Derivative phenylsulfonylacetate and their salts, derivatives sulfonamide as a source of compounds for their production, herbicide tool and method of combating weeds

 

(57) Abstract:

The invention relates to new derivatives of sulfonylurea of the formula I, where R1group CO-Q-R5; R2is hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms; R3- alkylsulfonyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1-4 carbon atoms or dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part, alkylsulphonyl with 1-6 carbon atoms in the alkyl part, with the alkyl part can be single or multiply substituted with halogen, alkoxygroup with 1-4 carbon atoms, phenylcarbinol, phenylsulfonyl, phenyl residue which may be substituted by alkyl with 1 to 4 carbon atoms, formyl group of the formula-CO-CO-R1where R1means alkoxy with 1-4 carbon atoms, cycloalkylcarbonyl with 3-6 carbon atoms in cycloalkyl part, a group of the formula

< / BR>
moreover, if the group-CH2-NR2R3located in the para-position relative to the group of SO2the rest of the sulfonylureas, R3does not mean the unsubstituted alkylsulphonyl with 1-6 carbon atoms in the alkyl part, R2and R3together mean a group of the formula (CH2)m- Or-B1-(CH2)m1-B-, g is or sulfur, Q is an oxygen atom or the group-NR9-, T -, an oxygen atom or sulfur, R4is hydrogen or methyl, R5is hydrogen, alkyl with 1-4 carbon atoms, R6is alkyl with 1-4 carbon atoms, R7and R8independently from each other hydrogen or alkyl with 1-4 carbon atoms, unsubstituted or multiply substituted with halogen, R9is alkyl with 1-4 carbon atoms And is a group of the formula below, where Z is - CH= or-N=, one of the radicals X and Y represents hydrogen, halogen, alkyl or alkoxy with 1-3 carbon atoms, unsubstituted or substituted by halogen atoms and the other radical X or Y means hydrogen, alkyl or alkoxy with 1-3 carbon atoms, unsubstituted or substituted by halogen atoms, mono - or dialkylamino with 1-3 carbon atoms in each alkyl group, or their salts. The compounds of formula 1 possess herbicide action. They can be used as active ingredient in the herbicide agent, and method of weed control by treatment of the latter, or their seeds, or the biosphere compounds I, or its salt in an effective amount. The invention also describes the new intermediate products of the formula II to obtain the compounds I. 4 S. and 2 C.p. f-crystals, 4 PL.

The invention otnositelino and their salts, derived sulfonamida as a source of compounds for their production, herbicide tool and method of weed control.

From the application WO 89/10291 known derivative phenylsulfonylacetate that can be used as a herbicide.

The objective of the invention is the expansion of the Arsenal derivatives phenylsulfonylacetate that can be used as a herbicide.

The problem is solved proposed derivatives phenylsulfonylacetate General formula (I)

< / BR>
where R1group CO-Q-R5,

R2is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1-4 carbon atoms,

R3- alkylsulfonyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1-4 carbon atoms or dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part, alkylsulphonyl with 1-6 carbon atoms in the alkyl part, with the alkyl part can be single or multiply substituted with halogen, alkoxy group with 1-4 carbon atoms, phenylcarbinol, phenylsulfonyl, phenyl residue which may be substituted by alkyl with 1-4 carbon atoms, formyl group of the formula-CO-CO-R1where R1means alkoxy with 1-4 carbon atoms, cycloalkyl the -NR2R3located in the para-position relative to the group of SO2the rest of the sulfonylureas, R3does not mean the unsubstituted alkylsulphonyl with 1-6 carbon atoms in the alkyl part,

R2and R3together mean a group of formula-CH2)mB - or-B1-(CH2)m1-B-, where b and b1independently from each other mean sulfonyl or carbonyl, m = 3, 4, a m1= 2, 3,

W is oxygen atom or sulfur,

Q is an oxygen atom or the group-NR9-,

T is an oxygen atom or sulfur,

R4is hydrogen or methyl,

R5is hydrogen, alkyl with 1-4 carbon atoms,

R6is alkyl with 1-4 carbon atoms,

R7and R8independently of one another denote hydrogen or alkyl with 1-4 carbon atoms, unsubstituted or multiply substituted with halogen,

R9is alkyl with 1-4 carbon atoms,

A group of the formula

< / BR>
where Z is - CH= or-N=, one of the radicals X and Y represents hydrogen, halogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms, [mono (or dialkylamino with 1-4 carbon atoms in each alkyl group] , and the other radical X or Y means hydrogen, alkyl or alkoxy with 1-3 carbon atoms, unsubstituted or samisen the x2">

The invention relates to all stereoisomers are encompassed by formula (1) and their mixtures. Such compounds of formula (I) contain one or more asymmetric carbon atoms or double bonds, which are not specifically indicated in the General formula (I). Different specific configuration of stereoisomers, such as enantiomers, diastereomers, CIS-isomers and TRANS-isomers encompassed by formula (I). They are obtained by customary methods from mixtures of the stereoisomers or by stereotypically reaction using stereochemical pure starting materials.

The compounds of formula (I) can form salts in which the hydrogen group-SO2NH - substituted suitable for agriculture cation. Such salts are, for example, metal salts, in particular alkali or alkaline earth metals, especially sodium and potassium salts, and also ammonium salts or salts with organic amines.

In the first group of preferred derivatives phenylsulfonylacetate General formula (I) include compounds in which

R2hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms,

R3- alkylsulfonyl with 1 to 4 carbon atoms, haloalkylthio with 1-4 carbon atoms, forcarbon noalter with 1-4 carbon atoms, dialkylaminoalkyl with 1-4 carbon atoms in each alkyl part, alkylsulphonyl with 1-6 carbon atoms in the alkyl part, with the alkyl part may be substituted one or more times by halogen atoms, alkoxy group with 1-4 carbon atoms, formyl, cycloalkylcarbonyl with 3-6 carbon atoms in cycloalkyl part, a group of the formula

< / BR>
where W denotes an oxygen atom or sulfur,

R6is alkyl with 1-4 carbon atoms,

R7and R8independently of one another denote hydrogen or alkyl with 1-4 carbon atoms, unsubstituted or multiply substituted by halogen atoms, and their salts.

The second group preferred derivatives phenylsulfonylacetate General formula (I) include compounds in which

R2is hydrogen, alkyl with 1-4 carbon atoms,

R3- alkylsulfonyl with 1 to 4 carbon atoms, formyl, alkylsulphonyl with 1-4 carbon atoms in the alkyl part, unsubstituted or singly or multiply substituted by halogen atoms, cycloalkylcarbonyl with 3-6 carbon atoms in cycloalkyl part, a group of the formula

< / BR>
where W, T, R6-R8have the above meaning,

A group of the formula

< / BR>
where Z is - CH=, -N=,

one of the radicals X and Y UB>2CF3and the other radical X or Y represents alkyl with 1 to 2 carbon atoms, alkoxy with 1-2 carbon atoms, haloalkoxy with 1-2 carbon atoms, and their salts.

Derivative phenylsulfonylacetate General formula (I) can be obtained by known methods, for example, the fact that the compound of formula (II)

< / BR>
where R1-R3have the above meaning, is subjected to the interaction with a heterocyclic carbamate of formula (III)

R*-O-CO-NR4-A (III),

where R4and A have the above meaning, a R*means unsubstituted or substituted phenyl or alkyl with 1-4 carbon atoms, or

b) phenylsulfonylacetate formula (IV)

< / BR>
where R1-R3have the above meaning, is subjected to the interaction with aminoheterocycles formula (V)

H-NR4-A (V),

where R4and A have the above meaning,

or

in) sulfonylation formula (VI)

< / BR>
where R1-R3have the above meaning, is subjected to the interaction with aminoheterocycles above formula (V),

or

d) aminoheterocycles above formula (V) is subjected to interaction with phosgene in the presence of a base and subsequent interaction obtained when e is>/BR>< / BR>
where R1-R3have the above meaning, is subjected to the interaction with the cyanate M-OCN, where M - NH4, sodium or potassium, and aminoheterocycles above formula (V) in the presence of a base,

or

e) a sulfonamide of the above-mentioned formula (II) is subjected to interaction with the (thio)isocyanate of the formula (V')

W=C=N-A (V')

where W and A have the above meaning, in the presence of a base.

The reaction of a) - d) lead to the formation of compounds of formula (I), where W stands for oxygen. If necessary, oxygen W can be transferred at the nitrogen atom by known techniques.

The reaction of compounds of formulas (II) and (III) is preferably carried out in the presence of an employee as a catalyst base in an inert organic solvent, such as, for example, dichloromethane, acetonitrile, dioxane or tetrahydrofuran, at temperatures from 0oC to the boiling point of the solvent. At the same time as the base used, for example, organic aminoaniline, such as 1,8-diazabicyclo[5.4.0]undec-7-ene, in particular when R*= (substituted) phenyl, trimethylsilyl or triethylaluminium, in particular when R*= alkyl.

Source sulfonamides of the formula (II) represent ), where R2and R3mean hydrogen, and Q is oxygen, further explains the opportunities, which, with some modifications suitable to obtain the compounds (II), where R2and R3not mean hydrogen, and Q does not mean oxygen.

On the basis of unsubstituted or substituted medieninformatik formula (VIII), which is first transferred to the NITRILES of the formula (IX) by diazotization and interaction with potassium cyanide and copper according to the method of Sandmaier receive a sulfonamide of the formula (X) after saponification of the nitrile, the esterification of carboxylic acids and translation sulfonic acids in protected tert.butila the sulfonamide by known methods as an intermediate product (see scheme 1).

Scheme 1:

< / BR>
In addition, the sulfonamides of the formula (X) obtained from unsubstituted or substituted methylnitrobenzene acids of the formula (XI) by esterification, recovery nitro group, diazotization, and the combination with the sulfur dioxide in the presence of copper chloride (I) and aminolysis tert.- butylamine (see diagram 2).

Scheme 2:

< / BR>
Sulfonamides of formula (X) are also based on unsubstituted or substituted methylnitrosamino formula (XII). The diazotization and the combination with the cyanide cleareventlog acid of the formula (XIII).

The nitro group can be converted to tert-butylaminoethyl (see diagram 3).

Scheme 3:

< / BR>
Sulfonamides of formula (II) are obtained as follows: the compounds of formula (X) are galogenirovannyie on the side chains with the formation of compounds of the formula (XIV), in which the halogen atom is replaced by an amine or azide, followed by reduction to benzylamino formula (XV') and the further derivatization of the amino group and the removal of the protective tertbutyl known techniques, for example using triperoxonane acid. So get sulfonamides of the formula (II') (see scheme 4).

Scheme 4:

< / BR>
This method can also be applied to obtain other compounds of formula (II), and at the last stage of the process applied compound of formula (XV)

< / BR>
The carbamates of the formula (III) can be obtained by known methods.

The interaction of compounds of the formula (IV) with aminoheterocycles formula (V) are preferably in inert, aprotic solvents, such as dioxane, acetonitrile or tetrahydrofuran, at temperatures from 0oC to the boiling point of the solvent. The necessary starting compound of the formula (V) are known from the literature or they can get well-known --- >/P>Phenylsulfonylacetate formula (VI) are known or can be obtained by known methods and subject interaction with aminoheterocycles formula (V).

Vosganian compounds of the formula (V) according to method d) is carried out preferably in the presence of bases, such as spatial employed organic aminoaniline, such as triethylamine. Subsequent interaction with compounds of the formula (II) according to method d) can be carried out in a known manner.

Sulfochloride formula (VII) can be obtained from the corresponding sulfonic acids by conventional methods such as, for example, the interaction of the potassium salt with phosphoroxychloride or thionyl chloride in inert solvents such as acetonitrile and/or tetramethylsilane, or without them by heating under reflux.

The corresponding sulphonic acids are obtained from the corresponding nitro compound by the method described in scheme 2.

Alternatively, in some cases, sulfochloride formula (VII) is obtained by sulfonation followed by chlorination or sulfochlorinated suitable substituted esters of benzoic acid; the sulfonation or sulfochlorinated are investimenti (thio)isocyanates (V') with compounds (II) takes place at temperatures from -10oC to +100oC, preferably from 20 to 100oC, in an inert aprotic solvent, such as, for example, acetone or acetonitrile, in the presence of a suitable base, such as, for example, triethylamine or potassium carbonate.

Salts of compounds of formula (I) preferably get in inert polar solvents, such as, for example, water, methanol or acetone, at temperatures from 0 to 100oC. as suitable grounds for obtaining salts of the proposed compounds are used, for example, a carbonate of alkali metals such as potassium carbonate, or hydroxide of alkali or alkaline earth metals, such as, for example, sodium hydroxide or potassium hydroxide, and ammonia or ethanolamine.

The term "inertia solvent" refers to solvents which are inert under the respective reaction conditions, but which should not be inert under any conditions.

Derivative phenylsulfonylacetate General formula (I) are herbicide activity and therefore they can be an active ingredient herbicide funds, which is the third object of the invention.

The proposed product contains the active substance in effectivity in the form of any standard of drug. Such preparations can be, for example, wettable powders, soluble powders, water-soluble concentrates, emulsifiable concentrates, emulsions such as emulsions of the type water-in-oil and oil-in-water, spray solutions, suspension concentrates, dispersions based on oil or water mixed with oil solutions that are enclosed in capsules, suspensions, dust products, treaters, sprinkle the granules, granules for application to soil, microgranules, spray granules, suspension granules, adsorption granules, water dispersible granules, water-soluble granules, drugs intended for extremely fine distribution of the active principle, microcapsules and waxes.

Under "wettable powder" refers to drugs that are uniformly dispersible in water, which contain along with the active substance and a diluent or inert substance, also surfactants of ionic and/or nonionic type (wetting and dispersing agents), such as, for example, polyoxyethylene ALKYLPHENOLS, polyoxyethylene the fatty alcohols, polyoxyethylene fatty amines, sulfates simple polyglycolic ether alcohol IRN sly sodium, dibutylethanolamine sodium, oleoylethanolamide sodium. To obtain a wettable powder herbicide active substance is finely pulverized, for example, in conventional devices, such as hammer mills, blower mills, mills with jet blower, and together with the grinding or after it is mixed with auxiliary substances.

Emulsifiable concentrates are obtained by dissolving the active substance in an organic solvent, such as, for example butanol, cyclohexanone, dimethylformamide, xylene, high boiling fragrances or hydrocarbons, mixtures of organic solvents with addition of one or more surfactants of ionic or nonionic type (emulsifiers). As emulsifiers used, for example, alkylarylsulfonate calcium salts such as, for example, dodecylbenzenesulfonate calcium, or nonionic emulsifiers, such as, for example, a complex polyglycolic a fatty acid ester, a simple alkylarylsulphonates ether, simple polyglycidyl ether of fatty alcohol series, condensation products of propylene oxide and ethylene, a simple alkylhalides, complex sorbitane esters, such as, for example, a complex polyoxyethylenesorbitan ether fatty acids.

Powdered preparations are obtained by grinding the active substance with finely dispersed solids, such as, for example, talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water-based or oil. Get them, for example, by wet grinding by means available in tigole mills and, if necessary, by adding the above-mentioned surface-active substances.

Emulsions such as emulsions of the type oil-in-water, will get, for example, by means of stirrers, colloid mills and/or static mixers using aqueous organic solvents and, if necessary, the above-mentioned surface-active substances.

The granules are produced either by spraying the active substance capable of adsorption, granulated inert material or by applying concentrates of the active substance by means of adhesives, such as, for example, polyvinyl alcohol, polyacrylnitril sodium, mineral oil, to the surface of carriers as sand, kaolinites or granulated inert material. In addition, it is possible granulation suitable active substances izvestnymi> Dispersible in water, the granules get, as a rule, by the usual methods, such as, for example, spray drying, spray granulation in the fluidized bed, pelletizing plates, mixing using high-speed mixers and extrusion without the use of a solid inert material.

The granulates obtained using plates, fluidized bed, extruder, or by spraying.

The proposed product contains, as a rule, 0.1 to 99 wt.%, in particular 0.1 to 95 wt.% the active substance of the formula (I). The concentration of active substance in wettable powders is about 10 to 90 wt.%, and the balance up to 100 weight. % consists of conventional auxiliary substances. In emulsifiable concentrates, the concentration of the active substance is about 1-90, preferably 5-80 wt.%. Powdered preparations containing 1-30 wt.%, preferably 5-20 wt.% the active substance, and spray solutions contain approximately 0.05 to 80, preferably 2-50 wt.% the active substance. If dispergiruyushchie granules in water, the concentration of the active substance depends partly on whether the active substance in liquid or solid state, and type of excipients, fillers and t as the target additives proposed facility contains customary adhesives, the wetting and dispersing agents, emulsifying agents promoting penetration agents, preservatives, antifreeze agents, solvents, fillers, carriers, colorants, defoamers, retarding evaporation means, means affecting the pH and viscosity.

The fourth object of the invention is a method of combating weeds, which is that the compounds of formula (I) is applied on plants, their seeds or the biosphere in an effective amount.

The flow rate of the compounds of formula (I) depends on external conditions, such as temperature, humidity, the type of herbicide. It can vary within wide limits, for example, from 0.001 to 10.0 kg/ha or more of active substance, but preferably it is from 0.005 to 5 kg/ha.

Receipt of the proposed compounds of General formula (I) is illustrated by the following examples.

Example 1. Obtain N-tert-butyl-5-methyl bromide-2 - methoxycarbonylmethylene

A solution of 54.8 g (192 mmol) of N-tert-butyl-2-methoxycarbonyl-5 - methylbenzenesulfonamide in 420 ml of carbon tetrachloride is heated under reflux for 8 hours with simultaneous irradiation with fluorescent light in a nitrogen atmosphere n the shape, sequentially washed with a solution of sodium bisulfite, sodium bicarbonate solution and water, dried over sodium sulfate and fully concentrated under reduced pressure. Crystallization of the residue from diisopropyl ether and complex ethyl ester acetic acid, receive a 41.9 g (57%) of N-tert-butyl-5-methyl bromide-2 - methoxycarbonylmethylene with a melting point of 88-90oC.

Example 2. Obtain N-tert-butyl-5-azidomethyl-2 - methoxycarbonylmethylene

A solution of 25.5 g (70 mmol) of N-tert-butyl-5-methyl bromide-2 - methoxycarbonylmethylene and 5.9 g (90 mmol) of sodium azide in 240 ml of ethanol is heated under reflux for 6 hours. Then fully concentrated and the resulting residue extracted with a mixture of water and complex ethyl ester of acetic acid. In the result of thererofre crude product in an environment diisopropyl ether obtain 16.6 g (72,5%) N-tert - butyl-5-azidomethyl-2-methoxycarbonylmethylene with a melting point of 63-65oC.

Example 3. Obtain N-tert-butyl-5-aminomethyl-2 - methoxycarbonylmethylene

16.3 g (50 mmol) N-tert-butyl-5-azidomethyl-2 - methoxycarbonylmethylene dissolved in 300 ml of methanol and hydronaut in the presence of 5% of Pallady the silica gel column using as eluent a mixture of complex ethyl ester of acetic acid and methanol in the ratio, equal to 4:1. Obtain 11.2 g (74%) of N-tert-butyl-5-aminomethyl-2-methoxycarbonylmethylene as a viscous oil.

1H NMR (100 MHz, CDCl3): = 1,25 (s, N, C(CH3)3), 1,80 (Shir.s, 2H, NH2), of 3.95 (s, 3H, OCH3), of 4.00 (s, 2H, aryl-CH2), 6,20 (Shir.s, 1H, SO2NH), 7,58 (DD, 1H, aryl-H), 7,80 (d, 1H, aryl-H), 8,10 (DD, 1H, aryl-H).

Example 4. Obtain N-tert-butyl-5-atsetamidometil-2 - methoxycarbonylmethylene

To a cooled to a temperature of 0oC solution 2,01 g (6.7 mmol) of N-tert-butyl-5-aminomethyl-2 - methoxycarbonylmethylene and with 0.93 ml (6.7 mmol) of triethylamine in 30 ml of dichloromethane was added dropwise a solution to 0.63 g (8 mmol) acetylchloride in 10 ml of dichloromethane followed by a translation at room temperature for 2 hours. The mixture is then washed with water, dried and fully concentrated under reduced pressure. Obtain 2.1 g (91%) of N-tert-butyl-5-atsetamidometil-2 - methoxycarbonylmethylene as a viscous oil.

1H NMR (100 MHz, CDCl3): = 1,25 (s, N, C(CH3)3), was 2.05 (s, 3H, COCH3), of 3.95 (s, 3H, OCH3), 4,50 (s, 2H, aryl-CH2), x 6.15 (s, 1H, SO2NH), 6,38 (Shir. t, 1H, NH), 7,47 (DD, 1H, aryl-H), to 7.75 (d, 1H, aryl-H), 7,95 (DD, 1H, aryl-H).

Example 5. Getting 5-atsetamidometil-2 - meth is sulfonamide in 25 ml triperoxonane acid was stirred at room temperature for 14 hours and then evaporated. Crystallization of the residue from complex ethyl ester acetic acid gain of 1.33 g (76%) 5-atsetamidometil-2 - methoxycarbonylmethylene with a melting point of 173-175oC.

Example 6. Obtaining N-[(4,6-dimethoxypyrimidine-2 - yl)aminocarbonyl]-5-atsetamidometil-2 - methoxycarbonylmethylene.

A suspension of 1.3 g (of 4.54 mmol) 5-atsetamidometil-2-methoxycarbonylmethylene and 1.25 g (of 4.54 mmol) of N-(4,6-dimethoxypyrimidine-2-yl)phenylcarbamate in 20 ml of acetonitrile serves 0,69 g (of 4.54 mmol) of 1,8-diazabicyclo[5,4,0] undec-7-ene at a temperature of 0oC. After 2 hours at room temperature the mixture is diluted with water and diethyl ether and acidified with hydrochloric acid to pH 1-2. The precipitation onfiltered and dried. Get 1,32 g (62%) of N-[(4,6 - dimethoxypyrimidine-2-yl)aminocarbonyl]-5-atsetamidometil-2 - methoxycarbonylmethylene with a melting point of 149-150oC.

Summarized in tables 1-4 of the compounds of formula (I) are similar to examples 1-6.

The examples illustrate how the proposed herbicide kompoziciu.

Composition A. 10 weight. parts of the compound of example 1 is blended with 90 weight. parts of talc as inert substance and the resulting mixture is ground in shock mölln is 64 weight. parts containing kaolin quartz as inert substance, 10 weight. parts ligninsulfonate potassium and 1 weight. part oleoylethanolamide sodium as wetting agent and dispersant, and the resulting mixture was ground in a rod mill with getting legalisierung in water wettable powder.

The composition of the Century 20 weight. parts of compound No. 2 in table 1 was mixed with 6 weight. parts simple alkylphenol ether (trade product Triton X 207), 3 weight. parts simple isotridekanolethoxylate ether containing 8 mol of ethylene oxide, and 71 weight. part of paraffinic mineral oil (boiling within about 255 to above 277oC) and the resulting mixture is ground in a ball mill until a particle size below 5 microns. Get legalisierung in water dispersion concentrate.

Composition, 15 weight. parts of compound No. 4 in table 1 was mixed with 75 weight. parts of cyclohexanone as solvent and 10 weight. parts of oxyethylated Nonylphenol as emulsifier. Get emulsifiable concentrate.

Composition D. 75 weight. parts of compound No. 6 of table 1 is mixed with 10 weight. parts ligninsulfonate calcium, 5 weight. parts of lauryl sodium, 3 and powder granularit in the fluidized bed by injecting water into it. Get dispersible in water granulate.

The composition that is In a colloidal mill homogenized and pre-milled mixture of 25 weight. parts of compound No. 1 of table 2, 5 weight. parts of 2,2'-dynafilter-6,6'-disulfonic sodium, 2 weight. parts oleoylethanolamide sodium, 1 weight. part of polyvinyl alcohol, 17 weight. parts of calcium carbonate and 50 weight. parts of water. Then carry out the grinding to the desired size of the particles and the resulting suspension is sprayed and dried in the spray tower, equipped with a single nozzle. Get dispersible in water granulate.

The following experiments explain herbicide activity, which is determined by the following criteria: good activity - 50-70%; very good activity 70-100%.

Experience I. the Effect on the weeds in the pre-emergence treatment.

Seeds and isomnia pieces of mono - and decotigny weeds contribute in sandy clay soil in plastic pots. Then on the ground put the covering layer of the same land. Available in the form of a wettable powder or emulsion concentrate the following compounds of formula (I) and their salts diluted with water, taken in the amount of 600 to 800 l/ha of the resulting aqueous suspension or emulsion of nae in terms of weed growth. Optical assessment of damage to the plants is carried out after the shoot experimental plants 3-4 weeks compared to untreated control plants. The results of the experiments show that the investigated compounds exhibit good herbicide activity against a broad spectrum of weed grasses and plants. So, for example, at a flow rate of 0.3-0,005 kg/ha of compound N 1-69, are shown in table 1, compound No. 1 - 17, are shown in table 2, the compounds No. 1, 2, are given in table 3, and the compound No. 1 in table 4, show a very good herbicide activity against weeds such as Sinapis alba, Stellaria media, Chrysanthemum segetum and Lolium Polygonum.

Experience II. The effect on the weeds in the post-harvest processing

Seeds and isomnia pieces of mono - and decotigny weeds contribute in sandy clay soil in plastic pots and then on the ground put the covering layer of the same land. The pots are placed in a greenhouse under conditions of growth of the weeds. Three weeks after sowing the processing of experimental plants in the stage of development of the three leaf herbicides. Available as a wettable powder and emulsion concentrate the following compounds of formula (I) and their salts rabbaani in different doses. After 3-4 weeks of growing test plants in the greenhouse under optimal conditions determine the optical activity of drugs in comparison with untreated control plants. And during post-harvest processing of the proposed tools are good herbicide activity against a wide range of important from an economic point of view weeds and plants. For example, at a flow rate of 0.3-0,005 kg/ha of compound N 1-69, are shown in table 1, the compounds 1-17 N, are shown in table 2, the compounds No. 1, 2, are given in table 3, and the compound No. 1 in table 4, show a good herbicide activity against weeds such as Sinapis alba, Stellaria media, Chrysanthemum segetum and Lolium Polygonum.

Experience III. Tolerance to herbicides cultivated plants.

In other experiments the seeds of a number of cultivated plants and weeds put in a sandy clay soil in plastic pots and then on the ground put the covering layer of the same land.

Part of the pots treated according to experience II, and the remaining pots are placed in a greenhouse until the development of two or three true leaves in plants. Then treated according to experience II, and the above compounds of formula (I) ilcesi determine that pre-emergence, and during post-harvest processing of the proposed connection does not have any negative effects on dicotyledonous crops such as, for example, soybean, cotton, canola, sugar beets, potatoes, even if they are used in high doses. Some active substances't even have any negative effects on cereal plants such as, for example, barley, wheat, rye, sorghum ordinary, corn or rice.

1. Derivative phenylsulfonylacetate General formula I

< / BR>
where R1group CO-Q-R5;

R2is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms;

R3- alkylsulfonyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1 to 4 carbon atoms or dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part, with the alkyl part can be single or multiply substituted with halogen, alkoxygroup with 1 to 4 carbon atoms, phenylcarbinol, phenylsulfonyl, phenyl residue which may be substituted by alkyl with 1 to 4 carbon atoms, formyl group of the formula-CO-CO-R', where R' is alkoxy with 1 to 4 carbon atoms, cycloalkylcarbonyl with 3 - 6 ATO is UP> located in the para-position relative to the group of SO2the rest of the sulfonylureas, R3does not mean the unsubstituted alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part;

R2and R3together mean a group of the formula (CH2)mIn - or-IN1-(CH2)m1-Where and1independently from each other - sulfonyl or carbonyl; m = 3,4, m1= 2, 3,

W is oxygen atom or sulfur;

Q is an oxygen atom or the group-NR9-;

T is an oxygen atom or sulfur;

R4is hydrogen or methyl;

R5is hydrogen, alkyl with 1 to 4 carbon atoms;

R6is alkyl with 1 to 4 carbon atoms;

R7and R8independently from each other hydrogen or alkyl with 1 to 4 carbon atoms, unsubstituted or multiply substituted with halogen;

R9is alkyl with 1 to 4 carbon atoms,

A group of the formula

< / BR>
where Z is - CH = or-N=: one of the radicals X and Y is hydrogen, halogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms and the other radical X or Y is hydrogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms, mono - or dialkylamino with 1 to 3 carbon atoms in each alkyl group,

or with the 1 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, R3- alkylsulfonyl with 1 to 4 carbon atoms, haloalkylthio with 1 to 4 carbon atoms, phenylcarbinol, phenylsulfonyl, phenyl residue which may be substituted by alkyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1 to 4 carbon atoms, dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part, with the alkyl part may be substituted one or more times by halogen atoms, alkoxygroup with 1 to 4 carbon atoms, formyl, cycloalkylcarbonyl with 3 to 6 carbon atoms in cycloalkyl part, a group of the formula

< / BR>
where W is an oxygen atom or sulfur;

R6is alkyl with 1 to 4 carbon atoms;

R7and R8independently from each other hydrogen or alkyl with 1 to 4 carbon atoms, unsubstituted or multiply substituted by halogen atoms,

or their salts.

3. Derivative phenylsulfonylacetate General formula I under item 1 or 2, in which R2is hydrogen, alkyl with 1 to 4 carbon atoms, R3- alkylsulfonyl with 1 to 4 carbon atoms, formyl, alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, unsubstituted or mono - or multiply substituted

where W, T, R6-R8have the above significance, And is a group of the formula

< / BR>
where Z is - CH= , -N= , one of the radicals X and Y is hydrogen, alkyl with 1 to 2 carbon atoms, alkoxy with 1 to 2 carbon atoms, the group OCF2N, CF3or OCH2CF3and the other radical X or Y is alkyl with 1 to 2 carbon atoms, alkoxy with 1 to 2 carbon atoms, haloalkoxy with 1 to 2 carbon atoms,

or their salts.

4. Derivatives sulfonamida General formula III

< / BR>
where R1-R3are specified in paragraph 1 values

as starting compounds for obtaining derivatives phenylsulfonylacetate formula I on PP.1 - 3.

5. Herbicide remedy containing the active substance based on the derivatives of phenylsulfonylacetate and at least one additive, characterized in that as a derivative phenylsulfonylacetate it contains at least one compound of General formula (I)

< / BR>
where R1the group CO-Q-R5;

R2is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms;

R3- alkylsulfonyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1 to 4 carbon atoms or dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl care substituted with halogen, alkoxygroup with 1 to 4 carbon atoms, phenylcarbinol, phenylsulfonyl, the phenyl ostatu which may be substituted by alkyl with 1 to 4 carbon atoms, formyl group of the formula-CO-CO-R', where R' is alkoxy with 1 to 4 carbon atoms, cycloalkylcarbonyl with 3 to 6 carbon atoms in cycloalkyl part, a group of the formula

< / BR>
moreover, if the group-CH2-NR2R3located in the para-position with respect to the group SO the rest of the sulfonylureas, R3does not mean the unsubstituted alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part.

R2and R3together mean a group of the formula (CH2)mIn - or-IN1-(CH2)m1-B-, where b and b1independently from each other - sulfonyl or carbonyl, m = 3,4, m1= 2,3;

W is oxygen atom or sulfur;

Q is an oxygen atom or the group-NR9-;

T is an oxygen atom or sulfur;

R4is hydrogen or methyl;

R5is hydrogen, alkyl with 1 to 4 carbon atoms;

R6is alkyl with 1 to 4 carbon atoms;

R7and R8independently from each other hydrogen or alkyl with 1 to 4 carbon atoms, unsubstituted or multiply substituted with halogen;

R9is alkyl with 1 to 4 carbon atoms;

A group of the formula
tamaseni or substituted by halogen atoms, and the other radical X or Y is hydrogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms, mono - or dialkylamino with 1 to 3 carbon atoms in each alkyl group,

or its salt in an effective amount.

6. The method of combating weeds by treating the latter, their seeds or biosphere derivative phenylsulfonylacetate, characterized in that as a derivative phenylsulfonylacetate use at least one compound of General formula (I)

< / BR>
where R1group CO-Q-R5;

R2is hydrogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms;

R3- alkylsulfonyl with 1 to 4 carbon atoms, monoalkylbenzenes with 1 to 4 carbon atoms or dialkylaminoalkyl with 1 to 4 carbon atoms in each alkyl part, alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part, with the alkyl part can be single or multiply substituted with halogen, alkoxygroup with 1 to 4 carbon atoms, phenylcarbinol, phenylsulfonyl, phenyl residue which may be substituted by alkyl with 1 to 4 carbon atoms, formyl group of the formula-CO-CO-R', where R' is alkoxy with 1 to 4 carbon atoms, cycloalkylcarbonyl with 3 to 6 atoms in titsa in the para-position relative to the group of SO2the rest of the sulfonylureas, R3does not mean the unsubstituted alkylsulphonyl with 1 to 6 carbon atoms in the alkyl part,

R2and R3together mean a group of the formula (CH2)mIn - or-IN1-(CH2)m1-B-, where b and b1independently from each other - sulfonyl or carbonyl, m = 3,4, and m1= 2,3,

W is oxygen atom or sulfur;

Q is an oxygen atom or the group-NR9-;

T is an oxygen atom or sulfur;

R4is hydrogen or methyl;

R5is hydrogen, alkyl with 1 to 4 carbon atoms;

R6is alkyl with 1 to 4 carbon atoms;

R7and R8independently from each other hydrogen or alkyl with 1 to 4 carbon atoms, unsubstituted or multiply substituted with halogen;

R9is alkyl with 1 to 4 carbon atoms;

A group of the formula

< / BR>
where Z is - CH = or-N=; one of the radicals X and Y is hydrogen, halogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms, mono - or dialkylamino with 1 to 4 carbon atoms in each alkyl group and the other radical X or Y is hydrogen, alkyl or alkoxy with 1 to 3 carbon atoms, unsubstituted or substituted by halogen atoms, mono - or dialkylamino with 1 to 4 carbon atoms in each alkyl

 

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