N-[(1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide or their salts, are applicable in agriculture, herbicide tool and method of controlling undesirable plant growth

 

(57) Abstract:

Usage: N-[(1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide or their salts, are applicable in agriculture, herbicide tool and method of controlling undesirable plant growth. The essence of the invention: N-[(1,3,5-triazine-2-yl) aminocarbonyl] benzosulfimide General formula I indicated in the description, where R1is methyl or ethyl; R2- halogen, CF32 methoxyethoxy, C1-3alkylsulfonyl; R3is hydrogen, chlorine, fluorine, methyl or ethyl; with herbicide activity. Connection I get, for example, by reacting the corresponding sulfonylation derived from 2-amino 1,3,5-triazine. Herbicide agent, comprising the compound 1 in an effective amount. And method of controlling undesirable plant growth by processing plants or their habitats compound I or its salt in an effective amount, 3 S. and 2 C.p. f-crystals, 13 tables.

The present invention relates to new N-[(1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide General formula I

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where R1methyl or ethyl group; R2halogen, trifluoromethyl, 2-methoxyethoxy, C1-3alkylsulfonyl; R3hydrogen, chlorine, fluorine, metallinou controlling undesirable plant growth.

In the literature there are various N-[(1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide.

Thus, U.S. patent N 4120691, N 4127405 and the application for the European patent N 44807 describe sulfonylureas with herbicide action, the General formula which covers the proposed connection.

In U.S. patent N 4120691 described derivatives of A triazine and pyrimidine B, having the following structure:

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In the application for the European patent N 44807 described two sulfonylureas C alliancegroup in the ortho-position of the benzene ring of the General formula:

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R CH3C2H5.

In the application for the European patent N 44808 described two sulfonylureas D 2-chloroethoxy-substituent in the benzene ring of the General formula:

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Z is CH, n

In the application for the European patent N 48143 the two N-methylated sulfonylureas E General formula:

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Z is CH, N, without specifying characteristics.

In the application for the European patent N 388873 describes an ester of benzoic acid of General formula F:

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R CH3C2H5< / BR>
U.S. patent N 4127405 describes sulfonylurea derivatives with chlorine or trifluoromethyl-substituent in the ortho-position of the benzene ring, and lowsulfur (Glean).

However, none of the cited source does not describe in detail the proposed connection, different from the previously known for certain combinations of substituents and significantly improved herbicide action, which previously was impossible to predict.

In particular, the application for the European patent N 388873 describes the herbicide triazine derivatives, which differ from those proposed in the application triazines ester group in position 1 of the phenyl ring (see, respectively, R2).

The application for the European patent N 48143, the application for the European patent N 44807 and published application US N 4127405 describe herbicide derivatives sulfonamida that cover the proposed connection of their General formula. Proposed according to the invention the compounds of formula I with triptorelin the substituent in position 6 of the triazine ring differ in the selection of the substituents mentioned in these documents. In the above documents are not experimental or any other data for compounds of formula I.

The application for the European patent N 44808 considers the herbicide triazine different from the one proposed in the application connections substituents (X-A/m) (see respectively odlozenych in the application of the compounds, the heterocycle is a derivative of diazine instead of the triazine derivative.

In contrast to previously known compounds of formula I possess improved herbicide properties and exhibit high selectivity in such sensitive crops, such as rice or corn. In particular, they have a higher selectivity in comparison with the compounds of very similar structure, G and H, which differ from those proposed by the presence of CH3group in position 6 of the triazine ring.

Thus, this invention relates to compounds of formula I and their salts, applicable in agriculture.

Preferred N-[(1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide formula I, where R2means chlorine.

In the formula I C1-C3alkylsulfonyl designates methyl-, ethyl-, propyl - or isopropylacetanilide, halogen denotes fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine. Especially preferred are benzosulfimide, in which R2denotes chlorine.

Proposed invention sulfonylureas of the formula I get different ways, described in the literature. As an example, you should specify particularly preferred is known conditions (application for European patent N 162723) with approximately the stoichiometric quantity of a derivative of 2-amino-1,3,5-triazine III at a temperature of from 0 to 120oC, preferably from 10 to 100oC. the Reaction may be carried out at normal pressure or at pressures up to 50 bar), preferably at 1 to 5 bar, continuously or periodically.

It is advisable to apply for the reaction under appropriate conditions of inert solvents and thinners. As solvents can be used, for example, kalogeropoulou, in particular chlorinated hydrocarbons, such as tetrachloroethylene, 1,1,2,2 - or 1,1,1,2-tetrachlorethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, chloronaphthalene, dichloronaphthalene, carbon tetrachloride, 1,1,1 - or 1,1,2-trichloroethane, trichloroethylene, pentachloroethane, o-, m-, p-differental, 1,2-dichloroethane, 1,1-dichloroethane, 1,2-CIS-dichloroethylene, chlorobenzene, torbenson, Brabanthal, idental, o-, m-, p-dichlorobenzene, o-, p-, m-dibromobenzyl, o-, m-, p-chlorotoluene, 1,2,4-trichlorobenzene; a simple ester, for example a simple ethylpropyl ether, simple tert. -butyl ether, a simple n-butylethylamine ether, a simple di-n-butyl ether, simple diisobutenyl ether, simple dietarily ether, simple diisopropyl ether, anisole, phenetol, simple cyclohexylmethyl ether, simple diethyl ether, simple, dimethyl ether of ethylene glycol, tetrahydrofuran, nitrobenzene, o-, m-, p-chloronitrobenzene, o-nitrotoluene; NITRILES, such as acetonitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile; aliphatic or cycloaliphatic hydrocarbons, such as heptane, pinan, Noonan, o-, m-, p-timol, gasoline range boiling point of from 70 to 190oC, cyclohexane, methylcyclohexane, decalin, petroleum ether, hexane, naphtha, 2,2,4-trimethylpentane, octane; esters such as ethyl acetate, acetoacetic ether, isobutyl acetate; amides, for example, formamide, methylformamide, dimethylformamide; ketones, such as acetone, methyl ethyl ketone, and the corresponding mixture. It is advisable to use the solvent in an amount of from 100 to 2000 weight. preferably from 200 to 700 weight. with respect to the starting substances II.

Compound II, is required for the reaction, is generally used in approximately equimolar amounts (excess or deficiency, for example from 0 to 20% relative to the corresponding original substance (III). Starting material III can be added to one of the above diluents and then add the starting material II. However, a more appropriate starting material II to add to one of the previously mentioned solvents and then add the starting material III.

oC, preferably from 10 to 100oC.

As a reaction accelerator can be used, preferably, a tertiary amine, for example pyridine, ,,-picoline, 2,4-, 2,6-lutidine, 2,4,6-kallidin, p-dimethylaminopyridine, trimethylamine, triethylamine, three(n-propyl)amine, 1,4-diaza[2,2,2]bicicletta [DABCO] or 1,8-diazabicyclo[-5,4,0] -undec-7-ene in an amount of from 0.01 to 1 moles per mole of the original substance II.

The final matter I separated from the reaction mixture in the usual way after removal of the solvent or directly by sucking. The residue can be washed with water or dilute acid to remove basic impurities. Alternatively, the residue is dissolved in a solvent not miscible with water, and rinsed as described above. In this case the required final substances are released in pure form, respectively, they can be purified by recrystallization, extraction with stirring in an organic solvent, adsorbing impurities, or by using chromatography.

Usually the reaction is carried out in acetonitrile, simple tert.-butyl ether, toluene or methylene chloride in the presence of from 0 to 100 molar equivalents, preferably from 0 to 50 molar equivalents of a tertiary amine, such as, formula IV is treated in a known manner (application for European patent N 120814, the application for the European patent N 101407) in an inert organic solvent at temperatures between 0 and 120oC, preferably from 10 to 100oC, a derivative of 2-amino-1,3,5-triazine III. If this can be added bases, such as tertiary amines, allowing the reaction accelerates and improves the quality of the product.

Suitable bases for this purpose are, for example, tertiary amines, as described in the method And, in particular triethylamine or 1,4-diaza-bicyclo [2,2,2] octane, in the amount of from 0.01 to 1 moles per mole of the original substance IV.

As solvents it is expedient to apply the solvents specified in method A.

The solvent used in quantities of from 100 to 2000 weight. preferably from 200 to 700 weight. relative to the original substances IV.

Compound IV, required for the reaction, is generally used in approximately equimolar amounts (excess or deficiency, for example from 0 to 20% relative to the corresponding original substance (III). Starting material IV can be added to the diluent, and then add the original substance III.

In addition, you can also educt III add in one of these solvents or diluents removed before or during the reaction.

From the reaction mixture it is possible to allocate the final product I in the usual way as described in method A.

Method C. a Sulfonamide of the formula V is treated in a known manner (application for European patent N 2141777 and the application for the European patent N 101670) in an inert organic solvent approximately stoichiometric quantity of phenylcarbamate VI at a temperature of from 0 to 120oC, preferably from 20 to 100oC. the Reaction may be carried out at normal pressure or at pressures up to 50 bar), preferably at 1 to 5 bar, continuously or periodically.

If this can be added bases, such as tertiary amines, accelerating the reaction and improves the quality of the product. Suitable bases for this purpose are the reasons specified in the method And, in particular triethylamine, 2,4,6-kallidin, 1,4-diazabicyclo[2,2,2]octane [DABCO] or 1,8-diazabicyclo [5,4,0]undec-7-ene [DBU] in an amount of from 0.01 to 1 moles per mole of the original substance V.

As solvents or diluents suitable to use solvents or thinners specified in method A.

The solvent is used in an amount of from 10 to 2000 weight. preferably from 200 to 700 weight. relative to the educt V

You can also in one of these solvents add the educt V and then add carbamate VI. In both cases, as a catalyst, you can add one of these grounds before or during the reaction.

For the end of the reaction after the filing of the components is stirred for further 20 min to 24 h at a temperature of from 0 to 120oC, preferably from 10 to 100oC, in particular from 20 to 80oC.

Sulfonylureas of the formula I is recovered from the reaction mixture by conventional methods, as described in method A.

Method D. the Sulfonamide of the formula V is treated in a known manner (application for European patent N 234352) in an inert organic solvent to about the stoichiometric amount of isocyanate VII at a temperature of from 0 to 150oC, preferably from 10 to 100oC. the Reaction may proceed at normal pressure or at pressures up to 50 bar), preferably at a pressure of from 1 to 5 bar, continuously or periodically.

At the same time before or during the reaction may be added the basics of the s are the base, specified in method A, in particular triethylamine or 2,4,6-kallidin, in the amount of from 0.01 to 1 moles per mole of the original substance V.

As solvents it is expedient to apply the solvents specified in method A. the Solvent is used in an amount of from 100 to 2000 weight. preferably about 200 to 700 weight. relative to the educt V

The connection V, required for the reaction, is generally used in approximately equimolar amounts (excess or deficiency, for example from 0 to 20% relative to the original substances VII). Starting material VII can be added to one of the above diluents, and then add the original substance V. However, you can also add a sulfonamide, and then the isocyanate VII.

For the end of the reaction after the filing of the components is stirred for further 20 min to 24 h at a temperature of from 0 to 120oC, preferably from 10 to 100oC, in particular from 20 to 80oC. the Final product I can be isolated from the reaction mixture in the usual way as described in method A.

Used as starting substances sulfonylation formula II can be obtained in a known manner from the corresponding sulfonamides by vosganian (Houben-Weyl 11/2 (1985) 1106, U.S. patent N 4379769) ylcarbamate formula IV were obtained by analogy with the known reactions (for example, the application for the European patent N 120814). Sulfonylation formula II can be translated by reaction in an inert solvent, such as, for example, a simple ether or dichloromethane with phenol in the carbamates of the formula IV.

The carbamates of the formula VI receive by analogy with known methods (for example, an application for a European patent N 101670), in particular they can be obtained from the corresponding isocyanates VII and phenol.

The isocyanates of the formula VII is obtained from the amines of formula III by treatment with oxalylamino or phosgene (by analogy with Angew. Chem. 83 (1971) 407, the application for the European patent N 388873).

Sulfonamides can be obtained by reaction of the corresponding chlorides of sulfonic acids with ammonia (Houben-Weyl, Methods der organischen Chemie, volume 9 (1955) 605). Chlorides of sulfonic acids are produced either by the reaction of Meerwein (diazotization of the corresponding amines and salt catalyzed copper, sulfochlorinated), or by chlorosulfonylphenyl corresponding aromatic hydrocarbons, for example, chloride 2,5-dichlorobenzenesulfonate can be obtained from p-dichlorobenzene (Houben-Weyl, Methods der organischen Chemie, volume 9 (1955) 557 ff.).

2-Amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-amino-4-ethoxy-6-trifluoromethyl-1,3,5-triazine known in the liter is NT N 304282, published application US N 4599412). They are obtained by deprotonation of the corresponding sulfonation I in water or an appropriate inert organic solvent at a temperature of from -80oC to 120oC, preferably from 0oC to 60oC in the presence of a base.

Appropriate bases are, for example, hydroxides, hydrides, oxides or alkaline alcoholate or alkaline earth metals, such as sodium hydroxide, potassium and lithium methylate, ethylate and tert.-butanolate sodium, sodium hydride and calcium oxide calcium.

As solvents can be used, along with water, alcohols, such as methanol, ethanol and tert.-butanol, ethers, such as tetrahydrofuran and dioxane, acetonitrile, dimethylformamide, ketones, such as acetone and methyl ethyl ketone, and halogenated hydrocarbons.

The deprotonation can be carried out at normal pressure or at pressures up to 50 bar, preferably at normal pressure and gauge pressure up to 5 bar.

The object of the present invention are also herbicide means, including derivative N-[(1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide and target cadinene General formula I or its salts, acceptable in agriculture, in an effective amount; and a method of controlling undesirable plant growth by processing plants or their habitats derived N-[(1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide, using as the final compounds of General formula I or its salts that are acceptable in agriculture, in an effective amount.

The compounds I or herbicide products containing these compounds and their salts of alkali and alkaline earth metals, suitable for environment may very well be used to combat harmful plants in crops, such as wheat, rice or corn without damaging crop plants, the effect is noticeable even at a low rate of application of herbicide. They can be used, for example, in the form of directly sprayable solutions, powders, suspensions, also high-grade aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, opilivaya drugs, introduced into the soil, or granules by spraying, spraying, dusting, scattering or watering. Forms of application are determined depending on the purpose of use; in each case they must provide The compounds I are applied to obtain directly sprayable solutions, emulsions, pastes or oil dispersant. As inactive additives are considered, among others, mineral oil fraction having a boiling range from medium to high, such as kerosene or diesel oil, furthermore, the oil of coal tar, and oil of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, such as toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or highly polar solvents, such as N,N-dimethylformamide, dimethylsulfoxide, N is an organic or water.

Aquatic forms for application can be prepared from emulsion concentrates, dispersions, pastes, wettable powders or water dispersible granules by adding water. To obtain emulsions, pastes or oil dispersions, the substrates as such or dissolved in an oil or solvent, can gomogeniziruetsya in the water with wetting, grasping, dispersing or emulsifying means. In addition, can be obtained also concentrates consisting of active substance, wetting, by dilution with water.

As surface-active substances can be used alkali, alkaline earth ammonium salts of aromatic sulfonic acids, for example lignin-, phenol-, naphthalene - and dibutyldithiocarbamate, and also of fatty acids, alkyl - and alkylarylsulfonates, alkyl sulphates, sulphates simple lauric ether sulfates of fatty alcohol series, and also salts of sulfated hexa-, hepta - and octadecanol, and glycol ether of a fatty alcohol series, condensation products from sulphonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic with phenol and formaldehyde, a simple broadcast polyoxyethyleneglycol, the ethoxylated isooctyl-, octyl - or Nonylphenol, alkylphenol, tributyltinchloride ether, alkilammonia polyester alcohols, isotridecyl alcohol, condensates of ethylene oxide fatty alcohols, ethoxylated castor oil, easy polyoxyethyleneglycol ether or polyoxypropylene, acetate polyglycolide ester lauric alcohol, sorbitol complex ether, ligninases-spent sulfite liquor or methylcellulose.

Powdered drugs, drugs for soil and means for dusting could.

The granules such as pellets with sheath, impregnating and homogeneous granules, can be obtained by combining the active substance with solid fillers. Solid fillers are silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium, magnesium oxide, ground synthetic materials, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and vegetable products, such as cereal flour, flour from tree bark, wood and nut shell, cellulose powder or other solid fillers.

The compositions usually contain from 0.1 to 95 weight. preferably from 0.5 to 90 weight. the active substance.

Examples of the compounds.

I. 90 parts by weight of compound No. 1 (see tab. 1) is mixed with 10 weight parts of N-methyl-a-pyrrolidone and get the solution suitable for use in the form of tiny droplets.

II. 20 parts by weight of compound No. 1 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the product of the merger of 8 to 10 moles of ethylene oxide to 1 pray N-monoethanolamide oleic acid, 5 weight parts of calcium salts Daudet is the asle. By finely dispersing the solution in 100000 weight parts of water to obtain an aqueous dispersion containing 0.02 weight. the active substance.

III. 20 parts by weight of compound No. 1 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of Isobutanol, 20 parts by weight of the product of the joining of 7 moles of ethylene oxide to 1 pray isooctylphenol and 10 weight parts of the product of the joining of 40 moles of ethylene oxide to 1 pray castor oil. By dispersing the solution in 100000 weight parts of water to obtain an aqueous dispersion containing 0.02 weight. the active substance.

IV. 20 parts by weight of biologically active substances N 1 dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of from 210 to 280oC and 10 weight parts of the product of the joining of 40 moles of ethylene oxide to 1 mole of castor oil. By dispersion solution 100000 weight parts get the water dispersion containing 0.02 weight. the active substance.

V. 20 parts by weight of a biologically active substance No. 1 is well mixed with 3 weight parts of sodium salt diisobutyrate-a-sulfonic acids, 17 weight parts of sodium ligninsulfonate in a hammer mill. By dispersing the mixture in 20000 weight parts of water to obtain a solution for spraying, containing 0.1 weight. the active substance.

VI. 3 weight parts of the biologically active substance N 1 are mixed with 97 weight parts of fine kaolin. So get the tool for dusting, containing 3 weight. the active substance.

VII. 30 parts by weight of a biologically active substance No. 1 well stirred with a mixture of 92 parts by weight of powdered silica gel and 8 weight parts of paraffin oil, which is sprayed on the surface of this silica gel. In this way we obtain a composition of the active substance with good adhesiveness.

VIII. 20 parts by weight of a biologically active substance No. 1 well mixed with 2 weight parts of calcium salt of dodecylbenzenesulfonate, 8 weight parts polyglycolic ether fatty acids, 2 weight parts of sodium salt of a condensate of a phenol-urea-formaldehyde and 68 weight parts of a paraffinic mineral oil. Get a stable oily dispersion.

The application can be predskozuem and post-harvest. If the biologically active substance is poorly tolerated by some cultural thus, that leaves sensitive cultivated plants not astonished, while the active substance reaches the leaves growing below undesirable plants or on the bare earth surface (post-directed, lay-by).

Consumption rates of biologically active substances reach depending on the purpose of application, time of year, the plants and the growth stage from 0.001 to 1.0 kg/ha, preferably from 0.01 to 0.5 kg/ha

Given the variety of methods of applying the compounds proposed in the invention, and products containing these compounds, they can be used to eliminate unwanted plants found in a large number of cultivated plants. Discusses, for example, the following crops, which are presented in the table. 1.

To broaden the spectrum of action and to achieve sinergeticheskogo effect triethynylbenzene sulfonylureas of the formula I can be mixed with various representatives of other herbicide or regulating the growth of groups of biologically active substances and applied in conjunction with them. As such compounds for mixing can be used, for example, diazine, derivatives of 4H-3,1-benzoxazine, benzothiadiazine, 2,6-dinitroanilines, N-vinilkosmo the us, orally, derivatives benzofuran, derivatives, cyclohexane-1,3-dione, derivatives of quinoline-carboxylic acid, phenyloxy or heterooligomerization acid, and their salts, esters, amides, and others.

In addition, preferably the compounds of formula I alone or in combination with other herbicides to mix more with other means for protection of plants and use them together, for example with agents for weed control or phytopathogenic fungi or bacteria. In addition, it is mixed with solutions of mineral salts used to correct the lack of nutrients and trace elements. Can also be added neotomine oils and oil concentrates.

Below are examples of synthesis of compounds I.

1) 2-chloro-1-N-[(4-methoxy-6-trifluoromethyl-1,3,5-triazine-2-yl)aminocarbonyl]benzosulfimide

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A solution of 4.0 g (21 mmol) of 2-amino-4-methoxy-6-trifluoromethyl-1,3,5-triazine in 20 ml of acetonitrile were mixed at a temperature of 25oC with 4.5 g (21 mmol) of 2-chlorobenzalmalononitrile. Thus obtained solution was stirred for 21 h at 25oC. and Then under reduced pressure at a temperature of 40oC was removed rastie 3 hours The product was aspirated and dried in a vacuum at a temperature of 40oC. Obtained 6.5 g (75%].) the compounds with a melting point 166-186oC.

2) Sodium salt of 2-chloro-1-N-[(4-methoxy-6-trifluoromethyl-1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide

A suspension of 1.5 g (3.6 mmol) of 2-chloro-1-[(4-methoxy-6-trifluoromethyl-1,3,5-triazine-2-yl) aminocarbonyl]benzosulfimide in 10 ml of methylene chloride was mixed at a temperature of 25oC with 0.66 g (3.6 mmol) of a solution of sodium methylate (30 weight.) in methanol. The resulting homogeneous solution was stirred for 1 h at 25oC. After removal of volatile particles at a temperature of 60oC in vacuum obtained using a water-jet pump, has been specified a connection with quantitative yield by decomposition temperature 220-224oC.

Biologically active substances specified in the following table. 2, receives the same way.

Similarly, we can obtain the following connections:

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6-ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6 ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6 ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6 ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methox is hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6-ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6 ethoxy;

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or their sodium salts, where R3has the following meanings: hydrogen, 3-methyl, 4-methyl, 5-methyl, 6-methyl, 3-ethyl, 4-ethyl, 5-ethyl, 6-ethyl, 3-fluoro, 4-fluoro, 5-fluoro, 6-fluoro, 3-chloro, 4-chloro, 5-chloro, 6-chloro, 3-methoxy, 4-methoxy, 5-methoxy, 6-methoxy, 3-ethoxy, 4-ethoxy, 5-ethoxy, 6 ethoxy.

Application examples.

Herbicide N-[(1,3,5-triazine-2-yl) aminocarbonyl]benzosulfimide formula I on the growth of test plants shown in the following experiments in the greenhouse.

As containers for crops are plastic flower pots with a volume of 300 cm3and clayey sand with approximately 3% of humus as a substrate. Seeds of the test plants are sown separately by type.

For post-harvest processing are selected or nepoui a few days before the treatment in the tank for experiments.

Then depending on germination subjects plants at a height of from 3 to 15 cm are processed suspended or emulsified in water in the form of dispersions of biologically active substances sprayed through the nozzle. The consumption rate for post-harvest processing reaches of 0.06 or 0.03 kg/ha of active substance.

Pilot plants are placed in the greenhouse, and for thermophilic species of the temperature from 20 to 35oC, and to create a temperate climate, the preferred temperature is from 10 to 20oC. Experimental period lasts from 2 to 4 weeks. During this time caring for plants and analyze their response to individual processing. The assessment is carried out on a scale from 0 to 100. 100 means no germination of the plants or complete destruction of at least the exposed parts, and 0 means no damage or normal course of growth.

Plants used for experiments in the greenhouse, consist of species presented in table. 3.

is 0.06 or 0.03 kg/ha of active substance used in post-harvest processing, shows connection N 1 a very good effect on undesirable broadleaf plants when ignorenontxtables the results of biological studies, in which the proposed invention the active substance of example 1 is compared with the compound B, is known from U.S. patent N 4169719.

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In tables 5 and 6 compares the proposed invention the compounds of examples 1 or 3 substances G and H from the U.S. patent N 4127405.

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The results show very high selectivity.

Known compounds cause unacceptable damage on 85 or 70% in the culture of corn. The compounds of examples 1 or 3, on the contrary, when equally good herbicide exposure show only 10% damage cultivated plants.

High selectivity in sensitive crops rice, wheat and summer maize is achieved by using the proposed invention compounds N 7, as shown by the results presented in the following tables 7 and 8.

The following experience is a sodium salt of comparative compound H was compared with example 7. The results are presented in table. 9.

The results of the experiment demonstrate extremely high selectivity with high herbicide efficiency of the proposed invention the connection.

In the following table. 10 13 shows herbicide AK is the soup of the formula I

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where R1methyl or ethyl group;

R2halogen, trifluoromethyl, 2-methoxyethoxy,1- C3-alkylsulfonyl;

R3hydrogen, chlorine, fluorine, methyl or ethyl group,

or their salts, are applicable in agriculture.

2. N-[(1,3,5-triazine 2-yl)aminocarbonyl] benzosulfimide under item 1, where R2chlorine.

3. The compounds of formula I or their salts on PP.1 and 2, characterized in that they have a weed-killing activity.

4. Herbicide means, including derivative N-[(1,3,5-triazine--2 Il)aminocarbonyl] benzosulfimide and target additives, characterized in that as a function of N-[(1,3,5-triazine--2 Il)aminocarbonyl] - benzosulfimide it contains a compound of General formula I or its salts under item 1 in an effective amount.

5. The method of controlling undesirable plant growth by processing plants or their habitats derived N-[(1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide, characterized in that as a function of N-[(1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide used as a compound of General formula I or its salt under item 1 in an effective amount.

 

Same patents:

The invention relates to a new derived arylsulfonyl-triethynylbenzene formula I

which can find application in agriculture as a herbicide for weed control in cereal crops and flax, as well as herbicide composition based on it

The invention relates to the derived O-carbamidomethylation, specifically to methyl ether, 2-[[N-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)-N-methylaminomethyl]aminosulfonyl]benzoi Noi acid of the formula I

< / BR>
have a weed-killing activity, and herbicide compositions based on it

The invention relates to new derivatives of sulfamethoxypyrazine and herbicides containing them as active ingredients

The invention relates to herbicides that can be used against monocotyledonous and dicotyledonous weeds

The invention relates to methods seleting suppression of undesirable plant species in the presence of agricultural crops

The invention relates to a preparation containing a synergistic mixture of bromoxynil or one of its derivatives (I) c 2-[[(4,6-dimethoxypyrimidine-2-yl] amino-arbonyl] (aminosulfonyl)-N, N - dimethyl-3-pyridinecarboxamide (II)

The invention relates to a method of controlling undesirable vegetation using sulfonylureas

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: 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: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

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: agriculture, in particular method for controlling of weeds.

SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

FIELD: agriculture, herbicides.

SUBSTANCE: invention relates to herbicide composition based on derivative of sulfonylurea that comprises non-ionogenic surface-active substance, lignosulfonates as anion-active surface-active substance and highly dispersed amorphous silica as a carrier. Composition comprises chlorsulfuron as derivative of sulfonylurea and triethanolamine or diethanolamine additionally, and potassium dihydrogen phosphate as a stabilizing agent in the following ratio of components, wt.-%: chlorsulfuron, 18-22; non-ionogenic surface-active substance, 3-5; potassium dihydrogen phosphate, 9-12; triethanolamine or diethanolamine, 9-11; lignosulfonates, 3-10, and highly dispersed amorphous silica, the balance. Method involves mixing components in indicated ratios by steps for 3 stages. At the 1-st stage triethanolamine or diethanolamine is applied on surface of highly dispersed amorphous silica, at the 2-d stage - chlorsulfuron, and at 3-d stage - potassium dihydrogen phosphate, lignosulfonates and non-ionogenic surface-active substance. After keeping for 24 h at the room temperature mixing products from all three stages are combined. Invention provides enhancing stability of chlorsulfuron and biological activity of preparation based on thereof. Invention is designated for applying in agriculture.

EFFECT: valuable properties of herbicide composition.

4 cl, 2 tbl, 9 ex

FIELD: agriculture, in particular chemical agents for plant protection.

SUBSTANCE: sulfonylaminourea and phenoxyacetic acid derivatives-based herbicidal composition contains nonionic surfactant, anion-active surfactant sulfonol, kaolin as carrier, and carbon white. As sulfonylaminourea and phenoxyacetic acid derivatives it contains 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea and 2-methyl-4-chlorophenoxyacetic acid sodium salt, respectively. Additionally composition contains triethanolamine or diethanolamine, disubstituted potassium phosphate as stabilizer in the component ratio of (mass %): 2-methyl-4-chlorophenoxyacetic acid sodium salt 55-72; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea 0.3-0.4; nonionnic surfactant 0.05-0.15; sulfonol 0.05-0.15; triethanolamine or diethanolamine 0.15-0.2; carbon white 0.37-1.5; disubstituted potassium phosphate 1.0-2.0; and balance: kaolin. Composition components are separately applied on carrier surface. More specifically triethanolamine or diethanolamine is separately mixed with kaolin; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea, and carbon white are separately mixed with kaolin; disubstituted potassium phosphate, nonionic surfactant, and sulfonol are separately mixed with kaolin; and 2-methyl-4-chlorophenoxyacetic acid sodium salt also is separately mixed with kaolin. Mixtures are conditioned for 24 h at room temperature and then are blended to provide mentioned above component ratio in product.

EFFECT: herbicidal composition of increased activity and deferred hydrolysis in wetted powder.

3 cl, 6 ex, 2 tbl

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