SU368722A1 - INSECTICIDE - Google Patents

Description

one

The invention relates to the use as an insecticide of cyclopropanecarboxylic acid esters.

It is known to use as an insecticide / -2-allyl-4-hydroxy-3-methyl-2-cyclopentene-1-ovine ester with / - {"c-t / an (; - chrysanthemum monocarboxylic acid (allethrin).

In order to expand the range of highly effective insecticides with low toxicity for warm-blooded animals, it is proposed to use for this purpose cyclopropanecarboxylic acid ester of the general formula

Compounds of formula I can be obtained by reacting compounds of the general formula

SNGA

where Y, R, R, m and p are as defined above, A is halogen, or hydroxy, with cyclopropanecarboxylic acid of the general form

NOSE-

.0; s;

NZS CH where Y is oxygen or sulfur; R is hydrogen or methyl; R is methyl, 2-methyl-1-propenyl; 2-methoxycarbonyl-1-propenyl, phenyl, 3,4-methylenedioxyphenyl, if 25 is R-hydrogen, or R2 is methyl, if R is methyl; R and R are the same or different, halogen or methyl; m and p are O, 1.2 or 3.30 where R and R are as defined above. Among the esters of the formula I, the compounds listed in Table 2 have especially chain insecticidal properties. 1. In all examples, the amount of reagents is given in parts by weight. Example 1. 0.05 parts of compounds 1, 4 and 6 are dissolved in kerosene (up to 100 hours). Three spray liquids are obtained. Example 2. 0.2 parts of compounds 2, 5, 7, 8 and 10, 0.8 hours, piperonyl butoxide is dissolved in

T abl and a 1

room

Compound name

3-Phenoxy-benzyl-3 -3-phenylcyclopropanecarboxyl-3-phenoxybenzyl-2, 2-dimethyl-3 (3, 4-methylenedioxy) -phenylcyclopropanecarboxene

3 - (,) - Chlorophenoxybenzylchrnzanthemate) 2-Chloro-5-phenoxybenzylchrisanate 3- (2, 4-Dichlorophenoxybenzylchrisanmate)

3- (2-Chloropheno1 sibenzylchrisante1mat) 2,6-Dichloro-3-phenoxybenzylchrisantemate 3- (2, 4, 5-Trichlorophenoxybenzylchrisantemat) 3- (m-Chlorphenoxy) -benzyl-2, 2, 3-trimethylcyclopropanecarboxyl-2 D1et11L-4-chlorophenoxy) benzylchrysanthemate

3- (o-Tolyloxy) -benzylchrisantemate 3- (l-Tolyloxy) -benzylchrisant 3 - (/ g-Toliloks11) -benzylhr11anteant Z-Methyl-5-phenoxybenzylchristemate 2-Methyl-5-phenox 1benzylchristemat 3- (2, 2 Xyloxy) -benz11lchryzaitemate 3- (3, 4-Xyloxy) -benzylchrisanate 3 "(3, 5-Xyloxy) -benzylchrisantemate 3-Phenylthiobenzyl-chrysanthemate 3-Phenylthiobenzyl-2, 2, 3, 3-Tetramethylpropanecarboxle-Zach-2, 2, 3, 3-3 , 2-dnmetil-3-phenylcyclopropanecarboxylate 3-, g-Tolylthiobenzylchrisanate 3- «-Tolylthiobenzylchrisanate 3-o-Tolplthiobenzylhrizant.mat 3-l-Chlo rphenylthiobenzyl chrysanthemate

kerosene and bring to about 100 hours. 5 liquids are obtained containing 0.2% of the proposed compounds and 0.8% of pyeronylbutoxide as a synergist.

Example 3. 0.2 parts of compounds 16 and 20 and 0.8 parts of 0-to-methyl-O-propargylphenyl phosphanate (N IA-16388) are dissolved in kerosene (up to 100 parts). Get 2 fluids containing 0.2% of the proposed compounds and 0.8% sierhgist N IA-16388.

Example 4. 20 parts of compounds 1-8, 10, 12, 13, 15-20, 23-25, 10 hours. Coprol SM-200 (emulsifier trademark, manufactured by Togo Chemical Co.) and 70 parts of xylene are mixed. and get 20 emulsifiable concentrates containing 20 wt. % of the proposed compounds.

Example 5. 0.6 g of compounds 1, 4-6 and the yt / 7a of the c-chrysanthemum of compounds 1 and 19 are dissolved in 20 ml of methanol. The solutions are mixed with 99.4 g of a carrier consisting of a mixture of Tabu powder, pyrethrum and wood powder in the ratio 3: 5: 1. Methanol is evaporated and r

The rest of the MW added 150 ml of water, carefully moved, formed mosquitoes removed and dried them. 6 anti-mosquito coils are obtained, each containing 0.6% of the active substance.

Example 6 0.2 parts of compound 1, 0.2 parts of tetramethrin dissolved in a mixture of 7 parts of xylene and 7.6 parts of deodorized kerosene. The solution is loaded into an aerosol container, in

after the valve was attached, 85 parts of the propellant iodine were injected under pressure. Get the aerosol.

llpime 7: 0.4 parts of Compound 4 are dissolved in a mixture of 7 parts of xylene and 7.6 parts of deodorized kerosene with stirring. Get the aerosol, as in example 6.

11 g. Measure 8. 0.3 parts of methyl 3 and methyl nitrophos are dissolved in a mixture of 7 parts of xylene and 7.6 parts of deodorized kerosene. Get

aerosol, as in example 6.

11 g. And measure 9. 0.3 parts of compound 7, 0.2 parts of tetramethrin, 13.5 parts of deodorized kerosene and 1 part are mixed. Atmos 300 (trademark of an emulsifier produced by Atlas Chemical Co.) 50 hours of pure water are obtained and an emulsion is obtained, which is loaded into an aerosol container together with 35 parts of a mixture of deodorized propane and butane in the ratio of 1: 3. An aerosol is obtained.

Example 10. 1 part of compounds 1, 4 and 6 are dissolved in 20 parts of acetone, 99 parts of diatomite (300 mesh) are added to the solutions. The mixture is vanished; The mixture is stirred in a mortar and the acetone is evaporated. Get 3 dust.

Example 11. In a mortar mix thoroughly for 5 hours. compounds 1, 5h. Toyolignin ST (trademark filler, produced by Toyo Bosechi Ko) and 90 parts of clay CSM (trademark clay, produced by Cyclite Mineie Co.). The mixture is then supplemented with 10% water (by weight of the mixture) and thoroughly mixed again. The resulting mixture was granulated and existed in air. A granulated preparation is obtained.

Example 12. To a mixture of 25 parts of compound 4 and 5 hours. Coprol SM-200 was added 70 parts of talc (300 mesh) and mixed thoroughly in a mortar. A wettable powder is obtained.

Example 13. 1.5 g of compounds 9, 11-14,

17, 19, 21 and 22 are dissolved in 20 ml of methanol, each solution is thoroughly mixed with 98.5 g of the carrier indicated in Example 5. Methanol is evaporated, 150 ml of water are added to the residue, mixed thoroughly, molded into

spiral and dry. Get 9 mosquito coils containing 1.5% of the active ingredient.

Example 14. 0.2 parts of compounds 26-28, 30 and 32 are dissolved in kerosene (up to 100 hours) and

receive liquid preparations.

Example 15. A mixture of 0.1 parts of compound 20 and 0.4 parts of piperonylbutoxide was dissolved in kerosene (up to 100 hours) and a liquid preparation was obtained. Example 16. A mixture of 0.1 parts of compound 31 and

0.4 parts of sulfoxide 1,2-methylenedioxy-4- 2- (octylsulphenyl) propyl-1-benzene is dissolved in kerosene (up to 100 hours) and a liquid preparation is obtained.

Example 17. A mixture of 0.1 parts of compound 33 and 0.4 parts of MS-K-264 M- (2-ethylhexyl) -bicyclo- (2, 2,1) -hepta-5-en-2,3- Dicarboximide is dissolved in kerosene (up to 100 hours) and a liquid preparation is obtained.

Example 18. A mixture of 15 parts of compound 26, 3h. DDVP, 10 parts. Soprol SM-200 (emulsifier manufactured by Togo Kem Co.) and 72 parts of xylene are thoroughly mixed and an emulsifiable concentrate is obtained.

Example 19. A mixture of 20 parts of each of the compounds 29, 31 and 33, 10 hours. Coprol SM-200 and 70 parts of xylene are thoroughly mixed and 20% emulsifiable concentrates are obtained.

Example 20. Solutions of 2 parts (i-trans-chrysanthemums of compounds 26 and 27 in 20 ml of methanol are thoroughly mixed with 99 parts of the carrier indicated in example 5. After evaporation of methanol, the mixture is thoroughly mixed with 150 ml of water, dried and receive mosquito coils containing 1% active substance.

Example 21: 0.3 parts of compound 26, 0.2 parts of tetramethrin, 0.5 parts of methoxychlor, 7 parts of xylene and 7 parts of deodorized kerosene are carefully transferred, the resulting solution is loaded into an aerosol container. After the valve is installed, 85 parts of propellant are supplied to the container under pressure and an aerosol is obtained.

Example 22. 0.3 parts of compound 28, 0.3 parts of methyl nitrophos, 7 parts of xylene and 7.4 parts of deodorized kerosene are mixed, the resulting solution is treated as in Example 21, and an aerosol is obtained.

Example 23. A mixture of 0.3 parts of compound 27, 0.2 parts of tetramethrin, 0.5 parts of N IA-16388, 2.5 parts of chlorosen Nu (the trade mark of the product is “Dow Chemical Co., containing as active ingredient 1,1,1-trichloroethane) 5.5 parts of deodorized kerosene and 1 part of emulsifier Atmos 300 are emulsified in the presence of 45 parts of pure water. The emulsion is loaded into an aerosol container together with 25 parts of a mixture of deodorized butane and propane (3: I). Get the aerosol.

Example 24. A mixture of 1 part of compounds 26 and 28 and 5 parts of NIA-16388 is dissolved in 20 parts of acetone, the solution is shifted in a mortar with 99 parts of diatomite (300 mesh). After evaporation of the acetone, dusts are obtained.

Example 25. Mix thoroughly in a mortar for 5 parts of compound 30, 5 hours of Toayolignin ST and 90 parts of glia of CSM, then mix with 10% (by weight of the mixture) water, mix, granulate and dry the granules.

Example 26. Mix thoroughly in a mortar 25 parts of compound 32, 5 hours. Coprol SM-200 and 70 parts of talc (300 mesh). A wettable powder is obtained.

To determine the insecticidal effect

The preparations obtained were tested.

Test 1. Spray 5 ml of liquid preparations obtained in examples 1, 2, 3, 14, 15, 16 and 17 and 0.2% alleletrin (control).

After 20 seconds after spraying, the valve is opened and adult adults of their flies (100 pieces per group) are exposed to the effect of fog for 10 minutes. They are then placed in an observation chamber, where they are given food. Having kept in the chamber for 1 day at room temperature, count the number of killed eggs.

The results of the experiments are given in table. 2

table 2

Test 2. The emulsifying concentrates prepared in Examples 4, 18 and

19, is diluted with water 40,000 times, 1.5 liters of this emulsion is loaded into a 23X30 cm box of 6 cm high polystyrene. About 100 larvae of the northern mosquito are released into this box. The next day, more than 90% of the larvae die.

And from attempt 3. About 20 adult northern mosquitoes are released into a glass chamber (70 g), in which mosquito coils weighing 1 g are burned, manufactured in examples 5, 13 and 20. Spirals contain compounds I,

4-6, 9, 11-14, 17, 19, 21, 22, 27 and d-trans-hrnzantemates of compounds 1, 19 and 26. 20 minutes after the spirals were burned, the number of dead insects was counted. The death of mosquitoes is more than 80%.

Test 4. The insecticidal effect on adult flies of aerosols prepared in examples 6, 7, 8, 9, 21, 22, 23 is determined by the aerosol method of testing using the Pete Grady chamber.

The results of the experiments are presented in table. 3

8 Table 3

Test 5. In a 14 liter polypropylene jar, 10 l of water is poured, then 1 g of the granulated preparation of examples 11 and 25 is loaded. After 1 day, 100 larvae of the northern washing machine are released into the water. Within 24 hours, more than 90% of the larvae die.

Test 6. Petri dish (14 cm in diameter, 7 cm in height} is lubricated with oil on the inner side, and the bottom of the wall 1 cm high is not lubricated. Dust from compounds 1, 4, 6 will interfere with the bottom of the cup at 2 g / m, 26 and 28, obtained in examples 10 and 24.

Then cockroaches are released into the cup, which come into contact with the dusts for 30 minutes. After 1 day, more than 90% of cockroaches were still, and after 3 days more than 90% died.

Test 7. In Wagker pots, rice plants are sprung up, which emerge 45 days after sowing. The emulsifiable concentrates of compounds I, 6 and 30, prepared according to examples 4 and 19, the wettable powder obtained according to example 12, are diluted 400 times with water. The resulting liquid is applied to the plants (10 ml per

pot), then each pot is “covered with a wire mesh, under which 30 rice fleas are placed. After 24 hours, in all cases more than 90% of the fleas die.

Subject invention

Use of cyclopropanecarboxylic ester of the general formula

R

HOSSN - C: R / C

ABOUT

HjC CHS

oxygen or sulfur: hydrogen or methyl; methyl, 2-methyl-1-propenyl; 2-methoxycarbonyl-1-propenyl, phenyl, 3,4-methylenedioxyphenyl, if R is hydrogen, or R2 is methyl, if R is methyl;

are identical, whether different, halogen or methyl; O, 1, 2 or 3. Insecticide.