point 77 78oC.

EXAMPLE 2

Getting 4,6-sodium dichloro-2-methylthiopyrimidine

Suspen is heated to remove moisture. When the temperature reached 200oC, the mixture was cooled to approximately 85oWith and added 24.5 g (0,126 M) 4,6-sodium dichloro-2 - methylthiopyrimidine, while stirring. Then the mixture was heated while stirring at a temperature of approximately 144oC and a reduced pressure of about 150 mm RT. Art. slowly removing the solvent and the target connection by paragoni. This procedure is continued as long as the bulb was left with a very small amount of liquid. The distillate and residue were combined and diluted with ether and the resulting mixture was extracted with water several times. The remaining ether solution was dried with magnesium sulfate and concentrated under reduced pressure to obtain a residue. After boiling distillation fraction at approximately 127oC and at a pressure of 150 mm RT.article collected and received by the target compound (16.1 g) in the form of white crystals with a melting point of 31 of the 32oC.

EXAMPLE 3

Getting 4,6-dibromo-2-methylthiopyrimidine

A mixture of 20.0 g (0,126 M) 4,6 dihydroxy - methylthiopyrimidine, 150 g (0,523 M) oxybromide phosphorus and 600 g of acetonitrile was heated in a flask under reflux for 3 hours. Solids, which initially tended to rest the reduced pressure, and the residue was diluted with methylene chloride, and then gently water. Bodony layer was removed, and the organic layer was extracted several times with water, dried with magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in hexane and the resulting solution was dried with magnesium sulfate and concentrated under reduced pressure, resulting in received and 26.8 g of target compound in the form of a white powder with a melting point 82 84oC.

EXAMPLE 4

Getting 5-chloro-4-methoxy-2-methyl-6-hydrazinopyridazine

Received a mixture containing 21 g of 4,5-sodium dichloro-6-methoxy-2-methylpyrimidine (0,11 M), 25 ml of hydrazine hydrate is added and 25 ml of water, and heated it in a flask under reflux for 25 minutes Then the mixture was cooled and was extracted with methylene chloride. The extract was washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The solid residue was extracted with hexane, and dried, resulting in a received 12.8 g (theoretically 62) of target compound in the form of pantoprazole solid white color with a melting point 158 159oC.

The following compounds were obtained in a similar way using the methods described above and when the powder is not completely white with a melting point 153-154oWITH

4-methyl-2-methylthio-6-hydrazinopyridazine, in the form of a white powder with a melting point of 136 137oWITH

5-chloro-2-methylthio-4-hydrazinopyridazine, in the form of a white with a melting point 154 155oAnd

2-methylthio-4-hydrazinopyridazine, in the form of a powder, yellowish-brown with a melting point 138-139oC.

EXAMPLE 5

Getting 4-Fluorescent-2-methylthio-6-hydrazinopyridazine

A solution of 15.8 g (0,097 M) 4,6-Diptera-2-methylthiopyrimidine in 50 ml of ethanol was slowly added, with stirring, to a solution of 11.6 ml (12.0 g, 0,214 M) hydrazinoacetate in 100 ml of ethanol, keeping the temperature below 0oWith by external cooling. The reaction mixture was subjected to interaction with another 30 minutes, and then volatiles were removed by evaporation under reduced pressure. The residue was diluted with ethyl acetate and the resulting solution was extracted with water, dried with magnesium sulfate and concentrated under reduced pressure, resulting in a received 16.0 g of target compound in the form of a white powder with a melting point 153 154oC.

Elemental analysis for C5H7FN4S

Calculated: C, 34,5 N, OF 4.05; N, 32,2

Found: C, 34,5 N, OF 3.94; N, 32,2

EXAMPLE 6

Getting 4 - chloro-2-metalina, of 29.5 g (0.21 M) of potassium carbonate, 80 l of hydrazinoacetate and 80 ml of water, was heated in a flask with reflux condenser, stirring, for 30 min, because during this time, as was demonstrated by the analysis by HPLC, the reaction was completed. Then the mixture was cooled and was extracted with methylene chloride. The extract was dried with magnesium sulfate and concentrated under reduced pressure. Then the residue was mixed with hexane and the solids were removed by filtration, and dried, resulting in received of 34.7 g of target compound in the form of a solid yellow-brown color with a melting point 118 119oC.

EXAMPLE 7

Getting 2-benzylthio-8-chloro-7-methoxy-5-methyl,2,4-triazolo [1,5-C] pyrimidine

5-chloro-4-methoxy-2-methyl-6-hydrazinopyridazine (11.3 g, to 0.060 M) of 13.7 g (0.18 M) of carbon disulfide, 15.6 g (0,072 M) of sodium methoxide in the form of a 25 solution of methanol and 250 ml of ethanol were combined, stirred for 1 hour at room temperature and then was heated in a flask under reflux for 2 hours, because during this time, as was demonstrated by the analysis of HPLC, the reaction was completed. Then add benzylchloride (9,1 g 0,072 M), while continuing to heat under reflux and stirred. Solids immediately separated. ZZ do not show the reaction benzylidene ended. Then the mixture was cooled and added 10 ml of acetic acid. The resulting mixture was diluted with water to about 1 l and were extracted with methylene chloride. The extract was washed with water, dried with magnesium sulfate and concentrated under reduced pressure. The residue from evaporation triturated with hexane, filtered and dried. Then it was recrystallized from methanol and received 16.3 g (85 theoretically) of target compound in the form of not-quite-white powder with a melting point 115-116oC.

Elemental analysis for C14H13ClN4OS

Calculated: C, a 52.4; H, 4,08; n, 17,47

Found: C, 52,3; H, Android 4.04; n, 17,14

EXAMPLE 8

Obtaining 3-benzylthio-7-fluorescent-5-methylthio-1,2,4-triazolo [4,3-C] pyrimidine

4-Fluorescent-2-methylthio-6-hydrazinopyridazine (15.0 g, 0,086 M) of 15.5 ml (19.7 g, 0,258 M) of carbon disulfide, 48 ml (34.8 g, 0,344 M) of triethylamine and 400 ml of ethanol were combined, stirring, and after 15 minutes was heated in a flask with reflux condenser, while stirring, for 2.5 hours. The resulting mixture was cooled to room temperature, stirring, was added 16.4 g (0,129 M) benzylchloride, and then subjected to reaction for 3 hours. Volatiles were removed by evaporation when the Wali magnesium sulfate and concentrated under reduced pressure. The residue was pereirae with hexane and filtered, resulting in received of 20.9 g of target compound in the form of a yellow-orange powder with a melting point of 74 - 77oC. was also Attended by a small number of 2-benzyl-tis-7-fluorescent-5-methylthio - 1,2,4-triazolo [1,5-C] pyrimidine. Amri UV spectra showed compliance with the proposed structure and the presence of impurities.

The following compounds were obtained in a similar way, and the resulting products had NMR and UV spectra, the corresponding spectra of the assumed structures:

3 Benzylthio-7-chlorine-5-methylthio-1,2,4 triazolo [4,3-C] pyrimidine in the form of powder light yellow color with a melting point 131 132oC.

3 benzylthio-7-methyl-5-methylthio-1,2,4 triazolo [4,3-C] pyrimidine in the form of light yellow powder with a melting point of 138 139oWITH

3 benzylthio-7-bromo-5 - methylthio-1,2,4 triazolo [4,3-C] pyrimidine in the form of yellowish-brown powder with a melting point of 125 127oC

3 benzylthio-5-methylthio-1,2,4 - triazolo [4,3-C] pyrimidine in the form of powder is not completely white with a melting point 108 109oC; and

3 benzylthio - 8-chlorine-5-methylthio - 1,2,4 triazolo [4,3-C] pyrimidine in the form of a viscous oil red, containing znachitelnyy-7-fluorescent-5-methoxy-1,2,4-triazolo [1,5-c] pyrimidine

25 solution of sodium methoxide in methanol (1.9 ml, 0,0085 M) was added to a solution of 19.9 g (0,065 M) 3 benzylthio - 7 fluorescent-5-methylthio-1,2,4-triazolo [4,3 - C] pyrimidine containing a small amount of 2-benzylthio 7-fluoro - 5-methylthio-1,2,4-triazolo [1,5-C] pyrimidine and 11.2 g (0,065 M) of diethylmaleate in 250 ml of ethanol, with stirring, at room temperature, and then the reaction mixture was left to react for approximately one hour. Then was added acetic acid (4 ml) and the volatiles were removed by evaporation under reduced pressure. The residue was dissolved in methylene chloride and the resulting solution was extracted with water, dried with magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was pereirae with hexane, filtered and dried, resulting in a received 10.7 g of target compound in the form of a white powder with a melting point of 121 122oC. the NMR and UV spectra of the compounds showed compliance with the proposed structure.

Privedennye following compounds were obtained in a similar way and had NMR and UV spectra, the corresponding spectra of the assumed structures:

2 benzylthio-7-chlorine-5-methoxy-1,2,4-triazolo [1,5-C] pyrimidine, the powder is not completely white with temperature pirimidine, white powder with a melting point of 85 86oWITH

2 benzylthio-7-methyl-5-methoxy-1,2,4-triazolo [1,5-C] pyrimidine, white powder with a melting point 93 94oWITH

2 benzylthio-7-methyl-5-ethoxy-1,2,4 triazolo [1,5 - c] pyrimidine, white powder with a melting point of 77 78oC;

2 benzylthio-5-methoxy-1,2,4-tritolo[1,5] pyrimidine, powder light yellow-brown color with a melting point 96 97oWITH

2 benzylthio-8-chloro-5-methoxy-1,2,4-triazolo [1,5-C] pyrimidine, powder pale yellow color with a melting point 109 110oC

2 benzylthio - 7-chloro-5,8-dimethoxy-1,2,4 - triazolo [1,5-C] pyrimidine, powder light yellow-brown color with a melting point 94 95oC.

EXAMPLE 10

Getting 5-chloro-7-methoxy-2-benzylthio-1,2,4-triazolo [1,5] pyrimidine

2,4-dimethoxy-6-hydrazinopyridazine (48,4 g (0,28 M), to 121.6 g (1.6 M) of carbon disulfide, 145, 2mm g (1,44 M) of triethylamine, and 2 l of ethanol was combined stirring and after 30 min was heated in a flask under reflux for 2 hours. Then add benzylchloride of 40.4 g (0,32 M) and continued to reflux for another 1 hour. The mixture is then concentrated under reduced pressure, and the residue was combined with 800 ml of acetonitrile and 250 ml of phosphorus oxychloride. The mixture was heated with reverse Healy in a mixture of ice and methylene chloride. The organic phase was separated, filtered through silica gel and concentrated under reduced pressure. The residue was extracted with hot hexane and then hexane was removed by evaporation. The specified fraction was purified using preparative WISH and got about 5 g of the target compound. Substances, any insoluble in hexane was dissolved in hot carbon tetrachloride. As a result of filtration and evaporation of carbon tetrachloride was obtained oily substance, which hardens, if it add a small amount of acetone. It was combined with the pre-selected product was extracted with hot hexane. The residue was dried and got to 31.2 g (theoretically 36) of target compound in powder form blignault 95 color purity. The sample, which was then purified using HPLC melted at 140 141oC.

Elemental analysis for C13H11ClN4OS

Calculated: 50,89; N 3,61 N 18,26

Found: From 50,00; N 3,62; N 18,44.

The compound 8-bromo-5-chloro-7-methoxy-2 - benzylthio - 1,2,4-triazolo [1,5 - C] pyrimidine was obtained in a similar way; elemental analysis showed satisfactory results, its melting point is 124 125oC.

EXAMPLE 11oC. Then the mixture was stirred for another 30 minutes, after which the water layer was removed, and the organic layer was dried with sodium sulfate and concentrated under reduced pressure. The residue is triturated with hexane and obtained a solid product, which was isolated by filtration and dried, resulting in a received 1.6 g (theoretically 90) of target compound in the form of a white powder with a melting point of 100 101oC.

The following compounds were obtained in a similar way and had NMR and UV spectra corresponding to structures:

8-chloro-2-chlorosulfonyl-5-methoxy-1,2,4 triazolo [1,5-c] pyrimidine, white powder with a melting point of 122-124oWITH

2-chlorosulfonyl-7-fluorescent-5-methoxy-1,2,4 triazolo [1,5 - C] pyrimidine, white powder with a melting point of 106 107oWITH

7-chloro-2-chlorosulfonyl-5,8-dimethoxy 1,2,4-triazolo [1,5-C] pyrimidine, powder pale yellow color with a melting point 132 133oWITH

2-chlorosulfonyl-5-methoxy-1,2,4-triazolo[1,5 - C] pyrimidine, white powder with a melting point of 128 129oWITH<36 137oWITH

7-chloro-2-chlorosulfonyl-5-ethoxy-1,2,4 triazolo [1,5-C] pyrimidine, white powder with a melting point of 99 101oWITH

2-chlorosulfonyl-5-methoxy-7-methyl-1,2,4 triazolo [1,5 - C] pyrimidine, white powder; and

2-chlorosulfonyl - 5-ethoxy-7-methyl-1,2,4 triazolo [1,5-C] pyrimidine, white powder with a melting point of 104 to 106oC.

EXAMPLE 12

Getting 5-chloro-7-methoxy-2-chlorosulfonyl-1,2.4 - triazolo [1,5-C] pyrimidine

5-Chloro-7-methoxy-2-benzylthio-1,2,4 - triazolo [1,5-C] pyrimidine (10.0 g, 0,033 M), 200 ml of chloroform and 200 ml of water were combined and cooled in an ice bath. Then stirring was slowly added chlorine gas (10.2 g, 0,143 M) while maintaining the temperature below approximately 3oWith, and continued to stir for another 30 minutes. Then the organic phase was separated, dried with magnesium sulfate and concentrated under reduced pressure, resulting in received of 9.1 g (theoretically 97) of target compound in the form of a semi-solid substance is yellow. A small portion was purified by trituration with ether and was obtained a white powder with a melting point of 79 80oC.

Prividence following compound was obtained in a similar way

8-bromo-5-chloro-7-methoxy-2-chlorosulfonyl 1,2,4-triazolo [1,5- ,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamida

Anhydrous, iodide sodium (11,7 g 0,078 M) were placed in 50 ml of dry acetonitrile, stirring, was added 8.5 g (0,078 M) trimethylsilylmethylamine. Then to the mixture was added 6.3 g (0,039 M) 2,6 dichloroaniline and 7.9 g (0,078 M) of triethylamine. The mixture was stirred at room temperature for 30 minutes, then volatiles were carefully removed by evaporation under reduced pressure, and the residue was diluted with ether and filtered. Analysis by gas chromatography showed that the solution contains-trimethyl-silyl-2,6 - dichloroaniline about 97 purity. Then repeated the procedure for the deposition of undissolved substances ether, then the ether was removed by evaporation under reduced pressure. The residue was mixed with 50 ml of dry acetonitrile, 3,9 g (0,013 M) 8-chloro-2-chlorosulfonyl-7-methoxy-5-methyl-1,2,4 triazolo [1,5-c] pyrimidine, and 0.2 ml of 0.003 M) of dimethyl sulfoxide and the mixture was stirred over night. The mixture is then concentrated under reduced pressure and the solid residue was dissolved in 400 ml methylene chloride and the resulting solution was extracted twice with water, dried with sodium sulfate and filtered. Then was concentrated under reduced pressure and the residue was mixed with hexane, collected by filtration and dried, resulting in h is 255 256oWith decomposition.

Elemental analysis for C17H10Cl3N5O3S

Calculated: 36,94; N. OF 2.38; N 16,57

Found: 36,98; N 2,41; N 16,30.

Connection privedennye in Table 1, were obtained in a similar way and had satisfactory elemental (SLEEP) analyses and NMR spectra corresponding to the desired structures.

In a similar way there were obtained the following compounds: N-(2,6-dichlorophenyl)-5 - chloro-7-methoxy 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide powder not quite white

N-(2,6-sodium dichloro-3-were)-5-chloro - 7-methoxy-1,2,4-triazolo [1,5-C] pyrimidine-2 sulfonamide: so pl. 204 205oC;

N-(2,6-dichlorophenyl)-8-bromo-5-chloro-7 - methoxy-1,2,4 - triazolo [1,5 a] pyrimidine-2-sulfonamide powder;

N-(2,6 - sodium dichloro-3-were)-8-bromo-5-chloro-7-methoxy-1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide: powder yellow-brown; and

N-(2,6-sodium dichloro-3-were)-8-chloro-7 methoxy-5-methyl-1,2,4-triazolo[1,5-c] pyrimidine-2-sulfonamide: so pl. 231 - 232oC.

EXAMPLE 14

Obtaining N-(2,6-dichlorophenyl)-5,7-dimethoxy-1,2,4 - triazolo [1,5-C] pyrimidine-2-sulfonamida. N- ( 2,6 dichlorophenyl ) 5 chlorine 7 methoxy 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide (0.8 g, 0.002 ml) was mixed with 25 ml of methanolate and the resulting mixture was concentrated under reduced pressure. The residue was dissolved in methylene chloride and the solution was extracted with water, dried with sodium sulfate and concentrated under reduced pressure. The residue was mixed with carbon tetrachloride, collected by filtration and dried, resulting in a received 0.5 g of target compound in powder form is not quite white melting point 211 212oC.

Elemental analysis for C13H11Cl2N5O4S

Calculated: 38,62; N IS 2.74; N 17,33

Found: 38,09; N 2,82; N 17,18.

Privedennye following compounds and compounds, privedennye in Table 1A were obtained in a similar way and has shown satisfactory results when the elemental analysis and NMR analysis

N-(2,6-sodium dichloro-3-were)- 5,7-dimethoxy 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide so pl. 212 213oC;

N-(2,6-dichlorophenyl)-8-bromo-5,7-dimethoxy 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide so pl. 212 213oWith decomp. and N-(2,6-sodium dichloro-3-were)-8-bromo - 5,7-dimethoxy-1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamide: so pl. 228 229oC ( decomp.).

EXAMPLE 15.

Assessment of post-harvest herbicide activity

The most typical compounds of formula I were evaluated for post-harvest herbicide activity against the measures of the standard equipment they were sprayed water composition, containing certain concentrations of the compounds of the present invention. The formulations for spray made by mixing the required amount of the active ingredient and an emulsifier or dispersant in aqueous acetone medium for the formation of the emulsion or dispersion. Control plants were sprayed in the same way and similar compounds, which have no active ingredient. Then the plants were kept in the greenhouse under conditions promoting plant growth. Two weeks after treatment, the growth of the plants was rated on a scale from 0 to 100, where a score of 0 means no effect, and score 100 complete destruction of the plants. In the specified test 100 PP is 0.25 kg/ha of Compound (numbers taken from Table. 1) and the tested plant species, the applied dose and the obtained test results are presented below in Table 2. In table. 2A comparative post-harvest herbicide activity of 1,2,4-triazolo 1,5-pyrimidine-2-sulfonamides.

EXAMPLE 16

Assessment predsjedava herbicide activity

The most typical compounds of formula I were evaluated on preschedule herbicide activity against different species of plants. With this purpose, seeds of plants vicarial compounds, in the form of an aqueous emulsion or suspension made by sesivany the required quantity of active ingredient in water acetone media containing 0.1 mass. surfactants. Control pots were watered the same mixture, which has no active ingredient. Then the pots were placed in a greenhouse under conditions conducive to germination and growth of plants. 2 weeks after treatment, the growth of the plants was rated on a scale from 0 to 100, where a score of 0 means no effect, and score 100 complete destruction of the plants. Connections (numbers taken from Table 1), the tested plant species, the applied dose and the obtained test results are presented below in Table 3.

EXAMPLE 17

Obtaining herbicide compositions

Prepare a mixture of weighted number of connections substituted triazolo [1,5-c] pyrimidine-2-sulfonamida and balanced quantities to obtain the necessary sootnoshenia of ingredients in the final product nonionic polyglycoside surfactant (Pluronic P-105TM), anionic suspending agent (Darvan No. 1TM), sodium aluminosilicate (Veegum TM), silicone protivovospalitel (Dow Corning antifoam ATM), ENT, until the average particle diameter is not less than 5 microns. Then prepared mixture kantauoi gum (KelzarTMand Orte-phenylphenolate stabilizer (DowicideTMand a certain amount of this mixture to obtain the proper ratio of ingredients in the final product, stirring, was added to the previously obtained mixture. After which the mixture was diluted with sufficient amount of water until the desired concentration sulfonamidnuyu connection. The result has been a fluid aqueous suspension of compounds substituted triazolo [1,5-C] pyrimidine-2-sulfonamida, slightly gray. Some of these compositions are presented in privedennoi following Table. 4 These fluid suspensions have the same herbicide activity, and that the suspension described in Examples 14 and 15.

Higher herbicide activity of the compounds of the present invention with respect to the compounds of the prototype can be demonstrated by comparing the most hanatamago compounds described in EP 0244948, namely: (N-2,6 defloriani-5,7-dimethyl-1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamida, with the closest to him, the compounds of the present invention, (N-2,6-defloriani (mono and di ) substituted 1,2,4-triazolo [1,5-c] pinnately post-harvest herbicide activity of 1,2,4-triazolo [1,5-C] pyrimidine-2-sulfonamides has demonstrated the superiority of the compounds of the present invention with respect to the compounds of the prototype. Each of the compounds of the present invention far exceeds any proven connection of the prototype. Similarly, the comparison is carried out for the compounds of the present invention having other substituents on the aniline ring, also showed excellent herbicide properties of these compounds. In addition, it should be noted that the data presented in Tables 1 and 1A, clearly demonstrate that all compounds of the present invention are significantly better herbicides than the best connection of the prototype. TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT TTT

1. Herbicide composition comprising an active ingredient derived 1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamida and target additives, characterized in that as a derivative of 1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamida it contains a compound of General formula

< / BR>
where

X is OCH3OC2H5or CH3Y means och3OC2H5H, CH3, CF3, Cl, Br or F;

Z means OCH3N, CH3, Cl, Br or F;

And means F, Cl, Br, CO2(C1-C3-alkyl), CON(CH3)2, CF3or NO2;

B denotes H, F, CL, Br, CH3the blending of X and Y means OCH3or OC2H5,

in the following ingredients in wt.

The active ingredient 6-12

The target additive and the Rest

2. Herbicide composition under item 1, characterized in that it contains 2% non-ionic surfactants based on polyglycol, 0.5% of an anionic dispersing agent, 0.3% aminosilicone sodium, 0,05-0,08% xanthan resin, 0.05 to 1% orthophenylphenol, 0.05 to 1% of the silicone antifoam and 4.5% propylene glycol.

3. Herbicide composition according to p. 3, characterized in that it optionally contains 2% citric acid.

4. Herbicide composition according to any one of paragraphs. 1-3, characterized in that as a derivative of 1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamida it contains N-(2,6-dichloro-3-were)-5,7-dimethoxy-1, 2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamide, N-(2-methoxycarbonyl-6-forfinal)-7-chloro-5-methoxy-1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamide, N-(2-methoxycarbonyl-6-chlorophenyl)-7-fluoro-5-ethoxy-1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamide, N-(2-chloro-6-forfinal)-5-ethoxy-7-ftor,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamide, N-(2,6-dichlorophenyl)- 7-fluoro-5-ethoxy-1,2,4-triazolo-(1,5-C)-pyrimidine-2-sulfonamide, N-(2,6-differenl)-8-fluoro-5-methoxy-1,2,4-triazolo-(1,5-C) pyrimidine-2-solarpanel)-8-fluoro-5-methoxy-1,2,4-triazolo-(1,5-C) pyrimidine-2-sulfonamide.

 

Same patents:

The invention relates to new 2-imidazolin-2-yl)thieno - foroperational compounds, to intermediates used to obtain these compounds, and the way of dealing with these compounds with unwanted annual and perennial plants, namely 6-(2-imidazolin-2-yl)thieno - and furo[2,3-b] and 5-(2-imidazolin-2-yl)thieno - and furo[3,2-b]the pyridine compounds and the corresponding 2,3-dihydrothieno and 2,3-dihydropyrimidine with structural formulas (Ia) and (Ib):

< / BR>
whererepresents a single or double bond; R1represents a C1-C4alkyl; R2represents a C1-C4alkyl or C3-C6cycloalkyl; R1and R2together with the carbon atom to which they are joined, can form WITH3-C6cycloalkyl, optionally substituted stands; And represents СООR3CHO, CH2OH, COCH2HE, CONHCH2CH2OH, CONHOH or

R3hydrogen, C1-C12alkyl, which can be broken od is alkoxy, halogen, hydroxyl, C3-C6cycloalkyl, benzyloxy, fullam, phenyl, furfuryl, galopera, lower alkylphenyl, lower alkoxyphenyl, nitrophenyl, carboxyla, lower alkoxycarbonyl, cyano, C1-C4alkylthio or three (lower) alkylammonium; C3-C6alkenyl, optionally substituted by one of the following groups:1-C3alkoxy, phenyl, halogen or two WITH1-C3alkoxygroup or two halogen groups; C3-C6cyclooctyl, optionally substituted by one or two1-C3alkyl groups; C3-C10quinil, optionally substituted by phenyl, halogen or CH2IT; or the cation of an alkali metal or alkaline-earth metal (CA, BA) manganese, copper, iron, ammonium, or organic ammonium; RWITHand RDrepresent N or CH3; Represents N; COR4or SO2R5provided that when a represents a COR4or SO2R5and is a СOOR3the radical R3cannot be hydrogen or a salt-forming cation; R4represents a C1-C11alkyl, chloromethyl or phenyl, optionally substituted A5 alkyl or phenyl, optionally substituted one metalno, chloro - or nitro-group; W represents 0 or S; X represents 0, S or whenis a single bond, the group S 0; Y and Y', Z and Z' represent hydrogen, halogen, C1-C6alkyl, C1-C4hydroxy (lower) alkyl, C1-C6alkoxy, C1-C6acyloxy, benzoyloxy, optionally substituted by one or two1-C4alkyl, C1-C4alkoxygroup or halogen; C1-C4alkylthio, phenoxy,1-C4haloalkyl,1-C4haloalkoxy, nitro, cyano, C1-C4alkylamino,1-C4dialkylamino,1-C4alkylsulfonyl or phenyl, optionally substituted by one or more1-C4the alkyl, C1-C4alkoxy, halogen, or any combination of these two groups, where Y and Z are the same provided that Y and Z represent hydrogen, halogen, alkyl or alkoxy, and when Y and Y' or Z and Z' are the same group they are hydrogen or alkyl; and taken together, Y and Z form a ring in which YZ has the structural formula -(CH2)n- where n являе/www.fips.ru/fullimg/rupat2/19962/004.dwl/2058313-8t.gif" ALIGN="ABSMIDDLE">-=where L, M, Q, and R7each represent hydrogen, halogen, nitro, C1-C4lower alkyl, C1-C4lower alkoxy, methoxy, phenyl, phenoxy, provided that only one of the radicals L, M, Q or R7may have a value different from hydrogen, halogen, C1-C4the alkyl or C1-C4alkoxy; or a pyridine-N-oxides, when W represents oxygen or sulfur and a is COOR3; and when R1and R2not the same, the optical isomers of these compounds, except for the case when R3represents a salt-forming cation, their salts kislotoustoichivam

The invention relates to a pesticide composition on the basis of new chemical compounds having pesticidal activity, and is used for pest control

The invention relates to new ways of combating nematodes

The invention relates to a new class of pesticides, which are 1,4-bis-substituted-2,6,7-dioxabicyclo(2.2.2)octane

The invention relates to new derivatives of benzo(b)naphthiridine General formula

R(I) where R1hydrogen, alkyl or hydroxyl radical;

R2hydrogen, linear or branched C1-C4-alkyl, foralkyl, cycloalkyl, alkyloxyalkyl or alkylamino radical;

R3WITH1-C4-alkyl, and R4and R5different and mean hydrogen or C1-C4-alkyl;

or R3hydrogen or alkyl, or cycloalkyl and R4and R5individually, each means hydrogen;

R6hydrogen or fluorine;

n is 1 or 2, or their salts, possess antibacterial property

The invention relates to the field of pest control, in particular fungicidal means on the basis pyrrol-carbonitrile and methods of combating fungi

The invention relates to the derivatives of uracil and their use in agriculture, namely use as herbicides

FIELD: agriculture.

SUBSTANCE: invention describes a method for feeding potato and tomato with 6-benzylaminopurine an aqueous solution taken in the concentration 10-4 M and growing pants up to preparing harvest according to technology accepted for the culture crop. Invention proposes 3-fold treatment of plants for vegetation: at the lateral branching phase, at onset of forming economically value organs and immediately after the growth termination. Method provides the effective enhancing the productivity of the most important vegetable crops - tomato and potato.

EFFECT: improved enhancing method.

6 tbl, 4 ex

FIELD: organic chemistry, chemical technology, herbicides.

SUBSTANCE: invention describes a method for preparing compounds of the formula (I):

wherein each R1, R2, R3 means independently of one another (C-C6)-alkyl; R can represent also pyridyl; R4 and R5 in common with nitrogen atoms to which they are joined form unsaturated 5-8-membered heterocyclic ring that can be broken by oxygen atom; G means hydrogen atom. Method involves interaction of compound of the formula (II):

wherein R1, R2 and R3 have above given values; R6 is a group RR9N-; R7 is a group R10R11N-; each among R8, R, R10 and R11 means independently of one another hydrogen atom or (C1-C6)-alkyl in inert organic solvent being optionally with the presence of a base with compound of the formula (IV) ,

(IVa)

or (IVb) ,

wherein R4 and R have above given values; H x Hal means hydrogen halide. The prepared compound of the formula (I) wherein G represents ammonium cation is converted to the corresponding compound of the formula (I) by treatment with Brensted's acid wherein G represents hydrogen atom. Also, invention describes compound of the formula (II) wherein R1, R2, R3, R6 and R7 have above indicated values.

EFFECT: improved preparing method.

9 cl, 12 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

EFFECT: improved method for control, valuable properties of composition.

6 cl, 26 tbl, 3 ex

FIELD: agriculture, plant science, plant protection.

SUBSTANCE: the suggested herbicidal composition of selective action contains, except generally accepted additional substances for the composition, a mixture as an active substance including a) herbicidally efficient quantity of compound of formula (I) , where R1 and R3 each independently means ethyl, ethynyl, C1- or C2alkoxy; R4 and R5 forms together the group Z2-CR14(R15)-CR16(R17)-O-CR18(R19)-CR20(R21)-(Z2); R14, R15, R16, R17, R18, R19, R20 and R21 means hydrogen; G means hydrogen, -C(X1)-R30, -C(X2)-X3-R31; X1, X2, X3 means oxygen; R30, R31 each independently means C1-C10alkyl, or salts or diastereoisomer of compound of formula (I), and b) efficient quantity of antidote of formula IIa to prevent harmful action of herbicide, where R22 means hydrogen, alkaline-earth metal or ethyl, or of formula IIb , where R23 means hydrogen, alkaline-earth metal or ethyl, and method for selective control for weed plants and grasses in cultivated plants. Thus, the antidote decreases the damage of cultivated plants induced by herbicide of formula (I).

EFFECT: higher efficiency of plant protection.

3 cl, 4 ex, 4 tbl

FIELD: organic chemistry, agriculture, herbicide composition.

SUBSTANCE: invention relates to herbicide composition, containing conventional inert additives and mixture of a) herbicidically effective amount of substance satisfying the formula I [in formula R1 and R3 are the same or different C1-C4-alkyl; R4 and R5 together form groups of formulae: -C-R6(R7)-O-C-R8(R9)-C-R10(R11)-C-R12(R13)-(Z1), -C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-(Z2), or -C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3), wherein each R6-R29 is hydrogen; G is hydrogen or -C(X2)-X3-R31; X2 and X3 independently are oxygen; R31 is C1-C10-alkyl]; b) herbicidic synergic amount of at least one herbicide selected from group containing sulfonylureas, phenoxyacetic acids, as well as florsulam, tralcoxidim, klodinafol-propargil, phenoxaprop-P-ethyl, trifluramine, pendimethaline, picolinafen, etc. Composition also may contain safety effective amount of protective agent, such as chloquintocet-mexyl and additive (e.g., mineral oil or C8-C22-fat acid alkyl esters) in amount of 0-2 mass %. Also disclosed is method for selective controlling of weeds and grassy plants in cultural plants by treatment of cultural plants, seeds or seedlings thereof, or vegetation area thereof with claimed composition.

EFFECT: effective composition and method for weed controlling.

5 cl, 11 tbl, 7 ex

FIELD: organic chemistry, veterinary science.

SUBSTANCE: invention relates to a method for control over exto- and endoparasites taken among group including acariform mites, parasitoformous mites and nematodes parasitizing in animals, productive cattle and domestic animals. Method involves applying veterinary preparation comprising 1-[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro)urea and compound of the formula (i):

wherein R1 means one of radicals:

or ; R2 means -CH(CH3)-CH3, -CH(CH3)-C2H5, -C(CH3)=CH-CH(CH3)2 or cyclohexyl; R3 means hydrogen atom or hydroxy-group if a bond between atoms 22 and 23 represents a double bond, or it means hydrogen atom or group =N-O-CH3 if an ordinary bond presents between atoms 22 and 23; R4 means HO-, and the preparation can be in free form or in physiologically acceptable form. Invention provides preparing preparations with good tolerance and rapid effect and persistence with respect to different helminth-associated diseases, parasitiformous and acariformous mites being without adverse effect on normal behavior of animals.

EFFECT: valuable properties of compounds.

7 cl, 3 tbl, 8 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal composition containing synergetically effective amounts of (A) and (B) components, wherein (A) has formula II (R1 is C1-C6-alkyl, substituted with halogen; R2, R3 and R4 are hydrogen; R5 is rest of formula -B1-Y1, wherein B1 is direct bond and Y1 is acyclic C1-C6-hydrocarbon or cyclic C3-C6-hydrocarbon; F is -CH2-CH2-, -CH2-CH2-CH2- and CH2-O-; X are independently halogen or C1-C4-alkoxy; n = 0-2; and (B) represents one or more herbicides, selected from group containing isoprothuron, flufenacet, anylophos, ethoxysulphuron, mecoprop-(P), ioxinyl, florazulam, pendimethalin, MV 100, etc. Also disclosed is method for weed controlling using abovementioned composition.

EFFECT: composition with improved herbicidal action.

12 cl, 23 ex, 23 tbl

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, herbicides, agriculture.

SUBSTANCE: invention describes a composition showing the selective effect and comprising as conventional inert adjuvants and the following mixture as an active component: a) effective amount of compound of the formula (I): as a herbicide wherein each R1 and R3 means independently of one another (C1-C4)-alkyl; R4 and R5 mean the group: -C-R14(R15)-C-R16(R17)-O-R18(R19)-C-R20(R21)-(Z2) wherein R14, R15, R16, R17, R18, R19, R20 and R21 mean hydrogen atom; G means hydrogen atom, -C(X1)-R30, alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation; X1 means oxygen atom; R30 means hydrogen atom, (C1-C10)-alkyl, and salts and diastereomers of compounds of the formula (I) under condition that R1 and R3 don't methyl group simultaneously; b) effective amount of protective agent (antidote) for prevention of hazard effect of herbicide wherein antidote is taken among the group comprising clochintocet, clochintocet with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation, clochintocet-mexil, mefenpir, mefenpir with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation and mefenpir-diethyl, and c) additive comprising (C8-C22)-saturated acids alkyl ester or emulsified vegetable oil, or mineral oil taken in the amount 0.01-2% as measured to the spraying mixture mass. Also, invention describes a method for selective control of weed and grassy plants in cultural plant plantings that involves using the abovementioned composition for treatment. Invention provides the selective effect in control of weed and grassy plants, in particular, in cereals crops plantings.

EFFECT: improved control method, valuable agricultural properties of composition.

3 cl, 8 tbl, 2 ex

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