Derivatives of pyrimidine, method of weed control and herbicide composition

 

(57) Abstract:

Usage: in agriculture as a means of weed control. The inventive product pyrimidine derivatives total f ly I, where R is lower imidazole or allylthiourea or a group of the formula OR3where R3hydrogen, alkyl, possibly substituted cyano-, alkoxy-, alkylthio-, phenyl, phenylthio-, phenylsulfinyl, phenylsulfonyl, benzyloxy, alkylcarboxylic, alkoxycarbonyl or telemedicine group, or R3alkenyl, quinil, alkyleenamine, alkali metal or the group-CH2-C(O)-R4where R4phenyl or alkyl; R1hydrogen or alkyl; R2hydroxy, alkoxy group, possibly substituted with halogen, phenoxy-, benzyloxy-, alkoxycarbonyl, cycloalkyl C3-C6or alkoxygroup, or R2alkenyl, possibly mono - or disubstituted by halogen or phenyl, alkyloxy, phenyl, possibly substituted with halogen, alkyl or alkoxygroup, fenoxaprop, benzyloxy may semeena halogen, alkoxygroup, phenylaminopropyl or the group-OC(O)R5where R55alkyl, possibly substituted with halogen, cyclopropyl, phenyl, possibly sialogram; Y is oxygen or sulfur, when this is specified in the alkyl substituents is lower. In addition, the product pyrimidine derivatives total f - crystals II, where R is hydroxy, alkoxy or benzyloxy-, R1hydrogen, lower alkyl; and In alkoxygroup; y is oxygen or sulfur, and phenyl derivatives of f ly III, where y is oxygen; R is hydroxy or alkoxyaryl; R1alkyl in the above substituents is a lower alkyl; R2phenyloxy or benzyloxy, act as intermediate products for the synthesis of compounds f ly I. Method of weed control lead processing plants or areas where plants are cultivated, the connection f ly I, taken in an amount 0,016 1 kg/ha Herbicide composition includes the active ingredients connection f ly I in the amount of 2 to 30 wt. and the rest of the target additives. (I) (II) (III) 3 C. p. 2 C.p. f-crystals, 14 PL.

The invention relates to new derivatives of pyrimidine or triazine and their salts, in particular derivatives of pyrimidine or triazine represented by the General formula I, and also relates to a herbicide composition containing these derivatives, pyrimidine or triazine or their salts as active substances, which can be used on rysownika, soils upland conditions or areas in the indoor presence of herbicide activity 2 phenoxypyridine derivatives.

However, these connections do not always meet their herbicide action.

The proposed derivatives of pyrimidine or triazine with substituents in certain positions in the pyrimidine or triazine ring and the benzene ring have an excellent herbicide activity not only annual but also perennial weeds along with high security on agricultural crops, in particular rice.

The present invention provides a derivative of pyrimidine or triazine and salt, with a derivative of a pyrimidine or triazine represented by the General formula

Y where R is the lowest allylthiourea, lower dialkylamino, imidazole group, or a group of the formula OR3where R3is hydrogen, a lower alkyl group, possibly substituted by langroup, lower alkoxygroup, lower alkylthiol, phenyl group, phenylthiourea, phenylsulfonyl, phenylsulfinyl group, benzyloxycarbonyl, lower alkylcarboxylic, telemedicine group; or R3lower Alchemilla group, lower Alchemilla group, lower alkyleenamine, alkali metal, or a group of formula-CH2COR4where R4=phenyl, nor is l, lowest alkoxygroup, possibly substituted by a halogen atom, fenoxaprop, benzyloxycarbonyl, lower alkoxycarbonyl group, lower cycloalkyl group or a lower alkoxygroup or R2=lower alkenylacyl, possibly substituted by one or two halogen or phenyl group, lower alkyloxy, phenyl group, possibly substituted with halogen, lower alkyl group or lower alkoxygroup, fenoxaprop; benzyloxy, possibly substituted with halogen, lower alkoxygroup, phenylaminopropyl or a group of the formula-OC(O)R5where R5-lower alkyl group, possibly substituted with halogen, lower cycloalkyl group, phenyl group, possibly substituted with halogen, lower alkoxygroup or phenylaminopropyl;

A= lower alkoxygroup;= alkoxygroup, possibly substituted by two halogen atoms; Y=oxygen or sulfur; Z is a group Metin or nitrogen atom. In addition, a method of controlling weeds by treating the plants or the area on which plants are cultivated, pyrimidine derivatives of the formula I in number 0,016-1 kg/ha, and herbicide composition comprising it pyrimidine derivative of the General formula I as the active ingredient in the General formula I of the invention.

The proposed connection can be obtained, for example, in accordance with the following methods A-F.

S p o C o b A.

+ RHD Y

where R, R1, R2, A, B, Z and Y have the above meanings; HD acid forming a salt with an amine, for example the corresponding acid to form the sulfate, hydrochloride or etc.

The compound of General formula I of the present invention can be obtained by reacting compounds of General formula II with a compound of General formula III in the presence of a base in an inert solvent at a temperature in the range of 0aboutC to the boiling point of the solvent for from 30 minutes to 12 o'clock as the basis, you can use the carbonate, bicarbonate, acetate, alcoholate, hydroxide, hydride or oxide of an alkali metal such as sodium and potassium, or alkaline-earth metal such as magnesium and calcium. In addition, it is possible to use an organic base, for example pyridine, or a tertiary amine such as triethylamine.

As a solvent it is possible to use a solvent-based hydrocarbon, for example toluene, benzene, xylene, etc. solvent-based Alojamientos hydrocarbon, for example methylene chloride, chloroform, etc. rastvoritelyami ether, tetrahydrofuran, 1,4-dioxane or etc., aprotic polar solvent, for example N, N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide or similar solvent on the basis of ester, such as ethyl acetate, etc.

It is preferable examples of the combination of the solvent and the base is a mixture of methanol and potassium acetate and chloroform and triethylamine.

S p o C o b C.

The compound of General formula I of the present invention can be obtained by reacting compounds of General formula II with the amine of General formula IV, for example, hydrazines, aniline, oxyamine or etc., preferably in a solvent represented by the following formula specified reaction

Y + R Y

In the specified way you can use the same solvent and temperature interactions, which are used in method A. To one of the preferred reaction conditions include boiling in methanol solvent.

Compounds of General formula II used as starting material in the methods a and b, represent a new compound and can be obtained as shown in the following reaction schemes:

a) a Compound of General formula II where Y is oxygen atom or sulfur

H + Z

The compound of General formula II-I can be obtained by the interaction of compounds of General formula V with a compound of General formula VI in the presence of a base in an inert solvent at a temperature in the range of 0aboutC to the boiling point of the solvent. Used in this method, the base and the solvent can be the same as described above. As preferred examples of the combination of solvent and base, you can use a mixture of dimethylformamide and potassium carbonate or dimethylformamide and sodium hydride.

The compound of General formula V are known and can be obtained, for example, in accordance with the method described in journal of Pharmaceutical Iournal.

The compound of General formula V can be obtained in accordance with the following two stages of synthesis is represented by the following reaction formulas.

Stage 1

< / BR>
where Q is an alkyl group, alkoxyalkyl group or benzyl group; R and R1have the specified values.

Derived acerpenna General formula I acetalized ethylene glycol in the presence of a Lewis acid to obtain compounds of General formula 2. After this connection the General formula 2 is subjected to interaction with carbon dioxide in prisutstvie 3. The compound obtained is then atrificial standard method, and then remove the protective group acetylenic and hydroxyl groups sequentially or simultaneously with obtaining the target product. The compound of General formula 4 can also be obtained by reacting compounds of General formula 2 with a complex ester Alojamientos formic acid in the presence of an ORGANOMETALLIC compound, for example n-utility or finelite in an inert solvent, such as toluene or benzene.

Stage 2

__< / BR>
where R, R1and Q have the specified values.

Ftoridnoe derivative of General formula 7 hydrolyzing the oxidation in the presence of potassium permanganate and magnesium nitrate with obtaining a derivative of salicylic acid of General formula 8.

The compound obtained is then atrificial in the usual way and to obtain the target compound selectively removing the protective group of hydroxyl.

The compound of General formula V, where Y1a sulfur atom, can be obtained from compounds of General formula VII, as shown in the following reaction scheme

HH where R and R1have the specified values.

b) the Compound of General formula II where Y is the group-NH - or

R10

S p o C o b C.

The compound of the present invention can also be obtained by alkylation of the corresponding oxime alkylating reagent, as shown in the following diagram interaction. Examples of alkylating reagent include haloalkyl, halide of alkenyl, benzylchloride, ester Alojamientos aliphatic acid halide cycloalkyl, alkylsulfate or etc.

+R*11L Y

where R, R1, A, B, Y and Z have the above meanings; R11alkyl, phenyl, Alchemilla group; L is leaving group.

The compound of formula IX can be obtained, for example, by reacting compounds of General formula II with hydroxyamino salt of General formula X according to a similar method described in STRs interaction of compounds of General formula XI with a compound of General formula VI in the presence of a base in an inert solvent at a temperature in the range of 0aboutC to the boiling point of the solvent. Used in said method the base and the solvent can be the same as those used in the synthesis of compounds of General formula II in accordance with method A.

Y1H + L Y

where R, R1, A, B, Y1, Z and L have the specified values.

The compound of General formula XI used as starting material in this reaction, is a new compound that can be obtained for example by reaction of compounds of formula V with an amine salt of formula III is similar to the technique of the way And in accordance with the following reaction scheme

Y1H + R2-NH2H Y1H

where R, R1, R2, Y HD have the specified values.

S p o o b E.

The compound of the invention of General formula I, where R is a hydroxyl group, can be obtained by the reaction of catalytic hydrogenation-reduction of compounds of General formula I, where R benzoyloxy, in the presence of Nickel catalyst Raney, palladium mobiles etc.

+ H2< / BR>
where R1, R2, A, B, Y and Z have the specified values.

S p o C o b F.

The compound of the present invention can also be obtained on the trail of the For example, the compound of the present invention can also be obtained by condensation of a derivative of benzoic acid obtained by the method E, with ester residue having an appropriate leaving group, in the presence of a suitable base, e.g. potassium carbonate, sodium hydride or so on, in a suitable inert solvent, for example dimethylformamide, tetrahydrofuran, acetonitrile, toluene, or etc., at a temperature in the range from room temperature to 100aboutC.

Typical examples of intermediate compounds of General formula II or XI to obtain the compounds of the invention are given in the table. 2 and 3.

These intermediate products also have excellent herbicide activity and selectivity.

Preparation of sodium 2-[(4,6-dimethoxypyrimidine-2-yl)oxy] -6-1 (N-methoxyimino)ethyl]benzoate (compound No. 49) (I-682).

to 0.23 g of metallic sodium was added to 20 ml of methanol in a nitrogen atmosphere, and then stirred for 30 minutes 3.6 g of 2-[(4,6-dimethoxypyrimidine-2-yl)oxy] -6-[1-(N-methoxyimino)ethyl] benzoic acid, prepared according to the method of example 10, is added to the mixture and stirred at room temperature for 1 hour, the Methanol is distilled off under reduced pressure, the process of dry ethyl acetate and acetone. After that, the crystalline substance is dried under reduced pressure. The result 2,95 g (yield 80,0%) of target compound (so pl. 138-150about(C) in the form of a light brown powder.

P R I m e R 1. Obtaining methyl ester 2 [(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-[-1-(N-methoxyimino)ethyl] benzoic acid (compound 9).

5 g of methyl ester of 2-acetyl-6-[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid (so pl. 164-166aboutC), 3 g of hydrochloric ethanolamine and 3.6 g of triethylamine are added to 50 ml of chloroform. The resulting mixture is subjected to interaction within 8 h with stirring while boiling. The reaction liquid is poured into a large amount of water, and the chloroform layers are separated after washing with water. After drying the residue, the solvent is distilled off under reduced pressure. The oily product was then purified column chromatography using as a developer a solvent mixture of hexane/isopropyl ether. After recrystallization of the residue in a solvent mixture of hexane/isopropyl ether to obtain 3.2 g of the target compound in the form of colorless, transparent, prismatic crystals (so pl. 105-106aboutC) at 50% output.

P R I m m e R 2. Getting metrov the P> 3,3 g of methyl ester of 2-acetyl-6-[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid, 4.1 g of hydrochloric ethanolamine and 4.9 g of potassium acetate are added to 50 ml of methanol. The resulting mixture is subjected to interaction with stirring for 2 hours at the boil under reflux. The reaction liquid was poured into a large amount of water, and the resulting product is extracted with ethyl acetate after acidification with hydrochloric acid with subsequent sequential washing with an aqueous solution of sodium bicarbonate and water. After drying, the resulting evaporation crystalline substance was washed with isopropyl ether, obtaining 3.2 g of the named product (so pl. 105-106aboutWith 89%-om its output).

Comparative example 1. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-thio]-6-acetyl benzoic acid (intermediate compound 7).

10.2 g of 2-amino-6-acetylbenzoic acid is converted into the diazonium salt using a mixture containing of 14.2 ml of concentrated hydrochloric acid, 40 ml of water and 4.3 g of sodium nitrite, and then the obtained Sol, page gradually added dropwise to the aqueous solution of sodium disulfide derived from 14.3 g of hydrate sulfide nearline the introduction of the specified salt reaction solution is stirred for 2 h at room temperature until the complete termination of the reaction. The reaction solution was poured into a large amount of water, then add to it a concentrated solution of hydrochloric acid. Then the resulting product is extracted with ethyl acetate. To an ethyl acetate layer was added an aqueous solution of sodium bicarbonate, and dissolved in sodium bicarbonate substance is extracted. To the obtained aqueous solution was added 14.8 g of persulfate sodium, after which the resulting mixture is refluxed until the end of the reaction. To the reaction solution was added concentrated hydrochloric acid, the resulting product is extracted with ethylcatechol. The extract is dried and the solvent is distilled off under reduced pressure with the output of 10.1 g of 2-mercapto-6-acetylbenzoic acid in 90% yield.

to 10.1 g of 2-mercapto-6-acetylbenzoic acid thus obtained and 7.6 g of potassium hydroxide is then dissolved in a mixed solvent containing 20 ml of water and 30 ml of N,N-dimethylformamide. To the resulting solution was added 13.5 g of 4,6-dimethoxy-2-metalsalt - nyerimilang, and then the resulting solution was stirred at room temperature for 2 h and another 0.5 h at 60aboutC. the Reaction solution was poured into a large amount of water, followed extegetag oily product is extracted with simple ether, and then the extract is dried. The ether solution was passed through a short column with florasulam; after simple distillation of the ether gain of 6.1 g of 2-[(4,6-dimethoxypyrimidine-2-yl)thio]-6-acetylbenzoic acid.

After the suspension of 0.3 g of 60% sodium hydride in 40 ml of a solvent mixture of tetrahydrofuran and N,N-dimethylformamide (1:1) to the resulting suspension was added 2-[(4,6-dimethoxypyrimidine-2-yl-)thio]-6-acetylbenzoic acid, followed by stirring the resulting mixture for 30 minutes Then she added dropwise 1.3 g methyl iodide at room temperature, the resulting solution was refluxed for 2 h to complete the reaction. The reaction liquid is then poured into water and extracted with ethyl acetate. The extract is washed with water and dried by distillation of the solvent under reduced pressure. The resulting residue purified by chromatography to yield 5.8 g of the target product; so pl. 149-151aboutWith 32% yield.

P R I m e R 3. Obtaining methyl ester 2 [(4,6-dimethoxypyrimidine-2-yl)thio]-6-[1-(N-methoxyimino)ethyl] benzoic acid (compound 33).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)thio] -6-acetylbenzoic acid (1 g) and hydrochloric METAIRIE 15 minutes After cooling the mixed solution to room temperature, thereto was added 0.8 g of sodium carbonate and the resulting solution was refluxed for 3 hours the Reaction solution was poured into a large amount of water and precipitated in the resulting oily product is extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried by distillation of the ethyl acetate under reduced pressure. The resulting residue purified by chromatography to yield 0.65 g of the indicated compounds (refractive index 1,5709) in 59% yield.

P R I m e R 4. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6- (N'-acetylhydrazone)benzoic acid (compound 27).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)oxy] 6-formylindolo acid (0.7 g), acetylhydrazine (0.7 g) and 10 ml of methanol is placed in a 50 ml flask in the shape of an eggplant. The resulting mixture was stirred for 30 min at room temperature. The methanol is distilled off under reduced pressure, and the residue is dissolved in ethyl acetate. The organic layer is washed with water, 5% hydrochloric acid and saturated aqueous sodium chloride, then dried with anhydride magnesium sulfate. After filtering to the received product: distilled off under reduced pressure. The resulting solid product was washed with isopropyl ether to yield 0.7 g of the target compound, so pl. 144-146aboutWith 85% yield.

Comparative example 2. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-formylindolo acid (intermediate compound 18).

Potassium carbonate (13.8 g) and dimethylformamide (50 ml) was placed in 200 ml baklazhanovyuyu flask and then added 11.1 g of methyl ester of 2-formyl-6-hydroxybenzoic acid and 14.6 g of 4,6-dimethoxy-2-methanesulfonamido under stirring. This mixture was stirred at 80aboutC for 1 h and the resulting liquid was poured into ice-cold water after cooling. Released precipitated oily product is extracted with ethyl acetate and dried with anhydride magnesium sulfate. The ethyl acetate is distilled off under reduced pressure; the resulting residue purified by the method of column chromatography with the release of these compounds (i.e pl. 91-93aboutC). Yield 52%

P R I m e R 5. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6- (N'-phenylhydrazone)benzoic acid (compound 24).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]6-formylindolo acid (0.9 g), hydrochloric acid Hairdryer shall within 10 min at room temperature. The methanol is distilled off under reduced pressure and the residue is dissolved in ethyl acetate. The organic layer is washed with water, 5% hydrochloric acid and saturated aqueous salt solution, then dried with anhydride magnesium sulfate. After filtering, add a small amount of Florisil and the resulting product is stirred for 5 min. Florisil filtered off and the ethyl acetate is distilled off under reduced pressure. Obtain 0.9 g of the target product (without determining physical properties) at its output 78%

P R I m e R 6. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-(gidroksilaminami)benzoic acid (compound 19).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-formylindolo acid (2 g), hydrochloric acid Xiamen (0.8 g), potassium acetate (1.1 g) and 10 ml of methanol is placed in a 50 ml baklazhanovyuyu flask and stirred for 10 min at room temperature. The methanol is distilled off under reduced pressure, and the obtained residue was dissolved in ethyl acetate. The organic layer is washed with water, 5% hydrochloric acid and saturated aqueous salt solution, then dried with anhydride magnesium sulfate. After filtering to the received product add a small amount of Florisil Out 1.5 g of the named product (refractive index 1,5558) at exit 72%

P R I m e R 7. Obtaining methyl ester 2- [(4,6-dimethoxypyrimidine-2-yl)-oxy] -6-[(1-ethoxycarbonylethyl) acetimidoyl] benzoic acid (compound 22).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)oxy]6-gidroksiiminobetulonovoi acid (2 g), ethyl ester of 2-bromopropionic acid (3 ml) and 0.9 g of silver oxide are placed in a 50 ml baklazhanovyuyu flask and incubated over night at room temperature. Then to the resulting reaction solution was added 10 ml of acetone and 10 g of silica gel, acetone is distilled off under reduced pressure. After purification of the obtained product by the method of column chromatography obtain 0.7 g of the above compound (refractive index 1,5261) with 27% yield.

Comparative example 3. Obtain methyl ester of 6-[1-(N-methoxyimino)ethyl]salicylic acid (intermediate compound 21).

Methyl ester of 6-acetylsalicylic acid (1.2 g), hydrochloric acid methoxyamine (1.3 g) and potassium acetate (1.5 g) was added to 30 ml of methanol, and then stirred over night at room temperature. After completion of the reaction, the reaction liquid was poured into water, acidified with hydrochloric acid and extraction of the reaction product with ethyl acetate. Obtained cont the project receive the concentrated oily product. After cleaning the specified product by the method of column chromatography gain of 1.15 g of target compound (refractive index 1,5423) with 83% of its output.

P R I m e R 8. Obtaining methyl ester 2 [(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-[1-(N-methoxyimino)ethyl]benzoic acid (compound 9).

Methyl ester of 6-[1-(N-methoxyimino)ethyl]salicylic acid (1,15 g), 4,6-dimethoxy-2-methylsulfonylamino (1.12 g) and potassium carbonate (0.71 g) was added to 50 ml of dimethylformamide and heated at 100aboutC for 2 hours After cooling, the reaction liquid was poured into water, extracted into water and extracted with ethyl acetate. After washing the extract with water, the obtained product is dried and evaporated to yield the crude crystals of the methyl ester of 2-[(4,6-dimethoxyphenyl - midin-2-yl)oxy]-6-[1-(N-methoxyimino)- ethyl]benzoic acid. After washing the obtained product diisopropyl ether obtain 1.35 g of target compound (so pl. 105-106aboutWith 73% of its output).

Comparative example 4. Obtain methyl ester of 2-acetyl-6-[(4,6-dimethoxytrityl-2-yl)oxy]benzoic acid (intermediate compound 13).

Methyl ester of 6-acetylsalicylic acid (1 g) was added to a suspension rasure for 10 hours After addition to the above-mentioned mixture of 0.95 g of 2-chloro-4,6-dimethoxytrityl it is stirred during the day and night at room temperature. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The extract is washed with water, dried and after evaporation receive a crystalline product. After purification of the resulting product by the method of column chromatography receive the target connection (so pl. 151-156about(C) at 67% of its output.

P R I m e R 9. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-[1-(N-methoxyimino)ethyl] benzoic acid (compound 41).

Methyl ester of 2-acetyl-6-[(4,6-dimethoxytrityl-2-yl)oxy] benzoic acid (0.9 g), hydrochloric acid methoxyamine (0.68 g) and potassium acetate (0.8 g) was added to 30 ml of methanol and the resulting mixture is stirred during the day and night at room temperature. The resulting reaction solution was poured into water and extracted with ethyl acetate. After washing the extract with water, the washed product is dried and evaporated to obtain an oily substance. The treatment of the specified product by the method of column chromatography gain of 0.47 g of the specified connection, so pl. 131-135aboutWith 48% of its output.

Complex benzyl ester 2-[(4,6-dimethoxypyrimidine-2-yl-oxy]-6-[1-(N-methoxy - imino)ethyl] benzoic acid (compound 4) (1.5 g) obtained according to the method described in example 1 and 10% palladium mobiles (0.15 g) was added to 50 ml of methanol, and then to the resulting mixture add 83 ml of hydrogen with stirring at room temperature. After completion of the reaction, the palladium black is filtered off and the solvent is distilled off under reduced pressure. Thus obtained oily product was then purified column chromatography using as developing solvent a mixture of hexane/ethyl acetate. Obtain 1.1 g of the target compound, so pl. 125-127aboutWith 86% of its output.

P R I m e R 11. Obtaining the ethyl ester of 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-[1-(N-methoxyimino)ethyl] benzoic acid (compound 15).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)oxy]-6-[1-(N-methoxyimino)- ethyl] benzoic acid (2 g) obtained in example 8, was added to 50 ml of dimethylformamide and stirred to dissolve at room temperature. To the resulting solution was added to 0.23 g of sodium hydride, and then after the termination of the formation of hydrogen was added 1 g of methyl ethyl. The resulting mixture was first resulting oily product is extracted with ethyl acetate. The extract is washed with water, dried and evaporated. The remaining oily product is purified column chromatography using as developing solvent a mixture of hexane/isopropyl ether (10:1) to obtain 1.5 g of the target compound, so pl. 65-68aboutWith 69% of its output.

P R I m e R 12. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-[1-(N-amoxiillin)ethyl] benzoic acid (compound 11).

Methyl ester of 2-acetyl-6-[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid (1 g), hydrochloric acid amoxilin (1.18 g) and potassium acetate (1.18 g) was added to 30 ml of methanol, the resulting mixture was refluxed with stirring for 5 hours Then the reaction mixture was poured into cold water and extracted in ethyl acetate. The organic layer is formed as a result of this, washed first with diluted hydrochloric acid and then aqueous sodium bicarbonate solution and water. After drying and evaporation of the specified organic layer get a solid substance. The obtained solid is washed with n-hexane to obtain the target compound, so pl. 93-95aboutWith in the form of colorless crystals in a yield of 67%

P R I m e p 13. Polunin 14).

Methyl ester of 2-acetyl-6-[(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid (1 g) hydrochloric acid Alliaceae (1 g) and potassium acetate (0.9 g) was added to 30 ml of methanol and the resulting mixture is refluxed for 5 hours After the reaction mixture was poured into cold water and extracted in ethyl acetate. Thus obtained organic layer washed with sodium bicarbonate and water. The organic layer is washed so, then dried and evaporated. The remaining oily product was then purified by the method of column chromatography to obtain 0.54 g of target compound (so pl. 76-78about(C) in the form of a colorless transparent crystalline substance at its output 46%

Comparative example 5. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-propenylbenzene acid (intermediate 17).

3-Hydroxy-2-methoxycarbonylamino - none (0,78 g) and 2-methylsulphonyl-4,6-dimethoxypyrimidine (0.85 grams) is dissolved in 60 ml of dimethylformamide. To the resulting solution was added 0.15 g of sodium hydride (60% oil dispersion) under cooling with ice. The mixture is stirred at room temperature for 8 h, and then added ice water. The resulting reaction solution extragere is fester. After removal of the solvent by the method of column chromatography and crystallization simple isopropyl ether get to 0.92 g of target compound, so pl. 120-122aboutWhen 71,3% output.

P R I m e R 14. Obtain methyl ester of 6-[1-(N-methoxyimino)propyl] -2 [(4,6-dimethoxypyrimidine-2-yl)oxy] benzoic acid (compound 53).

Methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-oxy]-6-propenylbenzene Noi acid (0,62 g), hydrochloric acid methoxyamine (0.45 g) and potassium acetate (0,53 g) was added to 80 ml of methanol and refluxed for 6 hours Precipitated precipitated product is filtered off and the solvent is distilled off. Then to the specified product is added water and extracted with ethyl acetate. Then the product is washed with water and dried with anhydrous magnesium sulfate. After removal of the solvent, purification of the mixture by the method of column chromatography and crystallization of the pure product with a mixture of isopropyl ether/ethyl acetate receive 0,60 g of target compound, so pl. 75-77aboutWhen 89,5% output.

P R I m e R 15. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-N-formylamino-6-[1-(N-methoxyimino)ethyl] benzoic acid (compound 131).

Methyl ester 2-formylamino-6-[1-(N-methoxyimino)eties stirred at room temperature for 10 minutes. To the mixture was added 8.7 g of 2-methylsulphonyl-4,6-dimethoxypyrimidine and the resulting mixture is refluxed for 6 hours After cooling, the reaction solution was poured into cold water and extracted with ethyl acetate. The resulting organic layer was washed with water, dried and evaporated. The resulting residue is purified column chromatography. The result of 8.3 g of target compound, so pl. 147-149aboutWith 54% yield.

P R I m e R 16. Obtaining methyl ester 2-[(4,6-dimethoxypyrimidine-2-yl)-amino]-6-[1-(N-methoxyimino)ethyl] benzoic acid (compound 46).

Concentrated hydrochloric acid (1 ml) was added to a solution containing of 1.34 g of methyl ester of 2-[(4,6-dimethoxypyrimidine-2-yl)-N-formylamino] -6-[1-(N-methoxyimino)ethyl] benzoic acid in 50 ml of methanol. The mixture was incubated at room temperature overnight. The reaction solution was poured into ice water and extracted with ethyl acetate. Formed in the organic layer is successively washed with aqueous sodium bicarbonate solution and water, dried and evaporated. The obtained residue purified by the method of column chromatography to obtain 0.87 g of the target compound, so pl. 82-84about

When using this compound as a herbicide on rice field to land in a mountainous area, orchards, lands that are not used in agriculture, or similar active component can be applied in different formulations depending on the purpose.

The proposed herbicide can be used in pure form or it can be prepared in various forms, is commonly used as a herbicide compositions, such as wetting the powder, granule, emulsifiable concentrate or powder when mixed with an inert liquid or solid carrier, a surface-active agent, a dispersant or adjuvant, traditionally used in the preparation of agricultural chemicals.

As the carrier used in the preparation herbicide compositions can be applied solid carrier such as talc, bentonite, clay, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate or urea, or a liquid carrier such as isopropyl alcohol, xylene, cyclohexanone or methylnaphthalene. As the surfactant and dispersant can be used, for example, ester oxysterol acid, arrowy ether or polyoxyethylene monoalkyl ether of sorbitol. Adjuvant you can specify, for example, carboxymethylcellulose, polyethylene glycol or the Arabian gum. Before applying the herbicide can be diluted to the appropriate concentration or make it without dilution.

The proposed connection is usually used in an amount of from 1 g to 10 kg per 1 ha, preferably from 1 g to 5 kg/ha, especially preferably 10-500 g / ha as an active ingredient.

A number of compounds of the invention in the aforesaid composition can be varied depending on the form of the composition, method of application, the location of the treated area, time of application, and so on, So this number cannot be determined in advance, it usually ranges from 1 to 5aboutpreferably 10-20 wt. in wettable powder, from 0.1 to 90, preferably 0.5 to 40 wt. in emulsifiable concentrate, and 0.01-10, preferably 0.1 to 1 wt. in the granule.

The proposed herbicide may be suitable for control of various weeds in recognice when processing them irrigated soil before and after the emergence of weeds or when the processing of the leaves. In addition, this herbicide can be used to control various weeds on lands under seruga lands, not used in agriculture, processing them in the soil before or after emergence of the weeds or by processing the leaves.

If soil treatment herbicide bring in a dose of from 1 g to 10 kg, preferably from 1 g to 5 kg, most preferably 10-500 g of the active component on ha When processing leaves the specified herbicide is diluted to a concentration of 1-10000 h/million Most preferably used as active ingredient in a dose of 10-100 g / ha of rice fields and from 500 g to 1 kg per square, not occupied for agricultural crops.

If desired, the proposed connection can be used in combination with insecticides, sterilizers, other herbicides, plant growth regulators, fertilizers or etc.

Examples of other known herbicides used in combination with the proposed compound include 4-nitrophenyl-2,4,6-trichlorphenol(chlorine nitrogen), 2,4-dichlorophenyl-3-methoxy-4-nitrophenyl (chlorotoxin), methyl ester 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid (bifenox), S-4-chlorbenzoyl ether diethylthiocarbamate acid (thiobencarb), S-ethyl ester of peligrosas-1-thiocarbonic acid (molinate), S-1-methyl-1-phenethyl ether PI is ebutiful)-N-(6-methoxy-2-pyridil)-N-me - tilokarat (peribuccal), methyl-3,4-dichloraniline (SVEP), 0,0-aminobutiramida S-(2-phenylcarbonylamino) phosphorodithioate(bensulide), S-2-methylpiperidine 0,0-dipropyl-phosphorodithioate (piperophos), N-(butoxymethyl)- 2-chloro-2,6-diethylacetanilide (butachlor), 2-chloro-2,6-diethyl-N-(2-propoxyethyl) acetanilide (pretilachlor), 2-(benzothiazole - 2-yloxy) N-methyl-acetanilide (mefenacet), (RS)-2-bromo-3,3-dimethyl-N, -dimethyl - benzyl)butyramide (bambuti), 2,4-dichlorophenoxyacetic acid and ethyl ester of 2,4-dichlorophenoxyacetic acid, 4-chloro-o-tolylacetylene acid (MSRA) and ethyl ether 4-chloro-o-tolylacetate acid, ethyl ester 4-chloro-o-triacetoxy acid (Tibetology ether 4-chloro-o-tolylacetate acid), 4-(4-chloro-o-tolyloxy)butyric acid (MSRV), 2-(2-naphthyloxy)propionanilide (nitroanilide), 2-(2,4-dichloro-3-methylphenoxy)propionanilide (clomipram), 2-(1,2-dimethylpropyl)-4-ethylamino-6-methylthio-1,3,5-triazine (deltamethrin), 2,4-bis (isopropylamino)-6-methylthio-1,3,5-triazine(prometryn), 1-(, -dimethylbenzyl)-3-(paratool)mochaui - (damron), 5-tertbutyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazol-2(3H))- it (oxadiazon), 4-(2,4-dichlorobenzoyl)-1,3-dimethyl-5-pyrazolyl-paratoluenesulfonyl (pyrazolate), 2-[4-(2,4-dichloro-3-methyl-benzoyl)-1,3-dimethylpyrazole), 3-isopropyl-1H-2,1,3-benzothiadiazin-4(3H)-she-2,2 - dioxide (bentazon), methyl 2-[[[(4,6-dimethoxypyrimidine-2-yl)aminocarbonyl] amino-sulfonyl]methyl] benzoate (benzylfentanyl), ethyl-5-[3-(4,6-dimethoxypyrimidine-2-yl)aridoculture] -1-methylpyrazole-4 - carboxylate (pyrazosulfuron), etc.

The following are examples of formulations of the herbicide composition of the present invention. In these examples, the term "part" refers to wt.h.

P R I m e R 1. Preparation of composition (wettable powder). 10 h of compound (11), 0.5 h of emulgen 810 (trade name of Kao Corporation), 0.5 h of Demol N (trade name of Kao. Corporation), 20 h Canelita 201 (trade name Kunimine Kogyo K. K.) and 69 h Gilita SA (trade name Jecklite Company Ltd) is mixed to a homogeneous state and pulverized into powder to obtain wettable powder.

P R I m m e R 2. Preparation of composition (wettable powder). 10 h connection 14, 0.5 h of emulgen 810, 0.5 h of Demol N, 20 h Canelita 201, 5 h Complexa 80 and 64 h Gilita SA is stirred until a homogeneous state and then crushed to obtain wettable powder.

P R I m e R 3. Preparation of composition (emulsifiable concentrate). 30 parts of compound 1, 60 h in a mixture of xylene and isophorone taken in an equivalent amount, and 10 provide additional exit emulsifiable concentrate.

P R I m e R 4. Preparation of composition (pellet). 10 h of compound (9), 80 h of the filler, which is a mixture of talc and bentonite (1:3), 5 h white black, 5 h surfactants Sobol 800A and 10 h of water is stirred to obtain a paste-like material. Then, this paste-like material ekstragiruyut through a sieve with holes of 0.7 mm in diameter, after which the extrudate is dried and cut into particles of 0.5-1 mm in length to obtain granules.

P R I m e R 5. Preparation of composition (granulated mixture). 2 parts of compound (9), 5 h of methylbenzophenone, 83 h of the filler, which is a mixture of talc and bentonite at a ratio of 1:3, 5 h white black, 5 h surfactants of Sarpola 800A and 10 h of water are thoroughly mixed to obtain a paste-like material, which is then ekstragiruyut through a sieve with holes of 0.7 mm in diameter, dried, and cut into particles of 0.5-1 mm in length to obtain granules.

The compound of the invention of General formula I exhibits an excellent herbicide action at minimum dose for a long period of time relative to annual weeds from the phase of budding to the stage of growth, such as chicken millet (Echin ochloa orusgalli), Cyperus fan (Cyperus difformis), Monochoria (Monochoria vaginalia) or so on, and perennial weeds, for example the. redlagaemoe connection is also effective as a herbicide on various weeds such as broadleaf weeds, including Highlander pepper (Polygonum lapathifolium), amaranth thin (Amarauthus Viridinis), white pigweed (Chenopodium album), starwort average (Stellaria media), canetic Theophrastus (Abutilon theophrasti), breast prickly Sida spinosa), morning glory (Ipomea spp.), cocklebur (Xanthium Strumarium), or etc., perennial and annual weeds family site, including syt purple (Cyperus zotundus), Chufu (Cyperus esculeutus), (Cyperus brevifolius), Cyperus fan (Cyperus mierairia), Cyperus fan of Ribnica (Cyperus iria), or etc., weeds of the family of rice, including chicken millet (Echinochloa crusgalli), weed blood (Digitaria sanguinalis), spickle green (Setaria viridis), annual bluegrass (Poa annua), sorghum Halep (Sorghum halepense), Alopecurus smooth (Alopecurus aelgualis), wild oats (Avena fatua), or etc.

In addition, the proposed herbicides are characterized by high security in respect of crops, particularly rice, wheat, barley, grain sorghum, pulses, cotton, sugar beet, etc.

Herbicide activity of the compounds of the present invention is disclosed hereinafter with reference to the examples of the test.

And with n s t a n d s 1 (check herbicide action when processing >, sow the seeds of barnyard millet (EU), Monochoria (Mo), bulrush (Sc) after compaction and leveling of the soil and subsequent flooding it with water to a depth of 3 see the next day wettable powder obtained in accordance with example 1, the composition is diluted with water and applied dropwise on the soil of the pot in the amount of 1 kg/ha as an active ingredient. After that, the pot is grown in the greenhouse. The evaluation is made on the 21st day after the treatment in accordance with the rating specified in the table. 4 and 5. The results are shown in table. 6.

And with n s t a n d s 2 (check herbicide steps in the processing of upland soil conditions).

In a plastic pot filled with upland soil conditions (surface area of 120 cm2), sowing the seeds of barnyard millet (EU), mountain pepper (Ro), chirici thin (Am), Marie white (Ch) and Siti fan of Ribnica (su) and zaravnivayut soil. The specified number of wettable powder prepared in accordance with example compositions 1, diluted with water and uniformly sprayed on the surface layer of soil by a small atomizer in quantities of 1000 l/ha dose of active ingredient 1 kg/ha. After that pot is cultivated in the greenhouse, and the evaluation is made on the 21st day after obrublennyh herbicides. The test results are given in table. 8.

And with n s t a n d s 3 (herbicide action in the processing of the leaves on upland field conditions).

In a plastic pot filled with upland soil conditions (surface area of 120 cm2), sowing the seeds of barnyard millet (EU), mountain pepper (Ro), chirici thin (Am), Marie white (CH) and site fan-shaped rice (Cy) and cultivated in a greenhouse for 2 weeks. The specified number of wettable powder prepared according to the method of example 1, diluted with water and causing a small spray on the foliage of plants in quantities of 1000 l/ha dose of active ingredient 1 kg/ha Plants cultivated in the greenhouse, and then on day 14 after treatment, assess the standard specified in table. 4. The compounds listed in the table. 7, is used as a comparative herbicides. The results are given in table. 9.

And with n s t a n d s 4 (test for selective effect on agricultural crops in the processing of rice soils).

During the growing vessel Wagner (the surface area of 1/5000 and filled with soil from Ribnica, seeded chicken millet (EU), Monochoria (Mo) and bulrush (Bogolub) (Sc) after irrigation, sealing and lining: polyester taffeta is more on the depth of the water layer 3, see The next day specified number of wettable powder prepared according to the method of example compositions 1, diluted with water and dropwise contribute to the soil surface. The plants cultivated in the greenhouse and 30 days after treatment assessment of herbicide action and phytotoxicity in accordance with the standards specified in the table. 4 and 5. The compounds listed in table. 7, are used as herbicides for comparative analysis. The results are shown in table. 10.

And with n s t a n d s 5 (test for selectivity crops soil from the field, the material conditions).

In a plastic pot (surface area of 600 cm2) filled with soil taken from the field, the material conditions, plant the seeds of soybean cultural (Gl), cotton, barnyard millet, sorghum Halep (So), Alopecurus smooth (Al), mountain pepper (Po), thin amaranth (Am) and Mary white (Ch) and zaravnivayut soil. The next day specified number of wettable powder prepared according to the method of example 1, diluted with water and evenly applied on the soil surface by a small atomizer in quantities of 1000 l/ha Then the plants cultivated in the greenhouse and on day 21 after obrabotke, listed in the table. 7, are used as herbicides for comparative analysis. The results are shown in table. 11.

And with n s t a n d s 6 (test for selectivity crops during the processing of foliage clad in the conditions).

In a plastic pot (surface area of 600 cm2) filled with soil material conditions, planting rice, cotton, chicken millet (EU), Highlander pepper (Rho), the thin amaranth (Am) and pigweed white (Ch) and cultivated in a greenhouse for 2 weeks. The specified number of wettable powder prepared according to the method of example 1, diluted with water and applied to foliage of a small sprayer. The plants cultivated in the greenhouse and on day 14 after treatment of leaves evaluate herbicide action and phytotoxicity. The compounds listed in the table. 7, is used as a comparative herbicides. The results are shown in table. 12.

And with n s t a n d s 7 (herbicide action when using a combination of herbicides by soil treatment with Ribnica).

In a ceramic pot (surface area 1/400) filled with soil from Ribnica, put chicken millet (EU), Monochoria (Mo), bulrush (Sc), syt, veero the m transplanted 2 tsadka rice (DG) of plastron a 2.0 to a depth of 2 cm and flood to a depth of 4 cm water. The next day specified number of mixed granules obtained by the method of example 5 composition is uniformly spread over the surface. Then the plants are cultivated in the open air and on the 61st day after treatment assess herbicide action and phytotoxicity in accordance with the standards shown in the table. 4 and 5. The results obtained are presented in table. 13.

And with n s t a n d s 8 (selectivity to crops N 2 soil of rice fields).

During the growing vessel Wagner (the surface area of 1/5000 and filled with soil from the rice fields, sow chicken millet (EU) after irrigation, compaction and leveling of the soil. Then in the transplanted vessel 2 Rostock paddy rice (DG) of plastron a 2.0 to a depth of 2 cm and sink to the depth of the water layer 3 see After cultivation in a greenhouse specified quantity (active ingredient, g/10a) wettable powder prepared according to the methods of example 1, diluted with water and dropwise contribute to the soil surface. The plants cultivated in the greenhouse and on the 30th day after treatment assessment of herbicide action and phytotoxicity in accordance with the standards specified in the table. 4 and 5. Compounds listed the table. 14.

1. Derivatives of pyrimidine General formula

< / BR>
where R is lower allylthiourea lowest dialkylamino, imidazole group, or a group of the formula OR3where R3hydrogen, a lower alkyl group, possibly substituted by cyano, lower alkoxygroup, lower alkylthiol, phenyl group, phenylthiourea, phenylsulfinyl, phenylsulfonyl groups, benzyloxycarbonyl, lower alkylcarboxylic, lower alkoxycarbonylmethyl, telemedicine group, or R3lower Alchemilla group, lower Alchemilla group, lower alkyleenamine, alkali metal, or a group of formula-CH2COR4where R4phenyl, lower alkyl, NH2lowest di-Alk-amino group;

R1hydrogen or lower alkyl;

R2hydroxyl, lower alkoxygroup, possibly substituted by a halogen atom, fenoxaprop, benzyloxycarbonyl, lower alkoxycarbonyl group, lower cycloalkyl group or a lower alkoxygroup, or R2lowest alkenylacyl, possibly substituted by one or two halogen atoms or a phenyl group, a lower alkyloxy, phenyl group, possibly substituted with halogen, lower alkyl groupeuropean, phenylaminopropyl or a group of the formula-OC(O)R5where R5lower alkyl group, possibly substituted with halogen, lower cycloalkyl group, phenyl group, possibly substituted with halogen, lower alkoxygroup or phenylaminopropyl;

A lower alkoxygroup;

B alkoxygroup, possibly substituted by two halogen atoms;

Y is oxygen or sulfur.

2. Method of weed control by treating the plants or the area on which plants are cultivated, pyrimidine derivative, characterized in that, in order to enhance herbicide activity, as derived pyrimidine is used as a compound of General formula

< / BR>
where R is lower allylthiourea, imidazole group, or a group of the formula OR3where R3hydrogen, a lower alkyl group, possibly substituted by cyano, lower CNS group, a lower alkylthiol, phenyl group, phenylthiourea, phenylsulfinyl group, phenylsulfonyl group, benzyloxycarbonyl, lower alkylcarboxylic, lower alkoxycarbonylmethyl or telemedicine group, or R3lower Alchemilla group, lower Alchemilla group, lower alcaligenaceae group, alkali metal or g is B>1
hydrogen or lower alkyl;

R2hydroxyl, lower alkoxygroup, possibly substituted by a halogen atom, fenoxaprop, benzyloxycarbonyl, lower alkoxycarbonyl group, lower cycloalkyl group or a lower alkoxygroup, or R2lowest alkenylacyl, possibly substituted by one or two halogen atoms or a phenyl group, a lower alkyloxy, phenyl group, possibly substituted with halogen, lower alkyl group or lower alkoxygroup, fenoxaprop, benzyloxy, possibly substituted with halogen, lower alkoxygroup, phenylaminopropyl, or the group General-OC(O)R5formula, where R5lower alkyl group, possibly substituted with halogen, lower cycloalkyl group, phenyl group, possibly substituted with halogen, lower alkoxygroup or phenylaminopropyl;

A lower alkoxygroup;

B lower alkoxygroup, possibly substituted by two halogen atoms;

Y is oxygen or sulfur,

the number 0,016 1.0 kg/ha.

3. Herbicide composition comprising an active ingredient derived pyrimidine, and the target additives, characterized in that, in order to enhance herbicide activity, he as derived pyrimido formula OR3where R3hydrogen, a lower alkyl group, possibly substituted by cyano, lower CNS group, a lower alkylthiol, phenyl group, phenylthiourea, phenylsulfinyl group, phenylsulfonyl group, benzyloxycarbonyl, lower alkylcarboxylic, lower alkoxycarbonylmethyl or telemedicine group, or R3lower Alchemilla group, lower Alchemilla group, lower alcaligenaceae group, alkali metal or the group of General formula-CH2COR4where R4phenyl, lower alkyl, NH2lowest di-Alk-NH-group;

R1hydrogen or lower alkyl group;

R2hydroxyl, lower alkoxygroup, possibly substituted by a halogen atom, fenoxaprop, benzyloxycarbonyl, lower alkoxycarbonyl group, lower cycloalkyl group or a lower alkoxygroup, or R2lowest alkyloxy, possibly substituted by one or two halogen atoms or a phenyl group, a lower alkyloxy, phenyl group, possibly substituted with halogen, lower alkyl group or lower alkoxygroup, fenoxaprop, benzyloxy, possibly substituted with halogen, lower alkoxygroup, phenylaminopropyl Issa cycloalkyl group, phenyl group, possibly substituted with halogen, lower alkoxygroup or phenylaminopropyl;

A lower alkoxygroup;

B lower alkoxygroup, possibly substituted by two halogen atoms;

Y is oxygen or sulfur,

in the following ingredients, by weight.h.

Active ingredient 2 30

The target additive and the Rest

4. Derivatives of pyrimidine General formula

< / BR>
where R is the hydroxy-group, the lowest alkoxygroup, benzyloxy;

R1hydrogen, lower alkyl;

A lower alkoxygroup;

B lower alkoxygroup;

Y is oxygen or sulfur.

5. The compound of General formula

< / BR>
where Y is oxygen;

R is the hydroxy-group, the lowest alkoxygroup;

R1lower alkyl;

R2lower alkoxy, benzyloxy-, fenoxaprop.

 

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23 cl, 17 sch, 9 tbl, 11 ex

FIELD: organic chemistry, agriculture.

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5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, herbicides, agriculture.

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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.

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40 cl, 16 sch, 12 tbl, 65 ex

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9 cl, 5 tbl, 18 ex

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EFFECT: enhanced assortment of pest controlling agents based on nitromethylene derivatives.

2 cl, 15 tbl, 9 ex

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