SU289539A1 - INSECTICIDE COMPOSITION - Google Patents

Description

This invention relates to insect control agents. An insecticidal composition is proposed, containing as an active ingredient synthetic pyrethrin analogs of the general formula CH-C-O-CHj-NR II 6 in which R is hydrogen or methyl; R - is hydrogen, methyl, ethyl, phenyl or ethoxyphenyl; R is methyl or ethyl; R is methyl or ethyl; R is a group necessary to form a nitrogen-containing heterocycle. The compounds of this formula are prepared in a known manner. In tab. 1 is a list of compounds corresponding to the formula. Example 1: 0.4 parts of compound 1 was dissolved in 5 parts of xylene. The volume of the solution was adjusted to 100 hours by the addition of purified kerosene. An oil formulation was obtained. 5 10 15 20 25 100 hours with the addition of purified kerosene. An oil formulation was obtained. Example 3. In 3h. xylene was dissolved in 0.2 h. Compounds 3 and 1 part piperonylbutoxide. Purified kerosene was added to the solution to a volume of 100 h. An oil composition was obtained. Example 4. 25 parts of compound 5 were mixed with 5 parts of sorpol SM-200 (a surfactant sold by the Japanese company, Togo Chemical Co., and a mixture of polyoxyethylene alkylphenyl ether and calcium alkylaryl sulfonate). The resulting mixture was thoroughly triturated with 70 parts of talcum (300 mash) in a mortar to obtain a wettable powder. Example 5 A solution of 0.2 parts of compound 6 was prepared in 5 parts of xylene. The volume of the solution was brought to 100 hours by the addition of purified kerosene, an oil composition was obtained. Example 6 A solution of 0.2 parts of compound 7 was prepared in 5 parts of xylene. By adding purified kerosene, the solution volume was adjusted to 100 h. An oil composition was obtained.

Table 1

Continuation

By adding purified kerosene, the solution volume was adjusted to 100 h. An oil composition was obtained.

Example 8. 0.2 parts of compound 9 and 1 part of sulfoxide were dissolved in 5 parts of xylene. The solution volume was adjusted to 100 hours by the addition of purified kerosene. An oil formulation was obtained.

Example 9 10 parts of compound 10, 10 parts of sorpol SM-200 and 80 parts of xylene were displaced and dissolved when transferred. An emulsifiable concentrate was obtained.

Example 10. 0.5 parts of compound 11, 2 parts of methoxychlor, 5 parts of xylene and 7.5 parts of purified kerosene were mixed, dissolved and poured into an aerosol bottle, where they were then poured

85 parts of propellant (for example, freon, vinyl chloride monomer or liquefied petroleum gas) under pressure. Received aerosol.

Example 11. 0.2 parts of compound 12 were dissolved in pure kerosene, the volume of the solution was adjusted to 100 hours.

Example 12. 1.5 g of compound 12 were dissolved in 20 ml of acetone and the solution was shifted from 98.5 g of talc. After distilling off the acetone, a dust was obtained.

Example 13. 10 parts of compound 12. 10 parts of sorpol 2020 (a topical active substance manufactured by the Japanese company Togo Chemical Co. and a mixture of alkylphenyloxy ester of polyoxyaltienium calcium alkylarylsulfonate) and 80 parts of xylene were mixed and dissolved with stirring. Received emulsified, ICE concentrate.

Example 14. 0.4 parts of compound 12, 0.5 parts of sumition, 5 parts of xylene and 9.1 parts of pure kerosene were mixed. A solution was obtained, which was poured into an aerosol bottle, to which 85 parts of propellant (for example, freon, vinyl chloride or liquefied petroleum gas) were then supplied under pressure. Received aerosol.

Example 15 0.2 parts of compound 12 and 1 part of piperonyl butoxide were dissolved in pure kerosene. The volume of the solution was adjusted to 100 parts, and an oil composition was obtained.

Example 16 0.2 parts of compound 12 and 0.5 parts of CHD were dissolved in 5 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. An oil formulation was obtained.

Example 17. 0.5 part of compound 12 and 1 part of sevine were mixed with 98.5 parts of talc. Received dust.

Example 18. 0.2 parts of compound 12, 0.2 parts of allethrin, 2 parts of piperonylbutoxide, 5 parts of xylene and 7.6 parts of pure kerosene were mixed until a solution was formed, which was poured into an aerosol vial. 85 hours of propellant (for example, freon, vinyl chloride or liquefied petroleum gas) were fed into it under pressure. Received aerosol.

Example 19. 0.4 parts of compound 12, 2 parts of piperonylbutoxide and 1L6 parts of pure kerosene were mixed with 1 part of atmosphere-300 (the registered name of the emulsifier manufactured by Atlas Chemical Co.). 50 parts of water were added to the mixture, then it was poured into an aerosol bottle together with 35 parts of a mixture (3: 1) of deodorized butane and propane. Received aerosol.

Example 20: 0.4 parts of compound 13 and 2 parts of niperonyl butoxide was dissolved in 7 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. Pppl / chali oil composition.

Example 21 0.2 parts of compound 17 were dissolved in 5 parts of xylene. The addition of pure kerosene brought the volume of the solution to 100 hours. An oil composition was obtained.

Example 22 0.5 g of compound 17 was dissolved in 20 ml of methanol. The resulting solution was evenly mixed with 99.5 g of the smoke stack substrate (a mixture of Tabu powder, pyrethrum and wood powder in a ratio of 5: 3: 1). The methanol was evaporated, the mixture was thoroughly mixed with 150 ml of water. Fumigant sticks were formed from the resulting mixture.

Example 23. 0.4 parts of compound 17, 2 parts of piperonylbutoxide, 2 parts of methoxychlor, 5 parts of xylene and 5.6 parts of pure kerosene were mixed and poured into an aerosol bottle, to which 85 parts of propellant were then injected with iodine. Received aerosol.

Example 24 0.2 parts of compound 17 and 0.5 parts of sumition were dissolved in 5 parts of xylene. The solution volume was adjusted by adding pure kerosene to 100 h. An oil composition was obtained.

Example 25 0.1 parts of compound 17 and 0.2 parts of DDUR dissolved in 3 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. An oil formulation was obtained. Example 26 A solution was prepared from 0.2 g of compound 17 in a cooTBTCTvvromeM amount of chloroform. The surface of the asbestos sheet, 2.5X1.5 cm in size, 0.3 cm thick, was uniformly impregnated with a solution. An asbestos sheet of the same size was laid on the sheet thus treated and a fibrous fumigant insecticidal composition was prepared, which was heated on an electric plate. As a fibrous substrate, it is possible, apart from asbestos, to use wood pulp and other materials similar to asbestos.

Example 27. A solution of 0.25 g of compound 17 and 0.25 g of allerin in 20 ml was prepared.

methanol and evenly mixed with 99.5 g of the substrate smoke bombs (a mixture of Taboo powder, crushed rice bran and wood powder in a ratio of 5: 3: 1). After evaporation of the methanol, the residue was thoroughly mixed with 150 ml of water and the smoke bombs were molded.

Example 28. 0.5 g of compound 18 was dissolved in 20 ml of methanol. Raster was treated as described in example 18 with the manual and received

smoke bombs.

Example 29. A solution of 0.9 parts of compound 19 and 0.5 parts of natural pyrethrin extract (20% of the active principle) were prepared in 5 parts of xylene. The solution volume was adjusted to

100 hours of pure kerosene added. An oil formulation was obtained.

Example 30 1.5 parts of compound 21 and 5 parts of piperoptoyl butoxide were dissolved in 30 ml of acetone. The solution was mixed with 93.5 parts of talc. Then

acetone was evaporated. Received dust.

Example 31 A solution of 0.7 g of compound 22 in 20 ml of methanol was prepared and worked up as described in example 18. Received a smoke bomb.

EXAMPLE 32 0.2 parts of compound 23 and 1 part of piperonyl butoxide was dissolved in 5 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. An oil formulation was obtained.

Example 33 0.5 parts of P1 27 and 2.5 parts of piperonyl butoxide were dissolved in 7 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. An oil formulation was obtained.

EXAMPLE 34 A solution of 0.2 parts of compound 28 and 0.1 parts of 3,4,5,6-tetrahydrophthalimide methyl ester of hrnanthemic acid (phthaltrine) in 5 parts of xylene was prepared. The volume of the solution was adjusted to 100 hours with the addition of kerosene. An oil formulation was obtained.

Example 35. A solution of 1 g of compound 30 in 20 ml of methanol was prepared and treated in the manner described in example 18. A smoke bomb was obtained. Example 36. 0.4 parts of compound 37 were dissolved in pure kerosene. The volume of the solution was adjusted to 100 hours. An oil composition was obtained. Example 37. 15 parts of compound 37, 20 parts of sorpol 2020 were mixed with 65 parts of xylene, dissolved with stirring to give an emulsifiable concentrate. Example 38 0.3 parts of compound 39 and 1.5 parts of piperonylbutoxide were dissolved in 7 parts of xylene. The solution was mixed with kerosene up to a volume of 100 hours and an oil composition was obtained. Example 39. 10 parts of compound 40, 10 hours of sor-15 SM-200 floor and 80 parts of xylene were stirred until dissolved and an emulsified, icy concentrate was obtained. Example 40 0.2 parts of compound 48 and 0.5 parts of sumition were dissolved in 5 parts of xylene. The addition of pure kerosene brought the volume of the solution to 100 hours. An oil composition was obtained. Example 41 0.5 parts of compound 51 and 2.5 parts of piperonylbutoxide were dissolved in pure quinoa. The solution volume was adjusted to 100 parts and an oil composition was obtained. Example 42. 5 parts of compound 52, 25 parts of piperonylbutoxide, 20 parts of sorpol 2020 and 50 parts of xylene were stirred until dissolved. An emulsifiable concentrate is obtained. Example 43 0.5 parts of compound 55 were dissolved in 5 parts of xylene. The addition of pure kerosene brought the volume of the solution to 100 hours. An oil composition was obtained.35 Example 44. A solution of 3 parts of compound 58 was prepared in 30 ml of acetone. The solution was mixed with 97 parts of talc. The mixture was thoroughly ground in a mechanical grater, then the acetone was evaporated and a dust mixture was obtained. 40 Example 45. 0.4 parts of compound 59 and 0.5 parts of sumation were dissolved in 5 parts of xylene. The solution volume was adjusted to 100 hours with the addition of pure kerosene. An oil formulation was obtained. Example 46. 0.5 parts of compound 69 was dissolved in 45 parts of xylene, diluted with pure kerosene to a volume of 100 parts, and an oil composition was obtained. Example 47. 0.5 parts of Compound 70 and 0.5 parts of Sumition were dissolved in 5 parts of xylene, the volume was adjusted to 50 hours with pure kerosene and an oily composition was obtained. Example 48. 5h. Compounds 71, 5 parts of ANS, 10 parts of sorpol 2020 and 80 parts of xylene were mixed and an emulsifiable coicentrate was obtained. 55 Below are examples of tests for the insecticidal activity of the proposed compounds. Example 49. Twenty adult houseflies were placed in a glass jar with a capacity of 70 SL1, into which 0.7 ml of each oil composition prepared in examples 7, 11, 21, 29 and 34 was injected under a pressure of 60 kg. 9 then. the number of paralyzed flies and the KTso (the time required to paralyze half of the insects) were determined. 65 The results are shown below. Insecticidal composition Oil composition according to the example of KTjo, sec 7 ... 120 11 ... 45 21 ... 68 29 ... 62 34 ... 75, 1% oil composition phthaltrna .96 Example 50. In 20 cm mosquitoes were placed in a 0 cm glass jar. 0.7 ml of each oil of the composition according to examples 1, 3, 5, 8, 32 and -17 was injected into the cavity and KTso was fixed as described above. Got the following results. Insecticidal composition KTso, sec. Oil composition according to example 1 ... 3 ... 5 ... 8 ... 32 ... 36 ... 47 ..., 2% oil composition of alleletrin. Example 51. 20 adult mosquitoes were placed in a 0 cm glass jar. Single-frame smoke bombs, obtained from the rimers 22, 27, 28, 31 and 35, were ignited from both hens and placed in the middle of the can. Then, the number of paralyzed mosquitoes was counted. KTzo was calculated. The results are given below. Insecticidal composition Smoke checker following the example of e, min 22 ... 10 27 ... 10.5 28 ... 11.5 31 ... 13.5 35 ... 10.5, 5% fumigant allelet. . .12.5 Example 52. The insecticidal effects on aerosols of indoor houseflies according to examples 10, 14, 18, 17, and 23 were tested according to the method of testing aerosols using a Peet rady camera. The results are shown in Table. 2. Table 2 Conversion Factor: 1 foot “0.02832 g. OTA is the standard test method for the aerosol co-ordination of US chemical companies.

Example 53. Pour 200 ml of liquid obtained by diluting 5000 times with water of emulsifiable concentrates according to examples 9, 13, 39, 42 and 48 into glasses of 300 ml. 30 mosquito larvae in the last stage were placed in each glass. In all cases, a 100% mortality rate was observed on the second day.

Example 54. Oil compositions according to examples 16, 24, 25 and 40 were sprayed plywood sheets at the rate of 50 ml / m and dried. Then, glass circular tubes 10 cm in diameter, oiled inside, were put on the sheets and 10 adult Prussian cockroaches were placed in them. After 24 hours of continuous contact, the number of paralyzed insects, including those killed, was counted.

The results are shown.

Paralyzed

following the example of insects, 96

70,100,100

95

Example 55. 4500-day-old rice sprouts were planted in Wagner’s hillside planks. The plants were pollinated with dust (at the rate of 300 L1g per pot) obtained in examples 12, 17 and 44. Then the plants were covered with a net, under which 30 adult rice cicadas were placed. After that, KTso was calculated, and after 24 hours the number of surviving and dead insects was counted.

The results are shown in Table. 3

Table 3

Example 56. In the pots of Wagner 1/50000 see fig. 45 days after the occurrence of sprouting, they were sprayed (at the rate of 100 ml per pot) with the liquid obtained according to examples 13, 37 and 42. Then, the RRT on adult rice cyclings and the percentage of dead insects after 24 hours were determined. The results are shown in Table. four.

Table 4

Example 57. The compounds of the formula I were individually dissolved in pure kerosene and oil preparations of a given concentration were prepared.

5 ml of the oil preparation was sprayed for 10 seconds using a Campbell instrument. After 20 seconds, 100 adult houseflies were let in and kept nx for 10 minutes. Then they were transferred to the observation chamber. The number of knock-down insects was counted, and after day I, the number of surviving and dead insects was noted and KTso and the percentage of dead were determined.

The test results are given in table. five.

Table 5

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Example 58. Oil preparations of compounds 12, 13, 22 and 23 and the corresponding chrysanthemic esters, i.e. phthaltrin, 1, 2, 3, 6-tetrahydrophthalimide methyl ester of chrysanthemic acid, 1,2-di, were prepared.

methyl succinimidmethyl ester of chrysanthemic acid and iso-iroylidene-succinimidmethyl ester of chryazaemotemic acid. Used device Kemebel. They tested each individual separately and determined the percentage of dead house flies at three test concentrations. Based on the results obtained, the insecticidal activity of the LDso of the tested compounds was determined.

The results are presented in table. 6

Table 6

Example 59 Compounds 12, 17, and 22, as well as their corresponding chrysanthemum esters

acids, i.e., phthaltrin, chrysanthemic acid dimethylmaleimidyl ester and chrysanthemic acid 1,2dimethylsuccinimidimethyl ester were dissolved separately in deodorized kerosene and oil preparations of certain concentrations were obtained. Twenty adult mosquitoes were placed in a glass jar of 70 kg. 0.7 ml of the above preparations were injected into the chamber under a pressure of 9 kg. Determine KTso- Results are presented in Table. 7

Table 7

A retrine, as well as a solid or liquid carrier, characterized in that a compound of the general formula 13 I I CH-C-0-CHg-NT 1 / R-Y8X539 14 is taken as the iiretrin analogue in which R is hydrogen or methyl; R - is hydrogen, avenging, ethyl, phenyl or ethoxyphenyl; R3 is methyl or ethyl; R is methyl or ethyl; The RS group is required to form a 5 nitrogen-containing heterocycle.