Way to destroy parasites, acarid and shellfish

 

(57) Abstract:

Usage: agriculture, chemical way to destroy parasites, acarid and shellfish. The inventive treatment of parasites, acarid and shellfish perform a derivative of pyrrole are shown in the description of the formula. 9 table.

The invention relates to chemical methods of plant protection, particularly to a method for killing parasites, acarid and shellfish.

Know the use of nitropyrrole for combating insects and mites. However, the known nitropyrrole are not effective when they are used in chemical methods of plant protection.

The aim of the invention is to increase the efficiency of the method.

This goal is achieved by treatment of parasites, acarid and shellfish, as well as their distribution and habitat derivative of pyrrole of the formula

(I) where W is a cyano - or nitro-group;

X is cyano, bromine, chlorine, iodine or trifluoromethyl;

Y is hydrogen, bromine, chlorine, iodine or trifluoromethyl;

Z is hydrogen, bromine, chlorine, iodine;

B is hydrogen, C1-C6-alkyl, C1-C2-alkyl, substituted C1-C4-alkoxygroup, possibly substituted by chlorine, alkyl, impregnated the sludge, substituted benzoyl chloride, trimethylsilyl or COR, where R is lower alkyl, phenyl or cyano in the amount of 0.05 to 4 kg/ha.

The present invention is illustrated by the following examples.

P R I m e R 1. Obtain 1-methyl-5-nitropyrrole-2-carbonitrile.

To a solution of 300 mg of 5-nitropyrrole-2-carbonitrile (2.14 mmol) in 15 ml of acetone is added 360 mg of potassium carbonate (2.6 mmol) and 0.165 ml of methyl iodide (1.6 mmol, 372 mg). The mixture is then stirred at room temperature for 24 hours the Reaction mixture is poured into a mixture of ice water (100 ml) and a drop-down cake, which is formed at the same time, is going to obtain 200 mg (62% ), so pl. 86-87about1-methyl-5-nitropyrrole-2-carbonitrile.

P R I m m e R 2. Getting 1-ethoxymethyl-5-nitropyrrole-2-carbonitrile.

To a solution of 560 ml of 5-nitropyrrole-2-carbonitrile (4 mmol) and 20 ml of dry THF is added 515 mg of tert butoxide potassium (4.6 mmol). After the addition of 0.45 ml chloromethylation ether (4.8 mmol) to the mixture, it mixes for 4 h, then diluted with ether (30 ml) and water (50 ml). The organic layer is separated, washed with water MgSO4(20 ml) and dried over MgSO4. After evaporation of the solvent is obtained red oil (600 ml, 75% ) 1 is % : C 49,40 H 4,07 N 21,30

P R I m e R 3. Getting diethylacetal 3-TRIFLUOROACETYL-3-cyanopropionic aldehyde.

To stir at 40-45aboutWith the suspension washed with hexane sodium hydride (5.5 g of 60% dispersion, 0.14 mol) in 200 ml of dried tetrahydrofuran is added dropwise a solution of ethyl ester triperoxonane acid (15 g, 0.11 mol) and diethylacetal 3-cyanopropionic aldehyde (17 g, 0.11 mol) in 100 ml dry tetrahydrofuran. Original grey suspension slowly turns into light brown color. The reaction mixture was stirred at 50-55aboutWith overnight maturity reaction by slow addition of 2-propanol (15 ml). Evaporation with a rotary evaporator volatile elements gives a dark oil, to which is added 150 ml of water at pH 7. Unreacted educt removed by washing the aqueous layer with diethyl ether (3 x 30 ml). The basic aqueous phase is acidified and then 12 n hydrochloric acid and extracted with ethyl acetate (2 x 100 ml). The combined organic layers are washed once with saturated sodium bicarbonate solution (40 ml) and once with brine (15 ml) before drying over magnesium sulfate. Evaporation using a rotary evaporator gives reddish is as eluent, to produce the target product (9 g, 32% ) as a yellow oil.

P R I m e R 4. Obtaining 3-TRIFLUOROACETYL-3-cyanopropionic aldehyde.

A mixture of 4,4-diethylacetal-2-triftoratsetilatsetonom aldehyde (5.0 g, 0.02 mol) and oxalic acid dihydrate (1.2 g, 0.01 mol) in 75 ml of water is heated to the boiling temperature under reflux for 20 minutes then the mixture is cooled, is added sodium bicarbonate (1.7 g, 0.02 mol) and then with 100 ml of ethyl acetate. The layers are separated and the organic phase is washed once with brine (15 ml) before drying over magnesium sulfate. Evaporation with a rotary evaporator gives a dark oil which is used immediately in the next reaction stage.

P R I m e R 5. Getting 2-(trifluoromethyl)-pyrrole-3-carbonitrile.

The crude aldehyde, selected from the previous stage (4.5 g) is dissolved in 50 ml of glacial acetic acid, then add ammonium acetate (1.5 g, 0.02 mol). The mixture is heated to 65-70aboutC for one hour, cooled, and then poured into 100 ml of water. Is extraction with ethyl acetate (2 x 75 ml), then carry out the washing with bicarbonate combined organic phases until then, until there is no longer acid. Red is hell to silicagel, using a mixture of hexane and ethyl acetate (4: 1) as eluent, to give 2-trifluoromethyl-3-cyanoprop (0.7 g, 4.3 mmol, 22% (based on acetal) as a pale yellow solid, so pl. 122-124aboutC.

P R I m e R 6. Obtaining 1-(ethoxymethyl)-2-(trifluoromethyl)-pyrrole-3-carbonitrile.

Mix a solution of 2-trifluoromethyl-3-cyanoferrate (1.0 g, 6.2 mmol) in dry tetrahydrofuran is treated with NaH (0,30 g, 7.5 mmol) as a 60% dispersion in oil in a nitrogen atmosphere at room temperature. After 20 min, the reaction mixture is treated dropwise with a solution chloromethylation ether (0,77 g, 8.1 mmol) in dry tetrahydrofuran, stirred vigorously for 3 h and treated with a mixture of 1N HCl solution and ethyl acetate. The phases are separated and the organic phase is washed with brine, dried over MgSO4and concentrated in vacuo to obtain a residue. Flash chromatography of the residue using silica gel and a mixture of hexane and ethyl acetate (3: 5: 1), gives the above-named compound as a pale yellow oil 0,83 g (61% ).

P R I m e R 7. Obtaining 4,5-dibromo-2-(trifluoromethyl)-pyrrole-3-carbonitrile.

To a solution of 2-(trifluoromethyl)-pyrrole-3-carbonitrile (1.0 g, 6.2 mmol) in 40 ml of tetrahydrofuran is Chi at room temperature, then quench the reaction with saturated aqueous sodium thiosulfate solution (5 ml). Added water (15 ml) and diethyl ether (50 ml) and the layers separated. The organic layer is washed with brine (10 ml) and dried over magnesium sulfate. Evaporation rotary evaporator to give a crude solid, which is subjected to flash chromatography using a mixture of hexane and ethyl acetate (2: 1) with addition of acetic acid (2 ml per 300 ml of solvent as eluent Target 2-trifluoromethyl-3-cyano-4,5-depomedrol (0.8 g, 2.5 mmol, 40% ) is allocated in the form of a pale yellow solid.

P R I m e R 8. Obtaining 4,5-dibromo-1-methyl-2-(trifluoromethyl)-pyrrole-3-carbonitrile.

To a solution of 2-trifluoromethyl-3-cyano-4,5-depomedrol (0.5 g, 1.6 mmol) in 30 ml of dry tetrahydrofuran is added to parts of tertbutoxide potassium (0.2 g, 1.9 mmol). Painted in pink color to the solution allow to mix for 20 min, and then gently add methyl iodide (0.6 g, 4.2 mmol). The resulting suspension stirred for 5 h, after which the reaction is extinguished by adding 10 ml of water. Also will be added diethyl ether (50 ml) and the layers separated. The organic phase is washed with brine (10 ml) and dried over magnesium sulfate. The issue is agely, using a mixture of hexane and ethyl acetate (4: 1) as eluent, to obtain N-methylated pyrrole (0.4 g, 1.2 mmol, 77% ) as a pale yellow solid, so pl. 123-125aboutC.

Using a similar technique and replacing the alkylating agent at chloromethyl - ethyl ester, get 4,5-dibromo-1-(ethoxymethyl)-2-(trifluoromethyl)-pyrrole-3-carbonitrile in the form of a white solid substance, so pl. 65-67aboutC.

P R I m e R 9. Obtaining 3,4-dibromo-5-nitropyrrole-2-carbonitrile.

Sample 5-nitropyrrole-2-carbonitrile (0.4 g, of 0.003 mol) is easily dissolved in 10 ml of the diluted solution of sodium hydroxide (0.4 g, 0.01 mol). Is added dropwise bromine (0.96 g, 0,006 mol), resulting in precipitation of the solids. An additional amount of 10% sodium hydroxide solution is added until, until all the solid has dissolved. Then the solution is stirred for 15 min, then acidified with dilute hydrochloric acid. Drop down a white precipitate is collected and dried. The reaction product (0.5 g, 56% ) has so pl. 181-186aboutC.

P R I m e R 10. Getting 3,5-dibromo-4-nitropyrrole-2-carbonitrile.

4-nitropyrrole-2-carbonitrile (0.6 g, 0,042 mol) is easily dissolved in 15 ml is osowaniu solid precipitate. Then sodium hydroxide (10% solution) is added to until the solid has dissolved. The resulting solution stirred for 15 min, after which the solution is acidified with diluted hydrochloric acid. Drop down a white precipitate (1.0 g, 83% ) has so pl. 170-175aboutC.

Calculated for

C5HBr2N3O2% :

C 20,35 H 0,33 N 14.24 From Br 54,20

Found, % :

C 20,72 H 0,23 N 14,16 Br 53,50.

P R I m e R 11. Getting 2,4,5-trichlorphenol-3-carbonitrile.

To a stirred mixture of 1.50 g (16.3 mmol) pyrrole-3-carbonitrile in 50 ml of glacial acetic acid is rapidly added dropwise to 4.1 ml (51,0 mmol) chloride Sulfuryl with a syringe through a rubber septum. During this addition the temperature of the reaction mixture increases from about 22 to 32aboutC. the Mixture was stirred 1.5 h, and then diluted with 100 ml of water. The resulting solids are collected by filtration and washed with water. After drying, the output is of 2.23 g (70% ) of a white solid substance, so more than 300 squareaboutC.

P R I m e R 12. Getting 2,4,5-tribromophenol-3-carbonitrile.

To a stirred mixture of 1.50 g (16/3 mmol) pyrrole-3-carbonitrile in 20 ml of chloroform is added dropwise and rises to 38aboutWith and forms a sticky solid mass, which requires adding an additional amount of chloroform (25 ml) and some reheated to achieve good mixing. The mixture is stirred for additional 2 h at room temperature, the solid reaction product is collected by filtration and washed with chloroform. The collected solids are 4,55, Concentration of the filtrate gives in addition of 0.58 g of the reaction product. The combined solids are transformed into Samoobrona condition with boiling methylene chloride. After cooling and filtering receive 3,66 g of a pale orange powder, so pl. 253-255aboutC.

Analysis.

Calculated for

C5HBr3N2IN % : C 18,26 H 0,31 N CHARGED 8.52

Br 72,91

Found, % :

WITH 18,28 H 0,35 N CHARGED 8.52

Br 72,74

P R I m e p 13. Getting 2,4,5-triumviral-3-carbonitrile.

4-cyanoprop-2-carboxylic acid (1,36 g, 0.01 mol) is added to the heated suspension of sodium bicarbonate (to 16.8 g, 0.2 mol) in water (150 ml). After all the acid has dissolved, the solution of iodine (8,3 g 0,033 mol) and potassium iodide (11,0 g, 0.66 mol) in water (50 ml) is slowly added with stirring within one hour. The mixture is heated Perdue nutrients are, carefully washed with water and dried. Column flash chromatography on silica gel filled in methylene chloride, gives the reaction product in the form of a yellow solid by crystallization of their acid ethyl ester (0.65 g); so pl. 257-258aboutC.

P R I m e R 14. Obtain 1-methyl-2,4,5-trichlorphenol-3-carbonitrile.

To stir the mixture 0,70 g (6.2 mmol) of tert-butoxide potassium in 25 ml dry THF under nitrogen atmosphere is added dropwise from a dropping funnel to 1.00 g (5,12 mmol) of 2,4,5-trichlorphenol-3-carbonitrile in 20 ml of dry THF over 15 minutes After 15 min with a syringe over 10 min is added dropwise to 0.50 ml (8,03 mmol) methyl iodide. Solid substances are formed and after stirring for about 3 h the mixture is diluted with 100 ml of water. The cloudy mixture is extracted twice with ethyl acetate and the combined organic layers are washed successively with diluted NaOH, water and saturated salt solution. After drying over magnesium sulfate the organic mixture is filtered and concentrated under vacuum to obtain 0,99 g not quite white solid. Purification by chromatography on silica gel, using methylene chloride, gives 0,68 g not quite white solid. Cleaning here turns into a slurry using hexane and removed by filtration; so pl. 110-114aboutC.

Analysis.

Calculated for C6H3Cl3N3, % :

C of 34.40 H 1,44 N 13,38 Cl 50,78

Found, % :

C 34,25 H 1,50 made 13.36 N Cl 50,88

P R I m e R 15. Obtain 1-methyl-2,4,5-tribromophenol-3-carbonitrile.

To stir a mixture of 0.87 g (of 7.75 mmol) tertbutoxide potassium in 30 ml of dry THF under nitrogen atmosphere is added dropwise from a dropping funnel 2,10 g (6,39 mmol) of 2,4,5-tribromophenol-3-carbonitrile in 20 ml of dry THF. After 15 min is added with a syringe within 2 min of 0.64 ml of 10.3 mmol) methyl iodide. After several hours at room temperature the mixture is diluted with 100 ml of water and 75 ml of ethyl acetate. The separated aqueous phase is extracted again with ethyl acetate and the combined organic layers are washed with dilute sodium hydroxide, water and saturated salt solution. After drying over magnesium sulfate the mixture is shaken with activated charcoal and filtered. Concentration under vacuum gives a white solid, which turns into a slurry using hexane and precrystallization from ethyl acetate to obtain the above compound as a white solid, so pl. 151-152aboutC.

Using similar materil in the form of a white solid; so pl. 138-139aboutC.

P R I m e R 16. Obtain 1-benzyl-2,4,5-tribromophenol-3-carbonitrile.

To a stirred mixture of 1.00 g (totaling 3.04 mmol) of 2,4,5-tribromophenol-3-carbonitrile and 0.68 g (6.1 mmol) of tertbutoxide potassium in 30 ml of dry THF under nitrogen atmosphere is added 1,10 ml of benzyl bromide. The mixture is heated to boiling under reflux and stirred overnight. After dilution with 100 ml of water and 150 ml ethyl acetate the organic mixture is separated and washed with brine, dried over magnesium sulfate and concentrate under vacuum to obtain 2,34 g orange oil. Oil is pounded into powder under a mixture of hexane and ether (5: 1) to obtain white solid collected by filtration (0,81 g); so pl. 100-103aboutC. the Filtrate gives a second material mass (0.11 g); so pl. 100-103aboutC.

P R I m e R 17. Obtain 1-allyl-2,4,5-tribromophenol-3-carbonitrile.

To a solution of 2,4,5-tribromophenol-3-carbonitrile (2.0 g, 6.1 mmol) in anhydrous tetrahydrofuran (20 ml) is added by portions at room temperature tertbutoxide potassium (0.75 g, 6.7 mmol), after 30 min is added dropwise allyl iodide (1.12 g, 6.7 mmol) and the mixture is then heated under reflux for 2 hours On The P> P R I m e R 18. Obtaining the ethyl ester of 2,4,5-tribromo-3-cyanoprop-1-acetic acid.

To a solution of 2,4,5-tribromophenol-3-carbonitrile (2.0 g, 6.1 mmol). After 30 min is added dropwise ethyl ester bromoxynil acid (1.12 g, 6.7 mmol) and the mixture stirred for 4-5 h at room temperature. The treatment described in example 15, the method gives the reaction product as a white solid (0,42 g); so pl. 140-143aboutC.

P R I m e R 19. Getting 2,4,5-tribromo-1-acylpyrrole-3-carbonitrile.

To a solution of 2,4,5-tribromophenol-3-carbonitrile (2.0 g 6.1 mmol) in anhydrous tetrahydrofuran (20 ml) is added by portions at room temperature tertbutoxide potassium (0.75 g, 6.7 mmol). After 30 min is added dropwise ethyl iodide (1.04 g, 6.7 mmol). The reaction mixture was stirred at room temperature for 30 min, and then heated under reflux for 90 minutes the Mixture is cooled, diluted with water and extracted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride solution and dried (Na2SO4). Evaporation of the solvent and crystallization from a mixture of ether and hexane gives a solid which is further purified column f the acetate in methylene chloride. Analytically pure sample eventually crystallizes from a mixture of methylene chloride and hexane as a white solid (1.55 g); so pl. 108,5-109,5aboutC.

In a similar way described to obtain 2,4,5-tribromo-1-acylpyrrole-3-carbonitrile in example 19, using the required centricolimpio and the appropriate alkylating agent, receive below for more counterparts (table. 1).

P R I m e R 33. Getting 2,4,5-tribromophenol-1,3-dicarbonitrile.

To a solution of 2,4,5-tribromophenol-3-carbonitrile (1.50 g, 4,56 mmol) in anhydrous tetrahydrofuran (20 ml) is added by portions at room temperature tertbutoxide potassium (614 mg, 5,74 mmol). After 15 min is added dropwise a solution of CYANOGEN bromide (177 mg, 5,74 mmol) in tetrahydrofuran (5 ml). The reaction solution is stirred at room temperature overnight and becomes cloudy. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is washed with water and saturated aqueous sodium chloride and dried over Na2SO4. Evaporation of the solvent and crystallization of the residue from ether gives a white solid (1.20 g); so pl. 195,0-197,5aboutC.

P R I m e R 34. Poluchenii should add pyrrol-2-carbonitrile (2.6 g, or 0.027 mmol). Added a few milliliters of dioxane, the mixture became homogeneous. Then added in small portions at 28-35aboutWith and with periodic cooling 12,96 g of bromine (of 0.081 mol). Before the end of the addition, the solids begin to precipitate. The contents brought back into solution by adding 10% sodium hydroxide. Then the remaining bromine is added to the solution, stirred for 15 min prior to acidification of the mixture with diluted hydrochloric acid. White solid (7.4 g, 84% ) is collected and after drying has so pl. 215-218aboutC.

Calculated for C5HN2Br3, % :

C 18,25 H 0,30 N 8,51 Br 72,92.

Found, % :

C 18,06 H 0,37 N 8,39 Br 72,72

P R I m e R 35. Getting 3,4,5-tribromo-1-methylpyrrole-2-carbonitrile.

3,4,5-tribromo-pyrrol-2-carbonitrile (1.0 g, of 0.003 mol) was dissolved in a mixture of acetone and dimethoxyethane. Added potassium carbonate (0.45 g, 0,0033 mol) and methyl iodide (0,478 g, 0,0033 mol). After stirring over night at room temperature the reaction mixture is poured into water and filtered. The pressed residue on the filter is dried in air, to obtain the above compound as a white solid 0.8 g (80% ); so pl. 115-119aboutaboutC.

P R I m e R 36. Getting 3,5-dibromo-pyrrole-2,4-dicarbonitrile.

Pyrrole-2,4-dicarbonitrile (0.5 g, 0,004 mol) is easily dissolved in 15 ml of water containing sodium hydroxide (0.5 g, 0.012 mol). Then added bromine (1,34 g 0,008 mol) and the solution stirred for 15 minutes Thin layer chromatography (90/10 methylenchloride/acetonitrile) shows that the reaction was not completed. The additional amount of bromine is added and the reaction can be traced by TLC. When the reaction completed, the mixture is acidified and going white solid. Solid (0,47 g, 40.8 per cent ) after recrystallization from dichloroethane (30 ml) is so pl. 227-232aboutC.

Calculated for C6HBr2N3, % :

C 26,20 H 0,36 N 15, 28 Br 58,15

Found, % :

C 26,25 H 0,58 N 15,17 Br 58,35

P R I m e R 37. Getting 3,5-dibromo-1-methylpyrrole-2,4-dicarbonitrile.

A sample (1.0 g, being 0.036 mol) of 3,5-depomedrol-2,4-dicarbonitrile easily dissolved in 20 ml of acetone. Added anhydrous potassium carbonate (0.64 g, 0,0046 mol) and at a time when the slurry is mixed, is added methyl iodide (0.68 g, 0,0047 mol). The reaction may contact the TWT. The reaction product (0,77 g, 74% ) has so pl. 175-178aboutC.

Calculated for C7H3Br2N3, % :

C 29,08 H 1,04 N 14,54 Br 55,33

Found, % :

C 29,09 H 1,42 N 14,54 Br 54,95.

P R I m e R 38. Obtain 3-bromo-2,5-dichloro-4-nitropyrrole.

The specified connection can be obtained by dissolving the sample of 2,5-dichloro-3-nitropyrrole (0.54 g, of 0.003 mol) in 10 ml of dilute sodium hydroxide (0.25 g, 0,006 mol) and the addition of bromine. Before you add the bromine may be subject to an additional number of reasons. When the addition is complete, the solution may be acidified with diluted hydrochloric acid to the target reaction product is dropped into the sediment.

P R I m e R 39. Getting 4-(trifluoromethyl)-pyrrole-3-carbonitrile.

A mixture of paracrystalline (to 0.72 g, 3.2 mmol) and sodium hydride (0.09 g, 3.8 mmol) in anhydrous ethyl ether is treated dropwise with a solution of 4,4,4-triftoruksusnaya (0,38 g, 3.2 mmol) in ether and dimethyl sulfoxide for 35 min, stirred at room temperature for 20 min and the reaction is extinguished by water. The phases are separated and the water phase is extracted with ether. The organic phase is collected, washed with brine, dried over MgSOaboutC.

P R I m e R 40. Obtaining 2,5-dibromo-4-(trifluoromethyl)-pyrrole-3-carbonitrile.

A mixture of 4-(trifluoromethyl)-pyrrole-3-carbonitrile (0.10 g, to 0.63 mmol) and sodium acetate (0.2 g, 2.4 mmol) in acetic acid is treated dropwise with a solution of bromine (0,23 g, 1.4 mmol) in acetic acid, stirred for 6 h at 25aboutC and poured into an aqueous solution of metabisulfite. The resulting mixture is filtered and pressed on the filter residue is washed with water and dried with air to obtain the above compound as a white solid 0.11 g (58% ); so pl. 198-200aboutC.

P R I m e R 41. Obtaining 2,5-dibromo-1-methyl-4-(trifluoromethyl)-pyrrole-3-Carboni - trile.

A solution of 2,5-dibromo-4-(trifluoromethyl)-pyrrole-3-carbonitrile (0.10 g, 0.30 mmol) in tetrahydrofuran is treated solid tertbutoxide potassium (0,053 g, 0.49 mmol), stirred for 1 h at 25aboutC, treated dropwise iodide stands (0,067 g, 0.47 mmol), stirred for 2 h at 25aboutthe successively with water and brine, dried over MgSO4and concentrated under vacuum to obtain the above compound in the form of a white solid 0.09 g; so pl. 101-104aboutC.

P R I m e R 42. Obtaining 4,5-dibromo-1-methylpyrrole-2-carbonitrile.

A solution of 1-methylpyrrole-2-carbonitrile (1.06 g, 0.01 mol) in tetrahydrofuran is treated with N-bromosuccinimide (5.34 g, 0.03 mol) at 25-30aboutC, stirred for 18 h at 25aboutC and concentrated under vacuum to obtain a residue. The remainder is transferred to carbon tetrachloride, filtered and the filtrate concentrated under vacuum to obtain a solid residue. Recrystallization from a mixture of ethanol and water gives the above-named compound as a gray solid; T. pl. 104-105aboutC.

P R I m e R 43. Obtaining the ethyl ester of 4-(trifluoromethyl)-pyrrole-3-carboxylic acid.

The solution tertbutoxide potassium (8,11 g of 0.075 mol) in tetrahydrofuran at -60aboutWith treated dropwise with a mixture of ethyl ether 4,4,4-trifurcating acid (10.5 g, 0,063 mol) and a pair of tolylsulfochloride (12.2 g, 0,063 mol) in tetrahydrofuran for 1 h, stirred at -60aboutC for 30 min, the mixture was allowed to warm to room tempesti are washed with saline, dried (MgSO4) and concentrated under vacuum to obtain a solid residue. Recrystallization from 1,2-dichloroethane gives the above-named compound in the form of reddish-brown solid, 7/3 g (56% ); so pl. 163-164aboutC.

P R I m e R 44. Obtaining the ethyl ester of 1-methyl-4-(trifluoromethyl)-pyrrole-3-carboxylic acid.

The solution tertbutoxide potassium (4.5 g, 0.04 mol) in tetrahydrofuran is treated dropwise with a solution of ethyl ester of 4-(trifluoromethyl)-pyrrole-3-carboxylic acid (8,3 g, 0.04 mol) in tetrahydrofuran for 20 min at 20-25aboutC, stirred for 30 min, treated dropwise iodide stands (5.7 g, 0.04 mol), stirred at room temperature for 24 h and poured into water. The resulting mixture is extracted with ether and the combined extracts are washed with saline, dried (MgSO4) and concentrated under vacuum to obtain a brown oily residue. The residue is distilled using a distillation apparatus Kugellager, to obtain a resinous solid at 80-85aboutC/0.2 mm RT. Art. the Solid is purified using ether and basic alumina to obtain the above-named compound in the form of instructions on how to apply the 1-methyl-4-(trifluoromethyl)-pyrrole-3-carboxylic acid.

A mixture of ethyl ester of 1-methyl-4-(trifluoromethyl)-pyrrole-3-carboxylic acid (4.4 g, 0.02 mol) and 4n. solution of sodium hydroxide (5 ml, 0.02 mol) in ethanol is stirred for 24 h at room temperature, diluted with water and extracted with ether. The aqueous phase is acidified 10% HCl solution and filtered. Pressed on the filter residue is washed with water and dried under vacuum at 45aboutIn order to obtain the above-named compound in the form of not-quite-white solid, 2.4 g (62% ); so pl. 210-212aboutC.

P R I m e R 46. Obtain 1-methyl-4-(trifluoromethyl)-pyrrole-3-carbonitrile.

A mixture of 1-methyl-4-(trifluoromethyl)-pyrrole-3-carboxylic acid (1,93 g, 0.01 mol) in acetonitrile at 40-45aboutWith treated dropwise chlorosulfonylisocyanate (of 1.41 g, 0.01 mol), heated at 40aboutC for 24 h, cooled to room temperature, treated with dimethylformamide (1,46 g, 0.02 mol) is heated at 40aboutC for 8 h, cooled to room temperature and poured into water. The resulting mixture is extracted with ethyl acetate. The extracts are combined, washed successively with water and brine, dried (MgSO4) and concentrated under vacuum to obtain an oil, dried (MgSO4) and concentrated under vacuum to obtain a yellow oily residue. Distillation apparatus Kugellager at 100-110aboutWith/2 mm RT. Art. gives the above-mentioned reaction product in the form of a white solid, 0.95 g (54% ).

P R I m e R 47. Getting phenyl ether 2,3,5-tribromo-4-cyanoprop-1-carboxylic acid.

A mixture of 7.0 g of 2,4,5-tribromophenol-3-carbonitrile and 2.9 g of tertbutoxide potassium in tetrahydrofuran is treated with 13.8 g of phenyl ether of Harborview acid, heated under reflux at boiling temperature for 12 h, cooled, poured into water and filtered. Hard pressed on the filter residue is washed with water and dried under vacuum to obtain the above compound. Sample precrystallization from a mixture of ethyl acetate and methylcyclohexane to obtain colorless crystals; so pl. 128-129aboutC.

P R I m e R 48. Obtaining methyl ester 2,3,5-tribromo-4-cyanoprop-1-carboxylic acid.

A solution of 2,4,5-tribromophenol-3-carbonitrile (3.0 g, 0,091 mol) in tetrahydrofuran is treated portions and tertbutoxide potassium (1,33 g, 0.012 mol) at room temperature, stirred for 2.5 days, poured over MgSO4and Kon concentrated under vacuum to obtain a brown solid residue. The remainder precrystallization from a mixture of ethyl acetate and hexanol, to obtain said compound in the form of reddish-brown solid, 1.4 g (39.5 per cent ), so pl. 119,5-122aboutC.

Using this method and substituting the appropriate chloroformate, are obtained the following compounds

< / BR>
OCH= CH2112-113

OCH2CH= CH286-89

P R I m e R 49 . Getting 2,4,5-tribromo-1-(parachlorophenyl)-pyrrol-3-carbonitrile.

A mixture of 2,4,5-tribromophenol-3-carbonitrile (5.0 g, 0.015 mol) and tertbutoxide potassium (2.0 g, 0.018 mol) in dry tetrahydrofuran stirred for 10 min at room temperature, treated dropwise with a solution of acid chloride of perchlorobenzene acid (3.25 g, 0.019 mol) in tetrahydrofuran is heated under reflux at the boiling temperature for 3 h, cooled and diluted with a mixture of water and ethyl acetate. The organic phase is separated, washed with brine, dried over Na2SO4and concentrated under vacuum to obtain a reddish brown solid residue. Recrystallization from benzene gives the above-named compound in the form of the Yu method and replacing the acid chloride by parameterising acid get 2,4,5-tribromo-1-(pharmacokientic)-pyrrol-3-carbonitril, so pl. 86-89aboutC.

P R I m e R 50. Insecticidal and acaricidal evaluation of cyano - and nitro-pyrrole.

In these tests assessments are carried out using the technical substance dissolved in a mixture of acetone and water (50: 50). All concentrations given in the description, depend on the use of active ingredient. Tests are conducted in the laboratory at a temperature that is supported approximately at the 27aboutC. grading System used is the following: with = no effect 5= 56-65% death 1= 10-25% death 6= 66-75% death 2= 26-35% loss 7= 76-85% death 3= 36-45% loss 8= 86-99% death 4= 46-55% death 9= 100% death

10 = low

dressing.

Tested insect species and acarides used in these estimates, together with the specific testing procedures, described below.

Larvae of the 3rd age, South scoop meadow Spodoptera eridania.

Foliage Lima beans, blown up to 7-8 cm in length, is immersed in the test solution with shaking for 3 and placed under the hood to dry. The foliage is then placed in a Petri dish 100 x 10 mm, containing moistened filter paper on the bottom and ten larvae of the 3rd age. Contents cha and any obstacle with normal shedding.

Spodoptera eridania - 7-day rest.

Plants treated at the specified test, see under the action of lamps of high intensity in the greenhouse for 7 days. These lamps dual action bright Sunny day in June in new Jersey and continue the length of a day for 14 hours After 7 days the foliage probiraetsya and tested as above.

Aphis fabae - mixed age stage, aphids beet.

A pot containing a single plant nasturtiums Fropacodum sp height of approximately 5 cm, infected, approximately 100 to 200 aphids per day before the test. Each pot sprayed test solution for 2 turns at the turning circle at a speed of 4 rpm under the hood, using atomized sprayer type 154 deciles. The tip of the sprayer is held at a distance of 15 cm from the plant and the jet is directed so as to obtain full coverage of plants and aphids. Sprayed the pots are placed side by side in a tray, covered with white enamel, and are contained within 2 days, after which the estimation is made on mortality.

Fetranychus urticae (R-resistant strain), 2-spotted spider mite.

The Lima bean plant with primary leaves, loose 7-8 cm in length, when selecting the main colony, and placed on each leaf of the tested plants. This is done for 2 h before treatment to allow the clamp to move everywhere on the subject of plant and lay their eggs. The size of the cut of the piece changes to get about 100 mites per leaf. During the processing of a piece of leaf, used for transferring mites, is removed and discarded. Infected ticks plants are immersed in the test solution for 3 with shaking, and placed under the hood to dry. Plants are kept for 2 days before making the assessment the death of an adult, using the first sheet. The second sheet is kept at a distance for another 5 days before recorded observations of the loss of eggs and/or newly hatched butterflies.

Dialrotic undecimpunetata hawrdi - South blaska Dlinnaya 3rd age.

One cm3pulverized talc is placed in wide-mouthed glass jar with a screw lid and a volume of 30 ml One ml of the corresponding acetone solution applied by pipette to the talc to provide a 1.25 and 0.25 mg of active ingredient on the jar. Jars are placed under a weak current of air until, until you evaporate the acetone. The dried talc l wet soil in each jar. The jar lid and the contents thoroughly mixed in a mixer of the type of Vortex. Following this, ten dlinnoyu flea beetles 3rd stages are added to each jar and the jars partially closed by a cover that is air exchange for the larvae. Spraying for 6 days before it is counted mortality. Missing larvae are presumed dead, as they decompose quickly and can't be found. The concentration used in this test correspond approximately to 50 and 10 kg/ha, respectively.

The data obtained are presented in table. 2.

When there are two or more tests with this connection, the estimates are averaged. In addition, when tests were not conducted, the evaluation is represented by a minus sign (-).

P R I m e R 51. Insecticidal evaluation.

Insecticidal evaluations are conducted with solutions of the tested compounds dissolved or dispersed in mixtures of acetone and water (50: 50). The test compound is a technical matter, dissolved or dispersed in said mixtures of acetone and water in sufficient quantity to ensure are presented in table. 3 to the E. 38. The used methods are described below for assessments against specific insect species. When there are two or more tests using the same connection, are reported averages of the test results.

Empoasca abrupta - adult, Cicada potato (sapadnoj the potatoes).

Leaf beans and Lima length of 5 cm is immersed in the test solution for 3 with shaking and placed under the hood to dry. The sheet is placed in a Petri dish 100 x 10 mm, containing moist filter at the bottom of the Cup. In each Cup is added about 10 adults of cicadas and processing continues for 3 days before calculations are made death (mortality).

Heliotis vivscens - scoop tobacco 3rd age extent (stage).

Cotton cotyledons are immersed in the test solution and dried under the hood. After drying each semados is cut into four pieces, ten parts are placed separately in plastic medical cups with a volume of 30 ml containing a piece of moist dental swab length 5-7 mm In each Cup is added one larva of the third age, a cardboard cover is placed on the Cup. Processing to be kept for 3 days, Priglashenie, the larvae (caterpillars) of the 3rd age, scoop southern meadow.

The connection is introduced into the composition in the form of an emulsion containing 0.1 g of the test substance, 0.2 g of emulsifier type of emulsifier E-620, 10 ml of acetone and 90 ml of water. This mixture is diluted 10-fold with water, to obtain for each test emulsion with a concentration of 100 M. D. optionally carried out subsequent 10-fold dilution with water. The Lima bean plant with primary leaves, crushed up to 7-8 cm in length, are cut by at least 3 cm above the soil level to avoid contamination of soil bacteria that cause the decomposition of the stem during the test. The cut stems are placed in the subjects of the emulsion and each stem is wrapped with a small amount of cotton wool to hold the stem out of the bottom of the bottle and to limit evaporation and volatilization of compounds. Tests conducted over 3 days at 27aboutWith to allow the compounds to penetrate into the plant. Following this, one leaf is removed from the plant and placed in a Petri dish 100 x 10 mm 10 Sovkome meadow. Counting the deaths and monitoring spoilage of food (feeding) are performed after 3 and 5 days. This method is derivative are presented in table. 3.

Blatella germanica - test bait, adult male German cockroach.

0.1% bait is obtained by measuring pipette 1 ml of an acetone solution of the test compounds 1000 M. D. concentration of 1 g corn flour in wide-mouthed bottles with a volume of 30 ml. Bait is dried by passing a weak current of air in the bottle is placed in wide-mouthed Mason jar with a volume of 1 pint (0,57 l) and added 10 adult red cockroaches. Lattice cover served on the Bank and a small piece of cotton wool soaked in 10% wage honey, put on top of the slatted cover. Estimates of deaths are carried out after 3 days.

Blatella germanica - test sediment, adult male German cockroach.

1 ml of an acetone solution of the test substance 1000 M. D. concentration is applied by pipette slowly to the bottom of the Petri dishes size 150 x 15 mm in order to obtain a uniform coating as possible. After drying the precipitate in each Cup placed 10 adult males red cockroaches and the lid is covered. Estimates of deaths are carried out after 3 days.

The data obtained are given in table. 3 and 4.

P R I m e R 52. Evaluation of test compounds against slug is by mixing 0.10 g technical matter with 1,90 g bait, consisting of 46% unprocessed bran, 6% Melissa and 48% water. One test scene is set for each processing by placing 2 g of bait on the cover from downlevel (28,3 g) banks and putting the lid on 8-unlevel (226,4 g) Cup, waxed and sheathed inside moist filter paper. Each Cup is infected 5 gathered in a field snails species Arion subfuscus. Plastic lid with small holes through it is placed on top of each Cup. Test sets and catches collected on the field snails. Subjects processing are examined periodically and indications of death removed after 3 and 4 days. Snails that do not respond to injections, are considered lost. Snails, which react much more slowly than the untreated control snails, are considered lost.

The connection of the Death of snails

species Arion

subfuscus, %

2,4,5-tribromophenol-3 - carbonitril 100

2,4,5-trichloro-1-methyl - pyrrole-3-carbonitrile 100

2,4,5-tribromo-1-metier - rol-3-carbonitril 100

1-benzyl-2,4,5-triglochin - rol-3-carbonitril 100

1-benzyl-2,4,5-tribromo - rol-3-carbonitril 100

2,4,5-tribromophenol-1,3 - dicarbonitrile 100

1-(ethoxymethyl)-5-nutropin - rol-2-carbonitril 100

Ousa concentration, 1 ml of each test solution adds to 1 g of unprocessed bran. Then the acetone is removed by evaporation. Primakova composition obtained by mixing 1 g processed by the given method unprocessed bran with 1 ml mellasovii mixture consisting of 4 ml of molasses and water (30 ml). Thus obtained Primakova the composition is placed on the lid 1-unlevel (28,3 g) banks, which is then placed on the bottom of the 8-unlevel (226,4 g) cups of wax-coated paper, which is coated with the inside moist filter paper. Each Cup is affected then 5 snails. Control Cup, which contains 0% of the test compounds in bait compositions are also prepared and infected with. Subjects processing are examined daily for 4 days and the percent power and death are recorded. The data obtained are presented in table. 5.

P R I m e R 53. Evaluation of errorcorrection and nitropyrrole as a means of combating land snails of the species Helix aprorce Helix aprosca, bought from Words Biologicl Supply company. Compound produced in the form of baiting mixtures as follows: 5% bait is obtained by blending technical substance (50 mg) in trubunal the bait (950 mg). Note the th boat (7 ml) polystyrene. Posted by bait is inserted into a plastic vessel (500 ml) with one wet dental swab. Then in each treatment added two snails and top each vessel tightly covered with a transparent plastic cover with holes for aeration. The vessels are examined 24 h after the start of testing. The data obtained are presented in table. 6.

P R I m e R 54. Experience on terrestrial snails with errorcorrection.

Bulimulus maria (terrestrial snails from Carolina Biological Supply company code 480) tested in 30 ml wide-mouthed jars, used 5% bait with corn flour, i.e., 25 mg compounds mixed in 450 mg of corn flour. The bait is watered every 2 days. One snail is added to each jar and lid are covered loosely on top of the cans. Faeces show the power of snails. Death is observed by testing the animal with a spatula. If the animal is alive, the cuts are obvious. Slow leakage and/or complete disappearance in the shell shows the death. Connection Loss for

1 week, %

2,4,5-tribromo-1-metier - rol-3-carbonitril 100

P R I m e R 55. The activity of pyrrole on freshwater snails.

Freshwater watery snails flannum pond water, which is subjected to aeration by using a filter on the tank bottom. Some members of the pyrrole series are compiled in aerated tap water (pH identical with pond water) at two dosages of 100 and 33 M. D. Compounds have relatively low solubility in water at 100 memorial plaques , but under stirring and the action of ultrasound solubility is significantly improved. Three healthy snails are added to each Cup with a volume of 150 ml, containing 80 ml of the treated water. Examinees concentrations are 100 and 33 M. D. Untreated control is also included. The connection M. D. Death for 18 h, % 2,4,5-tribromo - rol-3-carbonitril 100 100

33 100 2,4,5-trichloro-1 - methylpyrrole-3 - carbonitrile 33 100 2,4,5-tribromo-1 - methylpyrrole-3 - carbonitrile 33 100

P R I m e R 55. The activity of pyrrole on pond snails (fisadi).

Fisadi species Physa obtained from Words Biologicl Supply company, are used to estimate arilpirolul. Several members errorcorrecting series are compiled in aerated tap water at two dosages of 10 and 1 M. D. Three healthy snails are immersed in 10 ml of the treated water in 20-ml scintillation vials. Cover loosely covered on each bottle. The connection M. D. Death for 18 h, %

aboutC. the death of the larvae was assessed at 72 h after treatment. Individual concentrations of the insecticide was repeated 4 times (one sheet with 10 larvae per copy). Data on the destruction of the larvae were subjected to probit analysis to obtain values LC50(lethal concentration - 50% ). The results are presented in table. 7.

P R I m e R 57. Analyses were performed in order to determine the toxic effects of some acaricidal compounds on dvuperistye spider mite (Tefranychus an artical). Infected larvae of the tick sheets beans, still on the plants, were loaded on 3 in acetone/water (50: 50) acaricide solutions. Then, the treated plants were kept in the laboratory at a constant temperature 27about50(lethal concentration - 50% ). The results are presented in table 8.

P R I m e R 58.

Every cell in 1 m2containing soil and a few leaves of lettuce-salad, added 17 individuals netted slug Deroceras reticulatum. 2 days to manually enter a pesticide bait. Each treatment was duplicated 3 times and after 3 days was determined by the percentage of the death of the slug. The results are presented in table. 9.

P R I m e R 59. 2,4,5-tribromo-1-(hydroxymethyl) pyrrole-3-carbonitrile (ester) was mixed to homogeneity with components dry bait when the concentration of the active ingredient of 0.5 and 1.0 wt. % . The components of the dry bait consisted of 90 wt. % finely ground feed for poultry based on corn and soybeans and 10 wt. % wheat starch. The dry ingredients were mixed with lager beer in the ratio of 500 g of beer at 1150 g of dry product. This mixture was extrudible through a sieve with round holes of 2.5 mm, was cut into pieces 4-6 mm in length and dried. After that, prepare a 0.5% bait containing 1-methyl-2,4,5-tribromophenol-3-carbonita - Rila.

4% bait (Baye) from methiocarb and 5% bait from metaldehyde (Desangosse) are finished commercial products.

the wounded and habitat derivative of pyrrole, characterized in that a derivative of pyrrole is used as a compound of the formula

where W is cyano or nitro-group;

X is cyano, bromine, chlorine, iodine and trifluoromethyl;

Y is hydrogen, bromine, chlorine, iodine or trifluoromethyl;

Z is hydrogen, bromine, chlorine, iodine;

B is hydrogen, C1- C6-alkyl, C1- C2-alkyl, substituted C1- C4-alkoxygroup, possibly substituted by chlorine, allyl, PROPYNYL,1- C2-alkyl, substituted by cyano or hydroxy-group, unsubstituted or substituted by chlorine, benzyl, substituted benzoyl chloride, trimethylsilyl or COR, where R is lower alkyl, phenyl or cyano in the amount of 0.05 to 4 kg/ha

 

Same patents:

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to novel trifluoromethylpyrrole carboxamides of the formula (I):

wherein R1 means hydrogen atom (H), (C1-C4)-alkyl; R2 means (C1-C4)-alkyl, (C1-C4)-halogenalkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, cyano-group or (C1-C6)-alkylcarbonyl; A means the group of the formula:

, or wherein R3 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C2-C6)-alkenyl, (C3-C7)-cycloalkyl, (C1-C4)-alkyl-(C3-C7)-cycloalkyl, (C4-C7)-cycloalkenyl, (C1-C4)-alkyl-(C4-C7)-cycloalkenyl, phenyl, naphthyl or phenoxy-group, or substituted phenyl, or substituted phenoxy-group wherein substituted represent 1-3 groups taken independently among an order comprising halogen atom, (C1-C4)_alkyl, (C1-C4)-alkoxy-, cyano-group, (C1-C4)-alkylcarbonyl, (C1-C4)-halogenalkyl, (C1-C4)-halogenalkoxy-, methylenedioxy-, difluoromethylenedioxy-group or phenyl; R4 means hydrogen, halogen atom or (C1-C4)-alkyl; each among R5, R6 and R7 means (C1-C6)-alkyl. Compounds of the formula (I) are used for control of phytopathogen organisms or for prophylaxis in damaging cultured plants by these organisms.

EFFECT: valuable properties of compounds.

10 cl, 3 tbl, 1 sch, 12 ex

FIELD: organic chemistry, agriculture, insecticides.

SUBSTANCE: invention relates to a substituted anilide derivative of the formula (I): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2; Z represents oxygen atom; Q means a substitute represented by any of the following formulae: Q1-Q3, Q6, Q8-Q12, Q14-Q19, Q21 and Q23 (wherein each among Y1 that can be similar or different represents halogen atom, (C1-C6)-alkyl group, and so on); Y2 represents (C1-C6)-alkyl group or halogen-(C1-C6)-alkyl group; Y3 represents (C1-C6)-alkyl group, halogen-(C1-C6)-alkyl group or substituted phenyl group; p represents a whole number from 1 to 2; q represents a whole number from 0 or 2; r represents a whole number from 0 to 2. Also, invention proposes a chemical for control of pests of agricultural and fruit crops. The chemical comprises substituted anilide derivative of the formula (I) as an active component and represents insecticide, fungicide or acaricide. Also, invention proposes a method for addition of the chemical for control of pests of agricultural and fruits crops. Also, invention proposes aniline derivative represented by the general formula (II): wherein R1 represents hydrogen atom, (C1-C6)-alkyl group; R2 represents hydrogen atom, halogen atom or halogen-(C1-C6)-alkyl group; R3 represents hydrogen atom, halogen atom, (C1-C6)-alkyl group, hydroxyl group or (C1-C6)-alkoxy-group; t = 1; m = 0; each among X that can be similar or different represents (C2-C8)-alkyl group, hydroxy-(C1-C6)-alkyl group or (C3-C6)-cycloalkyl-(C1-C6)-alkyl group; n = 1 or 2. Invention provides the development of anilide derivative as insecticide, fungicide and acaricide against pests of agricultural and fruit crops.

EFFECT: valuable properties of compound.

5 cl, 6 tbl, 27 ex

FIELD: organic chemistry, herbicides.

SUBSTANCE: invention describes phenyl-substituted heterocyclic 1,3-ketoenols of the formula (I): wherein R1 and R3 mean independently of one another ethyl or (C1-C2)-alkoxy-group; Q means the group of the formula (Q1): or (Q2): wherein R4 and R5 in common with atoms to which they are joined form 5-7-membered cycle that can comprise additionally anellated alkylene chain consisting of 2-6 carbon atoms that, in turn, can comprise two heteroatoms taken among oxygen atom, and indicated cycle can be substituted with halogen atom, hydroxy-group, (C1-C6)-alkoxy-group, (C1-C6)-alkoxy-(C1-C6)-alkoxy-group, (C1-C4)-alkylcarbonyloxy-group, hydroxy-(C1-C4)-alkoxy-group, hydroxycarbonyl-(C1-C2)-alkoxy-group, methoxycarbonyl-(C1-C2)-alkoxy-group, methoxyimino-, methoxyethoxyethoxy-group; R6 and R7 means (C1-C10)-alkyl; R8 means hydrogen atom; X means oxygen atom; R20 means (C1-C10)-alkyl, and also agronomically acceptable salts and isomers of these compounds. Also, invention describes a method for preparing compounds of the formula (I), herbicide agent and a method for control of weed growth based on compounds of the formula (I). Invention provides preparing compounds possessing the herbicide activity.

EFFECT: improved preparing method, valuable properties of compounds and agents.

5 cl, 28 tbl, 5 ex

FIELD: agriculture, fungicides.

SUBSTANCE: claimed method includes treatment of contaminated cultural plants or cultivation area thereof with effective amount of composition, containing A) N-sulfonylvaline amide of formula I 1, wherein R1 represents hydrogen or haloprenyl; and R1 represents C1-C4-alkyl, in combination with B) methalaxyl, or fluozinam, or mancoceb, or chlorithalonyl, or strobyluzine, or pyraclostrobine, or acibenzolar-S-methyl, or dimethoform, or fludioxonyl, or cimoxanyl, or imazalyl in synergistically effective amounts. Fungicide composition containing effective combination of A and B in synergistically effective amounts in combination with agriculturally acceptable carrier and optionally with surfactant.

EFFECT: composition of increased fungicidal action due to synergic effect.

8 cl, 12 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to incecticidal/acaricidal agent of synergetic action having general formula I wherein W, Y and Z are independently hydrogen or C1-C4-alkyl; A and B together with carbon atom to which they are bonded form C3-C6-cycloalkyl monosubstituted with C1-C4-alkoxyl; G is carbon or -COOR, wherein R is C1-C4-flkyl and compound selected from group containing chloropyriphos, oxydimenton methyl, acephat, methiocarb, thiocarb, pyrimicarb in synergic ratio.

EFFECT: agent of high efficiency to control pests and mites.

2 cl, 8 tbl, 7 ex

FIELD: organic chemistry.

SUBSTANCE: invention describes C2-phenyl-substituted cyclic ketoenols of the general formula: wherein W means hydrogen atom, alkyl with 1-6 carbon atoms; X means alkyl with 1-6 carbon atoms, alkenyl with 2-6 carbon atoms; Y means hydrogen atom, methyl, ethyl, isopropyl, alkenyl with 2-6 carbon atoms, ethynyl; Z means hydrogen atom, alkyl with 1-6 carbon atoms under condition that at least one of residues W, X, Y or Z means a chain with at least 2 carbon atoms but only one of residues X and Y can mean alkenyl with 2-6 carbon atoms; CKE means one of the following groups: , , and wherein A means hydrogen atom, alkyl with 1-6 carbon atoms; B means hydrogen atom, alkyl with 1-6 carbon atoms; A and B in common with carbon atom to which they are bound mean cycloalkyl with 5-6 carbon atoms wherein the ring carbon atom can be substituted with oxygen atom and can be substituted with alkyl with 1-6 carbon atoms or alkoxyl with 1-6 carbon atoms; A and B in common mean group of the formula: D means hydrogen atom or phenyl substituted with fluorine atom if CKE means group of the formula (4); G means hydrogen atom (a) or one of groups of the formula: or wherein R1 means alkyl with 1-6 carbon atoms, alkoxymethyl with 1-2 carbon atoms; R2 means alkyl with 1-4 carbon atoms; A and Q1 in common mean alkanediyl with 3-4 carbon atoms; Q2 means hydrogen atom. Invention provides preparing compound of the formula (I) possessing with insecticide, acaricide and herbicide activity.

EFFECT: valuable properties of compounds.

2 cl, 8 tbl, 32 ex

FIELD: agriculture, fungicides.

SUBSTANCE: claimed composition contains two components as active ingredients in synergistically effective amount in combination with respective filler, wherein component 1 represents O-methyloxime of 2-[α-{[(α-methyl-3-fluoromethylbenzyl)imino]oxy7}ortho-tolyl]-glyoxylic acid methyl aster, and component II represents compound selected from group containing II1 4-(2,2-difluoro-1,3-(benzodioxol-4-yl)-pyrrol-3-carbonitrile (fludioxanyl); II2 4-(2,3-dichlorophenyl)-pyrrol-3-carbonitrile (phenpiclonyl); II3 1-methylcyclohexanecarboxylic acid (2,2-dichloro-4-hydroxyphenyl)-amide (phenhexamide); II4 2-{2-[6-(2-cyanophenoxy)-pyrimidine-4-yloxy]phenyl}-3-methoxyacrilic acid methyl ester (azoxystrobin); II5 methoxyimino-(2-ortho-tolyloxymethylphenyl)-acetic acid methyl ester (cresoxymemethyl). Method for controlling and preventing of plant diseases also is disclosed. Claimed method includes application of stricken plant parts with component I and component II on any order or simultaneously in synergistically effective amount.

EFFECT: fungicide of high activity.

3 cl, 6 tbl, 4 ex

FIELD: agriculture, organic chemistry.

SUBSTANCE: invention relates to agent for controlling of plant pathogen fungi containing compound of general formula I as active ingredient, wherein X represents =N-; E represents NO2 or CN; R representsthiazolulmethyl or pyridylmethyl substituted with halogen; A represents hydrogen; Z represents C1-C4-alkylamino group; or A and Z together with atoms bonded thereon form thiazolidine, imidazolidine, hexahydro-1,3,5-triazine, N2- and N5-substituted with two C1-C4-alkyl in alkyl group, 6-membered saturated heterocycle fragment including additionally oxygen and N-(C1-C4)alkyl heterogroup; and fungicide compound selected from group containing cyproconazole, triadimenol, methalaxide, azoxistrobin, kresoximmethyl, etc., in weight ratio compound of formula I/fungicidal agent of 1:(0.1-10). Also disclosed is insecticide agent containing compound of formula I and compound selected from group containing cyproconazole, azoxistrobin, kresoximmethyl, biterthanol, tiram, methalaxide, etc. in ratio of 1:(0.1-10).

EFFECT: enhanced assortment of agents for controlling of plant pathogen fungi and agents for insect controlling.

4 cl, 15 tbl, 15 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention relates to an insecticide-acaricide agent comprising a mixture of compound of the formula (I): wherein X means halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; W, Y and Z mean independently of one another hydrogen atom (H), halogen atom, (C1-C4)-alkyl, (C1-C4)-alkoxyl; A means H, (C1-C6)-alkyl; B means H, methyl or ethyl; A and B in common with carbon atom to which they are bound form saturated unsubstituted (C3-C6)-ring or substituted with (C1-C4)-alkoxy-group; D means H, (C1-C6)-alkyl; G means H or one of the following groups: (b) or (c) wherein L means oxygen atom (O); M means O; R1 means (C1-C10)-alkyl, (C3-C6)-cycloalkyl that if necessary can comprise one nitrogen atom (N) or O; R2 means (C1-C10)-alkyl and agonist, respectively, antagonist of nicotine acetylcholine receptors chosen from the group comprising compounds of formulas: (IIa) (IIe) (IIg) (IIh) (IIi) (IIk) (IIl) and (IIm) taken in synergetically effective ratio.

EFFECT: valuable biological properties of substances.

6 cl, 22 tbl, 6 ex

FIELD: organic chemistry, insecticides.

SUBSTANCE: invention describes an insecticide agent comprising synergetic mixture of compound of the formula (I): wherein W, X, Z, R and G have values given in the invention claim and one of the following compounds: lufenuron, triflumuron, novaluron, fluphenoxuron, emamectin, methoxyphenozide, endosulfan, fipronil, ciromazin, indoxacarb. Insecticide activity of the proposed agent is higher as compared with sum of activities of individual active substances.

EFFECT: enhanced activity of agent.

2 cl, 23 tbl, 6 ex

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