Substituted derivatives of pyridinesulfonamide, herbicide composition, derivatives pyridinesulfonamide

 

(57) Abstract:

Usage: agriculture as a herbicide funds. The inventive product - substituted derivatives of pyridinesulfonamide formula I specified in the text of the description, where R1- C1-5-alkyl, C1-3-homogeneity,1-2-alkoxy, C1-2-alkyl, vinyl, WITH3-6-cyclohexyl, phenyl. Product - derived pyridinesulfonamide formula II, as specified in the text of the description, where R1has the specified values. Herbicide composition with compounds of the formula I in amounts of 1 to 75 wt.h. 3 S. and 1 C. p. F.-ly, 8 PL.

The invention relates to the field of derivative pyridinesulfonamide, in particular to substituted derivative pyridinesulfonamide formula I, herbicide compositions, derived pyridinesulfonamide formula II.

Known derivative pyridinesulfonamide. However, herbicide activity is not high enough.

The aim of the invention is to find new compounds with higher herbicide activity and allows you to get the herbicide compositions on their basis, as well as refined and herbicide composition.

In accordance with one aspect of the invention provides substituted derivative of pyridinesulfonamide or its salt represented by the General formula I

< / BR>
where R1and R2may be each independently a member selected for the group, including unsubstituted or substituted alkyl group, unsubstituted or substituted alkeneamine group, unsubstituted or substituted cycloalkyl group and unsubstituted or substituted phenyl group, or are connected to each other to form -(CH2)ngroup, in which n is an integer of 2-5, X and Y each independently represents a member selected from the group comprising alkyl groups and alkoxygroup.

According to another aspect of the invention provides a method of obtaining a substituted derivative of pyridinesulfonamide or its salt represented by the General formula I

R1SO SO2NHNH where R1and R2can be either each independently a member selected from the group, including substituted alkyl groups, unsubstituted or substituted alkeneamine group, unsubstituted or substituted cycloalkyl group, unsubstituted or substituted phenyl group or are connected to each other to form -(CH2)ngroup, in PPy and alkoxygroup, the method consists in the reaction of substituted pyridine derivative represented by the General formula II

(II)where R1and R2take these values and Z1is a member selected from the group comprising-NH2group, NCO group, and-NHCO2R3group, where R3is alkyl or aryl, with a pyrimidine derivative represented by the General formula III

Z (III) where X and Y take the values specified and Z2represents-NH2group, when Z1NCO group, or-NHCO2R3group, and is a member selected from the group including: -NCO group and NHCO2R3group, where R3adopt these values, if Z1-NH2group.

According to another aspect of the invention provides a herbicide containing as an active ingredient substitution derived pyridinesulfonamide or its salt represented by the General formula I

R1SO SO2NHNH (I) where R1and R2can be either each independently a member selected from the group comprising: unsubstituted or substituted alkyl group, unsubstituted or substituted alkyl group, unsubstituted or substituted cycloalkyl group and unsubstituted or substituted phenyl group, the first independent member, selected from the group comprising alkyl groups and alkoxygroup.

According to an additional aspect of the invention provides substituted pyridine derivative represented by the General formula (II-1

(II-1)where R1and R2can be either each independently a member selected from the group comprising: unsubstituted or substituted alkyl group, unsubstituted or substituted alkeneamine group, unsubstituted or substituted cycloalkyl group and unsubstituted or substituted phenyl group, or are connected to each other to form -(CH2)ngroup, in which n is an integer of 2-5.

In the definitions of R1and R2in the General formula (I), the substituents that may be contained in the substituted alkyl groups and substituted alkenyl groups include halogen atoms, alkoxygroup etc., substituents that may be contained in the substituted cycloalkyl groups include halogen atoms, alkyl groups, alkoxygroup, etc., and the substituents that may be contained in the substituted phenyl groups include halogen atoms, alkyl groups, haloalkyl group, nitro group and so on, the Number of substituents contained in such substituted group can ravnets the e true for deputies, which, in turn, may be contained in the above-mentioned substituents, the replacement of the substituted groups represented by R1and R2.

In the General formula (I) alkyl groups, and alkyl fragments that can be included in the definition of R1, R2X and Y include groups with 1-5 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, which may be linear or branched terms of isomerism aliphatic chain. Alchemilla group, which may be included in the definition of R1includes group, such as vinyl. Cycloalkyl groups that can be included in the definition of R1and R2include group with 3-6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The halogen atoms that can be included in the values of R1and R2include fluorine atoms, chlorine, bromine and iodine.

Of the compounds of formula (I) substituted derivative pyridinesulfonamide may include a number of compounds of optical isomers, depending on the substituent(s) R1and/or R2; among the most preferred compounds include: 6-[(N-ethyl-N-methyl-sulfonyl)amino] -N-[[4, 6-dimethoxypyrimidine-2-yl) amino] carbonyl]-2-Piri is reincorporated (compound 18), and 6-[(N-ethyl-N-isopropylphenyl)amino] -N-[[4,6-dimethoxypyrimidine-2-yl) amino] carbonyl] -2-pyridinesulfonamide (compound 22).

Substituted derivative of pyridinesulfonamide General formula (I) can be obtained, for example, the proposed method embodiment which is reflected in the following schemes reactions /A/-/D/:

+ R_____ (I)

+ _____ (I)

+ H_____ (I)

+_____(I)< / BR>
The diagrams reactions /A/-/D/ R1, R2X and Y agree to the above values and R3is alkyl or aryl. An alkyl group, including the definition of R3can be any alkyl group, as described in connection with the definitions of R1, R2X and y as the aryl groups included in the definition of R3, may be mentioned phenyl, phenyl substituted by at least one chlorine atom, phenyl, substituted by at least one of the stands, naphthyl, etc.

Reaction A is carried out in the presence of base, reaction /B/, /C/ and /D/, if desired, can also be carried out in the presence of a base. Examples of such bases include tertiary amines such as triethylamine and 1,8-diazabicyclo[5.4.0]-7-undecene.

Reaction /A/, /B/, /C/ and /D/ can be carried out in the presence of a solvent, if necessary. Examples Rast and chlorobenzene; unsubstituted or substituted cyclic or acyclic aliphatic hydrocarbons, such as chloroform, carbon tetrachloride, methylene chloride, dichloroethane, trichloroethane, hexane and cyclohexane; ethers, such as diethyl ether, dioxane and tetrahydrofuran; NITRILES, such as acetonitrile, propionitrile and Acrylonitrile; esters such as methyl acetate and ethyl acetate; aprotic polar solvents such as dimethylsulfoxide and sulfolane etc.

The reaction temperature in the case of reaction /A/ is usually in the range of from -20 to 100aboutWith, preferably in the range of 0-40aboutC and the reaction time for the reaction of /A/ is usually in the range of 0.01 to 24 hours, preferably in the range of 0.1 to 1.5 hours the reaction Temperature for the reaction of /B/ is usually in the range of 0-150aboutC and the reaction time for the reaction of /B/ is usually in the range of 0.1 to 24 hours, the reaction Temperature for the reaction of /C/ is usually in the range of 0-150aboutC and the reaction time for the reaction /C/ usually intervale 0.1 to 24 hours, the reaction Temperature for the reaction of /D/ is usually in the range of -20 to +150aboutC and the reaction time for the reaction of /D/ is usually in the range of 0.1 to 24 hours

The original compound of General formula (II-1) diagrams of reactions of /A/ and /B/ of the invention can be synthesized, for example, according to one B> and R2each independently is a member selected from the group comprising: unsubstituted or substituted alkyl group, unsubstituted or substituted alkeneamine group, unsubstituted or substituted cycloalkyl group and unsubstituted or substituted phenyl group; n takes on the values specified in connection with General formula (I); t and Tabouteach independently is a member selected from the group comprising: a chlorine atom, a bromine atom, a iodine atom; Ph means phenyl; Et means these Bu(t) denotes tert-butyl and aq. means an aqueous solution. Substituted alkyl, alkeline, cycloalkyl and phenyl groups included in the definition of R1and R2the same as defined in connection with the definitions for R1and R2.

The original compound represented by the reaction scheme /C/ by the formula (II-2) may be obtained, for example, according to the following reaction scheme /H/:

The reaction scheme for the /H/

(I) CH3(CH2)3NCO

(II-1) TO (II-2)

(2) COCl2, xylene

The original compound represented by the reaction scheme for the /D/ of the formula (II-3) can be synthesized, for example, according to the following reaction scheme I:

The reaction scheme for the /I/ (II-1) to (II-3)

R1, R2and R3in the diagrams is eacli, the reaction time, the use or not use, and type and quantity of solvent (optionally used), the type and number of bases, can usually be easily selected by analogy with the reaction conditions for such reactions, unless otherwise specified. Salt mentioned substituted derivative of pyridinesulfonamide can be easily obtained in the usual manner.

The examples serve to more pick illustrate the invention, but they should not be construed as limiting the scope of invention.

P R I m e R synthesis 1. Synthesis of 6-[(N-ethyl-N-methylsulphonyl)amino]-N-[[(4,6-demeton - Sipiagin-2-yl) amino] carbonyl] -2-pyridinesulfonamide (compound 2 in table.2).

1) In an autoclave mix 13 g of 2-benzylthio-6-bromopyridine, 80 ml of aqueous ammonia (about 40 wt.) and a catalytic amount of copper chloride (I) and heated 4 h at 120aboutC. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:3) and obtain 5.7 g of 2-amino-6-benzoylthiophene, those who Ana, to the mixture mix 1,67 g of powdered potassium hydroxide and then stirred at room temperature. The resulting mixture is cooled with ice to a chilled mixture are added dropwise to 6.1 g methanesulfonanilide, after which the reaction mixture is stirred for about a day at room temperature. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:1) and obtain 1.5 g of N-(6-benzylcyanide-2-yl)methanesulfonamide c melting point 123-125aboutC.

3) Obtained at the previous stage N-(6-benzylcyanide-2-yl) methanesulfonamide (1 g) is mixed with 15 ml of tetrahydrofuran, the mixture is cooled with ice, add 0.15 g of sodium hydride (60 wt.), and the mixture is stirred at room temperature. Then added to the mixture of 3.56 g of ethyliodide and the resulting mixture is boiled for about a day. Upon completion of the reaction, the reaction mixture is transferred into the water, weakly acidified with hydrochloric acid and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate and concentrate what Finance with a mixture of ethyl acetate hexane (1:1) and obtain 0.8 g of white crystals of N-(6-benzylcyanide-2-yl)-N-ethylmethanesulfonate.

4) Obtained in the previous phase 3 N-(6-benzylcyanide-2-yl)-N-athleten - sulfonamide (0.8 g) is mixed with 10 ml of acetic acid and 10 ml of water, the mixture is cooled in the range from -5 to 0aboutWith and through the cooled mixture is passed chlorine gas. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate, and then through it in an hour passed at room temperature ammonia gas. After completion of the reaction, the reaction mixture is filtered, the filtrate is concentrated under reduced pressure and leave for some time. Followed by washing the hardened residue with ethyl acetate and n-hexane gain of 0.62 g of 6-[(N-ethyl-N-methylsulphonyl)amino] -2-pyridinesulfonamide (intermediate compound 2 in table.1) with a melting point 140-143aboutC.

5) Obtained in stage 4 6-[(N-ethyl-N-methylsulphonyl)amino]-2-pyridinesulfonamide (0.2 g) is mixed with 0.2 g of phenyl-(4,6-dimethoxypyrimidine-2-yl)carbamate and 7 ml of acetonitrile to the mixture with stirring 0.11 g of 1,8-diazabicyclo[5.4.0]-7-undecene, and the mixture was incubated 1 h at room temperature. Upon completion of the reaction, the reaction tons of water and after drying obtain 0.25 g of the desired product (compound 2) with a melting point 145-147aboutC.

P R I m e R the synthesis of 2. Synthesis of 6-[(N-ethyl-N-ethylsulfonyl)amino]-N-[(4,6-dimethoxy - pyrimidine-2-yl) amino] carbonyl] -2-pyridinesulfonamide (compound 18 in table.2)

1) Mix 2 g of 2-amino-6-benzoylthiourea and 30 ml of tetrahydrofuran, to the mixture of 0.52 powder of potassium hydroxide, after stirred at room temperature. The resulting mixture was cooled with ice, to the cooled mixture is added dropwise 2,38 g acanaloniidae and stirred for 30 min at room temperature. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:1) and obtain 0.9 g of N-(6-benzylcyanide-2-yl)acanalonia with a melting point 87-92aboutC.

2) Obtained at the previous step 1 N-(6-benzylcyanide-2-yl)ethanallen-amide (0.85 grams) is mixed with 15 ml of tetrahydrofuran, the mixture is cooled with ice, add of 0.13 g of sodium hydride (60 wt.), then stirred at room temperature. Then add 2 g of ethyliodide and the resulting mixture is boiled for 1.5 hours On the anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:1) and obtain 0.75 g of oily N-(6-benzylcyanide-2-yl)-N-athletesthe-amide.

3) Obtained in stage 2 of N-(6-benzylcyanide-2-yl)-N-acylethanolamine (0.75 g) is mixed with 20 ml of acetic acid and 15 ml of water, the mixture is cooled from -5 to 0aboutWith and through the cooled mixture is passed chlorine gas. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate and then through it in an hour passed at room temperature ammonia gas. After completion of the reaction, the reaction mixture is filtered, the filtrate is concentrated under reduced pressure and leave for some time. Subsequent washing of the cured residue with ethyl acetate and n-hexane obtain 0.6 g of 6-[(N-ethyl-N-ethylsulfonyl)amino]-2-pyridylsulfonyl-amide (intermediate compound 17 in table.1) with a melting point 115-118aboutC.

4) Obtained in stage 3 6-[(N-ethyl-N-ethylsulfonyl)amino]-2-pyridinyl - foamed (0.21 g) is mixed with 0.2 g of phenyl-(4,6-dimethoxypyrimidine-2-yl)carbamate and 7 ml acetonitrile 30 min lead reaction. Upon completion of the reaction, the reaction mixture is transferred into the water and weakly acidified with hydrochloric acid. The formed precipitate is filtered off and washing with water followed by drying obtain 0.25 g of the desired product (compound 18) with a melting point 165-170aboutC.

P R I m e R synthesis 3. Synthesis of 6-[(N-ethyl-N-isopropylphenyl) amino]-N-[[(4,6-dimethoxypyrimidine-2-yl)amino] carbonyl] -2 - pyridinesulfonamide (compound 22 of table.2).

1) In an autoclave mix 12 g 2-benzylthio-6-bromopyridine, 70 ml of an aqueous solution of ethylamine (40 wt.) and a catalytic amount of copper chloride (I) and heated 4 hours at 180aboutC. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:10) and obtain 5.5 g of oily 2-benzylthio-6-Ethylenediamine.

2) Mix 2 g obtained in stage 1 2 benzylthio-6-Ethylenediamine with 2,33 g isopropylacetanilide, and the mixture is stirred for about a day at 80-100aboutC. Upon completion of the reaction to the reaction will contentresult under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (1:10) and obtain 0.2 g of oily N-(6-benzylcyanide-2-yl)-N-ethylisopropylamine.

3) Obtained in stage 2 of N-(6-benzylcyanide-2-yl)-N - ethylisopropylamine (0.2 g) is mixed with 25 ml of acetic acid and 20 ml of water, the mixture is cooled from -5 to 0aboutWith and for the reaction through the cooled mixture is passed chlorine gas. Upon completion of the reaction, the reaction mixture is transferred into water and extracted with methylene chloride. The extract is washed with water, dried over anhydrous sodium sulfate, after which it for the reaction miss 30 min at room temperature with gaseous ammonia. After completion of the reaction, the reaction mixture was filtered and the filtrate concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (3:1) and obtain 0.12 g of oily 6-[(N-ethyl-N-isopropylmalonic)amino]-2-pyridine - sulfonamida (intermediate compound 21 in table.1).

4) Obtained in stage 3 6-[(N-ethyl-N-isopropylphenyl)amino]-2-pyridine - lonarid (0.12 g) is mixed with 0.11 g phenyl-(4,6-dealers which at room temperature for 30 min conducting the reaction. Upon completion of the reaction, the reaction mixture is transferred into the water, weakly acidified with hydrochloric acid and extracted with methylene chloride. The extract is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue is purified column chromatography on silica gel with elution with a mixture of ethyl acetate-hexane (4:1) and obtain 0.11 g of the desired product (compound 22) with a melting point 163-166aboutC.

Representative examples of intermediate compounds of General formula (II-1), synthesized essentially the above methods are listed in table.1, and representative examples of substituted derivatives of pyridinesulfonamide General formula (I) obtained essentially the present method are listed in table.2.

As active ingredients of herbicides substituted derivative pyridinesulfonamide or their salts of the present invention, as will become apparent from the examples of tests that have a broad spectrum herbicide action in low dosages, while security for soybean, wheat, cotton, etc.

The proposed herbicide can be made in a variety of areas, including agricultural land, such as upland fields, the garden is zavodskie surroundings. The method of applying a herbicide may be arbitrarily selected from a method of processing soil application and processing method by applying to the foliage. Herbicide may be applied in the form of a composition, such as a dust, granules, dispersible in water, granules, wettable powder, emulsifiable concentrate, soluble concentrate suspension concentrate, which is produced by mixing the proposed substituted derivative of pyridinesulfonamide or its salt as an active ingredient usually with the carrier and, if necessary, in addition to other various excipients selected from diluents, solvents, emulsifiers, strukturator, surfactants, etc. are Acceptable ratio by weight in the mixture of the active ingredient for agricultural additives may be in the range of(1:99)-(90:10), preferably in the range(5: 95)-(75: 25). With a reasonable amount intended for the use of an effective component, cannot be uniquely specified because it varies depending on weather conditions, soil conditions, shape of the composition, the type of processed weed and time of herbicide application. However, the quantity of active component usually is The proposed herbicide may be used in mixture or combination with, at least one ingredient or component selected from other agricultural chemicals, agricultural additives, reduce the phytotoxic agents, etc. with the aim to improve his action and purpose. The herbicide can be used in mixture or combination with another herbicide, and in this case can sometimes be achieved in a synergistic effect.

Examples of other herbicides.

Derivatives phenoxypropionate, such as:

ethyl ester()-2-[4-[(6-chloro-2-honokalani)oxy]phenoxy propionic acid (trivial name visuotactile);

ethyl ester()-2-[4-[(6-chlorine-benzoxazolyl)oxy]phenoxy] propionic acid (trivial name phenoxo - propanil);

butyl ether()-2-[4-[[5-(trifluoromethyl)-2-pyridinyl] oxy] phenoxy] propionic acid (trivial name fluazifop butyl);

methyl ester 2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl]oxy] phenoxy] propionic acid (trivial name galaxion methyl);

2-ethoxyethyl ester 2-[4-[[3-chloro-5-(trifluoromethyl)-2-pyridinyl] oxy] phenoxy]propionic acid (trivial name haloxyfop atotal);

(R)-2-[[(1-methylethylidene)amino] oxy] - Lowy ester 2-[4-[(6-chloro-2-honokalani)oxy] the s how:

sodium 5-[2-chloro-4-(trifluoromethyl)Hairdryer - oxy]-2-nitrobenzoate (trivial name acifluorfen sodium);

()-2-ethoxy-1-methyl-2-oxoethyl - 5-[2-chloro-4-(trifluoromethyl) -phenoxy]-2-nitrobenzoate (trivial name lactofen); 5-[2-chloro-4-(trifluoromethyl)phenoxy] -N-(methylsulphonyl)-2-nitrobenzamide (trivial name fomesafen);

derivatives haloganated, such as:

2-chloro-N-(2-ethyl-6-were)-N-(2 - methoxy-1-methylethyl)ndimethylacetamide (trivial name metolachlor);

2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)ndimethylacetamide (common name alachlor);

derivatives of imidazolinone, such as:

()-2-[4,5-dihydro-4-methyl-4-(1-IU - telecel)-5-oxo-1H-imidazol-2-yl] 5-ethyl-3-piridinkarbonovaya acid (trivial name imazethapyr); 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl] -3-fineliner Bo-new acid (trivial name imazaquin);

derivatives dinitroaniline, such as:

2,6-dinitro-N, N-dipropyl-4-(trifter - methyl)aniline (trial name trifluralin);

N-(1-ethylpropyl)-3,4-dimethyl-2,6-di - nitroaniline (trivial name of pendimethalin);

derivatives of carbamate, such as:

3-[(methoxycarbonyl)amino] phenyl-(3-were)carbamate (trivial name phenmedipham);

xantiana, such as: 2-[1-(amoxiillin)butyl]-5-[2-(ethylthio)propyl] -3-hydroxy-2-cyclohexen-1-he (trivial name sethoxydim);

and other connections, such as:

3-(1-mutilation)-(1H)-2,1,3-benzothia-diazen-4(3H)-one-2,2-dioxide (trivial name bentazon);

ethyl-4-[[[[(4-chloro-6-methoxy-2-pyrimi-dinyl)amino] carbonyl)] amino] sulfonyl]benzoate (trivial name chloroaromatic);

4-(2,4-dichlorophenoxy)butyric acid (common name 2,4-DB);

3-(3,4-dichlorophenyl)-1-methoxy-1-metalmachine (trivial name linuron);

4-amino-6-(1,1-dimethylethyl)-3-(methyl-thio)-1,2,4-triazine-5(4H)-he (trivial name of metribuzin);

7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid (trivial name endothall);

S-ethyldipropylthiocarbamate (trivial name VOC);

()-2-ethoxy-2,3-dihydro-3,3-dimethyl 5 - benzopyrroloindolic (trivial name ethofumesate);

5-amino-4-chloro-2-phenyl-3(2H)-pyrido-Zinon (trivial name of the ozone chloride).

Substituted derivative of pyridinesulfonamide or its salt can be used as an active ingredient of a herbicide in amounts of 0.05-5 g/and in combination with other compounds listed in an amount of 0.01-50 g/A. In particular, the derivative is the amount of 0.2-5 g/a, and derivatives haloganated and dinitroaniline derivatives can be used in amounts of 5-30 g/a in combination with the substituted derivatives of pyridinesulfonamide or its salt of the present invention. In addition, a synergistic effect can be achieved by using as another herbicide following compounds in mixture or combination with the herbicide of the present invention.

Derivatives of sulfonylurea, such as:

methyl-2-[[[[(4-methoxy-6-methyl-1,3,5-tri - Azin-2-yl)amino]-carbonyl] amino] sulfonyl] benzoate (trivial name metsulfuron); methyl-2 -[[[[ N-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)methylamino] carbonyl] amino] sulfonyl]benzoate (trivial name tribenuronmethyl);

2-chloro-N-[[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)amino] carbonyl] benzosulfimide (trivial name chlorsulfuron);

methyl-3-[[[[(4-methoxy-6-methyl-1,3,5-tri - Azin-2-yl)amino]carbonyl] amino]sulfonyl]-2-thiophenecarboxylate (trivial name timetorun-methyl);

derivatives phenoxypropionate, such as:

methyl ester()-2-[4-(2,4-dichlorphenoxy)phenoxy]propionic acid (trivial name dichloromethyl);

derivatives of imidazolinone, such as:

a mixture of methyl-6-(4-isopropyl-4-Noah called imazamethabenz);

and other connections, such as:

1,2-dimethyl-3,5-diphenyl-1H-Pirat - Lee-methyl sulfate (trivial name difenzoquat-methyl sulfate);

3,5-dibromo-4-hydroxybenzonitrile (trivial name bromoxynil);

4-hydroxy-3,5-diogenite (trivial name ioxynil);

2,4-dichlorophenoxyacetic acid (common name 2,4-D);

S-(2,3,4-trichloro-2-propenyl)-bis(1-IU-telecel)carbonation (trivial name of triallate);

4-chloro-2-methylphenoxyacetic acid (trivial name MSRA);

3,6-dichloro-2-piridinkarbonovaya acid (trivial name clopyralid);

0-(6-chloro-3-phenyl-4-pyridazinyl)-S-OK - til-thiocarbonate (trivial name peridot);

3,6-dichloro-2-methoxybenzoic acid (trivial name dicamba);

N'-(3,4-dichlorophenyl)-N,N-dimetil-Cavina (common name Diuron);

4-amino-3,5,6-trichloro-2-pyridinol-oil acid (trivial name picloram);

N, N-dimethyl-N'-[3-(trifluoromethyl)Fe-Neil] urea (trivial name fluometuron); 2-[[4-chloro-6-(ethylamino)-1,3,5-triazine-2-yl]amino]-2-methylpropionitrile (trivial name cyanazine);

N-(3,4-dichlorophenyl)propanamide (trivial name propanil);

N,N'-bis(1-methylethyl)-6-(methylthio)real name DSMA);

monosodium salt of methylarsonic acid (trivial name MSMA);

2-chloro-1-(3-ethoxy-4-nitrophenoxy)-4- (trifluoromethyl)benzene (trivial name oxyflourfen);

0,0-bis-(1-methylethyl)-S-[2-[(peninsul - radioactive)amino]ethyl] phosphorodithioate (trivial name bensulide);

2-(3,4-dichlorophenyl)-4-methyl-1,2,4-oxa - thiazolidin-3,5-dione (trivial name metasol);

4-chloro-5-(methylamino)-2-[3-(triptime - Tyl)phenyl] -3(2H)-pyridazinone (trivial name norflurazon);

2-chloro-6-(4,6-dimethoxypyrimidine-2-ylthio)benzoate;

ethyl-2-chloro-6-(4,6-dimethoxypyridine - DIN-2-ylthio)benzoate;

sodium-2-chloro-6-(4,6-dimethoxypyridine - DIN-2-ylthio)benzoate.

Substituted derivative of pyridinesulfonamide or its salt as an active ingredient of the herbicide of the present invention may be used in amounts of 0.05-5 g/a in combination with the above as examples of other compounds with an amount of 0.01-50 g/A.

Examples of tests using the proposed herbicide.

Example test 1. Pots with an area of 100 m2fill upland soil, and then in pots sown the seeds of various plants. Cultivated plants receive the following notation:

Rice (Oryza sal is to (Xanthium strumarium) (XA)

Bindweed purple (Ipomaea purpurea) (IP)

Breast prickly Sida spinosa) (SI)

Sirica thin (Amarathus viridis) (AM)

Chicken millet (Echinochioa crus-qalli) (EC)

Weed large (Digitaria adscendens) (DI)

When each plant reaches a given growth stage (stage 1.3-3 leaf rice stage from primary leaf to 1.2 sheet for soybeans, stage 2.3-4.1 worksheet for corn, stage from the appearance of the cotyledons to 1.1 sheet for cotton, stage 2.2-3 sheet for wheat, stage 1-3,2 sheets for cocklebur, stage in the 0.3-2 worksheet for bindweed purple, stage in the 0.1-1.8 sheet for breast barbed, stage 0.3-2.4 sheet serizy thin, phase 1.7-2.3 sheet for millet cock and stage 1.4-3.1 sheet Rosicky large), weigh the specified amount of the herbicide in the form of a wettable powder is diluted with water to 5 l/a, is mixed in the amount of 0,2 about. in terms of the resulting composition with agricultural strukturator, and then applied to the foliage of the plant a small sprayer. The course of development of the plants observed visually after 17-29 days after application to the foliage of identifying the degree of growth control, as measured by a 10-point scale (1 is the same as in the untreated pot, 10 excellent growth control). The results are shown in table.x sow seeds of various plants. Inoculated plants are indicated as follows:

Soybean (Glycine max) (GL)

Chanticleers(Abutilon avicennae) (AB)

The Eastern Cassia (Cassia oblusifolia) (CA)

When each plant reaches a specified stage of growth stage in 0.1 sheet for soybeans, stage 1.1 sheet for nachalnika Theophrastus and stage in 0.1 sheet for Cassia East), give a certain amount of the herbicide of the present invention in the form of a wettable powder is diluted with water to 5 l/a, is mixed in the amount of 0,2 about. in terms of the resulting composition with agricultural strukturator and a small sprayer applied to the foliage of plants. The course of development of the plants observed visually after 28 days after application to the foliage of identifying the degree of growth control, which is assessed on a 10-point scale, as in the example test 1. The results are shown in table.4.

P R I m e R test 3. Pots with a surface area of 1/3000 and 1/10000 and fill with dry soil and sow seeds of various plants. Plants are grown are marked as follows: Plant Name 1/3000 and soybean (Glycine max) (GL) 1/10000 and cocklebur (Xant-

hium strumarium) (XA) 1/10000 and bindweed purple

(Ipomoea purpu-

rea) (IP) 1/10000 sirica thin

(Amoranthus Viri gallery-

each plant reaches a certain stage of growth (stage 0.5 sheet for soybeans, stage 1 sheet for cocklebur, stage 1.1 sheet for purple bindweed, stage 1.4 sheet serizy thin, stage 1,2 sheet for cantica Theophrastus and stage 0.2 sheet for Cassia East), weigh the specified amount of the herbicide in the form of a wettable powder is diluted with water to 5 l/a, mixed with agricultural strukturator in the amount of 0,2 about. in terms of the resulting composition and a small sprayer applied to the foliage of plants. Visual inspection of soybean and other plants spend later, respectively, 18 and 24 days after spraying the foliage with the identification of the degree of growth control on a 10-point scale, as in example 1. The results are shown in table.5.

P R I m e R test 4. Pots with a surface area of 1/3000 and 1/10000 and fill upland soil and sow seeds of various plants. Plants are grown are marked as follows: Plant Name 1/3000 a soybean (Glycine max) (GL) 1/10000 a cocklebur (Xant-

hium strumarium) (XA) a 1/10000 bindweed purple

(Ipomoea purpu-

ren) (IP) 1/10000 sirica thin

(Amaranthus Viri gallery-

dis) (AM) 1/10000 canetic Theophrastus

(Abutilon avicennae) (AB) a 1/10000 Cassia East

(Cassia obtusifolia) (CA)

When each plant reaches a certain Ladoga, stage 1.2 sheet serizy thin, stage 1.3 sheet for cantica Theophrastus and stage 0.2 sheet for Cassia East), weigh the specified amount of the herbicide in the form of a wettable powder is diluted with water to 5 l/a, mixed with agricultural strukturator in the amount of 0,2 about. in terms of the resulting composition a small sprayer applied to the foliage of plants. Visual inspection of soybean and other plants hold, respectively, after 20 days and 25 days after spraying the foliage with the identification of the degree of growth control on a 10-point scale. The results are shown in table.6.

P R I m e R test 5. Pots with a surface area of 1/10000 and fill with dry soil and sow seeds of various plants. Plants are grown denote as follows:

Wheat (Triticum) (TR)

The wild oats (Avena fatua) (AV)

When each plant reaches a certain stage of growth (stage 2.1 sheet for wheat and stage 1 worksheet for wild oats), weigh the specified amount of the herbicide in the form of a wettable powder is diluted with water to 5 l/a, mixed with agricultural strukturator in the amount of 0,2 about. in terms of the resulting composition and neoliberally foliage determine the degree of growth control on a 10-point scale. The results are shown in table.7.

P R I m e R test 6. Pots with a surface area of 1/10000 and fill with dry soil and sow seeds of various plants. Plants are grown are marked as follows:

Cotton (Gossypium) (GO)

The Eastern Cassia (Cassia obtusifolia) (CA)

Weed large (Digitaria adscendens) (DI)

When each plant reaches a certain growth stage (stage of emergence of the cotyledons of cotton, stage 0.2 sheet for Cassia Eastern and stage 2.9 sheet Rosicky large), weigh the specified amount of the herbicide in the form of a wettable powder is diluted with water to 5 l/a, mixed with agricultural strukturator in the amount of 0,2 about. in terms of the resulting composition and a small sprayer applied to the foliage of plants. The evolution of plants observed visually after 28 days after spraying the foliage with the identification of the degree of growth control on a 10-point scale. The results are shown in table.8.

Examples of formulations of the herbicide.

P R I m e R 1. Composition, wt.h.

Clay (brand name Gulit) 97

Polyoxyethylenated-

phenyl ether, pre-

WriteLine mixed-

what you mix with each other and crushed with the formation of dust.

P R I m m e R 2. Composition, wt.h. The connection 22 75

Polymer type policer-

oil acid (firms

Menno name (Demol EP, powder) 13,5 NaCl 10 Dextrin 0,5

Alkylsulfonate (firms

Menno name TR-89121) 1

These components are placed in a high-speed granulator, add 20 wt. water granularit and after drying receive dispersible granules in water.

P R I m e R 3. Composition wt.h. Kaolin 78

The condensation product

sodium salt nafta-

inculpability

with formalin (firms

Menno name Lavalin FAN) 2

Sulfate netropolis-

setlinecolor-

the first ether, prior

sory mixed

with a white soot (firms

Menno name Sobol 5039) 5

White carbon black (trade-

Noah name Corplex) 15

A mixture of listed components are mixed with compound 2 in the ratio by weight of 9:1 with the formation of a wettable powder.

P R I m e R 4. Composition, wt.h. Diatomaceous earth 63

Ammonium salt

sulfate, polyacetate-

lanakiladallas

ether, prior

sory mixed

with a white soot (firms

Menno name Decool W-66) 5

Diallylsulfide-

zinat, e 18 30

The above components are mixed with one another with formation of a wettable powder.

P R I m e R 5. Composition, wt.

Microporosity

talc (branded on-

naming Nai Filler N 10) 33

Diallylsulfide-

zinat, pre-

but mixed with white

soot (branded on-

naming Sobol 5050) 3

A mixture of sulfate Poliak-

siterenacuajocom-

th ether with carbon

Tom polyoxide-

denominatio-

the first broadcast, pre-

satisfactory mixed

with a white soot (firms

Menno name of MARPOL 5073) 4 Connection 22 60

The above components are mixed with each other to obtain wettable powder.

P R I m e R 6. Composition, wt. Connection 2 4 Corn oil 79

The mixture dialkyl-

focaccina, Poliak-

setrenderer-

the first ether, Poliak-

seatile-(gidrirovanny-

Noah castor oil)

esters polyglyceryl-

on with fat sour

Tami (branded on-

naming Sobol 3815) 15

Bentonite-alkylamino first complex 2

These components are uniformly mixed together and crushed in Duino-the crusher (manufactured by Willy FL Barchiesi the th formula I

< / BR>
where R1- C1- C5is an alkyl group, a C1- C3-halogenated,1- C2-alkoxy-C1- C2is an alkyl group, vinyl group, WITH3- C6-cycloalkyl group or a phenyl group possibly substituted with halogen, triptorelin group or a nitro-group;

R2- C1- C4is an alkyl group or1- C3-halogenation group;

or R1and R2together may form - /CH2/ngroup, where n = 3 or 4, substituents X and Y independently of each methyl group or methoxy group.

2. Connection on p. 1, characterized in that the substituent R1- C1- C5is an alkyl group, a C1- C3-halogenation group or3- C6-cycloalkyl group, the substituent R2- C1- C4is an alkyl group or1- C3-halogenation group, and the substituents X and Y independently of one another methyl group or methoxy group.

2. Herbicide composition comprising active ingredient - substituted pyridinesulfonamide connection and the target additives, characterized in that as substituted pyridinesulfonamide of seeding>1- C3-halogenation group, vinyl group, WITH3- C6-cycloalkyl group or a phenyl group possibly substituted with halogen, triptorelin group or a nitro-group:

R2- C1- C4is an alkyl group, a C1- C3-halogenation group;

R1and R2together may form - (CH2)ngroup, where N takes a value of 3 or 4;

X and Y are independently from each other methyl group or methoxy group in the following ingredients, by weight.h.:

The active ingredient is 1 - 75

Targeted supplements - the Rest is up to 100

4. Derivatives pyridinesulfonamide General formula II

< / BR>
or Deputy R1- C1- C5is an alkyl group, a C1- C3-halogenation group1- C2-alkoxy-C1- C2is an alkyl group, vinyl group, WITH3- C6-cycloalkyl group or a phenyl group possibly substituted with halogen, triptorelin group or a nitro-group;

R2- C1- C4is an alkyl group or1- C3-halogenation group, or R1and R2together form -(CH2)ngroup, where N = 3 or 4.

Priority>-halogenated,3- C6-cycloalkyl; R2- C1- C4-alkyl, C1- C3-halogenated or R1and R2together may form -(CH2)ngroup, where n = 3 to 4; X and Y are methyl; methoxy group; the compound (II) under item 4, where R1, R2are there values that connection I.

12.07.91 connection 1 p. 1, where R1- vinyl, phenyl, possibly substituted by a halogen atom, trifluoromethyl or nitro-group; the compound (II) under item 4, where R1has the same meaning as in the compounds I.

 

Same patents:

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The invention relates to new derivatives of 3(2H)-pyridazinone and to their pharmaceutically acceptable salts, possessing inhibitory activity against the aggregation of platelets, cardiotonic activity, vasodilating activity, anti-SRS-A activity, to processes for their preparation and to pharmaceutical compositions containing them as active ingredient

The invention relates to new biologically active compounds, namely, the derivative of 4-aminophenol of the formula I

XNROR1where R1represents a group WITH/ABOUT/УZ;

Y represents a single bond, 0, NR7or; Z represents hydrogen, pyridyl; phenyl which may be substituted with halogen, nitro, lower alkoxy or carboxy; lower alkyl which may be substituted by hydroxy, lower acyloxy, carboxy, lower alkoxycarbonyl, CONR8R9, phenyl/lower/ alkoxy, phenyl, halogen, cyano or NR10R11;

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X 4.5-dihydropyrazolo or pyrazolyl, which may be substituted WITH3-C6-cycloalkyl or phenyl which can be substituted by trihalomethyl;

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The invention relates to the production of new proizvodnyh of thiazolidine that are used in pharmaceutical compositions

The invention relates to a method for obtaining complex diesters of alkyl substituted 4-hydroxy-piperidino connection of some complex organic esters, in particular to a method for producing a complex of diesters of alkyl-substituted 4-hydroxy-piperidino compounds of esters of dicarboxylic acids using a catalyst system containing the basic inorganic compound and a polar aprotic organic compound

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

The invention relates to synergistic herbicide composition, comprising as active components 1-[4,6-dimethoxypyrimidine-2-yl]-3-[3-trifluromethyl-2 - pyridylsulfonyl] urea ( hereinafter called "Compound a") and salt Isopropylamine or trimethylsulfonium N-(phosphonomethyl)glycine (hereafter referred to as "Compound B") in a mass ratio of 1:2.5 to 40

The invention relates to chemical methods of plant protection, in particular to a method of controlling undesirable vegetation using sulfonylureas

The invention relates to chemical means of protection of plants, particularly to herbicide compositions based on derivatives of sulfonylurea

The invention relates to chemical means of plant protection specifically to the herbicide agent on the basis of sulfonylurea derivatives and method of weed control using herbicide tools

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

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