A derivative of uracil

 

(57) Abstract:

Usage: agriculture as a herbicide. The inventive derivative of uracil f-ly I, where R1group f-ly III, where R2trifluoromethyl; R4hydrogen, fluorine or chlorine; R5group f-l IV, V, SCH2CO2CH3or N(R6)(SO2R7) where R6hydrogen, methyl, ethyl or methylsulphonyl; R7is methyl, ethyl, n-propyl, n-butyl, 3-chloropropyl or 2,2,2-triptorelin. 7 Il. 17 table. The structure of the compounds f-l: I, III, IV, V:

The invention relates to a new derivative of uracil with herbicide action.

A huge variety of herbicides was obtained and used in practice for the protection of important agricultural crops, such as rice, soybean, wheat, corn, cotton, beets, etc. from weeds to increase the productivity of these crops. In accordance with the places of application of herbicides can be roughly classified into the following three stages: a herbicide for upland fields; herbicides for rice fields and herbicides for non-arable lands. Each type of herbicides might be further divided into subclasses according to the method of application, such as Herbi>With the increase in recent years of people around the world cannot deny the fact that the productivity of the main agricultural crops has a major impact on the economy of food production in each country, and thus increase the productivity of the main crops at the present time is of paramount importance. People engaged in agriculture, still need herbicides that are capable of economically and efficiently destroy or suppress the growth of weeds and not harm agricultural crops.

Herbicides must meet the following requirements: high herbicide effect in the use of small quantities; short residual action (chemicals that preserve their action in the soil for a long time, cause damage to subsequent cultivated plants; the rapid destruction of weeds after application of the herbicide (providing the possibility of sowing and transplantation subsequent crops in a short time after the application of chemicals; the smallest number of herbicide treatments, a wide range of weeds, destroyed or suppressed on the change of various weeds, such as broadleaf weeds, grassy weeds and perennial weeds); various ways of treatment (herbicide effect is enhanced if the herbicide can be applied in various ways, such as soil, leaves and other); causing harm to cultivated plants (cultivated fields, where they grow cultivated plants and weeds, it is desirable to use herbicide was destroyed only weeds).

However, still not received herbicides, which could satisfy all the above requirements.

It is known that some compounds derivatives of uracil have herbicide action. For example, in Handbook of pesticides "Pesticide Manual: ed. 8th, C. 89, publ. The British Council for the protection of agricultural crops by The British Crop Protection Council, 1987, describes bromacil as one of the herbicides that have oralloy structure.

Known also following heterocyclic derivatives that can serve as the active ingredient for herbicides.

(1) 3-Arylaryl-alkalemia, alkenilovyh and alkenylsilanes ethers represented by the following General formula:

where R1(1-8)-alkyl, (2-6) With alkenyl, (2-6)-quinil, (2-8) and the
R4Voort, fluorine or (1-4)-alkyl,

R5(1-4)-alkyl, (1-4)-haloalkyl, or R4and R5can submit together three or tetramethylene (in which R6and R7independently represent (1-4)-alkyl, and m is 1 or 2) and X 0, 0-C(0), 0-C(0)-C(0)-0 (Japan patent (Kokai) N 63-107967).

(2) Compounds represented by the following formula:

where R1hydrogen, (1-4) C-alkyl, (1-4)-haloalkyl formyl or (2-6) With alkanoyl;

R2a simple ester or a residue containing (thio) carbonyloxy or sulfonyloxy, and this residue is directly linked to the benzene nucleus And through the oxygen atom;

R3halogen or cyano;

R4hydrogen or halogen;

R5hydrogen, halogen or (1-4) C-alkyl;

R6(1-4)-alkyl, or (1-4)-haloalkyl, or R5and R6may together represent a three - or tetramethylene, and salt compounds of the indicated formula in which R1hydrogen, (Japan patent (Kokai) N 63-41466).

(3) Benzothiazolinone derivative represented by the General formula:

O where R is hydrogen, lower alkyl, lower alkenyl, lower quinil, lower haloalkyl and lower haloalkyl, lower haloalkyl, lower alkoxy-lower alkyl, lower alkoxy ness heterocyclic derivatives, represented by the General formula:

S where X is an oxygen atom or sulfur and Z is:

H2)nin which G is a hydrogen atom or halogen;

As the halogen atom or a nitro, (NO);

E is a hydrogen atom, a halogen atom, WITH N, NO2, NH2, OH, SH, OR1where R1(1-5)-alkyl, (3-6)-cycloalkyl, (3-6)-cycloalkyl-(1-2)-quinil, (2-4)-alkenyl, (3-4)-quinil.

Q in which Qandand Qbindependently from each other, an oxygen atom or a sulfur atom;

R1aa hydrogen atom or (1-3)-alkyl;

R1ba hydrogen atom, (1-5)-alkyl, (2-5)-alkenyl, (3-5)-quinil, (2-3)s-haloalkyl, (1-2)-alkoxy-(1-2)-alkyl, (3-4)-cycloalkyl-(1-2)-alkyl, (3-6)-cycloalkyl, CH2CO2-(1-3)-alkyl or CH(CH3)-CO2-(1-2) C-alkyl, or R1aand R1btogether form a 4-6-membered lactone ring, composed of a methylene chain; group

N in which R1aand Qahave the same values as defined above, and R1cand R1drepresent independently each other a hydrogen atom, (1-5)-alkyl, (2-5)-alkenyl, (3-5)-quinil, (2-5)-haloalkyl, (3-6)-cycloalkyl or (3-6)-cycloalkyl-(1-2)-alkyl, or R1dand R1ctogether form a 5-7-membered ring composed of methylene chain;

CH2CN, tetrahydropyran hydrogen, (1-3)-alkyl, CH2CO2-(1-3)-alkyl or PINES3or (1-2)-alkoxy-(1-2)-alkyl; SR3in which R3has the same meaning as R1described above; CO2R5in which R5a hydrogen atom, (1-5)-alkyl, (3-6)-cycloalkyl or (3-6)-cycloalkyl(1-2)-alkyl; other6in which R6(1-5)-alkyl, (3-6)-cycloalkyl, (3-6)-cycloalkyl-(1-2)-alkyl, (2-4)-alkenyl or (3-4)-quinil; or NOR7in which R7a hydrogen atom, (1-5)-alkyl, (3-6)-cycloalkyl, (3-6)-cycloalkyl-(1-2)-alkyl, (2-4)-alkenyl or (3-4)-quinil; L atom of hydrogen or halogen; Y is an oxygen atom or a sulfur atom; n is 0 or 1 and J is a hydrogen atom, halogen atom, (1-5)-alkyl, (3-6)-cycloalkyl, (3-6)-cycloalkyl-(1-2)-alkyl, (2-4)With alkenyl, (3-5)-quinil, (1-5)-halogen - alkyl, (3-4)-haloalkyl, (3-4)-haloalkyl, (1-2)-alkoxy-(1-2)-alkyl; CH2CN, CH2CO2R8where R8a hydrogen atom, (1-5)-alkyl, (3-6)-cycloalkyl or (3-6)-cycloalkyl-(1-2)-alkyl; or CH2CH2CO2R9where R9a hydrogen atom, (1-5)-alkyl, (3-6)-cycloalkyl or (3-6)-cycloalkyl-(1-2)-alkyl (Japan patent (Kokai) N 1-250388).

(5) Compounds represented by the following formula:

where R1hydrogen, (1-4)-alkyl, (2-4)-alkenyl, (2-4)-quinil, (2-6)-alkoxyalkyl (2-6)-alkoxyalkyl;

R3halogen or nitro;

R4hydrogen or halogen;

R5hydrogen, halogen, (1-4)-alkyl, chloromethyl, methyl bromide, hydroxymethyl, (1-5)-alkoxy-methyl, (1-5)s-alkylthiomethyl, cyano, nitro or thiocyanato;

R6hydrogen, (1-4)alkyl or (1-4)-foralkyl, or R5and R6together represent tri - or tetramethylene in which one methylene group may be replaced by oxygen or sulphur, or these groups may be substituted by (1-3)-alkyl;

X is oxygen or sulfur, in which (1) when R5fluorine, R6(1-4)-alkyl or (1-4)-foralkyl, and (n) when R5cyano, R6hydrogen or (1-4)-alkyl, and X is oxygen, and salts of compounds of the aforesaid formula wherein R1and/or R2represents hydrogen (Japan patent (Kokai) N 61-221178).

(6) Tetrahydropyrimidine derivatives represented by the following formula:

O where R1(1-5)-alkyl, (3-5)With alkenyl, (3-5)-quinil or (1-3)-alkoxymethyl, X is hydrogen, fluorine or chlorine, and a is a group of the formula

OR-N - in which R2hydrogen or methyl;

R3hydrogen or methyl, and the nitrogen atom attached to the benzene ring (Japan patent (Kokai) N 61-85385).

(7) Tetrahydropyrimidine proizvodyostvennye;

R2hydrogen or methyl (Japan patent (Kokai) N 61-30586).

(8) Tetrahydropyrimidine derivatives represented by the following formula:

where R1alkyl, alkenyl, quinil, alkoxyalkyl or alkoxylalkyl;

R2hydrogen or methyl (Japan patent (Kokai) N 61-76476).

(9) Tetrahydropyrimidine derivatives represented by the following formula:

O where R (1-5)-alkyl, (3-5)With alkenyl, (3-5)-quinil or (1-3)-alkoxymethyl, and X is hydrogen or fluorine (Japan patent (Kokai) N 61-43188).

(10) Herbicide compounds having the General formula:

where X is hydrogen or hydroxy;

R1hydrogen or halogen;

R2alkyl, cycloalkyl, phenyl, alkenyl and substituted derivatives of the above compounds (U.S. patent N 3981715).

(11) Herbicide compounds having the General formula:

where X is hydrogen or hydroxy;

R1hydrogen or halogen;

R2alkyl, cycloalkyl, phenyl, alkenyl, and replaced derivatives of these compounds (U.S. patent N 3869457).

(12) Compounds of the formula:

where R1hydrogen, (1-4)-alkyl, (3-4)With alkenyl, (3-4)-quinil or (1-4)-haloalkyl;

R2is

-(-O or, when R1haloalkyl, hydrogen, (1-8)-alkyl, (2-8)-Alki is UP> hydrogen, fluorine or (1-4)-haloalkyl, and their enol ethers or salts (WO 88/10254).

There arose an urgent need for the development of herbicide, which can satisfy the above requirements (1) (7), namely herbicide, which exhibits a selective effect, without causing damage to cultivated plants, finds excellent herbicide effect at a low dose for a wide variety of weeds, and also able to show the desired effect as soil and in the processing of the leaves.

The studies of the present inventors, it was found that derivatives of uracil with haloalkyl group in 6-position and a phenyl group at the 3-position, which has a special Deputy represented by the General formula (I), has the ability of penetrating movement in plants and very high herbicide activity and compared with conventional herbicide compounds specified derivatives of uracil can be used to handle both soil and foliage, and have in this quick and highly effective herbicide action even at very low doses against a wide variety of weeds, including perennial weeds, oblada of the invention, provides uracil derivative represented by formula I:

in which R2trifluoromethyl or pentafluoroethyl; R4hydrogen or fluorine; AND2hydrogen, methyl, ethyl, propyl, allyl, steamed, 1-methylpropenyl, cyanomethyl, methoxymethyl, benzyl, orsometimes, parameterbased, or picolyl.

According to the second aspect of the invention provides a derivative of uracil, which is expressed by the formula I-a:

in which R4hydrogen, fluorine or chlorine

R5represents a group SCH2CO2CH3or SO2R24where R24methyl, ethyl, n-propyl, isopropyl, n-butyl, 3-chloropropyl or 2,2,2-triptorelin;

R25hydrogen, methyl, ethyl or methylsulphonyl.

Derivatives of uracil of the present invention, represented by formulas I and Ia, possess the characteristics of novelty.

In accordance with the purposes of the present invention of the uracil derivative expressed by formula I and I-a, preference is given to compounds of the following formulas(1), (2), (3) and (4).

1) Derivatives of uracil, expressed by the formula (1)

in which R2trifluoromethyl or metaphorical; R4hydrogen or fluorine; AND2is hydrogen, methyl, ethyl, propyl, allyl, propyl, 1-methylpiperazine, expressed by the formula (2)

< / BR>
3) Derivatives of uracil, expressed by the formula (3)

in which R6represents or

4) Derivatives of uracil, expressed by the formula (4)

in which R4hydrogen, fluorine or chlorine; R24methyl, ethyl, n-propyl, isopropyl, n-butyl, 3-chloropropyl or 2,2,2-triptorelin; R25hydrogen, methyl, ethyl or methylsulphonyl.

Derivatives of uracil according to the present invention can be synthesized in accordance with reaction schemes shown in Fig. 1-7.

(1) In scheme 1 phenyl-ISO(thio)cyanate (VI) is subjected to interaction with complex beta-aminoacridone ester (V) with the formation of the first stage uracil derivative (1') and after allocation specified derivative or without selection 1-position brazilero ring alkiliruya that allows you to get the uracil derivative of formula (1) in the second stage.

The reaction of the first stage.

Typically phenyl-ISO(thio)cyanate (VI) is used in quantities of 0.5 to 1.5 equivalent, preferably 0.9 to 1.1 equivalents with respect to a complex beta-aminoacridone ether (V).

The reaction may proceed without solvent, but is commonly used solvent for accelerating the reaction. As examples of the solution of the Academy of Sciences, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, and N,N-diethylaniline; acid amides, such as formamide, N, N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane; water and mixtures thereof. Among them, preferred aliphatic hydrocarbons, amides, acids, sulfur containing compounds and mixtures thereof.

The reaction may proceed without reason, but usually uses a base in an amount of from 0.5 to 10 equivalents, preferably 1.0 to 2.0 equivalents relative to the complex of beta-aminoacridone ether (V). As the base can be used, for example, organic bases containing nitrogen such as pyridine, triethylamine and 1,4-diazabicyclo-2,2,2-octane; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and a metal alcoholate, such as methylate NAIS potassium.

The reaction temperature is typically 40-200aboutC, preferably from room temperature to the temperature of reflux distilled reaction mixture.

The reaction time is usually from 10 min to 72 h, preferably 30 min 24 h

After the reaction derivative (1') can be separated by acidification of the reaction product of a mineral acid, such as hydrochloric acid or organic acid, such as acetic acid, triperoxonane acid, p-toluensulfonate or similar.

The reaction of the second stage.

In the second stage reaction derivative (1') alkiliruya using an alkylating agent in an amount of from 1.0 to 10 equivalents, preferably 1.0 to 5.0 equivalents with respect to derivative (1'). As the alkylating agent can be used, for example, alkylene acid, such as dimethylene acid and ditissima acid, and alkylhalogenide, such as methyl chloride, ethylchloride, bromide, ethylbromide, methyliodide and ethyliodide.

The reaction may proceed without solvent, but usually to accelerate the reaction solvent used. As examples of solvents used for the above mentioned purpose described in visr; aromatic hydrocarbons, such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; acid amides, such as formamide, N,N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane; water; and mixtures thereof. Among these solvents, preferred aliphatic hydrocarbons, amides, acids, sulfur containing compounds and mixtures thereof.

In the above reaction is commonly used base in an amount of from 1.0 to 10 equivalents, preferably 1.0 to 2.0 equivalents relative to the derivative (1'). As the base can be used organic bases containing nitrogen such as pyridine, triethylamine and 1,4-diazabicyclo-2,2,2-octane; and inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate. Among them, preferred inorganic bases such as sodium hydride and potassium carbonate.

Telegracia reaction mixture.

The reaction time is usually 10 minutes to 96 hours, preferably from 30 minutes to 48 hours.

(2) In accordance with scheme 2 N-phenyl carbamate (VII) is subjected to interaction with complex beta-aminoacridone ester (V) with the formation of the first stage uracil derivative (1') and after the selection derivative (1') or without selection 1 position brazilero ring alkiliruya that allows you to get the uracil derivative of formula (1) in the second stage.

The reaction of the first stage.

N-Phenylcarbamate (VII) is typically used in quantities of 0.5 to 1.5 equivalent, preferably 0.9 to 1.1 equivalents with respect to a complex beta-aminoacridone ether (V).

This usually requires that the reaction was attended by the solvent. The solvent can be used, for example, aliphatic hydrocarbons such as heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-DNA, such as dimethylsulfoxide or sulfolane; alcohols such as methanol, ethanol, propanol and butanol; water; and mixtures thereof. Among them, preferred aliphatic hydrocarbons, amides, acids, sulfur containing compounds and mixtures thereof.

In the reaction described above is commonly used base in the amount of 0.5-10 equivalents, preferably 1.0 to 2.0 equivalents relative to the complex of beta-aminoacridone ether (V). The base used in the above reaction include inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate; metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium, and allylmercaptan metals, such as methylmercaptan sodium and ethylmercaptan sodium. Among them, preferred inorganic bases such as sodium hydride and a metal alcoholate such as sodium methylate.

The reaction is carried out at a temperature of usually up to 0-200aboutC, preferably from room temperature to the temperature of reflux distilled reaction mixture.

The reaction time is generally 10 min to 72 h, preferably 30 min to 2 h

After completion of the reaction derivative (1') can vyd the banking acid, such as acetic, triperoxonane acid and para-toluensulfonate acid.

The reaction of the second stage.

Alkylation derivative (1') can be carried out under the same reaction conditions as in the second stage of the process of scheme 1.

(3) In scheme 3 phenyl-ISO(thio)cyanate (VI) is subjected to interaction with N-substituted beta-aminoacridone complex ester (VIII), which allows to obtain a derivative of uracil of the formula (1) as a result of the implementation of one stage. You can apply the same reaction conditions used in the process according to scheme 1.

(4) According to scheme 4 N-phenyl (carbamate (VII) subject to the interaction of N-substituted beta-aminoacridone complex ester (VIII), which allows to obtain a derivative of uracil of the formula (1) for one stage. The reaction may be conducted in the same reaction conditions as used in the process according to scheme 2.

(5) In scheme 5 phenylisocyanate (VI-a) is subjected to interaction with beta-aminoacridone complex ester (V-a), resulting in the formation of uracil derivative (1-a) in the first stage, and after separation of the specified derivative (1'-a) or without selection 1-position brazilero ring metiliruetsa that leads to the formation of a derivative of uracil Faure is camping in the amount of 0.5 to 1.5 equivalent, preferably 0.8 to 1.2 equivalent with respect to beta-aminoacridone ether complex (V-a).

The reaction may proceed without solvent, but usually to accelerate the reaction solvent used. As examples of solvents used for this purpose in the reaction, may be mentioned aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane, water, and mixtures of these solvents. Among them, preferred aliphatic Uglevodorody, aromatic hydrocarbons, amides, acids and sulfur containing compounds and mixtures thereof.

The reaction may proceed without reason, but is commonly used base in the amount of 0.5-10 equivalents, preferably from 1.0 to use for example, organic bases containing nitrogen such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine and 1,4-diazabicyclo- (2,2,2)octane; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and a metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium. Among them, preferred sodium hydride, sodium hydroxide and potassium hydroxide.

The reaction temperature is usually from -70 to 200aboutC, preferably from -30aboutWith up to the temperature of reflux distilled reaction mixture.

The reaction time is normally 5 min to 72 h, preferably 10 min 12 PM

After completion of the reaction derivative (1') can be released by acidification of the reaction product of a mineral acid, such as hydrochloric acid or organic acid, such as acetic, triperoxonane acid, para-toluensulfonate acid or similar acids.

The reaction of the second stage.

In the second stage reaction derivative (1'-a) metiliruetsa using meteorologi agent in an amount of from 0.5 to 10 equivalents, preferably 0.8 to 5.0 equivalent, shall methylglucamide, such as methyl chloride, methyl bromide and methyliodide.

The reaction may proceed without solvent, but to accelerate the reaction is commonly used solvent. As examples of solvents used in the above reaction for this purpose, may be called aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; acid amides, such as N, N-dimethylacetamide, N,N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane; water; and mixtures thereof. Among them, preferred aliphatic hydrocarbons, aromatic hydrocarbons, ethers, ketones, NITRILES, amides, acids, sulfur containing compounds and mixtures thereof.

In the above reaction is commonly used base in an amount of from 0.5 to 10 equivalents, preferably from 0.8 to 3.0 equivalents relative who, such as pyridine, triethylamine, N,N-dimethylaniline, N, N-diethylaniline, 4-(N,N-dimethylamino)pyridine and 1,4-diazabicyclo(2,2,2)octane, and inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate. Among them, preferred inorganic bases such as sodium hydride and potassium carbonate.

The reaction temperature is usually from -30 to 150aboutC, preferably from -10aboutWith up to the temperature of reflux distilled reaction mixture.

The reaction time is usually 10 minutes to 96 hours, preferably 30 minutes to 48 hours

(6) According to the scheme 6 N-phenylcarbamate (VII-a) is subjected to interaction with complex beta-aminoacridone ether (V-a), resulting in a derivative of uracil, (1') in the first stage and after the selection derivative (1'-a) or without isolating it, in the second stage 1-position brazilero rings specified derived metiliruetsa, resulting in the formation of uracil derivative (1-a).

The reaction of the first stage.

Usually N-phenylcarbamate (VII-a) is used in quantities of 0.5 to 1.5 equivalent, preferably 0.8 to 1.2 equivalent with respect to beta-aminoacridone ether (V-a).

Usually tribulations hydrocarbons, such as hexane, heptane, ligroin and petroleum ether, aromatic hydrocarbons such as binol, toluene; xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide and N-organic; sulfur-containing compounds, such as dimethyl sulfoxide and sulfolane; alcohols such as methanol, ethanol, propanol and butanol; water; and mixtures thereof. Among them, preferred aliphatic hydrocarbons, aromatic hydrocarbons, amides, acids, sulfur containing compounds and mixtures thereof.

In the above reaction is commonly used base in the amount of 0.5-10 equivalents, preferably 1.0 to 3.0 equivalents relative to beta-aminoacridone ether (V-a).

The base used in the above reaction include organic bases containing nitrogen such as pyridine, triethylamine, N,N-dimethylaniline, N, N-diethylaniline, 4-(N, N-dimethylamino)pyridine and 1,4-diazabicyclo(2,2,2)octane; inorganic osnovaniya; the metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium, and allylmercaptan metals, such as methylmercaptan sodium and ethylmercaptan sodium.

Among them, preferred Neorganicheskie base such as sodium hydride and a metal alcoholate such as sodium methylate.

The reaction is carried out at a temperature of usually 0 to 200aboutC, preferably from room temperature to the temperature of reflux distilled reaction mixture.

The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 24 hours

After completion of the reaction derivative (1') can be emitted from the reaction mixture by acidification of the mineral acid, such as hydrochloric acid or organic acid, such as acetic acid, triperoxonane acid and para-toluensulfonate acid.

The reaction of the second stage.

Methylation derivative (1'-a) can be carried out under the same reaction conditions as in the second stage of the process according to scheme 5.

(7) In accordance with scheme 7 phenylisocyanate (VI-a) is subjected to interaction with N-methyl-aminoacridone ether (VIII-a), which allows to obtain a derivative of uracil of the formula (1-a) for Audemer 8 N-phenylcarbamate (VII-a) is subjected to interaction with N-methyl-beta-aminoacridone complex ester (VIII-a), that allows you to get a uracil derivative of the formula (1-a) in the exercise of one stage. The reaction may be conducted under the same conditions, which are used according to the scheme 6.

(9) According to scheme 9 sulfonylmethane (X-a) or sulfonovy anhydride (X-b) is subjected to interaction with laminirovannyy compound (IX), which allows to obtain a derivative of uracil of the formula (1-a) in the exercise of one stage.

Usually sulfonylmethane (X-a) or sulfonovy anhydride (X-b) is used in an amount of 0.3 to 10 equivalents, preferably 0.5 to 2.0 equivalents relative to laminirovannom the compound (IX).

The reaction may proceed without solvent, but usually to accelerate the reaction solvent used. As examples of solvents used in the reaction for this purpose, may be called aliphatic hydrocarbons, such as hexyne, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tration the-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof.

The reaction may proceed without reason, but usually uses a base in an amount of from 0.3 to 10 equivalents relative to laminirovannom the compound (IX). Also as a solvent can be used, the basis taken in large excess. As the base can be used, for example, organic bases containing nitrogen such as pyridine, triethylamine, N, N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine and 1,4-diazabicyclo(2,2,2)octane; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and a metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium. Among them, preferred organic bases containing nitrogen, and inorganic bases.

The reaction temperature is usually from -30 to 160aboutWith preferably from -10 to 130aboutC.

The reaction time is generally 10 min to 48 h, preferably 30 min 24 h

(10) According to scheme 10, aminirovanie compound (IX) is subjected to interaction with allermuir agent, resulting in Allaho highlight the acylated aminosidine (IX-a) sulfanilimide with the formation of the second stage N-arylsulfonamides compound (IX-b); after separation of the N-arylsulfonamides compound (IX-b) or without selection N-arylsulfonamides the compound (IX-b) at the third stage deacylases that allows you to get a uracil derivative of the formula (1-a).

The reaction of the first stage.

Usually allerease agent is used in amount of 0.5-5.0 equivalents, preferably 0.8 to 2.0 equivalents relative to laminirovannom the compound (IX). As Alliluyeva agent you can use acetylchloride, benzoyl chloride, acetic anhydride and formic acid, is preferred acetic anhydride.

The reaction may proceed without solvent, but is commonly used solvent for accelerating the reaction, as examples of solvents used in the reaction for this purpose, may be called aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluol, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; and tertiary amines such as pyridine and N,N-diethylaniline; acid amides such as N,N-dimethylacetamide, N, N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfate and sulfo them preferred aliphatic hydrocarbons, aromatic hydrocarbons, halogenated hydrocarbons and organic acids.

The reaction can be carried out without reason, but usually the base is used in amounts of 0.5 to 5.0 equivalents, preferably 0.8 to 2.0 equivalents relative to laminirovannom the compound (IX). As the base can be used, for example, organic bases containing nitrogen such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)-pyridine and 1,4-diazabicyclo(2,2,2)octane; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and a salt of acetic acid such as sodium acetate and potassium acetate.

The reaction temperature is usually from -30 to 200aboutWith preferably 0-130aboutC.

The reaction time is usually 10 minutes to 24 hours, preferably 30 minutes to 6 o'clock

The reaction of the second stage.

In the second stage, the reaction of the acylated aminosidine (IX-a) sulfonamides using sulfonylurea agent in the amount of 0.5-5.0 equivalents, preferably 0.8 to 2.0 equivalents, relative to the acylated aminosidine (IX-a). As sulfonylurea agentname anhydride, represented by the formula, R24O2-O-SO2R24(X-b).

The reaction may proceed without solvent, but usually to accelerate the reaction solvent used. As examples of solvents used in the above reaction for this purpose, may be called aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and machinetalker; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; amides of the acids, such as N, N-dimethylacetamide, N,N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane and mixtures thereof.

In the above reaction is commonly used base in the amount of 0.5-5.0 equivalents, preferably 0.8 to 2.0 equivalents relative to the acylated aminosidine (IX-a). As the base can be used organic bases containing nitrogen such as pyridine, triethylamine, N, N-dim is such as sodium hydride, potassium carbonate and sodium carbonate, and a metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium. Among them, preferred organic bases containing nitrogen, and inorganic bases.

The reaction temperature is usually from -30 to 160aboutC, preferably from -10 to 130aboutC.

The reaction time is usually 30 min to 48 h, preferably 1-12 o'clock

The third reaction stage.

Usually water, alkalis or acids are used in amounts of 0.5 to 3.0 equivalents, preferably 0.8 to 2.0 equivalents relative to N-arylsulfonamides the compound (IX-b).

As examples of the alkali may be called inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, metal alcoholate such as sodium methylate, sodium ethylate and tert-butyl potassium. Among them, preferred inorganic bases.

As examples of acids may be mentioned inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as acetic acid and triperoxonane acid.

The reaction may proceed without solvent, what, for example, aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons, tackie as chloroform and methylene chloride; alcohols, such as methanol and ethanol; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, triethylamine, N,N-dimethylaniline and N,N-diethylaniline; amides of the acids, such as N,N-dimethylacetamide, N,N-dimethylformamide and N-organic; organic acids such as formic acid, acetic acid and butyric acid; water; and mixtures thereof. Among them, preferred alcohols, ethers, ketones, tertiary amines, amides, acids, organic acids and water.

The reaction is carried out at a temperature of usually from -30 to 130aboutC, preferably from -10 to 100aboutC.

The reaction time is usually 10 to 48 h, preferably 30 min 24 h

(11) According to scheme 11, aminirovanie connection IX sulfonylurea, resulting in desulfonylation the compound (IX-c) at the first stage, and after separation disulfonic the lease with the formation of the uracil derivative of the formula (1-a) in the second stage.

The reaction of the first stage.

Usually sulfonylmethane (X-a) or sulfonovy anhydride (X-b) is used in an amount of 1.0 to 20 equivalents, preferably 2.0 to 5.0 equivalents relative to laminirovannom the compound (IX).

The reaction may proceed without solvent, but usually the solvent is used to accelerate the reaction. As examples of solvents used in the reaction for this purpose, may be called aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, halogenated hydrocarbons such as chloroform and methylene chloride; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine and N,N-diethylaniline; acid amides, such as dimethylacetamide, N, N-dimethylformamide and N-organic; sulfur-containing compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof.

The reaction may proceed without reason, but usually the base is used in an amount of 1.0 to 10 equivalents, preferably 2.0 to 3.0 equivalents with respect Ataraxie nitrogen, such as pyridine, triethylamine, N,N-dimethylaniline, N,N-diethyl - aniline, 4-(N,N-dimethylamino)pyridine and 1,4-diazabicyclo(2,2,2)octane; inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and alcoholate metals, such as sodium methylate, sodium ethylate and tert-butyl potassium. Among them, preferred organic bases containing nitrogen, and inorganic bases.

The reaction is carried out at a temperature of usually from -30 to 160aboutC, preferably from -10 to 130aboutC.

The reaction time is usually 30 minutes to 60 hours, preferably 1-30 hours

The reaction of the second stage.

Water, alkalis or acids are used in amounts of 0.5 to 3.0 equivalents, preferably from 0.8 to 2.0 equivalents relative to desulfonylation the compound (IX-c) for the purpose of hydrolysis.

As examples of the alkali may be called inorganic bases such as sodium hydride, potassium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and a metal alcoholate such as sodium methylate, potassium methylate and tert-butyl potassium. Among them, preferred inorganic compounds.

The reaction may proceed without solvent, but usually to accelerate the reaction solvent used. As examples of solvents used in the reaction for this purpose, may be called aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene; halogenated hydrocarbons such as chloroform and methylene chloride; alcohols, such as methanol and ethanol; ethers, such as diethyl ether, dioxane and tetrahydrofuran; ketones, such as acetone and methyl ethyl ketone; NITRILES, such as acetonitrile and isobutyronitrile; tertiary amines such as pyridine, trimethylamine, N, N-dimethylaniline, N,N-diethylaniline, 4-(N,N-dimethylamino)pyridine and 1,4-diazabicyclo- (2,2,2)octane; acid amides such as N,N-dimethylacetamide, N,N-dimethylformamide and N-organic; organic acids such as formic acid, acetic acid and butyric acid; water; and mixtures thereof. Among them, preferred alcohols, ethers, ketones, tertiary amines, amides, acids, organic acids and water.

The reaction is carried out at temperatures 5 min to 48 h, preferably 30 minutes to 24 hours

Derivatives of uracil according to the present invention can be used as a herbicide for upland fields, paddy fields and non-arable lands by soil treatment or processing of the leaves. They also show high herbicide activity at low doses against, for example, weeds growing on arable land, for example, broadleaf weeds family Solananceae, such as Solanum nigrum and Datura stramonium, weeds of the family Malvaceae, such as Abution theophrasti and Side spinosa, weeds Convolvulaceae, such as Spomea PPPs, or Spomoea purpurea, Calystegia PPPs, weeds family Amaranghaceae, such as be able to provide a lividis and Amatanthus retraflexus, weeds Composita, such as Xanthium pensylvanicum, Ambrosia artemisiaefolia, Helianthus annus, Galinsoga Cirsium arvense, Senecio vulgaris, Erigeren annus and Bidens pilosa, weeds Crucifera, such as Roppipa indica, Sinapis arvensis and psella Bursapastris, weeds Polygonaceae, such as Polyganum Blume and Polygonum convolvulus, weeds of the family Portulacaceae, such as Portulaca oleracea, in the family Chenopodiaceae, such as Chenopodium album, ficifolium and Kahias coporia, family Caryophy elaceae, such as Stellaria media, family Serophulariaceae, such as Verenica persica, weeds of the family Commelinaceae, such as Commelina communis, Gramineae weeds, such as Lamium amplexicaule and Lamium purpureum, weeds Euphorbiaceae, such as Euphorbia supina and Euphorbia maculata, weeds Rubiaceae, such as Galium spurium, Gabium apa is STV Graminaceous, such as Sorgham bicolor Panicum dichotomiflorum, Serghus halepence, Echinochloa crus-galli; Digitaria adscendens, Avena fatua, Eleusine indica, Setaria viridis and Alopecurus aequalis, weeds Cyperaseous, such as Cuperus rotundus and Cuperus esculentus; and weed the rice paddies; the family Alismataceae, such as Alisma canaliculatum, Sagittaria trifolia and Sagittaria pygmaea family Cyperaceae, such as Cyperus difformis; Cyperus Serotinus Scirpus juncoides and Eleocharis kuragiwai, weeds lariaceae, such as Lindemia puxidaria, weeds family Potenderiaceae, such as Monochoria Vaginalis, weeds Lythraceae, such as Rotala indica and Gramineae weeds such as Echinochloa Gremineae, such as Echinochloa crus-gali. Derivatives of uracil according to the present invention do not cause harm such important crops as wheat, corn, barley, soybeans, rice. In particular, since the derivatives of uracil (1-a) of the present invention do not exhibit phytotoxicity against soybean soil and incorporate into the soil, and also exhibit high herbicide activity at very low doses against weeds Abution theoprasti; Xanthium pensylvanicum, Spomoea PPPs. Spomoea purpurea, Calystegia PPPs. Amaranthus retraflexus, Polygonum Blume, Polygonum convolvulus, Portulaca oleracea, Chenopodium album, Datura Stramonium, Ambrosia artemisiaefolia, Bidens pilosa, Side spinosa, Sebsania exaltata and Solanum nigrum, derivatives of uracil (1-a) according to the present invention are very useful as the active ingredient of the herbicide composition.

Key compounds of the present invention as herbicides, they are usually mixed with a carrier, for example, a solid carrier such as clay, talc, bentonite, diatomaceous earth and white carbon (fine powder of silicon dioxide), or a liquid carrier such as water, alcohols (isopropanol, butanol, benzyl alcohol, perfilova alcohol and others ), aromatic hydrocarbons (toluene, xylene, and others), ethers (anisole and others ), ketones (cyclohexanone, isophorone and other), esters (butyl acetate, and others), acid amides (N-organic and other) and halogenated hydrocarbons (chlorobenzene, and others). If necessary, these may be joined by suitable adjuvants, such as surfactants, emulsifiers, dispersing agents, agents that facilitate the penetration of agents that increase the wetting ability, thickeners, agents that lower the freezing point, agents that prevent coagulation, stabilizers and similar agents, these compounds can be offered for practical use in a variety of ready-made forms, such as liquid formulations, emulsifiable concentrate, wettable powder, dry flowable drug, fluid compositions, dusty and granules.

In the herbicide composition of the present invention, the amount of the active ingredient of proizvodi the attachment of the carrier or diluent is 10-99,9 mass. per 100 wt.h. herbicide compositions.

More specifically, the preferred number of components in the composition (per 100 wt.h. herbicide compositions) uracil derivative according to the present invention in each composition are presented below.

Wettable powder, wt.h.

Derivatives of uracil

in the present image - retenu 5-80 Solid media 10-85 Surfactant 1-10 Other media 1-5 (for example, an agent that prevents coagulation and others). Emulsifiable concentrate, wt.h. A derivative of uracil according to the present invention 1 30 carrier Liquid 30 95 Surfactant 5 15 Fluid composition, wt.h. A derivative of uracil according to the present invention 5 70 carrier Liquid 15 65 Surfactant 5 12 Other media 5 30

(for example, an agent that lowers the freezing temperature, the thickening agent and others).

Granular wettable powder (dry flowable composition), wt.h. A derivative of uracil of the present invention 20 90 Solid carrier 10 60 Surfactant 1 20

Granules, wt. including uracil Derivative according to the present invention is 0.1 to 10 Solid carrier 90 to 99.99 Other media 1 5

Compounds of the present invention may St, regulating the growth of plants, synergists and similar substances in the course of obtaining or during application of the composition.

As herbicides, which can be mixed with the compounds of the present invention, can be mentioned (for example, compounds described in the Handbook of Farm chemical Handboor 1990).

In case of use of the compounds of the present invention in relation to soy as examples of preferred compounds which can be mixed with the compound of the present invention, can be named trifluralin, pendimethalin, alachlor, metolachlor, metribuzin, linuron, chlorimuron, ethyl, imazighen, imazethapyr, dinoseb, bifenox and clomazone.

The consumption rate of the compounds of the present invention varies depending on the place of application, time of application, method of application, the type of processed culture, etc. but usually the connection of the present invention is used in an amount of about of 0.0001-10 kg/ha, preferably 0.001 to 5 kg/ha when calculating the amount of the active ingredient.

Derivatives of uracil according to the present invention exhibit high activity of movement in plants and very high herbicide activity is tillage, embedded in the soil against a wide variety of weeds.

The present invention further explored in the following examples.

P R I m e R a 1. Synthesis of 3-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-1-methyl-6 - trifluoromethyl-2,4(1H/3H)-pyrimidinedione(compound a-1).

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0.18 g of 3-(7-fluoro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl)-6-trifluoromethyl - 2,4(1,3 N)-pyrimidinedione was added at room temperature in a solution of dimethylformamide (2 ml) suspended in it, 0.02 g of sodium hydride (frequency: 55%). After maturation for 20 min the solution was added 0.09 g dimethylsilanol acid, and the solution was stirred over night. Then dimethylformamide drove away and the residue was extracted with ethyl acetate by adding water. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then drove the ethyl acetate, the result of which was obtained the crude product. This crude product was purified using preparative thin-layer chromatography using a mixture of hexane and ethyl acetate (3:1) as developing solvent, which allowed us to obtain 0.15 g of the target compound as colorless viscous oil. After being left in oxazin-6-yl] -1-methyl-6-thrift ormetal-2,4% (1H, 3H)- pyrimidinedione (compound a-3).

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0.20 g of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)1-methyl-6-trifluoromethyl -2,4(1H,3H)-pyrimidinedione was added at room temperature to a solution of N, N-dimethylformamide (5 ml) suspended in it, 0.05 g of sodium hydride (purity: 55%). After maturation for 20 min to the solution was added 0.09 g of the hydrochloride of 2-chloromethylpyridine and the solution was stirred for 4 h

Then N,N-dimethylformamide drove away and the residue was extracted by adding ethyl acetate vday. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then ethyl acetate drove with the formation of the crude product. This product was purified using preparative thin-layer chromatography using a mixture of hexane and ethyl acetate (2:3) as developing solvent, the result of which was obtained 0.09 g of the target compound as pale yellow crystals.

P R I m e R a-3. Synthesis of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-1-methyl-6-three - vermeil-2,4(1H,3H)-pyrimidinedione (compound a-4).

O

O

of 0.85 g of 3-(7-fluoro-3-oxo-2H-1,4-benzoxazin-6-yl)-6-trifluoromethyl-2,4(1H, 3H)-Piri - medindia was dissolved in 8.5 ml of N,N-dimethylformamidine 4 hours After completion of the reaction of N,N-dimethylformamide drove away and the residue was extracted with ethyl acetate by adding water. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, and then ethyl acetate drove with the formation of the crude product. This product was purified by chromatography on a column using chloroform as a developing solvent, which allowed us to get to 0.53 g of the target compound as pale yellow crystals.

P R I m e R-1. Synthesis of 3-(4-chloro-2-fluoro-5-methoxy-carbonylmethyl)-1-methyl-6-trifluoromethyl -2,4(1H/3H)-pyrimidinedione (compound-1).

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To a suspension of 0.16 g of sodium hydride (purity 55%) in 5 ml of dimethylformamide at room temperature dropwise dobavlyali a solution of 1.5 g of 3-(4-chloro-2-fluoro-5-methoxycarbonylaminophenyl)-6-triptime - Teal-2,4(1H, 3H= -pyrimidinedione in 10 ml of dimethylformamide. After the evolution of hydrogen had ceased, was added 0,59 g dimethylsilanol acid and the resulting solution was stirred at room temperature for 3 hours the Reaction mixture was poured into 300 ml of water and was extracted twice with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride yokenny product was purified using preparative thin-layer chromatography (manifesting solvent: CHCl), and then use vysokoeffektivnoi preparative liquid chromatography ability (eluent:CHCN/HO (5:1), resulting in a 0.1 g of target compound in the form of a viscous oil.

P R I m e R s-1. Synthesis of 3-[4-chloro-2-fluoro-5-(5-methyl-1,3,4-oxadiazol-2-yl)Fe - Neil] -1-methyl - 6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (compound C-1).

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To a suspension of 0.31 g of sodium hydride (oil, purity 55%) in 13 ml of dimethylformamide was added dropwise at 25aboutWith a solution of 2.5 g of 3-(4-chloro-2-fluoro-5-)5-methyl-1,3,4-oxadiazol-2-yl(phenyl)-6-trifluoromethyl-2,4- (1H, 3H)-pyrimidinedione in 2 ml of N,N-dimethylformamide. After the evolution of hydrogen had ceased, was added 1,02 g dimethylsilanol acid for 15 minutes, the Mixed solution was stirred at room temperature for 2 h and was extracted with ethyl acetate by adding water. The extract was dried over anhydrous sodium sulfate. The solvent is then drove away and the residue was purified by high performance liquid chromatography using a mixture of acetonitrile and water (5:1) as eluent, resulting in 0,78 g of target compound.

P R I m e R s-2. Synthesis of 3-(4-chloro-3-ethanolgasoline)-1-methyl-6-three-vermeil-2,4(1H,3H)- pyrimidinedione (connection pyridine. To the resulting solution was added dropwise 0.16 ml of acanaloniidae at a temperature of not higher than 5aboutWith, and the mixed solution was stirred for 2 hours After the reaction was completed, pyridine was off and the residue was dissolved in ethyl acetate. The solution was washed with water, diluted hydrochloric acid and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate, and then ethyl acetate drove away, resulting in the obtained crude product. The obtained product was washed diisopropyl ether with the formation of 0.37 g of the desired product as light brown crystals.

P R I m e R s-3. Synthesis of 3-[4-chloro-3-(N-methyl)ethanolgasoline]-1-me - til-6-trifluoromethyl - 2,4(1H,3H)-pyrimidinedione (compound C-6).

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CF

0.25 g of 3-(4-chloro-3-ethanolgasoline)-1-methyl-6-trifluoromethyl - 2,4(1H, 3H)-pyrimidinedione was dissolved in 3 ml of dimethylformamide. To the resulting solution was added 0.17 g of anhydrous potassium carbonate and 0.08 ml iodotope bromide, and the mixed solution was stirred over night at room temperature. After drove dimethylformamide, the residue was dissolved in ethyl acetate. The resulting solution was washed with water and saturated aqueous knogo product. The resulting product was purified using preparative thin-layer chromatography (manifesting solvent mixture of hexane and ethyl acetate 3:2), which was obtained 0.18 g of target compound as white crystals.

P R I m e R s-4. Synthesis of 3-[4-chloro-2-fluoro-5-bis(methanesulfonyl)AMINOPHENYL]-1-methyl-6-trifluoromethyl - 2,4(1H,3H)-pyrimidinedione (compound C-10).

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To a suspension of 0.05 g of sodium hydride (purity 60%) and 5 ml of tetrahydrofuran at a temperature of 0aboutWith 0.5 g) was added 3-(4-chloro-2-fluoro-5-methanesulfonamido - phenyl)-1-methyl-6-trifluoromethyl - 2,4(1H, 3H)- pyrimidinedione. Then to the resulting suspension was added dropwise to 0.11 ml of methane - sulphonylchloride. After stirring for 7 h, the reaction mixture was poured into a mixture of ice water and was extracted with ethyl acetate. An ethyl acetate extract layer was washed saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. Then the ethyl acetate drove with the formation of the crude product. The obtained product was washed with diethyl ether education 0.50 g of the desired product as white crystals.

P R I m e R s-5. Synthesis of 3-(4-chloro-2-fluoro-5-isopropylphenyl-AMINOPHENYL)-1-methyl-6 - trifluoromethyl-2,4-(1H,3H)-pyrimidinedione (soy which was storyli in 5 ml of benzene. To the resulting solution was added and 0.61 ml of acetic anhydride, and the resulting solution was heated under reflux for 1 h After distillation of the benzene obtained crude product was washed with hexane to form a 3-(5-acetylamino-4-chloro-2-forfinal)-1-methyl-6-trifluoromethyl-2,4 (1H,3H)-pyrimidinedione in the form of white crystals.

So pl. 263-266aboutC.

1H-NMR (d6-DMSO) (ppm): 2,15 (3H, c); 3,47 (3H, c.); is 6.54 (1H, c.); and 7.7 (1H, d, J 9 Hz), of 7.90 (1H, d, J 8 Hz), of 9.56 (1H, broad singlet).

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To a suspension of 0.11 g of sodium hydride (oil, purity 60%) in 10 ml of tetrahydrofuran was added to 1.00 g of the obtained 3-(5-acetylamino-4-chloro-2-forfinal)-1-methyl-6-three-vermeil - 2,4(1H,3H)-pyrimidinedione at a temperature of 0aboutWith, and then added dropwise to the resulting suspension were added to 0.30 ml of isopropylacetanilide. After stirring for 2 h the reaction mixture was poured into a mixture of ice water and was extracted with ethyl acetate. An ethyl acetate extract layer was washed saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. Then the ethyl acetate drove with the formation of the crude product. The resulting product was purified using preparative thin-layer chromatography (manifesting solvent: Socinians] 1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione in the form of a colorless viscous oil.

Range 1H-NMR (CCl3) (h/m): 1,45 (6N, D. J 7 Hz), of 1.97 (3H, s), 3,47 (3H, s), 4,10 (1H, Quaternary Quartet, J 7 Hz), 6,23 (1H, s), 7,29 (1H, d, J 7 Hz), was 7.36 (1H, d, J 9 Hz).

< / BR>
of 0.47 g of the obtained 3-[4-chloro-2-fluoro-5-(N-acetyl)isopropylbenzylamine - Neil] -1-methyl-6-trifluoromethyl-2,4(1H,3H)- pyrimidinedione was dissolved in 5 ml of tetrahydrofuran. To the resulting solution was added 0.04 g of sodium hydroxide and 0.06 ml of water, after which the mixed solution was stirred for 4 hours After completion of the reaction, the reaction mixture was poured into diluted hydrochloric acid and was extracted with ethyl acetate. An ethyl acetate extract layer was washed with water and saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate. Then drove acid ethyl ester with the formation of the crude product. The resulting product was purified using preparative thin-layer chromatography (manifesting solvent: a mixture of hexane and ethyl acetate 3/1), resulting in 0,29 g of target compound in the form of a colorless viscous oil.

P R I m e R s-9. Synthesis of 3-(2,4-dichloro-5-ethanolgasoline)1-methyl-6 - trifluoromethyl - 2,4(1H,3H)-pyrimidinedione (compound C-21)

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To a mixture of 1.00 g of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-thriftway 0.56 g of acanaloniidae. The resulting mixture was stirred over night. After twice washing the reaction mixture with water the mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Dichloromethane drove with the formation of the crude product. The obtained product is washed with diisopropyl ether, the resulting 1.40 g of 3-[5-bis(econsultancy)amino-2,4-dichlorophenyl] -1-methyl-6-triptime - Teal-2,4(1H, 3H)-pyrimidinedione in the form of light yellow crystals.

Melting point: 221 223aboutC.

Range 1H-NMR (d6-DMSO) (h/m): 1,48 (6N, T. J 7 Hz), 3,49 (3H, s), 3,61 (4H, K. J 7 Hz), 6,27 (1H, s), 7,56 (1H, s), to 7.67 (1H, s).

< / BR>
< / BR>
In 8 ml of dioxane was dissolved 0,80 g of the obtained 3-[5-bis(econsultancy)amino-2,4-dichlorophenyl] -1-methyl - 6-Cryptor - methyl-2,4(1H, 3H)-pyrimidinedione and to the resulting solution was added 0.12 g of sodium hydroxide (93%) and 2 ml of water. After stirring the mixed solution for 4 h were added diluted hydrochloric acid to acidification of the resulting solution. The reaction mixture was extracted with ethyl acetate. The extract obtained an ethyl acetate layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous sulfa is OSU preparative thin-layer chromatography (manifesting solvent mixture of hexane and ethyl acetate 3/2), the result of which was received and 0.46 g of the desired product as white crystals.

Reference example. Synthesis of 3-[5-bis(methanesulfonyl)amino-2,4-dichlorophe-Neil]-1-methyl-6 - trifluoromethyl-2,4(1H,3H)-pyrimidinedione (intermediate product).

< / BR>
< / BR>
To a mixture of 1.00 g of 3-(5-amino-2,4-dichlorophenyl)-1-methyl-6-trifluoromethyl-2,4 (1H, 3H)-pyrimidinedione, of 0.60 g of triethylamine and 10 ml of dichloromethane at a temperature of not higher than 5aboutWith added 0,46 g methanesulfonanilide. The resulting mixture was stirred over night. After twice washing the reaction mixture with water the mixture was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Dichloromethane drove with the formation of the crude product. The obtained product is washed with diisopropyl ether, the resulting 1.40 g of the desired product as white crystals.

Melting point: not lower than 300aboutC.

Range 1H-NMR (d6-DMSO) (h/m): 3,50 (6H, c.); 4,20 (3H, c.); 6.35mm (1H, c.), at 7.55 (1H, c.), the 7.65 (1H, c.).

Derivatives of uracil according to the present invention synthesized in accordance with the above examples and on the basis of the techniques described in the above examples or diagrams in Tavastia with the present invention, not limited to the compounds shown in table. 1-6.

Below shows examples of finished compositions in which the compounds are applied according to the present invention.

P R I m e R of structure 1. Wettable powder, wt.h.

The compound a-1 to this - Adamu invention 50 Cycle PFP (clay coli - new type, manufactured by Cycle industries Co. Ltd.) 43 Sobol 5050 (anionic surfactant ve substance is made of fir - my Toho chemical Co. Ltd.) 2 Rooks 1000 C (anionic in supercial-active substances, manufactured by Toho chemical Co. Co., Ltd.) 3 Corplex 80, substance, pony procedure temperature measurement speeds (white coal, carried upon the firm Shionogi Far maceutical To. Ltd) 2

The above substances are uniformly mixed and pulverized with the formation of a wettable powder.

Example of compound 2. Emulsifiable concentrate, wt.h. The compound a-1 to present the overarching invention 3 Xylene 76 Isophorone 15 Sobol 3005 X (a mixture neion - aqueous surfactant and anionic surfactant, manufactured by Toho chemical Co. Ltd.) 6

The above substances are evenly mixed with the formation of the emulsifiable concentrate.

Example of compound 3. Fluid product, wt.h. The compound a-1 to present properly izobretennoj Toho chemical Co. Co., Ltd.) 0.5 to 1% aqueous solution of Rodopoli (thickener produced by the firm Ro-Poulenc) 20 ethylene Glycol (substance, nausea temperature measurement speeds) 8 Water 28,5

The above substances are uniformly mixed to obtain a fluid drug.

Example of compound 4. Granular wettable powder (dry flowable preparation), wt. including Compound a-1 to this - Adamu invention: 75 Isobar 1 (anyone surfactant, manufactured by Ku - Rara Isoprene chemical Co. Ltd.) 10 Unilex P (anionic surfactant manufactured by San Kokusaku pulp K. K.) 5 Corplex 80 (white carbon, manufactured by SIO - feet pharmaceutical Co. Co., Ltd.) 10

The above substances are uniformly mixed and pulverized with the formation of the dry flowable of the drug.

Example of compound 5. Wettable powder, wt.h. Connection-1 on this - Adamu invention 50 Cycle PFP (clay coli - new type, manufactured by Cycle ind. Co. Ltd.) 43 Sobol 5050 (anionic surfactant manufactured by Toho chemical Co. Ltd.) 2 Rooks 1000 C (anionic surfactant manufactured by Toho chemical Co. Ltd.) 3 Corplex 80 (antifreeze, white coal produced by the company Shionogi Pharm. Co. Ltd.) 2

The above substances are uniformly mixed and grinded with the formation of smachavariani 3 Xylene 76 Isophorone 15 Sobol 3005 X (a mixture of nei - traditional surfactants and anionic surfactants, manufactured by Toho chemical Co. Ltd.) 6

The above substances are uniformly mixed with the formation of the emulsifiable concentrate.

Example of compound 7. Fluid product, wt.h. Connection-1 on this - Adamu invention 35 Agrisol S-711 (nonionic surfactant, manufactured by Kao Corp. ) 8 Rooks 1000 (anyone surfactant, manufactured by Toho chemical Co. Ltd. ) 0.5 to 1% aqueous solution through the floor (thickener pressed upon by the company rhône-Poulenc) 20 ethylene Glycol (substance, nausea temperature for marzenia) 8 Water 28,5

The above substances are uniformly mixed with the formation of a fluid drug.

Example of compound 8. Granules, wt.h.

Connection-1 on this - Adamu invention 0.1 Bentonite 55,0 Talc 44,9

The above substances are uniformly mixed and pulverized, and then kneaded with stirring, with the addition of minor amounts of water, granularit using an extrusion granulator and dried to form granules.

Example of compound 9. Granular wettable powder (dry flowable preparation), wt. including Connection-1 on this - Adamu invention 75 Isobar 1 (anionic surfactant manufactured by Ku - Rara Isoprene chemical Co. Ltd.) 10 Unilex P (anionic surfactants, send.) 10

The above substances are uniformly mixed and pulverized with the formation of the dry flowable of the drug.

An example of the structure 10. Wettable powder, wt.h. Connection-1 on this - Adamu invention 50 Cycle PFP (clay, kaoline the first type, manufactured by Cycle industries, Co. Ltd.) 43 Sobol 5050 (anionic surfactant manufactured by Toho chemical Eng. Ltd.) 2 Rooks 1000 C (anionic surfactant manufactured by Toho chemical Co. Ltd.) 3 Corplex 80, substance, pony procedure temperature measurement speeds (white coal, carried upon the firm Shionogi Pharm. Co. Ltd. ) 2

The above substances are uniformly mixed and pulverized with the formation of a wettable powder.

Example of compound 11. Emulsifiable concentrate, wt.h. Connection-1 on this - Adamu invention 3 Xylene 76 Isophorone 15 Sobol 3005 X (a mixture of nei district surfactant and anionic surfactant, manufactured by Toho Ke - MikaL To. Ltd.) 6

The above substances are uniformly mixed to obtain emulsifiable concentrate.

An example of the structure 12. Fluid product, wt.h. Connection-1 infusion - the overarching invention 35 Agrisol S-711 (nonionic surfactant, manufactured by Kao Corp.) 8

Rooks 1000 C (anionic surfactants,

manufactured by Toho chemical Co. Ltd.) 0,5

1>lowering the freezing point) 8 Water 28,5

The above substances are uniformly mixed to obtain a fluid drug.

Example of compound 13. Granules, wt.h. Compound C-1 of the present invention: 0.1 Bentonite 55 Talc 44,9

The above substances are evenly mixed and grinded, and then kneaded with stirring and the addition of a small amount of water, granularit using an extrusion granulator and dried to form granules.

P R I m e R composition 14. Granular wettable powder (dry flowable preparation), wt.h. Connection-1 on this - Adamu invention 75 Isobar 1 (anionic surfactant manufactured by Kur - ray Isoprene chemical Co. Ltd.) 10 Unilex N (anionic surfactant manufactured by San Kokusaku pulp K. K.) 5 Corplex 80 (white carbon, manufactured by Shionogi Pharm. Co. Ltd.) 10

The above substances are uniformly mixed and pulverized with the formation of the dry flowable of the drug.

Example of compound 15. Wettable powder, wt.h. Connection-7 on this - Adamu invention: 50 Cycle PFP (clay kao - lanovogo type of product apparent firm Cycle In castris To. Ltd.) 43 Sobol 5050 (anionic surfactant manufactured by Toho chemical Co. Ltd.) 2 Rooks 1000 (anyonone Pharm. Co. Ltd.) 2

Substances mentioned above are uniformly mixed and pulverized with the formation of a wettable powder.

Example 16. Emulsified concentrate, wt.h. Connection-7 on this - Adamu invention 3 Xylene 76 Isophorone 15 Sobol 3005 X (a mixture of non - ionic surfactant and anionic surfactant, manufactured by Toho chemical Co. Ltd.) 6

The above substances are evenly mixed with the formation of the emulsifiable concentrate.

An example of the composition of 17. Fluid product, wt.h. Connection-7 on this - Adamu invention: 35 Agrisol S-711 (nonionic surfactant, manufactured by Kao Corp. ) 8 Rooks 1000 C (anionic surfactant manufactured by Toho chemical Co. Co., Ltd.) 0.5 to 1% aqueous solution Ro Gopala (thickener produced by the company rhône-PU - Lenk) 20

Ethylene glycol (substance

lowering the freezing point) 8 Water 28,5

The above substances are evenly mixed with the formation of a fluid drug.

Example of compound 18. Granules, wt.h. Connection-7 on this - Adamu invention 0.1 Bentonite 55,0 Talc 44,9

The above substances are mixed until smooth and crushed, then knead with stirring, with the addition of a small amount of water, granularit using the extra the nd powder (dry flowable preparation), wt. including the Connection-7 on this - Adamu invention 75 Isobar 1 (anionic top - surface-active substance manufactured by the Kur - ray Esopral chemical Co. Ltd.) 10 Unilex N (anionic surfactant manufactured by the Seine Kokusaku pulp K. K.) 5

Corplex 80 (white carbon,

manufactured by SIO - feet Pharm. Co. Ltd.) 10

The above substances are uniformly mixed and pulverized with the formation of dry bulk drug.

An example of the structure 20. Wettable powder, wt.h. Connection-11 on this - Adamu invention 50 Cycle PFP (clay, kaoline the first type, manufactured by Cycle industries Co. Ltd.) 43 Sobol 5050 (anionic surfactant manufactured by Toho chemical Co. Ltd.) 2 Rooks 1000 C (anionic surfactant manufactured by Toho chemical Co. Ltd.) 3 Corplex 80 (antifreeze, white coal produced by the company Shionogi Pharm. Co. Ltd.) 2

The above substances are uniformly mixed and pulverized with the formation of the dry flowable of the drug.

Example of compound 21. Emulsifiable concentrate, wt.h.

Connection-11 on this - Adamu invention 3 Xylene 76 Isophorone 15 Sobol 3005 X (a mixture of nei district surfactant and anionic surfactant, manufactured by Toho chemical Co. Ltd.) 6

The above substances are mixed equal to apart, wt.h. Connection-11 infusion embracing of the invention 35 Agrisol S-711 (nonionic surfactant, manufactured fir - my Kao Corp.) 8 Rooks 1000 C (anionic surfactant manufactured by Toho chemical Co. Ltd.) 0.5 to 1% aqueous solution Ro Gopala (thickener produced by the company rhône-Poulenc) 20 ethylene Glycol (substance, nausea freezing temperature 8 Water 28,5

The above substances are evenly mixed with the formation of a fluid drug.

Example of compound 23. Granules, wt. including the Connection-11 on this - Adamu invention 0.1 Bentonite 55,0 Talc 44,9

The above substances are evenly mixed and crushed, then knead with stirring, with the addition of a small amount of water, granularit using an extrusion granulator and dried to form granules.

An example of the structure 24. Granular wettable powder (dry flowable preparation), wt. including the Connection-11 in this submission to the invention 75 Isobar 1 (anionic surfactant manufactured by Kur - ray Isoprene chemical Co. Ltd.) 10 Unilex N (anionic surfactant manufactured by San Kokusaku pulp K. K.) 5 Complex 80 (white carbon, manufactured by si - onogi Pharm. Co. Ltd.) 10

The above substances are mixed evenly and crushed with the formation of dry tech is constituent of the concentrate, fluid mixture and granulated wettable powder diluted in their 50-1000 times with water, and then applied so that the active ingredient was delivered at a dose of 0.0001-10 kg/ha.

The usefulness of the compounds of the present invention as active ingredients of herbicides will be clearly seen from the results of examples of the tests described below.

Example 1 tests. Test for herbicide action when tillage.

Sterilized deluvial soil was placed in plastic box size 15 x 22 x 6 cm, Then in the box were sown in a mixture of seeds of barnyard grass Echinochloa crus-galli, Rosicky blood Digitaria adsendens, annual sedges Cyperus microiria, black nightshade Solanum nigrum, galinsoga hairy Galinsoga ciliate, garesnica Indian Rorippa indica, rice, Oriza sativa, corn Zeu mays, wheat Triticum aestivum, soybean Glycine max and cotton Cossipium herbaceum and covered with a soil layer of thickness about 1 cm, and then the test liquid herbicide was sprayed uniformly on the soil surface using a small sprayer so, to view the active ingredient was applied at a predetermined rate. Each test liquid herbicide were prepared by dilution with water of the composition obtained according sootvetstvuyuschim examples costly their herbicide effects on these different types of weeds and crops, and evaluated in accordance with the following standard grading scale. The results are shown in table. 7-11.

Standard grading scale: 5 degree of suppression of the growth is more than 90% (plants almost completely faded); 4 degree of suppression of the growth of 70-90% 3 degree of suppression of the growth is 40-70% 2 degree of suppression of the growth of 20-40% are 1 degree of suppression of the growth is less than 5% (almost not effective).

The degree of inhibition of growth was determined by the following formula after measuring the weight of the ground part of the plants in the treated area and weight on the raw site:

Degreegrowtherysuppression< / BR>
Example 2 testing. Test for herbicide action in the processing of the leaves.

In plastic box size 15 x 22 x x6 cm, containing sterilized deluvial soil, sown patches of seeds of barnyard grass Echinochloa crus-galli, Rosicky blood Digitaria adscendens, annual sedges Cyperus microria, black nightshade Solanum nigrum, galinsoga hairy Galinsoga cilitae, garesnica Indian Rorippa indica, rice Oryza sativa, soybean Glycine max, wheat Triticum aestivum, maize Zea mays, cotton Cossipium herbackum and sugar beet Beta vulgaris, and covered with soil to a thickness of about 1 cm When the plants were grown to the stage of 2-3 leaves, the test liquid herbicide evenly sprayed on the foliage rustici herbicide were prepared by dilution with water of the composition, obtained according to the respective examples of the compositions described above, and sprayed the entire foliage of the weeds using a small sprayer. Four weeks after spraying, the test liquid herbicide tested its herbicide effect on these types of weeds and useful plants and evaluated on the same scale that was used in test example 1. The results are shown in table. 12-16.

Example 3 tests. Test for herbicide action in the irrigated field.

Alluvial soil were placed in pots Wagner area of 1/5000 ar, and then they poured water for dilution of the soil and the formation of miniature models, resembling jelly rice field with a layer of water above the soil depth of 2 cm Then these pots were sown mixture of seeds of barnyard grass Echinochloa crus-galli, Monochoria Monochoria vaginalis, rotala Indian Rotala indica and bulrush Scirpus

juncoides. In the soil layer was placed the tubers of sedges perennial Cyperus serotinus and arrowhead Sagittaria pymaea, and then transplanted the seedlings of rice in stage 2.5 leaves. The pots were placed in a greenhouse with a temperature of 25-30aboutTo ensure normal plant growth. On day 2 after seeding diluted liquid herbicide subjected to the test, to benaloh in a given number. Three weeks after the application of liquid herbicide tested its herbicide effect on rice and these types of weeds and evaluated on the same scale that was used in test example 1. The results are shown in table. 17.

The underlined characters in the table. 7-16 indicate the following:

N: barnyard grass (Echinochloa crus galli);

M: weed blood (Digitaria adsendens);

K: annual sedge (Cyperus microiria);

H: black nightshade (Solanum nigrum);

D: galinsoga hairy (Galinsoga ciliate);

I: gershnik Indian (Rorippa indica);

R: rice (Oryza sativa);

T: corn (Zea mays);

W: wheat (Triticum aestivum);

S: soybean (Glycine max);

C: cotton (Cossipium herbaceum);

B: sugar beet (Reta vulgaris).

As control compounds were used bromacil having the following structure:

A DERIVATIVE of URACIL General formula

< / BR>
where R1a group of General formula

< / BR>
R2trifluoromethyl;

R4hydrogen, fluorine or chlorine;

R5the connection formulas

< / BR>
< / BR>
-SCH2CO2CH3< / BR>
< / BR>
where R6hydrogen, methyl, ethyl or methylsulphonyl;

R7methyl, ethyl, n-propyl, isopropyl, n-butyl, 3-chloropropyl or 2,2,2-triptorelin.

 

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Derivative oxazole // 2032677
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FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes substituted benzoylcyclohexanediones of the general formula (I):

wherein m = 0 or 1; n = 0 or 1; A means a single bond or alkanediyl (alkylene) with 1-4 carbon atoms; R1 means hydrogen atom or unsubstituted alkyl with from 1 to 6 carbon atoms; R2 means methyl; R3 means hydrogen atom, nitro-, cyano-group, halogen atom, alkyl with from 1 to 4 carbon atoms substituted with halogen atom, alkoxy-group with from 1 to 4 carbon atoms or alkyl sulfonyl with from 1 to 4 carbon atoms; R4 means nitro-group, halogen atom, unsubstituted alkyl with from 1 to 4 carbon atoms of that substituted with halogen atom; Z means heterocycle, and herbicide agent based on thereof. Also, invention describes substituted derivatives of benzoic acid of the general formula (III):

wherein values n, A, R3, R4 and Z are given above. These compounds represent the parent substances used for preparing compound of the formula (I). Compounds of the formula (I) elicit high and selective herbicide activity.

EFFECT: valuable properties of compounds.

7 cl, 8 tbl, 7 ex

FIELD: agriculture, in particular herbicide compositions.

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

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

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