Derivatives of uracil, intermediate compounds, herbicide composition and method of weed control

 

(57) Abstract:

Usage: the products of chemical means of plant protection, chemical method of plant protection. The essence of the invention: derivatives of uracil f-ly 1, where R1-triptoreline or panafcortelone group; R2-methyl, amino group; Q is one of the following groups Q1-Q3where R3is a hydrogen atom, methyl; R4,R5and R6each independently represents an unsubstituted or substituted with halogen, C1-C4- alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4- quinil, C1-C4- alkoxy, C1-C3- alkyl; X is hydrogen or fluorine; Y is an oxygen atom or a sulfur atom, provided that Q denotes the Q3, R2is methyl, and intermediate products to obtain a derivative of uracil. Herbicide composition comprises a derivative of uracil in the amount of 0.05 to 5.0, targeted supplements the rest. Method of weed control by processing areas, where they grow derivatives of uracil in the amount of 0.002 - 1 kg/ha 1 Il., 28 table.

The invention relates to the derivatives of uracil and their use in agriculture, namely use="ptx2">

However, they have low herbicide activity or have poor selectivity for crops and weeds.

The aim of the invention is the synthesis of new derivatives of uracil and increase herbicide activity.

This goal is achieved by derivatives of uracil of the formula

(I) where R1- triptorelin group or panafcortelone group;

R2is a methyl group or amino group;

Q - any one of formulas

where R3is a hydrogen atom or a methyl group;

R4, R5and R6- each unsubstituted or galizana1-C4-alkyl or C3-C4-Alchemilla group3-C4-Alchemilla group or1-C4-alkoxy(C1-C3)-alcalina group;

X is a hydrogen atom or fluorine;

Y is an oxygen atom or a sulfur atom, provided that when Q is Q3then R2denotes a methyl group.

These derivatives of uracil exhibit high herbicide activity against various weeds at high selectivity between crops and weeds.

Compounds of the present invention can be obtained Razi X have the above meanings, get in any way from the number below.

Method A.

The compound (Q-1: R2=CH3) are obtained by reacting compounds of the formula

(II) where R1, R3, R4and X have the above meanings, with meteorous reagent.

Communication is usually carried out in an inert solvent at a temperature of about 0-100aboutC for about 0.5 to 10 hours

Metymirumi the reagent is used in an amount of about 1-3 equivalents to one equivalent of the compound (II). Examples meteorologi reagent are methyl chloride, methyl bromide, methyliodide, dimethylsulfate etc.

Examples of the inert solvent are aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, xylene, toluene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), tertiary amines (e.g. pyridine, triethylamine, N, N-diethylaniline, tributylamine, N-methylmorpholine), acid amides (for example, formamide, N, N-dimethylformamide, ndimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, sulfolan) and so on, They can be used is ulpanat etc.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and extracted with an organic solvent followed by concentration. If desired, the resulting product can be subjected to any conventional methods of purification, such as chromatography, distillation or recrystallization.

The way Century.

The compound (Q-1: R2=CH3; X=F) are obtained by reacting compounds of the formula

(III) where R1and R3have the above meanings, with a compound of the formula

R4- Z, (IV) where Z is tsepliaeva group such as halogen atom (e.g. chlorine, bromine, iodine), or sulfonyloxy (for example, methanesulfonate, p-toluensulfonate); R4has the given value.

The reaction is usually carried out in the presence of a base in an inert solvent at a temperature of about 0-100aboutC for about 0.5 to 10 hours

Typically, the compound (IV) and the base are used respectively in amounts of about 1-1,2 equivalent of about 1-3 equivalents to one equivalent of the compound (III). As a basis you can use inorganic base (e.g. sodium hydroxide, hydrox, the sodium ethylate), or etc.

Examples of the inert solvent are aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), golozhabernyi hydrocarbons (e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), fatty acids (e.g. formic acid, acetic acid, oleic acid), alcohols (e.g. methanol, ethanol, isopropanol, tert-butanol, octanol, cyclohexanol, methylcellosolve, diethylene glycol, glycerin), esters (such as ethyl formate, ethyl acetate, diethylmalonate), nitro compounds (for example, nitroethane, nitrobenzene), a nitrile (e.g. acetonitrile, isobutyronitrile), tertiary amines (e.g. pyridine, triethylamine, N, N-diethylaniline, tributylamine, N-methylmorpholine), acid amides (for example, formamide, N, N-dimethylformamide, ndimethylacetamide), aqueous ammonia, water, etc. They can be used separately or in combination.

PEFC is ü poured into water and the precipitated crystals are collected by filtration. Alternative reaction mixture is shaken in combination with water and a water-immiscible organic solvent for extraction, after which the extract was concentrated. If desired, the resulting product can be any of the conventional methods of purification, such as chromatography, distillation or recrystallization.

Method C.

The compound (Q-1:R2=NH2) are obtained by reacting the compound (II) with aminimum reagent.

Communication is usually carried out in an inert solvent at a temperature of about 0-100aboutC for about 0.5 to 10 hours

Miniraise the reagent is used in an amount of about 1-1,2 equivalent to one equivalent of the compound (II). As amineralo reagent can be used 2,4-dinitrophenoxy or etc.

Examples of the inert solvent are aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), tertiary amines (e.g. pyridine, triethylamine, N, N-diethylaniline, tributyl the example, dimethyl sulfoxide, sulfolan), and so on, They can be used separately or in combination.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and extracted with an organic solvent followed by concentration. If desired, the resulting product may be subjected to any conventional methods of purification, such as chromatography, distillation or Perek - retalitate.

In accordance with the above methods (A), (B) or (C) receive the proposed connection.

Typical ways to obtain these compounds in the following examples.

P R I m e R 1. To a solution of 1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl] -4-trifluoromethyl-1,2,3 ,6 - tetrahydropyrimidin-2,6-dione (2.0 g) in dimethylformamide (10 g) added methyliodide (0.5 g) and potassium carbonate (1.6 g) and the resulting mixture heated at 80-100aboutC, followed by stirring for 3 hours After completion of the reaction, the reaction mixture was poured into water and the precipitated crystals are collected by filtration, washed with water, dried and purified column chromatography to obtain 1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl] -3-methyl-4-trift the J=2,5 Hz, 2N), of 4.66 (s, 2H), 6,33 (s, 1H), make 6.90 (d, J=11 Hz, 1H), 6,98 (d, J=6 Hz, 1H).

P R I m m e R 2. A mixture of 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzo - casin-3(4H)-she (1.4 g) and ethyl 3-amino-4,4,4-trifurcation (0,92 g) dissolved in dimethylformamide (0,92 g), and then add sodium hydride (0.2 g). The resulting mixture was stirred for 30 min, cooled with ice and heated under reflux for 3 hours After cooling, add methyliodide (1.0 g) and the resulting mixture was stirred at 40aboutC for 30 minutes After completion of the reaction, the reaction mixture is combined with water and extracted with diethyl ether. The organic layer is concentrated and purified column chromatography or silica gel to obtain 1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl] -4-triptime-yl-3 - methyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (0.3 g).

P R I m e R 3. To a solution of 1-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl] -3-methyl-4-trifluoromethyl-2,2,3,6 - tetrahydropyrimidin-2,6-dione (2.3 g) in dimethylformamide (10 g) was added chloromethylation ester (1.0 g) and potassium carbonate (1.7 g) and the resulting mixture was heated at 40-50aboutC for 30 minutes After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate (30 ml), washed with water, dried and Konz is)-on-6-yl] -3-methyl-4 - Cryptor - methyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (1.8 g).

P R I m e R 4. A mixture of 5-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzo - casin-3(4H)-she (1.4 g) and ethyl 3-amino-4,4,4-trifurcation dissolved in dimethylformamide (5.0 g), and then add sodium hydride (0.2 g). The resulting mixture was stirred for 30 min, cooling on ice and heated under reflux for 3 hours After cooling, add 2,4-dinitrophenoxy (1.2 g) and the resulting mixture was stirred at 40aboutC for 3 hours After completion of the reaction, the reaction mixture is combined with water, extracted with ethyl acetate and concentrated. The residue is purified column chromatography on silica gel to obtain 1-[7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl] -3-amino-4 - trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (0.2 g).

Similarly receive the remaining compounds (Q-1), are given in table.1.

In addition, for example, the compound (1:Q=Q2) formula

(Q-2) where R1, R2, R5and Y have the above meanings, receive the following ways:

Method D. the Compound (Q-2):R2=CH3) are obtained by reacting compounds of the formula

(V) where R1, R5and Y have the above meanings, with meteorous reagent.

aboutC for about 0.5-8 hours

As a rule, metymirumi reagent and dehydrohalogenating agent used respectively in amounts of about 1-1,2 equivalents and about 1-3 equivalents to one equivalent of the compound (V). As meteorologi reagent can be used methyliodide, methyl bromide, methyl chloride, dimethylsulfate etc. Examples dehydrohalogenating agent is an organic base (e.g. pyridine, triethylamine, N,N-diethylaniline), inorganic bases (e.g. sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, alkoxides of alkali metals (e.g. sodium methylate, sodium ethylate), etc.

Examples of the inert solvent are aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), golozhabernyi hydrocarbons (e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone (for example, formamide, N, N-dimethylformamide, ndimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, sulfolan), water, etc. They can be used separately or in combination.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and the precipitated crystals are collected by filtration. Alternative reaction mixture is shaken in combination with water and a water-immiscible organic solvent for extraction, and the extract was concentrated. If desired, the resulting product may be subjected to any purification method, such as chromatography, distillation or recrystallization.

The way it Is.

The compound (Q-2:R2=NH2) are obtained by reacting the compound (V) with aminimum reagent.

The reaction is usually carried out in an inert solvent at a temperature of about 20-100aboutC for about 0.5-8 hours

Miniraise reagent is usually used in an amount of about 1-3 equivalents to one equivalent of the compound (V). As amineralo reagent can be used 2,4-dinitrophenoxy etc.

Examples of the inert solvent are aliphatic, ensol, toluene, xylene), golozhabernyi hydrocarbons (e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), tertiary amines (e.g. pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine), acid amides (for example, formamide, N,N-dimethylformamide, acetamide), sulfur compounds (for example, dimethylsulfoxide, sulfolan), etc.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and the precipitated crystals are collected by filtration. Alternative reaction mixture is shaken in combination with water and a water-immiscible organic solvent for extraction, and the extract was concentrated. If desired, the resulting product may be subjected to any conventional methods of purification, such as chromatography, distillation or recrystallization.

Typical ways to obtain the compounds (Q-2) shown in the following examples.

P R I m e is g) in dimethylformamide (10 g) added methyliodide (0.5 g) and potassium carbonate (1.6 g) and the resulting mixture heated at 40 to 80aboutC for 3 hours After completion of the reaction, the reaction mixture was poured into water and the precipitated crystals are collected by filtration, washed and dried. The residue is purified column chromatography to obtain 1-[3-sec-butyl-6-fluoro-2(3H)-benzothiazole-5-yl] -3-methyl-4-triptime - Teal - 1,2,3,6-tetrahydropyrimidin-2,6-dione (1.0 g).

H-NMR (ppm)/CDCl3, 60 MHz: from 0.90 (t, J=7 Hz, 3H), of 1.48 (d, J=7 Hz, 3H), 1,6-2,3 (m, 2H), 3.45 points (s, 3H), 4.0 to 4.5 (m, 1H), and 6.3 (s, 1H), 7,03 (d, J=6 Hz, 1H), 7,32 (d, J=10 Hz, 1H).

P R I m e R 6. To a solution of 1-[6-fluoro-3-propargyl-2(3H)-benzoxazolone-5-yl] -4-trift - ormetal-1,2,3,6 - tetrahydropyrimidin-2,6-dione (2.0 g) in dimethylformamide (10 g) added methyliodide (0.5 g) and sodium hydride (0.4 g) and the resulting mixture was heated at 40-50aboutC for 3 hours After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and the organic layer concentrated under reduced pressure. The residue is purified column chromatography to obtain 1-[6-fluoro-3-propargyl-2(3H)-benzoxazolone-5-yl]-3-me - til-4-trifluoromethyl - 1,2,3,6-tetrahydropyrimidin-2,6-dione (0.3 g).

P R I m e R 7. To a solution of 1-[6-fluoro-3-sec-butyl-2(3H)-benzothiazole-5-yl] -4-Tr - iformity-1,2,3,6 - tetrahydropyrimidin-2,6-dione (2.0 g) in dimethylformamide (10 g) was added sodium hydride (0.3 g) and 2,4 reaction mixture is poured into water, extracted with ethyl acetate and concentrated. The residue is purified column chromatography on silica gel to obtain 1-[6-fluoro-3-sec-butyl-2(3H)-benzothiazole-5-yl]-3-amino-4-triptime - Teal - 1,2,3,6-tetrahydropyrimidin-2,6-dione (0.4 g).

Similarly receive the compound (Q-2), are given in table.2.

In addition, for example, the compound (1:Q=Q3) formula

(Q-3) where R1and R6have these values get below way.

Method F.

The compound (Q-3) are obtained by reacting compounds of the formula

(VI) where R1has the above significance, with a compound of the formula

R6-Z (VII) where R6and Z have the above values.

Communication is usually carried out in the presence of a base in an inert solvent at a temperature of about 0-100aboutC for about 0.5-12 hours

The compound (VII) and the base are used respectively in amounts of about 1-1,2 equivalent of about 1-1,5 equivalents to one equivalent of the compound (VI). As a basis you can use inorganic base (e.g. sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride, alkoxide Selous aliphatic hydrocarbons (for example, hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), golozhabernyi hydrocarbons (e.g. chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethyleneglycol dimethyl ether), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone), fatty acids (e.g. formic acid, acetic acid, oleic acid), alcohols (e.g. methanol, ethanol, isopropanol, t-butanol, octanol, cyclohexanol, methylcellosolve, diethylene glycol, glycerin), esters (such as ethyl formate, ethyl acetate, butyl acetate, diethylmalonate), nitroso - organisations (for example, nitroethane, nitrobenzene), NITRILES (e.g. acetonitrile, isobutyronitrile), tertiary amines (e.g. pyridine, triethylamine, N,N-diethylaniline, tributylamine, N-methylmorpholine), acid amides (for example, formamide, N, N-dimethylformamide, ndimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, sulfolan), aqueous ammonia, water, etc. They can be used separately or in combination.

After completion of the reaction, the reaction mixture by beraut filtering. Alternative reaction mixture is shaken in combination with water and a water-immiscible organic solvent for extraction, and the extract was concentrated. If desired, the resulting product can be subjected to any conventional methods of purification, such as chromatography, distillation or recrystallization.

Typical mode to obtain the compounds (1-3) shown in the following example.

P R I m e R 8. To a solution of 1-[6-fluoro-1,2,3,3-tetrahydroquinoxalin-2-one-7-yl]-3--methyl-4 - trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (2.0 g) in dimethylformamide (10 g) was added sodium hydride (500 mg) and propylbromide (1.0 g), the mixture was heated at 40-50aboutWith in an hour. After completion of the reaction, the reaction mixture was poured into water and the precipitated crystals are collected by filtration, washed and dried to obtain 1-(6-fluoro-1-propargyl-1,2,3,4-tetrahydroquinoxalin-2-he-7-yl)-3-methyl-4 - trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (1.0 g).

Similarly receive join (Q-3), are given in table.3.

The original compound (II) or (V) can be obtained according to the following scheme

where R7- C1-C6is an alkyl group, R8- C1-C6is an alkyl group; R< the scheme is further explained in detail.

1) Obtaining the compound (II) or compound (V) from compound (VIII) or the compound (X).

The compound (II) or compound (V) can be obtained by reacting compound (VIII) or the compound (X) with the compound of the formula

R1(NH2)C= CHCOOR9(XII) where R9- C1-C6is an alkyl group; R1has the above value, usually in the presence of dehydrogenating reagent in an inert solvent at a temperature of about 0-200aboutC for about 0.5 to 10 hours

In General, the compound (XII) and dehydrogenative the reagent is used respectively in amounts of about 1-1,2 equivalent of about 1-1,2 equivalent to one equivalent of the compound (VIII) or the compound (X). As dehydrogenating reagent can be used an inorganic base (e.g. sodium carbonate, potassium carbonate, sodium hydride), alkali metal alkoxide (e.g. sodium methylate, sodium ethylate), etc.

Examples of the inert solvent are aliphatic hydrocarbons (e.g. hexane, heptane, ligroin, petroleum ether), aromatic hydrocarbons (e.g. benzene, toluene, xylene), ethers (e.g. diethyl ether, diisopropyl ether, dioxane, tetr the Lin, tributylamine, N-methylmorpholine), acid amides (for example, formamide, N, N-dimethylformamide, ndimethylacetamide), sulfur compounds (e.g. dimethyl sulfoxide, sulfolan), and so on, They can be used separately or in combination.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and extracted with an organic solvent followed by concentration. If desired, the resulting product can be subjected to any conventional purification method such as chromatography, distillation or recrystallization.

The compound (II) or compound (V) can be metilirovanie or minirovat without selection, obtaining the compound (I-I) or the compound (1-2).

Typical mode to obtain the compound (II) or compound (V) in the following example.

P R I m e R 9. To a solution of 3-isopropyl-6-fluoro-5-methoxycarbonylamino-2(3H)-Ben - satiation (2.8 g) in N,N-dimethylformamide (10 g) was added sodium hydride (0.4 g) and ethyl 3-amino-4,4,4-trifurcation (0.9 g), the mixture was heated under reflux for 3 hours After cooling, the reaction mixture is poured into water and extracted with ethyl acetate. The organic layer concen-trifluoromethyl-1,2,3,6-tetrahydro-pyrimidine-2,6-dione (0.8 g).

H-NMR (ppm/) CDCl3, 60 MHz/: of 1.55 (6H, d, J=7 Hz), 4,4-5,5 (1H, m), 6,17 (1H, c), 7,0 (1H, l, J=6 Hz), 7,25 (1H, d, J=9 Hz), from 9.0 to 10.1 (1H, m).

Similarly receive the compound (II) and compound (V), are given in table. 4 and 5.

2) obtaining the compound (VIII) or the compound (X) from the compound (IX) or the compound (XI).

The compound (VIII) or the compound (X) can be obtained by reacting compound (IX) or the compound (XI) with the compound of the formula

Cl OR10(XIII) where C1-C6-alcalina group, in the presence of dehydrohalogenating reagent, in the presence or absence of an inert solvent at a temperature of about 0-150aboutC for about 0.5 to 10 hours

Typically, the compound (XIII) and dehydrohalogenated the reagent is used respectively in amounts of about 1-1 .5 equivalent of about 1-1,5 equivalents to one equivalent of the compound (IX) or the compound (XI). As dehydrohalogenating reagent can be used an organic base (e.g. pyridine, triethylamine, N,N-diethylaniline), inorganic base (e.g. sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride), alkali metal alkoxide (e.g. sodium methylate, sodium ethylate), etc.< xylene), golozhabernyi hydrocarbons (e.g. chloroform, carbon tetrachloride), ethers (e.g. diethyl ether, dioxane), etc.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture is poured into water and extracted with an organic solvent followed by concentration. If desired, the resulting product can be subjected to any conventional purification method such as chromatography, distillation or recrystallization.

Typical mode to obtain the compound (VIII) or the compound (X) in the following example.

P R I m e R 10. A mixture of 6-amino-7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-she (2.1 g) in N,N-diethylaniline (1.5 g) and methylcarbamate (1.0 g) dissolved in 1,2-dichloroethane (10.0 g) and the resulting mixture heated under reflux for 3 hours After cooling, the reaction mixture is washed with water and the organic layer concentrated. The residue is washed with methanol to obtain 7-fluoro-6-methoxycarbonylamino-4-propargyl-2H-1,4-benzo - casin-3(4H)-she (2.0 g).

Similarly receive the compounds (VIII) and compound (X), are given in table. 6 and 7.

The compound (IX) can be obtained by the method disclosed is B>12each stands WITH1-C6is an alkyl group; R1and R3have the above values.

The reaction in each stage in the diagram is explained in more detail below.

3). Obtaining compound (III) or compound (VI) from compound (XIV) or compound (XV).

The compound (III) or the compound (VI) can be obtained by subjecting the compound (XIV) or the compound (XV) reductive cyclization. Reductive cyclization can be accomplished, for example, by treating the compound (XIV) or compound (XV) with a reducing agent such as iron powders, or by catalytic reduction of compound (XIV) or compound (XV).

Processing of metal powders can be accomplished with the use of iron powders (Crocus) in an amount of about 2.5 to 10 equivalents to one equivalent of the compound (XIV) or compound (XV) in the presence of a minor amount of acid (e.g. acetic acid, karnavati acid) in an inert solvent at a temperature of about 50-200aboutC for about 0.5-10 hours Examples of the solvent are toluene, 1,2-dichloroethane, methyl isobutyl ketone, acetic acid, water, etc. are Also suitable mixture of these solvents.

After completion of the reaction, the reaction mixture can be subjected to conventional post-processing. For example, the reaction mixture is filtered, the filtrate is combined with water and the resulting mixture is extracted with an organic solvent followed by concentration. If desired, the resulting product can be subjected to any traditional methods of purification such as recrystallization or column chromatography.

Typical ways to obtain compound (III) or compound (VI) is shown in the following examples.

P R I m e R 11. A suspension of 1-(2-fluoro-4-butyloxycarbonyl-5-nitrophenyl)- -3-methyl-4-trifluoromethyl - 1,2,3,6-tetrahydropyrimidin-2,6-dione (10 g), water (3 g) and iron powder (8 g) in acetic acid (50 g) is heated under reflux for 3 hours After completion of the reaction, the reaction mixture was filtered using pelita, the filtrate is combined with water and extracted with ethyl acetate. The organic layer is concentrated and the residue purified column chromatography to obtain 1-[7-fluoro-2H-1,4-benzoxazin-3(4H)-on-6-yl] -3-methyl-4 - trifluoromethyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (8.0 g), so pl. 224-225aboutC.

aboutC.

4). Obtaining the compound (XIV) from compound (XVI).

The compound (XIV) can be obtained by reacting compound (XVI) with the compound of the formula

R11O (XVIII) where R3and R11have the values given, usually in the presence of a base in an inert solvent at a temperature of about 25-200aboutC for about 0.5 to 10 hours In this reaction, the compound (XVIII) and the base can be used respectively in an amount of about 1.0 to 1.2 equivalent of about 1.0 to 4.0 equivalents to one equivalent of the compound (XVI). As a basis you can use inorganic base, such as potassium fluoride, potassium carbonate or sodium hydride. Examples of the solvent are aromatic hydrocarbons (e.g. toluene, xylene), ha is the dioxane), etc.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing. For example, the reaction mixture pour in water and extracted with an organic solvent followed by concentration. If desired, you can take any conventional method of purification, such as chromatography or recrystallization.

A typical option for obtaining the compound (XIV) in the following example.

P R I m e p 13. A suspension of 1-(2,4-debtor-5-nitrophenyl)-3-methyl-4-trifluoromethyl-1,2,3, 6-tetrahydropyrimidin - 2,6-dione (10.0 g), butylglycol (5.0 g) and potassium fluoride (10.0 g) in dioxane (30.0 g) is heated under reflux for 4 hours After completion of the reaction, the reaction mixture was poured into water and extracted with ethylacetate followed by concentration. The residue is purified column chromatography on silica gel to obtain 1-(2-fluoro-4-butyloxycarbonyl-5-nitrophenyl)- 3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydro-pyrimidine-2,6-dione (11,0 g), so pl. 110-113aboutC.

5). Obtaining the compound (XV) from compound (XVI).

The compound (XV) can be obtained by reacting compound (XVI) with the compound of the formula

R12O (IXX) where R12has a given value, usually in the presence of base the connection (IXX) and the base can be used in amounts of about 1.0 to 1.2 equivalent of about 1.0 to 4.0 equivalents to one equivalent of the compound (XVI). As a basis it is possible to use an organic base such as triethylamine. Examples of the solvent are aromatic hydrocarbons (e.g. toluene, xylene), golozhabernyi hydrocarbons (e.g. dichloromethane, 1,2-dichloroethane), ethers (e.g. tetrahydrofuran, dioxane), etc.

After completion of the reaction, the reaction mixture is subjected to ordinary post-processing, for example, the reaction mixture was poured into water and extracted with an organic solvent followed by concentration. If desired, you can take any conventional method of purification, such as chromatography or recrystallization.

A typical option for obtaining the compound (XV) in the following example.

P R I m e R 14. A suspension of 1-(2,4-debtor-5-nitrophenyl)-3-methyl-4-trifluoromethyl-1,2,3,6 - tetrahydropyrimidin-2,6-dione (10.0 g), acylaminoacyl (5.0 g) and triethylamine (6,1 g) in dioxane (50 g) is heated under reflux for 4 hours After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. The extract is dried in the presence of magnesium sulfate and concentrated. The residue is purified column chromatography on silica gel using a mixture of hexane and ethyl acetate, full (12.0 g).

H-NMR (ppm)/CDCl3, 60 MHz: 1,33 (2H, t), 3,53 (3H, s), 4,0 (2H, d), 4,27 (2H, HF), 6,27 (1H, s), to 6.43 (1H, d), 8,11 (1H, d), of 8.3 to 8.8 (1H, m).

6). Obtaining the compound (XVI) from compound (XVII).

The compound (XVI) is obtained by nitration of the compound (XVII) with nitric acid in concentrated sulfuric acid is usually at a temperature of about 0-30aboutC for approximately 0.3 to 3 o'clock When the nitration using nitric acid is used in an amount of about 1 to 1.5 equivalents to one equivalent of the compound (XVII). Subsequent processing of the reaction mixture after completion of the nitration can be performed in the traditional way.

A typical option for obtaining the compound (XVI) in the following example.

P R I m e R 15. A solution of 1-(2,4-differenl)-3-methyl-4-trifluoromethyl-1,2,3,6-Tetra - hydropyridine-2,6 - dione (30,6 g) in concentrated sulfuric acid (100 g) is cooled to 5aboutWith, and then added dropwise 61% solution of nitric acid (10.3 g) at a temperature below 10aboutC, followed by stirring the mixture for 3 hours After completion of the reaction, the reaction mixture was poured into water and the precipitated crystals are collected by filtration and dried to obtain 1-(2,4-debtor-5-nitrophenyl)-3-methyl - 4-Cryptor - methyl-1,2,3,6-tetrahydropyrimidin-2,6-dione (33,0 g), templet with traditsionnye solid or liquid carriers or diluents, as well as surface-active agents or auxiliary agents, in the form of traditional drugs, such as emulsifiable concentrates, wettable powders, suspension, water dispersible granules and suspensions. The content of the compound (I) as the active ingredient in such forms of the drugs is usually 0.02 to 80 wt. % , preferably about 0.05 to 70 wt.%. Examples of the solid carrier or diluent are fine powders or granules of kaolin, attapulgite, bentonite clay, terralba, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, synthetic hydrosilicate, etc. as the liquid carrier or diluent can lead aromatic hydrocarbons (e.g. xylene, methylnaphthalene), alcohols (e.g. isopropanol, ethylene glycol, cellosolve), ketones (e.g. acetone, cyclohexanone, isophorone), soybean oil, cotton, dimethylsulfoxide, N,N-dimethylformamide, acetonitrile, water, etc.

Surface-active agent used for emulsification, dispersion or wetting can be the substance of any type, for example, anionic or nonionic. Examples of surfactants include polyoxyethyleneglycol esters, polyoxyethyl - alkylaromatic esters, polyoxyethylene-polyoxypropylene block copolymer, a complex sorbitan-esters of fatty acids, complex polyoxyethylene-sorbitan-esters of fatty acids and other Examples of auxiliary agents are ligninsulfonate, sodium alginate, polyvinyl alcohol, Arabian gum, CMC (carboxymethyl cellulose), PAP (isopropylbenzyl phosphate), etc.

Practical options herbicide compositions in accordance with the present invention is shown in the following examples, in which parts are represented by mass. The number of the active ingredient corresponds to the number shown in the table. 2, 4 and 6.

Example of structure 1.

50 h of any one compound among compounds NN 1,2, 4-12, 14-18, 20, 21, 24 27-29. or 32-40, 3 hours ligninsulfonate calcium, 2 hours lauryl sodium and 45 p.m. synthetic hydrosilicate mix well until the powder state in order to obtain a wettable powder.

Example composition 2.

5 o'clock any connection from among compounds NN 1-40, 14 hours polyoxyethyleneglycol ether, 6 hours dodecyl - benzosulfimide calcium, 25 hours of xylene and 50 hours of cyclohexanone are well mixed to obtain emulsifiable concentrate.

, including ligninsulfonate calcium, 30 hours of bentonite and 65 hours of kaolin clay are well mixed to a powdery state. The mixture is then diluted with water, granularit and dried to obtain granules.

Example of compound 4.

25 including any compounds among compounds NN 1, 2, 4-12, 14-18, 20, 21, 24, 27-29, or 32-40 mixed with 3 hours of polyoxyethylene sorbitan monooleate, 3 hours carboxymethylcellulose and 69 hours water and sprayed up until the particle size of the mixture becomes less than 5 μm, obtaining a suspension.

Example of compound 5.

0,05 including any of the compounds NN 1-40, 1 h synthetic hydrosilicate, 2 hours ligninsulfonate calcium, 30 hours of bentonite and 66,95 including kaolin clay is thoroughly mixed with the simultaneous poroshkovaya. The mixture is then diluted with water, granularit and dried to obtain granules.

The compound (I) thus obtained in any suitable form of the drug, is used for pre-emergence or post-harvest destruction of undesired weeds by soil or leaves, and processing provenien flooding of the site. These processing methods include introducing into the surface of the soil before or after sowing, the incorporation into the soil before seeding or transplanting and so on Hardwood processing is it possible to make a direct entry in the weeds with care, in fact, to chemical substance not found on foliage culture.

The compound (I) can be used together with other herbicides to improve their activity as herbicides, and in some cases, you can expect a synergistic effect. In addition, compound (I) can be applied in combination with the insecticide, acaricide, nematocide, fungicide, growth regulator of plants, fertilizer, melioidosis means and so on, the Connection is also useful as a herbicide for gardens, pastures, lawns, forests, agricultural land, etc.

The dosage of compound (I) may vary depending on prevailing weather conditions, the composition used, the prevailing season, type of application, nature of the soil, type of crops and weeds, etc. As a rule, the dosage is about 0.01 to 80 g, preferably about 0.02 to 40 g of the active ingredient on ar. The proposed herbicide composition formed in the form of emulsifiable concentrate, wettable powder, water dispersible granules or suspension can be applied by dissolving it in water at a volume of about 1-10 l/ar, optionally with addition of an auxiliary agent such as an agent that increases smachivayushchee-active substance acid-based polyoxyethylene resin (ester), ligninsulfonate, salt abietinus acid, dinaftiletilena, paraffin, etc. Composition, made in the form of granules, usually can be used without dilution.

Biological data of compound (I) as a herbicide in the following examples, in which phytotoxicity relative of cultivated plants and weed-killing activity in relation to weeds see visually with respect to the degree of germination as well as growth inhibition, and note the index 0, 1, 2, 3, 4 or 5, where 0 indicates a lack of significant differences compared with untreated plants, and 5 indicates complete inhibition or death of the test plants.

The compounds listed in the table. 11, is used for comparison.

The test example 1.

Cylindrical plastic pots (diameter: 10, height 10 cm) filled with soil upland areas, then sow the seeds of barnyard grass-plushie millet, wild oats, ipomea and cantica Theophrastus and cover with soil. A certain amount of the test compounds prepared in the form of an emulsifiable concentrate as in example composition 2, diluted with water and the diluted composition is sprayed on the soil surface with the help of their 20 days then examine herbicide activity. The results are shown in table. 9.

The test example 2.

Cylindrical plastic pots (diameter: 10, height 10 cm) filled with soil upland areas, then sow the seeds of barnyard grass-plushie millet, ipomea, radish, cantica Theophrastus and wild oat and cultivated in a greenhouse for 10 days. A certain amount of the test compounds prepared in the form of an emulsifiable concentrate as in example composition 2, was diluted with water containing a substance that increases the wetting ability, and the diluted composition is sprayed on the foliage of the test plants by means of a small hand sprayer at a volume spray 10 l/ar. Then the subjects of the plants grown in the greenhouse for 20 days, after which examine herbicide activity. The results are shown in table. 10.

The test example 3.

Cylindrical plastic pots (diameter: 10, height 12 cm) filled with soil of flooded rice fields, seeds of barnyard millet (Echinochloa erpicola), broadleaf weeds, i.e. false bedrentsa, rotary branched, pomoynitska sow at a depth of 1-2 cm and Then pour in water to create conditions flooded area and carry out the more in the greenhouse. After 6 days (at this time, the weeds begin to germinate in pots by perfusion impose a certain amount of the test compounds prepared in the form of an emulsifiable concentrate as in example composition 2, and diluted with water (5 ml). The subjects of the plants grown in the greenhouse for another 20 days, after which examine herbicide activity and phytotoxicity.

The results are shown in table. 11.

The test example 4.

Kegs (HH cm) filled with soil upland areas, which at a depth of 1-2 cm sowing the seeds of rice, soybeans cultural, corn, ipomea, cantica Theophrastus, black nightshade, sorghum Halep and results of the analysis of green. A certain amount of the test compounds prepared in the form of an emulsifiable concentrate as in example composition 2, diluted with water, and the diluted composition is sprayed on the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 20 days, after which examine herbicide activity and phytotoxicity.

The results are shown in table. 12.

The test example 5.

Kegs (HH cm) filled with soil upland areas, katarzina black, amaranth spiked and results of the analysis of green. A certain amount of the test compounds prepared in the form of an emulsifiable concentrate as in example 2, diluted with water and the diluted composition is sprayed on the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 20 days, after which examine herbicide activity and phytotoxicity.

The results are shown in table.13.

The test example 6.

Kegs (HH cm) filled with soil from upland areas, which at a depth of 1-2 cm sowing the seeds of wheat, barley, mountain pepper, Veronica Persian violet field and cleaver. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water, and the diluted composition is sprayed on the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 27 Nam and investigate herbicide activity and phytotoxicity.

The results are presented in table. 14.

The test example 7.

Kegs (HH cm) on the tion, chickweed average, Veronica Persian and violet field. A certain amount of the test compounds prepared in emulsifiable concentrate as described in example 3, diluted with water and the diluted composition is sprayed on the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 27 DN, then measure herbicide activity and phytotoxicity.

The results are presented in table.15.

The test example 8.

Kegs (HH cm) filled with soil upland areas, which sow the seeds of corn, rice, ipomea, cocklebur, cantica Theophrastus, nesuhi canadian and black nightshade and cultured for 18 days in a greenhouse. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water and the diluted composition is sprayed on the foliage of the test plants by means of a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for another 20 DN, then investigate herbicide activity and phytotoxicity. During herbicides subjects rastenij plants varies depending on their type.

The results are presented in table. 16.

The test example 9.

Kegs (HH cm) filled with soil upland areas, which sow the seeds of corn, cocklebur, cantica Theophrastus, ipomea, black nightshade, millet batoshevo and results of the analysis of green and cultured for 18 days in a greenhouse. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water, and the diluted composition is applied to the foliage of the test plants by means of a small hand sprayer at a volume of 10 litres of spray on ar. Subjects plants further grown in the greenhouse for 20 days, after which examine herbicide activity and phytotoxicity. During herbicides subjects plants generally have 1-4 stage of maturation of leaves and height from 2 to 12 cm, however, the stage of growth of the test plants varied depending on their species.

The results are presented in table. 16.

The test example 10.

Kegs (HH cm) filled with soil upland areas, which sow the seeds of wheat, barley, mountain pepper, cleaver, chickweed average, Veronica Persian and pavlenkova in emulsifiable concentrate, as indicated in the example composition 2, diluted with water, and the diluted composition is sprayed on the foliage of the test plants by means of a small hand sprayer at a volume of 10 litres of spray on ar. The subjects of the plants grown in the greenhouse for 27 days, after which examine herbicide activity and phytotoxicity. During herbicides subjects plants generally have 1-4 stage of maturation of leaves and height from 2 to 12 cm, however, the stage of growth of the test plants varied depending on their species.

The test results are presented in table. 18.

The test example 11.

Pots Wagner (1/5000 ar) fill soil of flooded rice fields, which at a depth of 1 to 2 cm sowing the seeds of broad-leaved weeds (e.g. false bedrentsa, rotary branched, pomoynitska). Then, pour the water in order to create a flooded conditions and rice seedlings of the second stage of ripening leaves transplanted into the soil, after which the subjects of the plants grown in the greenhouse. After 4 Nam certain amount of the test compounds prepared in emulsifiable concentrate and diluted with water (10 ml), injected into the vascular perfusion. Subjects plants vity presented in table. 19. During processing, the water level in the vessel is maintained at 4 cm, and after 2 days the water allow to seep with the amount corresponding to the depth of 3 cm per day.

The test example 12.

Pots Wagner (1/5000 ar) fill soil of flooded rice land, which at a depth of 1 to 2 cm sowing the seeds of broad-leaved weeds (e.g. false bedrentsa, rotary branched, pomoynitska) and barnyard millet. Then, pour the water in order to create a flooded conditions, and there transplanted rice seedlings with 2 stage of maturation of the leaves, after which the subjects of the plants grown in the greenhouse. After 4 Nam certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, and diluted with water (10 ml), injected into the vascular perfusion. The subjects of the plants grown in the greenhouse for 20 DN, then investigate herbicide activity and phytotoxicity. The test results are presented in table. 20. During processing, the depth of water in the vessel is maintained at the level of 4 cm, and after 2 days allow water to seep with the amount corresponding to the depth of 3 cm per day.

The test example 13.

Cylindracea a depth of 1 to 2 cm sowing the seeds of barnyard millet, broadleaf weeds (e.g., false bedrentsa, rotary branched, pomoynitska) and bulrush. Then, pour the water in order to create a flooded conditions, and the subjects of the plants grown in the greenhouse. After 6 days (at this time, the weeds begin to sprout) a certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, and diluted with water (5 ml), bring in the vessels by perfusion. The subjects of the plants grown in the greenhouse for 20 days, after which examine herbicide activity. The test results are presented in table. 21.

The test example 14.

Kegs (HH cm) filled with soil upland areas, which at a depth of 1 to 2 cm sowing cotton seeds, corn, rice, cantica Theophrastus, cocklebur, ipomea, black nightshade, amaranth spiked and sesbania hemp. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, and razdavlennoi water, sprayed on the soil surface using a small hand sprayer at a volume of 10 l/ar. The subjects of the plants grown in the greenhouse for 20 DN, then explore gerbil is 15.

Kegs (HH cm) filled with soil upland areas, which at a depth of 1 to 2 cm sowing the seeds of corn, rice, cantica Theophrastus, ipomea high, black nightshade, amaranth spiked and results of the analysis of green. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water and the diluted composition is applied to the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 20 DN, then explore herbicidal activity and phytotoxicity. The test results are presented in table. 23.

The test example 16.

Kegs (HH cm) filled with soil upland areas, which at a depth of 1 to 2 cm sowing the seeds of barnyard millet, sorghum Halep, the results of the analysis of green and Rosicky blood. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water, and the diluted composition is applied to the soil surface using a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse in techinically in table. 24.

The test example 17.

Kegs (HH cm) filled with soil upland areas, which sow the seeds of corn, cocklebur, cantica Theophrastus, ipomea high and nightshade black and cultured for 18 Nam in the greenhouse. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water and the diluted composition is applied to the foliage of the test plants by means of a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 20 DN, then investigate herbicide activity and phytotoxicity. During treatment, subjects plants have mostly 1-4 stage of maturation of leaves and height from 2 to 12 cm, however, the stage of growth of the test plants varied depending on their species. The test results are presented in table. 25.

The test example 18.

Kegs (HH cm) filled with soil upland areas, which at a depth of 1 to 2 cm sowing the seeds of wheat, barley, mountaineer peppermint, chickweed average, Veronica Persian, Marie white and violet field. A certain amount of the test compounds prepared in emuleret the soil with a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 27 DN, then investigate herbicide activity and phytotoxicity. The test results are given in table. 26.

The test example 19.

Kegs (HH cm) filled with soil upland areas, which sow the seeds of corn, cocklebur, cantica Theophrastus, ipomea high, nesuhi canadian, black nightshade, barnyard millet and sorghum Halep and cultured for 18 Nam in the greenhouse. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water and the diluted composition is applied to the foliage of the test plants by means of a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 20 DN, then investigate herbicide activity and phytotoxicity. During treatment, subjects plants have mostly 1-4 stage of maturation of leaves and height from 2 to 12 cm, however, the stage of growth of the test plants varied depending on their species. The test results are presented in table. 27.

The test example 20.

Kegs (HH cm) filled with soil upland areas, in which C is letnego and Alopecurus myservicename and ultiroute for 27 Nam in the greenhouse. A certain amount of the test compounds prepared in emulsifiable concentrate, as indicated in the example composition 2, diluted with water and the diluted composition is applied to the foliage of the test plants by means of a small hand sprayer at a volume spray 10 l/ar. The subjects of the plants grown in the greenhouse for 27 DN, then investigate herbicide activity and phytotoxicity. During treatment, subjects plants have mostly 1-4 stage of maturation of leaves and height from 2 to 12 cm, however, the stage of growth of the test plants varied depending on their species. The results of the tests are presented in table. 28.

DERIVATIVES OF URACIL, INTERMEDIATE COMPOUNDS, HERBICIDE COMPOSITION AND METHOD OF WEED CONTROL.

1. Derivatives of uracil General formula I

< / BR>
where R1- triptoreline or panafcortelone group;

R2is methyl or amino group;

Q - one of the following groups:

< / BR>
where R3is hydrogen or methyl;

R4, R5and R6each independently unsubstituted or substituted with halogen, C1-C4-alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-Cthe Q denotes the Q3, R2is methyl.

2. The compound of General formula

< / BR>
where R1- triptoreline or panafcortelone group;

R3is hydrogen or methyl;

R4is unsubstituted or substituted with halogen, C1-C4-alkyl,

unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-C4-alkoxy-C1-C3-alkyl;

X is hydrogen or fluorine.

3. The compound of General formula

< / BR>
where R1- triptoreline or panafcortelone group;

R3is hydrogen or methyl.

4. The compound of General formula

< / BR>
where R1- triptoreline or panafcortelone group;

R5is unsubstituted or substituted with halogen, C1-C4-alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-C4-alkoxy-C1-C3-alkyl;

Y is oxygen or sulfur.

5. The compound of General formula

< / BR>
where R1- triptoreline or panafcortelone group.

6. The compound of General formula

< / BR>
where R3is hydrogen or methyl;

R4is unsubstituted or substituted with halogen, C1-C44-alkoxy-C1-C3-alkyl;

R7is methyl;

X is hydrogen or fluorine.

7. The compound of General formula

< / BR>
where R5is unsubstituted or substituted with halogen, C1-C4-alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-C4-alkoxy-C1-C3-alkyl;

R8is methyl;

Y is oxygen or sulfur.

8. Herbicide composition containing a derivative of uracil and target additives, characterized in that as a derivative of uracil is used as a compound of General formula I

< / BR>
where R1-- triptorelin group and panafcortelone group;

R2is methyl or amino group;

Q - one of the following groups:

< / BR>
where R3is hydrogen or methyl;

R4, R5and R6- each unsubstituted or substituted with halogen, C1-C4-alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-C4-alkoxy-C1-C3-alkyl;

X is hydrogen or fluorine;

Y is oxygen or sulfur;

when the Q denotes the Q3, R2is methyl,

and with the following ratio of components, wt.%:

< / BR>
where R1- triptoreline or panafcortelone group;

R2is methyl or amino group;

Q - one of the following groups;

< / BR>
where R3is hydrogen or methyl;

R4, R5and R6- each unsubstituted or substituted with halogen, C1-C4-alkyl, unsubstituted or substituted with halogen, C3-C4alkenyl, C3-C4-quinil, C1-C4-alkoxy-C1-C3-alkyl;

X is hydrogen or fluorine;

Y is oxygen or sulfur,

when the Q denotes the Q3, R2is methyl,

the dose of the compounds of General formula I 0,002 - 1 kg/ha

 

Same patents:

The invention relates to a series of racemic and optically active derivatives of pyrido[1,2-a] pyrazine, which are used as antidepressants and anxiolytics, as well as intermediates of these derivatives

The invention relates to the derivatives of pyrimidine, herbicide compositions and chemical method of weed control with their use

The invention relates to a process for the preparation of new heterocyclic derivatives of acrylic acid, possess valuable fungicidal properties and which can find application in agriculture

The invention relates to chemical methods of plant protection

The invention relates to new biologically active compounds - derivatives of pyrimidine exhibiting herbicide activity, which can find application in agriculture

The invention relates to pyrimidine derivative of the General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl-(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5with herbicide activity, and to a method of controlling undesirable vegetation by processing them in the locus, namely, that the treatment is carried out pyrimidine derivatives of General formula I:

where R1- alkyl-(C1-C4), O-alkyl-(C1-C4), halogen;

R2- alkyl-(C1-C4), O-alkyl(C1-C4);

n = 3-5;

Z = COOH, COO-alkyl-(C1-C4), CONHSO2C6H5in the amount of 1-10 kg/ha

The invention relates to methods of producing derivatives of 2-anilinopyrimidines or acid additive salts of novel biologically active compounds, which can find application in agriculture

The invention relates to derivatives of 2,4-bis-(pyridine)hintline, which can find application in agriculture for cotton defoliation

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

FIELD: organic chemistry, agriculture.

SUBSTANCE: method involves carrying out a seasonal single treatment of plant leaves with asymmetrical derivative of 4,6-bis-(aryloxy)pyrimidine of the formula: wherein X means chlorine atom (Cl), nitro- or cyano-group. Invention provides enhancing the long-term time of plants protection.

EFFECT: enhanced effectiveness and valuable properties of compounds.

6 cl, 6 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention relates to new derivatives of uracil of the formula [I] eliciting the herbicide effect, herbicide composition based on thereof and a method for suppression of weed growth. In the formula [I] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen atom (O) or sulfur atom (S); R1 means (C1-C3)-alkyl or (C1-C3)-halogenalkyl; R2 means (C1-C3)-alkyl; R4 means hydrogen atom (H) or methyl; R5 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl or (C3-C6)-halogenalkynyl; X1 means halogen atom, cyano- or nitro-group; X2 means hydrogen atom (H) or halogen atom; each among X3 and X4 means independently hydrogen atom (H), halogen atom, (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-, (C1-C6)-halogenalkoxy-, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy- or cyano-group. Also, invention relates to new intermediate substances used for preparing compounds of the formula [I] corresponding to formulae [VII] , [XXXIV] and [XXXIII] wherein in compound of the formula [VII] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen (O) or sulfur atom (S); in compounds of formulae [XXXIV] and [XXXIII] W means oxygen atom (O); R17 means oxygen atom (O); R4 means hydrogen atom (H) or methyl. Also, invention relates to methyl- or ethyl-[2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate not early described in the literature.

EFFECT: valuable herbicide properties of compounds.

23 cl, 17 sch, 9 tbl, 11 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

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