Derivatives of 1-phenylimidazole exhibiting insecticidal properties and insecticidal composition

 

(57) Abstract:

Usage: in agriculture as an insecticide. The inventive compound f - ly 1, where R is a hydrogen atom or methyl, X is fluorine atom, chlorine or nitro-group, Y is a chlorine atom or fluorine, Z is a hydrogen atom, fluorine or bromine. Obtained by reaction of halogen-substituted aromatic compounds with relevant azotosodyerzhascimi connections. Also described insecticidal composition containing 0.1 - 95 wt.% active compound, the remainder to 100 wt.% - target additives. Connection structure 1 2 S. p. f-crystals, 8 PL.

The invention relates to new derivatives of 1-phenylimidazole formula 1

CFN

where R represents a hydrogen atom or methyl;

x represents a fluorine atom, a chlorine atom or a nitro-group;

y represents a fluorine atom or a chlorine atom;

z represents a hydrogen atom, a fluorine atom, a chlorine atom or a bromine atom, a process for the preparation of these compounds and insecticides containing as active components of these compounds.

In U.S. patent 3 868 458, U.S. patent 3 940 484 and U.S. patent 3 996 366 indicated that certain imidazole derivatives used as active ingredients in insecticides.

As a result of intensive the uly 1 exhibit extremely high insecticidal activity, in relation to a wide range of harmful insects both in pure form and in compositions.

The synthesis example 1 (synthesis of compounds 10).

To a solution of 0.41 (2 mmol) 4 (5)-2-(chloro-1,1,2,2-tetraborate)of imidazole in 5 ml of N, N-dimethylformamide was added 80 mg (2 mmol) of sodium hydride in oil (60% ) while cooling with ice, followed by stirring at the same temperature for 10 minutes Upon completion of the reaction, to the reaction mixture dropwise added 0.50 g (2 mmol) of 3,4,5-trichlorobenzaldehyde, followed by stirring for 7 h at 80-90aboutC. After completion of the reaction, the reaction mixture was poured into water and extracted with ethyl acetate. Then the residue is washed with brine, dried over magnesium sulfate and concentrate under reduced pressure. The resulting product chromatographic on silica gel and get to 0.23 g of 1-(2,6-dichloro-4-triptoreline) -4-(2-chloro-1,1,2,2-tetraborate)imidazole, T. pl. 101,2aboutC.

The synthesis example 2 (synthesis of compound 23).

To a solution of 0.43 g (2 mmol) of 2-methyl-4-(5)-(2-chloro-1,1,2,2-tetraborate)of imidazole in 5 ml of N,N-dimethylformamide are added at the same time of 0.41 g (3 mmol) of anhydrous potassium carbonate and 0.47 g (2 mmol) of 3,5-dichloro-4-fermentatively, followed by stirring for 7 h p is live brine, dried over magnesium sulfate and concentrate under reduced pressure. Chromatography of the product on silica gel obtain 0.33 g of 1-(2,6-dichloro-4-triptoreline)-2-methyl-4-(2-chloro-1,1,2,2-tetraborate)imidazole, T. pl. 134,3aboutC.

Examples of compounds of the invention are synthesized by the methods described here are given in table.1.

The following are examples of compositions, in which all parts are given by weight and the compounds of the present invention is marked with the numbers listed in table.1.

Example of structure 1. Emulsifiable concentrate.

After dissolving 10 o'clock each of compounds (1) to(27) of the invention in 35 hours of xylene and 35 hours of dimethylformamide, to the solution was added 14 PM steelfinish ether of polyoxyethylene and 6 hours of dodecylbenzenesulfonate calcium. The resulting mixture is thoroughly mixed and the result is a 10% emulsifiable concentrate.

Example of compound 2. Wettable powder.

After adding 20 hours of connection 1-27 of the invention to a mixture of 4 hours lauryl sodium, 2 g calcium lignosulfonate, 20 hours a fine powder of synthetic hydrated silicon dioxide and 54 h diatomaceous earth, the mixture is stirred in a mixer for juice and receive a 20% wettable powder.

the oxide of silicon, 5 hours of dodecylbenzenesulfonate, 30 hours of bentonite and 55 including clay to 5 hours of compounds (1) to(27) of the invention the mixture is thoroughly stirred. After stirring to the mixture add the required amount of water. The mixture granularit using the pellet mill and after drying in the air get the 5% granules.

Examples of composition 4. Dust.

After dissolving 1 tsp connection 22 of the invention in an appropriate amount of acetone to the solution add 5 o'clock a fine powder of synthetic hydrated silicon dioxide, 0,3 including RAR and 93,7 including clay. The mixture is stirred in a mixer for juice and after evaporation of the acetone receive 1% dust.

Example of compound 5. Bulk concentrate.

After mixing 20 hours of connection 23 of the invention and 1.5 hours of trioleate from 28.5 hours of an aqueous solution containing 2 hours of polyvinyl alcohol, a mixture of finely crushed (to particles with a diameter less than 3 μm, using a sand eraser. Then to the powder add 40 hours of an aqueous solution containing 0.05 tsp xanthan gum and 0.1 PM alumomagnesium silicate, also add 10 hours of propylene glycol. The mixture was thoroughly stirred and receive a 20% bulk concentrate for aqueous suspensions.

Example of compound 6. Oil spray.

The village is arrowanas kerosene and receive a 0.1% oil spray.

Example of compound 7. Aerosol oil-based.

Mix and dissolve 0,1'clock compounds 1-27 invention, 0,2 hours of tetramethrin, 0,1 h d-phenothrin, 10 am, trichloroethane and 59.6 hours deodorized kerosene and the resulting solution is filled aerosol containers. After the establishment of the valve under pressure is injected through the valve 30 PM propylene (liquefied petroleum gas) and get an aerosol oil-based.

Example of compound 8. Water aerosol.

Mixed together and dissolved 0.2 h connection 24 of the invention, 0,2 h d-allethrin, 0,2 h d-phenothrin, 5 hours xylene, 3,4 including deodorized kerosene and 1 tsp emulsifier [ATMOS 300 (registered mark, AtLaS Chemical Co. Co., Ltd.)] and the resulting solution with 50 hours of distilled water is filled aerosol container. After establishing the container valve through it under pressure from the pump 40 hours of propellant (liquefied petroleum gas) with a water spray.

Example of compound 9. Mosquito spiral.

After addition of 0.3 part d-allethrin to 0.3 g of compound 20 of the invention, the mixture was dissolved in 20 ml of acetone. Then the solution is evenly mixed with with 99.4 g of a carrier for mosquito coil (tobacco crumbs: salesny por, molded and after drying receive mosquito spiral.

An example of the structure 10. Electric mosquito Mat.

A mixture of 0.4 g of compound 19 of the invention, 0.4 g of o allethrin and 0.4 g of piperonylbutoxide dissolved in acetone to a hollow volume of 10 ml. of the resulting solution (0.5 ml) uniformly impregnate the base material (a mixture of cotton lint and fiber mass, the cured plate) electric Mat size 2,5x1,5 cm and a thickness of 0.3 cm with obtaining electric mosquito Mat.

Example of compound 11. The fumigant.

After dilution with 100 ml of connection 16 of the invention in the required amount of acetone, the resulting solution is impregnated with a porous ceramic plate size 4x4 cm and a thickness of 1.2 cm with the receipt of fumigant.

An example of the structure 12. Poisoned bait.

After dissolving 10 mg of the compound 1-27 invention in 0.5 ml of acetone, the resulting solution was applied to 5 g of dry feed, pounded into powder. After drying of the powder is 5% poisoned bait.

An example of the composition 13. Oil solution.

95 hours of each of the compounds 6 or 12 of the invention was mixed with 5 hours of purified kerosene obtaining 95% oil solution.

Sample test 1 (insecticidal test on the nymphs of the brown plant of a flea).

Emulsifiable concentrate of the test compound, prepared in accordance with example 1, diluted with water (respectively to the concentration of 500,5 or 0.5 ppm) and in dilute solution at the moment submerged shoots of rice plants (approximately 12 cm). After drying in air shoots of rice plants are placed in a test tube for testing, which also put about 30 nymphs brown herbal flea beetle (Nilaparvata Lugens). Six days later reveal the presence of living and dead nymphs. Assessment tests indicate as follows:

and the lack of live insects

b live insects 5 or less

with live insects 6 or more

The results are shown in table.3.

Sample test 2 (insecticidal test on blaske dinosau South).

At the bottom of a polyethylene Cup with a diameter of 5.5 cm is placed filter paper of the same size, which is dotted 1 ml water diluted (50 who had 1, and on it placed in the quality of the food one germ of corn. In a bowl put about 30 eggs a flea dinosau South (Diabrotica undecumpynotata). Eight days after covering cups reveal the presence of living or dead hatched larvae. The criterion of the test results is as follows:

a lack of live insects

b live insects 5 or less

with live insects 6 or more

The results are shown in table.4.

Examples of test 3 (insecticidal test on blaske dinosau South).

5 ml of dilute aqueous emulsifiable concentrate of the test compound obtained according to example 1 are mixed with 50 g of sieved (16 mesh) soil. The concentration of active ingredient in soil set 0.25 or 0.125 h/million

Each soil sample contribute in a plastic Cup with a diameter of 5.6 cm and a height of 5.8 cm, in which sow two seeds of maize root length 2-3 cm Then into the Cup release 10 larvae flea dinosau South (Diabrotica undecimpunctata howardi) in the third larval stage. Two days later, count the number of treated insects (dead or moribund) and not exposed to processing insects (energetic) identifying effective is the ordinary mosquito).

Emulsifiable concentrate of the test compound obtained according to example 1, diluted with water and the diluted solution (0.7 ml) is added to 100 ml of deionized water (concentration of the active component of 3.5 ppm). In the mixture out 20 larvae of ordinary mosquito (Culex pipiens pallens) in the last larval stage. A day after the release of reveal mortality among larvae.

Evaluation criteria indicate as follows:

and 90% or higher

b is not less than 10% but less than 90%

with at least 10%

The results are shown in table.6.

Example test 5 (insecticidal test on the beetles).

At the bottom of a polyethylene Cup with a diameter of 5.5 cm is placed filter paper of the same size, which is dotted 0.7 ml water diluted (500 ppm) of the emulsifiable concentrate of the test compound, prepared in accordance with example 1. As food for filter paper evenly distribute 30 mg of sucrose. In the Cup run 10 adult male German cockroach (Prussak) (lattella germanica). Six days after covering cups determine the number of dead and alive insects to calculate mortality.

The result is polietileno Cup with a diameter of 5.5 cm is placed filter paper of the same size, which dotted 0.7 ml water diluted (500 ppm) of the emulsifiable concentrate of the test compound, prepared in accordance with example 1. As food for filter paper evenly distribute 30 mg of sucrose. In the Cup run 10 adult female flies home (Mysca domestica). After 48 h after covering the Cup determines the number of dead or living insects with detection of mortality (2 repeat). The results are shown in table.8.

1. Derivatives of 1-phenylimidazole General formula

< / BR>
where R is hydrogen, methyl;

X is fluorine, chlorine, nitro-group;

y is fluorine, chlorine;

Z is hydrogen, fluorine, chlorine or bromine,

exhibiting insecticidal properties.

2. Insecticidal composition containing a derivative of 1-phenylimidazole and target additives, characterized in that as the derived 1-phenylimidazole used as a compound of General formula

< / BR>
where R is hydrogen, methyl;

X is fluorine, chlorine, nitro-group;

y is fluorine, chlorine;

Z is hydrogen, fluorine, chlorine or bromine,

in an amount of 0.1 95,0 wt. target additives else.

 

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< / BR>
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EFFECT: valuable properties of compounds.

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EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

17 cl, 2 tbl, 74 ex

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12 cl, 3 tbl, 2 sch, 2 dwg, 8 ex

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EFFECT: improved method of synthesis, valuable medicinal properties of compounds and pharmaceutical composition.

13 cl, 97 ex

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SUBSTANCE: invention relates to substituted ω-azolylalkane anilides. Invention describes substituted ω-(1H-azol-1-yl)-N-phenylalkaneamides of the general formula (I): wherein Z and Y mean nitrogen atom of CH-group, or they represent the chain -C-CH=CH-CH=CH-C- simultaneously and forming in common an anellated ring; n means a whole number from 1 to 3; Rm are similar or different and mean hydrogen, halogen atom, alkyl group with number of carbon atoms from 1 to 4, alkoxy group, alkylenedioxy group, benzyloxy group, perfluoroalkyl group with number of carbon atoms from 1 to 4, nitro group, alkoxycarbonyl group, carboxyl group, halogenphenylthio group, halogenbenzoyl group; m means a whole number from 0 to 5, their salts with acids. Also, invention describes methods for synthesis of compounds of the formula (I) and their using as anti-aggregative preparations. Invention provides synthesis of novel compounds possessing the useful biological properties.

EFFECT: valuable properties of compounds, improved method of synthesis.

8 tbl, 11 ex

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