N-pyridylsulfonyl-n'-pyrimidinediamine or their salts with amines, bases, alkali or alkaline earth metal or quaternary ammonium bases, herbicide, and the vast growth of plants tool


(57) Abstract:

The invention relates to the compound N-pyridylsulfonyl-N'-pyrimidinylidene formula 1

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where R1denotes methyl or methoxy and R2denotes hydrogen or methyl; compounds and salts of these compounds with amines, bases, alkali or alkaline earth metal or Quaternary ammonium bases have good herbicide and regulating plant growth properties during selective use before and after germination. 2 S. and 2 C.p. f-crystals, 9 PL.

The invention concerns new N-pyridylsulfonyl-N'-pyrimidinylidene, acting as herbicides, method of production thereof, agents containing them as active substances, and their use for weed control, especially selectively in crops of useful plants, or for regulating and inhibiting the growth of plants.

Phenylsulfonylacetate with herbicide known from European patent application N 0103543. However, the active substances may not always meet the requirements of the degree and spectrum of activity. Thus there is a need for more effective and more selective of the active substance of the new sulfonylurea correspond to the formula I

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where R1denotes methyl or methoxy and

R2denotes hydrogen or methyl;

as well as salts of these compounds with amines, bases, alkali or alkaline earth metal or Quaternary ammonium bases.

The invention also includes salts that can form the compounds of formula I with amines, bases, alkali and alkaline earth metal or Quaternary ammonium bases.

From hydroxides of alkali and alkaline earth metal as a salt-forming should be noted hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular sodium and potassium.

As examples of amines suitable for the formation of ammonium cations considered as ammonia and primary, secondary and tertiary C1-C18-bonds alkylamines, C1-C4-oxyalkylene and C2-C4-alkoxyalkyl, for example, methylamine, ethylamine, n-Propylamine, Isopropylamine, chetyrekhyadernye butylamine, p-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylic, hexadecylamine, heptadecyl, octadecylamine, methyl-ethylamine, methyl-Isopropylamine, methyl-hexylamine, methyl-nonylamine, Meekel-octylamine, dimethylamine, diethylamine, di-n-Propylamine, di-Isopropylamine, di-n-butylamine, di-n-amylamine, di-isoamylamine, digoxigenin, gigatronik, dioctylamine, ethanolamine, p-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropylamine, N-butylethylamine, allylamine, p-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutene-2-amine, dibutyl-2-amine, n-hexenyl-2-amine, Propylenediamine, trimethylamine, triethylamine, tri-n-Propylamine, tri-Isopropylamine, tri-n-butylamine, tri-isobutylamine, three-Deut. -butylamine, tri-n-amylamine, methoxyethylamine and amoxicillin; heterocyclic amines such as pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, Hinkley and azepine; primary amines, such as, for example, anilines, methoxyaniline, ethoxyaniline, o,m, p-toluidine, phenylenediamine, benzidine, naphthylamines and o,m,p-chloraniline, in particular, triethylamine, ISO-Propylamine and Diisopropylamine.

In the compounds of the formula I R2represents preferably hydrogen. As the preferred individual compounds of formula I include: N-(3-deformationen-2-yl-sulfonyl)-N'-(4-methyl-6-methoxypyridine-2-yl)-urea.

The compounds of formula I can be obtained by converting

a) PIR R2have the meanings indicated in formula I, and R3denotes phenyl or 4-tolyl, in the presence of a base, or by converting

b) compounds of the formula IV

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where A denotes a or O=C=N-, and R3have the above significance, in the presence of a base using 2-aminopyrimidine formula V

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where R1has the value shown in the formula I, or by converting

c) pyridinesulfonamide formula II

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in the presence of a base using pyrimidinediamine formula VI

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where R1has the value shown in the formula I, or by conversion

d) the compounds of formula VII

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using the compounds of formula V

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where R1has the value shown in the formula I, in the presence of ammonium salts, phosphonium, sulfone or alkali metal cyanate of the formula VIII


where M denotes an alkali metal or the group R4R5R6R7Q, where R4, R5, R6and R9independently of one another denote C1-C18-alkyl, benzyl or phenyl, and the total number of C atoms is not greater than 36; and Q denotes a nitrogen, sulfur or phosphorus.

Conversion to compounds of formula I are carried out, the pre is s, as for example, benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloromethane, carbon tetrachloride or chlorobenzene, ethers, such as, for example, a simple diethyl ether, simple etilenglikolevye ether, simple diethylethylenediamine ether, tetrahydrofuran or dioxane, NITRILES, such as acetonitrile or propionitrile, amides, such as dimethylformamide, diethylformamide or N-methylpyrrolidinone. The reaction temperature is preferably in the range of (-20oC) and (+120oC).

Conversion proceed mainly with small heat release and can be carried out at room temperature. With the aim of reducing the time of reaction or also to begin the conversion, the reaction mixture is heated to boiling point in a short time. The time of reaction can be reduced by feeding a few drops of base as reaction catalyst. As bases are suitable, in particular, tertiary amines, such as trimethylamine, triethylamine, Hinkley, 1,4-diazabicyclo-(2,2,2)-octane, 1,5-diazabicyclo(4,3,0)non-5-ene or 1,5-diazabicyclo(5,4,0)undec-7-ene. As grounds for mohotatse, as for example, sodium hydroxide and potassium, carbonates, such as sodium carbonate and potassium or hydrogen carbonates, such as potassium bicarbonate and sodium.

The final products of formula I can be isolated by concentration and/or evaporation of the solvent and purified by recrystallization or trituration of the solid residue in solvents in which they are poorly soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.

Compounds of formulas II, III, IV, V, VI, VII and VIII are either known or can be obtained analogously to known methods. Variant of the method a) described for example in European patent application N 0103543, a variant of method (b) described, for example, in European patent application N 0101670. Variants of the method (c) and (d) described in European patent application N 0459949 or patent Switzerland N 662348.

For use according to the invention compounds of formula I, or products containing these compounds, discusses the various methods and technologies, such as the following:

i) seed Treatment.

a) seed Treatment active substance prepared in the form of a wettable powder by shaking the powder by VSAT to 4 g of the active substance of the formula I (50% up to 8.0 g of wettable powder): 1 kg of seed.

Seed emulsion concentrate of the active substance or an aqueous solution of the active substance of the formula I, prepared as a wetting powder according to method a) (wet dressing).

c) Dressing by immersing seed in broth containing up to 1000 hours per million of the active substance of the formula I within 1 to 72 hours and, accordingly, subsequent drying of seeds (treatment by immersion).

Treatment of seed or processing of germinated seedlings are naturally the preferred methods of application as the processing of the active substance is completely focused on the desired culture. Apply, as a rule, from 0.01 g to 4.0 g of active substance per 1 kg of seed, and by a technique, which allows to Supplement other active substances or minerals and which allows you to deviate from a threshold concentration above or below (re-treatment).

ii) Controlled the issuance of the active substance.

The active substance is applied in solution in mineral granular filler or polymerised granules (urea/formaldehyde) and dried. Dopolniteldnyh quantities after a certain period of time.

The compounds of formula I can be used unchanged, i.e., as obtained in the synthesis, however, they are preferably processed in the usual way AIDS used in the technology of formulation, for example, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, powdered preparations, granules or microcapsules. The application methods, such as sputtering, spraying, dusting, wetting, scattering or watering choose simultaneously with the tool, aimed at achieving a particular purpose and in accordance with the specified ratios.

The recipe, i.e. products containing the active substance of the formula I or at least one active substance of formula 1 and, respectively, one or more solid or liquid additives, the technology of preparation or composition to receive in a known manner, for example by stirring until smooth and/or grinding the active substances with additives, as for example solvents or solid fillers. In addition, you can apply a surface-active compounds (surfactants) upon receipt of the compounds.

SUB>12as for example, mixtures of alkyl benzenes, e.g. xylene mixtures or alkylated naphthalenes; aliphatic or cycloaliphatic hydrocarbons, such as paraffins, cyclohexane or tetrahydronaphthalen; alcohols, such as ethanol, propanol or butanol; glycols and their ethers and esters, such as propylene glycol or a simple ester dipropyleneglycol, ketones, such as cyclohexanone, isophorone or datetoday alcohol, strong polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or water; vegetable oils and their esters, such as rape, ricinulei or soybean oil; accordingly also silicone oils.

As particulate fillers, for example, powdered drugs and dispersible powders are used, as a rule, natural crushed rocks such as calcite, talc, kaolin, montmorillonite or attapulgite. To improve the physical properties can be added also highly dispersed silicic acid or highly dispersed polymerizate with absorptive capacity. As crushed adsorption granular fillers are considered porous materials, such as PE is or sand. In addition, there may be used a number of pre-granulated materials of inorganic or organic nature, in particular dolomite or crushed plant residues.

As surface-active compounds, depending on the type composed of the active substance of the formula I are considered non-ionic Catino and/or anionic surfactants with good emulsifying, dispersing and wetting properties. Under surfactants should be understood also mixtures of surface-active substances.

Suitable anionic surfactants can be of the so-called water-soluble Soaps and water-soluble synthetic surface-active compounds.

As a soap, you can specify alkaline salts, alkaline earth metal or substituted ammonium salts of the bases of the higher fatty acid series (C10-C22), as for example, salts of Na or K oil or stearic acid, or of natural mixtures of fatty acids are presented, which can be derived from coconut or melted animal fat. In addition, mention should also be methyl-turinawe substances, in particular, sulfonates of fatty alcohols, sulfates of fatty alcohols, from sulphonated benzimidazole derivatives or alkylarylsulfonates.

The sulfonates or sulfates of fatty alcohols, usually in the form of alkaline salts, alkaline earth metal or substituted ammonium salts of the base and have an alkyl radical with 8 to 22 C atoms, and alkyl includes alkyl portion of the acyl radicals, for example, salt of Na or Ca ligninsulfonate, complex ether modellserie acid or a mixture of sulfates of fatty alcohols derived from natural fatty acids are presented. This includes salts of esters of sulfuric acid and sulfonic acids products joining fatty alcohol-ethylene oxide. From sulphonated benzimidazole derivatives contain, preferably, 2 groups of sulfonic acids and one radical of the fatty acid number of from 8 to 22 atoms C. Alkylarylsulfonate are salts of Na, Ca or triethanolamine of dodecylbenzensulfonate, dibutylaminoethanol, or condensation products of naphthalenesulfonate-formaldehyde.

It also covers the corresponding phosphates, e.g. salts of ester of phosphoric acid product Pris is active substances, first of all, are considered derivative simple polyglycolic ether of aliphatic and cycloaliphatic alcohols, saturated or unsaturated fatty acid series and ALKYLPHENOLS, which can contain from 3 to 30 groups simple glycol ether, and from 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the ALKYLPHENOLS.

Other suitable nonionic surfactants are the water-soluble addition products of polyethylene oxide containing from 20 to 250 groups of simple ether of ethylene glycol and 10 to 100 groups of simple ether of propylene glycol, polypropyleneglycol, ethylenediaminetriacetic and alkylpolyethylenglycol with 1 to 10 carbon atoms in the alkyl chain. These compounds usually contain for each unit of propylene glycol from 1 to 5 units of ethylene glycol.

As examples of nonionic surfactants should specify nonylphenolethoxylates, simple polyglycolic ether rezinovogo oil, the addition products of polypropylene-polyethylene oxide, tributyltinoxide, polyethylene glycol and octylphenoxypolyethoxyethanol.

Cu is polyoxyethylenesorbitan-trioleate.

In the case of cationic surfactants, above all, speaks of the salts of Quaternary ammonium bases, which as Vice-N contain at least an alkyl radical with 8 to 22 C atoms and the other substituents are lower, respectively, halogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts are preferably in the form of halides, methylsulfate or ethylsulfate, for example, chloride of stearylamine or bromide benzyl-(2-chloroethyl)-ethylamine.

Surfactants used in the preparation of formulations that can be used in the proposed invention the tools described in particular in the following publications: Mc Cutcheon''s Detergents and Emulsifiers Annual. Mc Publishing Corp., Glen Rock, New Jersey, 1988; M. and J. Ash. Tycyclopedia of Surfactants, vol. I-III, Chemical Publishing Co. , New York, 1980-1981; Dr. Helmut Stache. Tensid-Taschenbuch, Carl Hanser Verlag, München/Wien 1981.

Herbicide formulations contain, as a rule, from 0.1 to 99%, in particular from 0.1 to 95% of the biologically active substance of the formula I, from 1 to 99% solid or liquid additive and 0 to 25%, in particular from 0.1 to 25% surfactant.

For use are preferred with the form.

Funds may also contain other additives, such as stabilizers, for example, respectively epoxydecane vegetable oil (epoxydecane coconut oil, rapeseed oil or soybean oil), defoamers, for example, silicone oil, preservatives, viscosity regulators, binders, adhesive additives, as well as fertilizers or other active ingredients to achieve the desired effect.

Preferred compounds are, in particular, as follows, wt.%:


The active substance is 0.1 to 50 (preferably) - 0,1 - 5

Solid filler to 99.9 - 90 (preferably) to 99.9 - 99

Suspension concentrates:

The active substance is 5 - 75% (preferably 10 - 50)

Water - 94 - 24 (preferably 88 to 30)

Surface-active agent is 1 to 40, preferably 2 to 30)

Wettable powders:

The active substance is 0.5 to 90 (preferably 1 to 80)

Surface-active agent is 0.5 to 20 (preferably 1 - 15)

Solid filler is 5 to 95, preferably 15 to 90)


The active substance is 0.1 to 30, preferably 0.1 to 15)

Solid - 99,5 - 70 (preferably 97 to 85)

The active substance of the formula I are used successfully with nollette, can be determined through experiments. It depends on the type of treatment, stage of development of plants and weeds, as well as from the application (place, time, method) and, based on these parameters, may vary in other limits.

The compounds of formula I are distinguished by properties that inhibit the growth of plants, and weed-killing properties that are great are their introduction into a culture of useful plants, in particular in cereals, cotton, soybeans, canola, sugar cane, plantation crops, maize and rice, and especially preferred is the use of them in the corn.

Obtaining compounds of formula I are explained using the following examples.

Example H1. Getting 2-isopropylthio-3-oksipiridina:

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To a solution of 16.4 g of 2-mercapto-3-oksipiridina (known from Tetrahedron 21. 2191, 1980) in 155 ml of dimethylformamide at a temperature of 5oC added in several portions 14 g of potassium-tert.-butyl. Then at a temperature of from 0 to 2oC added dropwise 12.5 ml of isopropylated within 15 minutes After 2-hour stirring, the reaction mixture was extracted at room temperature with 400 ml of ice water and 200 ml of ethyl acetate. After you install ve is shelled organic phases are washed three times with water 150 ml, concentrated in vacuo to a volume of 100 ml and extracted four times with an aqueous solution of caustic soda 2N 50 ml at a temperature of 0oC. Then the aqueous phase was adjusted with 2N hydrochloric acid to pH 7 to 8 b is extracted four times with ethyl acetate 50 ml After drying the organic phase, filtering through 100 g of silica gel, four washing with ethyl acetate 50 ml) and evaporation receive crystallizing the residue, which is triturated with petroleum ether and then filtered. Obtain 14.6 g of 2-isopropylthio-3-oksipiridina with a melting point 64oC.

Example H2. Getting 2-isopropylthio-3-deformationen:

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To a solution of 118,4 g 2 isopropylthio-3-oksipiridina in 560 ml of dioxane for 15 min add 464 ml of 30% aqueous sodium hydroxide solution dropwise. Then at a temperature of 80oC for 2 hours to enter 121 g of freon 22 and mix the following 90 minutes After cooling the reaction mixture to room temperature, extracted with a mixture of 2500 ml of ice water and 1000 ml of methylene chloride and the phases are washed four times with methylene chloride, 50 ml and once with 150 ml of ice water. Then peeled the organic phase is dried over sodium sulfate and evaporated in vacuum. After about what varicela get 105,7 g 2 isopropylthio-3-deformationen in the form of oil with n2D11,5088.

Example H3. Obtaining 3-deformationen-2-yl-sulphonamide:

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In a mixture of 105,7 g 2-Isopropenyl-3-deformationen, 1000 ml dichlorethane and 1723 ml of 1N hydrochloric acid is injected for 50 minutes at a temperature of from -5 to 0oC 142 g of gaseous chlorine. After 20 minutes stirring at a temperature of from -30oC for 15 min injected nitrogen. Then phase washed three times with ice water to 250 ml and 250 ml dichloromethane and purified organic phase is dried over sodium sulfate. This reaction mixture at a temperature of from -50 to -40oC for 40 min added dropwise to the mixture from 12267 g of ammonia in 250 ml of dichloromethane. After 15 hours stirring and subsequent filtration of the reaction mixture is evaporated, triturated with petroleum ether, the obtained crystalline agglomerate filtered and dried. Get 85,9 g 3-deformationen-2-yl-sulfonamide with a melting point of from 85 to 86oC.

Example H4. Obtaining N-(3-deformationen-2-yl-sulfonyl)-N'-(4-methyl-6-methoxypyridine-2-yl)-urea

The compound N 1.03:

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To a solution of a 4.03 g of 3-deformationen-2-yl-sulfonamida in 40 ml of acetonitrile alternately add equal to 4.97 g of N-(4-methyl-6-methoxyp the second mixture was concentrated in vacuo. Then, the thus obtained oily residue triturated 12 ml of 2N hydrochloric acid and diluted with 10 ml of water. Crystallized product is filtered and then washed with water and simple diethyl ether. Get N-(3-deformationen-2-yl-sulfonyl)-N'-(4-methyl-6 - methoxypyridine-2-yl)-urea (compound N 1.03) with a melting point of 151 to 154oC.

Similarly receive the compounds of formula I, are given in table. 1, as well as their intermediate products.

Examples of formulations for the active substances of formula I are given in table. 2.

The active substance is well mixed with additives and good ground in appropriate mills. Get a wettable powder which is well diluted with water, suspensions of any desired concentration. The results are given in table. 3.

The active substance is dissolved in methylene chloride, dispersed in the filler and then the solvent is evaporated in vacuum. The results are presented in table. 4.

The finely ground active ingredient is uniformly applied in the mixer on the filler moistened with polyethylene glycol. Thus obtained pellets in the shell, without dust. The results are presented in trout and then dried in an air stream. The results are given in table. 6.

Get ready to use powdered drug, active ingredient which is mixed with fillers and grind in an appropriate mill. The results are given in table. 7.

The finely ground active substance is mixed with ingredients until smooth. So get a suspension concentrate from which, by dilution with water it is possible to obtain suspensions of the desired concentration.

Biological examples.

Example B1. The effectiveness of herbicides when used before emergence.

Plastic pots filled expanded vermiculite (density: is 0.135 g/cm3, adsorption capacity of water: of 0.565 l/l). After saturation readsorbing vermiculite water emulsion of the active substance in deionized water containing the active substance in a concentration of 70 hours/million, sown the seeds of the following plants: Nasturtium officinalis, Agrotis tenuis, Stellaria media and Digitaria sanguinalis. Then experienced the vessels kept in a climatic chamber at a temperature of 20oC, covering approximately 20 Klux and a relative humidity of 70%. During the phase of germination from 4 to 6 Nam to increase local humidity pots cover sitepronews what about the fertilizer, available on the market. After 12 Nam after sowing analyzes the result of experience and assess the impact on the experimental plants according to the following scale: 1 plants do not sprout or completely destroyed; 2 - 3 very strong impact; 4 - 6 medium impact; 7 - 8 low impact; 9 no impact (as unprocessed pilot plant). The results are presented in table. 8.

Example B2. The effect of the herbicide after emergence (contact herbicide).

A few weeds as monocots and dicots are sprayed after emergence (in the development stage 4 - 6 leaves) water dispersion of the active substance according to example F6 dosage of from 8 to 500 g of active substance per hectare and maintain them at a temperature of 24 - 26oC and 45 - 60% relative humidity. After 15 DN after processing assessment experience.

After 3 weeks, evaluated the effectiveness of the herbicide on the nine-storeyed scheme (1 total defeat, 9 no effect) compared with the untreated control group. The records from 1 to 4 (in particular 1 to 3) indicate good and very good efficacy of the herbicide. Recording from 6 to 9 (in particular, from 7 to 9) indicate good endurance (in particular cultivated plants).

Comparison of the biological activity of the compounds of the proposed applications and connections from EP-A-O 103543.

Was investigated herbicide action for connections:

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(compound N 1.01 of proposed order) and

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(compound N 142 from EP-A-O 103543).

Preschedule impact (1B).

Monocotyledonous and dicotyledonous weed and crop plants were sown in plastic pots with the standard method. Immediately after vysielanie was treated with an aqueous suspension of the proposed connection (500 l of water/ha). The number of the tested active substances ranged from 8 to 15 g/ha subjects Then the plants were placed in a greenhouse with optimal conditions. The evaluation was performed 3 weeks after applying for the nine-storeyed scale Monitor (1 annihilation, 9 no action). Scale scores Monitor from 1 to 4 (in particular, from 1 to 3) indicate good to very good herbicide action. Estimates from 6 to 9 (in particular from 7 to 9 show a good to very good tolerance of cultivated plants.

Subjects plants: Alopecurus, Bromus, Avena, Lolium, Panicum, Sorghum, Digitiaria, Echinoclloa, Brachiarria, Rottboellia and Cyperus.

The data are summarized in the following table. 9.

As known from the prior art connection 142 when consumed 15 g/ha for Alopecurus, Lolium, Echinoclloa and Brachiarria have a deterrent effect, and all other weeds either not observed or observed very weak herbicide exposure.

1. N-Pyridylsulfonyl-N'-pyrimidinylidene formula I

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where R1methyl or methoxyl;

R2a hydrogen atom,

or their salts with amines, bases, alkali or alkaline earth metal or Quaternary ammonium bases.

2. N-(3-Deformationen-2-yl-sulfonyl) -N'-(4-methyl-6-methoxypyridine-2-yl)-urea under item 1.

3. Herbicide and the vast growth of plants means containing a derived N-pyridylsulfonyl-N'-pyrimidinediamine and auxiliary (target) additives, characterized in that as a derived N-pyridylsulfonyl-N'-pyrimidinylidene it contains a compound of formula I under item 1 in an effective amount.

4. Means on p. 3, characterized in that it contains the active substance of the formula I on p. 1 in an amount of 0.1 to 50%


Same patents:

The invention relates to compounds of formula (I) listed in the description, where R1represents a hydrogen atom or unsubstituted or substituted alkyl group; and A represents the number of cyclic or acyclic nitrogen containing groups

The invention relates to a new derived pikolinos acid, useful as components of the herbicide compositions, herbicide compositions containing it, which can be used in rice fields, cultivated fields and non-agricultural land

The invention relates to certain new derivative thimerisol, provides a way of obtaining them and relates to methods and compositions for use as antibacterial agents

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

The invention relates to new biologically active compounds that can be used as plant growth regulators

The invention relates to compounds of the formula


where R1represents hydrogen, lower alkyl, lower alkenyl, lower quinil, aryl lower alkyl, cycloalkyl lower alkyl, lower alkoxy lower alkyl, hydroxy lower alkyl, amino lower alkyl, mono - or di-lower alkyl, amino lower alkyl, formyl, lower alkylsulphonyl, amino lower alkylsulphonyl, lower alkoxycarbonyl, mono - or di-aryl-substituted lower alkyl, arylcarbamoyl lower alkyl, aryloxy lower alkyl, or lower alkylene

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X represents O or S;

W represents hydrogen, halogen, hydroxy, lower alkoxy, aryl lower alkoxy, nitro, trifluoromethyl or

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where R3represents hydrogen, lower alkyl or aryl lower alkyl, and R4represents lower alkyl or aryl lower alkyl; or alternatively the groupas a whole represents the

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R5is hydrogen, lower alkyl, aryl or aryl lower alkyl; and

Z predepression

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

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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