SU297153A1 - INSECTICIDE COMPOSITION - Google Patents

Description

This invention relates to insect control agents.

Insecticidal compositions containing the active ingredient based on pyrethrin analogs, as well as solid or liquid carrier are known.,,

It is proposed as a pyrethrin analogue to use a compound of the general formula

I d

СН-С-О СНо-Н

R

II o d

D

in which RI is hydrogen, methyl or ethyl; - hydrogen, methyl, ethyl or phenyl; Rs is methyl, ethyl or methoxyphenyl; R is methyl or ethyl; R3 is phenyl, furyl or benzofuryl, and phenyl and furyl may have as substituents lower alkyl, halogen, alkenyl, alkylene, benzyl, alkyl, a substituted benzyl group, tenyl or furfuryl, which may be replaced by lower alkyl .;

The compounds of the above formula are prepared in a known manner.

In tab. 1 given a list of compounds corresponding to this formula.

The following are examples of the preparation of compositions. Example 1: 0.4 parts of compound 1 are dissolved in purified kerosene, the volume is adjusted to 100 parts and a 0.4% oily preparation is obtained.

Example 2. 0.4 parts of compound 2 are dissolved in IB with purified kerosene, the volume is adjusted to 100 parts, and 0.4 o / o-oy is obtained.

Example 3. 10 parts of the compound 2, 10 hours. The Sorpol SM-200 (trade name, Togo Kadaki; K. K-) and 80 parts of xylene are dried with stirring. An emulsifiable concentrate is obtained .;

Example 4. 5 parts of compound 2, 5. Sumition, 20 h. Sorpola SM-200 and 70 h. Of xylene

dissolved at; stirring. Receive emulsifiable concentrate. |

When e. P.5. | 0.3 hours of compound 3, and 1.5 hours

piperonium lbutrxid is dissolved in purified kerosene, Dodobf volume up to 100 hours and get oily distillation,. ,, |

P r and m ef-6. i 10 parts of 4 and 20 hours. Sorpola 2020 (brand name, manufactured by; Togo Kagaku K-K.) is dissolved with stirring from 70 parts of xylene and Table 1

Continuation

Continuation

Example 7. 0.2 parts of compound 4 and part of Sumition are dissolved in purified kerosene, and the volume is up to 100 hours, and an oil preparation is obtained.

Example 8. 0.1 parts of compound 5 is a solution of purified kerosene, brought to volume

100 hours and get 0.1 o / o-oh oil composition.

Example 9. 0.4 parts of compound 5, 6 parts of xylene li 8.6 hours were mixed: purified kerosene. The resulting solution is transferred to an aerosol bottle. Then 85 hours of propellant (e.g., freon, vinyl chloride monomer or sigine oil and gas) are injected into it and an aerosol is obtained.

Example 10. 0.6 g of compound 5 is dissolved in 20 ml of methanol, then mixed with 99.4 g of a fumigantry base (mixture 5:; 3: I Tabu powder; pyrethrum and wood powder). After evaporation of the methanol, the mixture was diluted with 150 ml of water. .Ji3 the resulting mixture is molded fumigant-pali ki. ;

Example 11.: 1h. Compounds 5 are dissolved in 20 parts of acetone. The solution with | is mixed with 99 parts of diatomaceous earth (300-mesh), and the mixture is thoroughly ground on the mechanical. After distilling off the acetone, dust is obtained. |

SM-200 is dissolved in 80 parts of xylene and an emulsifiable concentrate is obtained.

Example 13. 0.02 parts of compound 5 and 0.15 parts of natural pyrethrin are dissolved in purified kerosene, the volume is adjusted to 100 parts, and an oil preparation is obtained.

Example 14. 0.02 parts of compound 1 and 0.2 parts of phthaltrin were dissolved in purified kerosene, the volume was adjusted to 100 parts, and an oil preparation was obtained.

Example 15. 0.04 parts of compound 5 are mixed, 0.36 parts of phthaltrin, 6 parts of xylene and 8.6 parts of purified kerosene are mixed and a solution is obtained, which is placed in an aerosol bottle. After adding 85 parts of the propellant under pressure, an aerosol is obtained.

Example 16. 0.1 parts of compound 5 and 0.5 parts of piperonylbutoxide were dissolved in purified kerosene, the volume was adjusted to 100 parts and an oily composition was obtained.

Example 17. A mixture of 0.4 parts of compound 5, 13.6 parts of purified kerosene and 1 part. Atmos-300 (the trade name of the emulsifying agent, i manufactured by Atlas Chemical opii.) Is emulsified by adding 50 parts of water. Then it is placed in an aerosol bottle together with 35 parts of a mixture of deodorized butane and propane (3: 1). Get the aerosol. Example 18 0.2 g of compound 5 is dissolved in an appropriate amount of chloroform. The solution is impregnated evenly on the surface of a piece of asbestos with a thickness of 0.3 hedgehog measuring 2.5 x 1.5 cm. An asbestos sheet of the same size is used to obtain a fibrous fumigant insecticidal composition on an electrically heated plate. As a fibrous substrate, in addition to asbestos, modsp use wood pulp and other materials similar to asbestos. Example 19. 5h. Compounds 5, 5 h. Togolignin ST (the brand name of the product manufactured by “Togo Boseki K.K.) and 90 hours. GSM Clay (the brand name of the product manufactured by“ Cyclet Kogyo K.K.) is thoroughly mixed on a grater. After adding 10% water, the granules are formed. Example 20. 0.2 parts of compound 7 are dissolved in purified kerosene, the volume is adjusted to 100 parts, and a 0.2 / o oil composition is obtained. Example 21 g of compound is dissolved in 20 ml of methanol. The solution is thoroughly mixed with 99 g of a fumigant base. After distilling off the methanol, the mixture is diluted with 150 ml of water and formed into fumigant sticks. Example 22. Mix 5 parts of compound 7, 5 parts. IPOs, 20 hours. Sorpola 2020 and 10 parts of xylene and get emulsifiable concentrate. Example 23. 0.2 parts of compound 7 and 0.2 parts of DDTP are dissolved in purified kerosene. The volume is adjusted to 100 parts and an oil preparation is obtained. Example 24. 0.2 parts of compound 9 are dissolved in purified kerosene, the volume is adjusted to 100 parts, and 0.2% oily preparation is obtained. Example 25 10 parts of compound 14, 20 parts of Sornol 2020 and 70 parts of xylene are mixed and an emulsifiable concentrate is obtained. Example 26. 0.3 part of compound 13 is dissolved in purified kerosene, the volume is adjusted to 100 parts, and an oil formulation is obtained. Example 27. 0.2 parts of compound 22 was dissolved in purified kerosene, the volume was adjusted to 100 parts, and an oil preparation was obtained. Example 28. 0.4 parts of compound 23 were dissolved in kerosene, the volume was adjusted to 100 parts, and an oil preparation was obtained. Example 29. In 20 methanol, 0.5 g of compound 24 is dissolved. The solution is mixed thoroughly with 99.5 g of fumigant substrate. The methanol is distilled off, the mixture is diluted with 150 ml of WATER and formed smoke bombs. Example 30. 15 parts of compound 25, 10 parts of Sorpol SM-200 and 75 parts of xylene are mixed and an emulsifiable concentrate is obtained. Example 31. 20 parts of compound 26 are mixed with 5 parts of Sorpol SM-200, then 75 parts of talc (300 mesh) is added and ground in a mortar. Get wettable powder. Example 32 0.2 parts of compound 28 was dissolved in kerosene, the volume was adjusted to 100 parts and an oil preparation was obtained. Example 33 0.5 parts of compound 31 are dissolved in kerosene, the volume is adjusted to 100 parts and an oil preparation is obtained. Example 34. Mix 20 parts of compound 31, 20 parts of Sorpol SM-200 and 60 parts of xylene to form an emulsifiable concentrate. Example 35: 0.3 parts of compound 33 and 1.5 parts of piperonylbutoxide were dissolved in kerosene, the volume was adjusted to 100 parts, and an oil preparation was obtained. Example 36 0.2 parts of compound 35 was dissolved in kerosene, the volume was adjusted to 100 parts and an oil preparation was obtained. Example 37. 5 parts of compound 37 and 20 parts of Sorpol 2020 are mixed with 75 parts of xylene to obtain an emulsifiable concentrate. EXAMPLE 38 0.5 parts of compound 27 is dissolved in kerosene, the volume is adjusted to 100 parts, and an oil preparation is obtained. Example 39. 25 parts of compound 36 and 5 hours are mixed. Sorpol SM-200. Then 70 parts of talc NWR mesh are added.). The mixture is ground in a mortar and a wettable powder is obtained. Example 40 0.5 parts of compounds 6, 7, 12, 16, 19, 26 and 34 are mixed with 2 parts of piperonyl butoxide and each of the mixtures obtained is dissolved in pure kerosene. The volume is adjusted in each case to 100 hours and oil preparations are obtained. Example 41. 25 parts of compounds 10, II, 13, 15, 17, 20, 21, 25, 28 and 30, respectively, are mixed with 15 hours. Sorpol SM-200 and 60 parts xylene. Receive emulsifiable concentrates. The resulting compositions are then checked for insecticidal activity. Example 42. In the glass chamber (70X70X70 SLG) 20 adult mosquitoes will interfere. Smoke bombs weighing 1 g each, obtained in examples 10, 21, and 29, are lit at both ends and melted in the center of the chamber. The number of paralyzed mosquitoes is then counted and the KTso (half the time required to achieve this effect) is determined. The results are shown below. Insecticidal composition KTso, m. Smoke boll, obtained in Example 1012 2113.5 2915 0.5% alleletrin boll 11.5 Example 43. 20 adult coma will interfere with a glass chamber (70x70x70 cm}). 0.7 ml oily preparations of examples 26, 28 and 36 are evenly injected into the cavity under pressure.

KTso, sec

insecticidal composition

The oil preparation obtained in example

280 260

26 28 36 220 300

0,2% - on alletrinova

145 oil per composition Example 45. Water to the desired concentration is added to the emulsifiable concentrates or wettable powders obtained in Examples 4, 6, 12, 22, 25, 30, 31, 34 and 37 separately. 200 ml of each of these formulations are placed in a 300 ml glass beaker. 30 mosquito larvae are placed in a glass. After one day, the number of survivors and dead were noted and the LCso (500/0 flying concentration) was calculated. The results are shown below. Insecticidal composition LCso (ppm) Emulsifiable concentrate obtained in example Wettable powder obtained in example 31 Emulsifiable concentrate obtained in example 34 37 Emulsified composition of Sumition Alletrin

A) Concentration of active principle.

Example 46. An oil composition obtained in examples 7, 13, 14 and 23 in an amount of 50 ml / m is sprayed onto the surface of a sheet of plywood and dried. Cylindrical glass rings with a diameter of 10 cm, coated on the inside with oil, are placed on each sheet. After that, 10 adult cockroaches-Russacks are placed in these glass cylinders. After continuous kon297153

12

Example 44. The insecticidal activity of the compounds obtained in examples 9, 15 and 17 in the form of aerosols is tested according to the method described in the Manual for Soaps and Chemicals, 1965. Adult flies are used as a test object. The results are shown in table 2,

table 2

Example 48. In Wagner's pots, 1/50,000 sow rice. 45 days after emergence of the seedlings, they are sprayed with the emulsions obtained in examples 4, 6, 12, 25 and 34, previously diluted to the desired concentration, at the rate of 10 ml per pot. Then the plants are covered with a net, under which I planted, 30 adult rice cyclings are grown. After 24 4Q.C, the number of surviving and dead insects is counted. within 24 hours, the number of paralyzed insects, including the dead, is counted. The results are shown below. Insecticidal com pact Amount of paralyzed insects, including dead, o / o The oil composition obtained in example 7 13 14 23 Example 47. In Wagner's pot 1/50000 sow rice. 45 days after sowing, the plants are sprayed with the dust obtained in Example 11 in an amount of 300 mg per pot using a spray bottle. The plants are then covered with a net and 30 adult paddies are placed inside the space covered by the net. After 24 hours, count the number of live and dead insects. The results are given below. Insecticidal composition Killed rice cicadas, 7o Dust, obtained in example 11,100 1.5o / on-dust Dust Malathion 100

Table 3

Table 4

Test object - adults

Housefly specimens.

Example 50. Oil preparations of compounds 4, 5, 7, and 9 and their corresponding monocarboxylic chrysanthemic acid esters, i.e., chrysanthemic acid 2,3,6-trichlorobenzyl ester of chrysanthemic acid, 5-benzyl-3-furylmethyl ester, are prepared. 4-allylbenzyl ester of chrysanthemum acid and 2,6-dimethyl-4-allylbenzyl ester of chrysanthemic acid. The resulting oil formulations are tested on houseflies using the Campbell instrument. The percentage of dead flies is counted with three test concentrations of each individual compound. Based on the results obtained, the insecticidal effect of each compound on house flies - LCgo (50% of the flying concentration) is calculated.

Example 49. The compounds of the above formula are dissolved separately in purified kerosene. Oil preparations of a certain concentration are obtained. 5 ml of each preparation is sprayed for 10 seconds using a Campbell instrument.

After 20 seconds, the shutter was opened and adult indoor flies (a group of about 100 flies) were pollinated for 10 minutes and then transferred to an observation chamber. The number of paralyzed flies is noted, the number of surviving and dead flies and the percentage of shot down and dead are counted in a day.

The results are shown in Table. four.

Continued and None

The results are shown in Table. five.

Table 5 Example 51. Compound 5 and the corresponding monocarboxylic chrysanthemic ester, i.e., 5-benzyl-3-furyl methyl chrysanthemic acid ester is dissolved separately in purified kerosene and a 0.2% oily suspension is prepared. About 20

KTso is the time during which half of the test insects are paralyzed.

Subject invention

An insecticidal composition containing the active ingredient based on nirethrin analogs, as well as a solid or liquid carrier, characterized in that a compound of the general formula is taken as a pyrethrin analog

R

.

CH-C-0-CH., - R

and about

in which RI is hydrogen, methyl or ethyl; ..

R is hydrogen, methyl, ethyl or phenyl;

R "is methyl, ethyl or methoxyphenyl;

R is methyl or ethyl;

R3 is phenyl, furyl or benzofuryl, and phenyl and furyl may have, as substituents, lower alkyl, halogen, alkenyl, alkylene, benzyl, alkyl, substituted benzyl group, tenyl or furfuryl, which may be replaced by lower alkyl. Adult house flies are placed in a glass jar (70 x 70 x 70 hedgehog) and 0.7 ml of each composition is injected uniformly under pressure. Then count the number of paralyzed flies. The results are shown in Table. 6. Table 6