SU675835A1 - 2-chloroalken-1-yl-thiophosphates possessing insecticidic activity - Google Patents

Description

Table 1

5 ml of benzene are boiled under reflux for 10 hours. The solvent is evaporated and the product is distilled under vacuum.

Example 2. Obtaining diethyl- (1-chloromethyl-2-vinyl chloride) thiophosphate.

A mixture of 0.06 g-mol diethyl- (1-chloromethyl-2-chlorovinyl) phosphite and 0.06 g-mol ser:

Table 2

in 15 ml of benzene is refluxed for 6 hours. The benzene is evaporated and the product is distilled.

Example 3. Obtaining ethyl- (2-chlorocyclohexen-1-yl) dimethylamidothiophosphate.

To a solution of 0.02 g-mol of ethyl- (2-chlorocyclohexen-1-yl) dimethylamidophosphite in 5 ml of benzene, 0.02 g-mol of sulfur was carefully added while the reaction mixture was cooled with water. The mixture is then refluxed for 3 hours. The benzene is evaporated and the product is distilled. Example 4. Preparation of ethyl- {2-chlorocyclohexen-1-yl) diethylamidothiophosphate. Through a mixture of 0.075 g-mol of ethyl- (2-chlorocyclohexen-1-yl) chlorophosphite and 0.08 g-mol of pyridine in 50 ml of benzene, 0.08 g-mol of hydrogen sulfide is passed at a temperature. Stir for 2 hours and filter. 0.09 g-mol of carbon tetrachloride is added to the filtrate and 0.16 g-mol of diethylamine is added dropwise with stirring and weak cooling. After two days, the reaction mixture is filtered. The filtrate is evaporated, the product is distilled in vacuo. Example 5. Preparation of 2-chlorocyclohexen-1-yl-bis-dimethylamidothiophosphate. To 0.03 gmol of 2-chlorocyclohexen-1-ylbis-dimethylamide phosphate, 0.03 gmol of sulfur was carefully added while the reaction mixture was cooled with ice water. After 2 hours, distil. Insecticidal activity of new compounds is studied in laboratory and field conditions. 6 laboratory experiments serve as biological test objects: rice weevil-Calandra oryzae Z., house flies (imago and larvae) - Musca domestica L. and cereal tl - Schisaphis graminum Rond. In the field onbitax, the effects of Compound 3 on cereal aphids are studied. Laboratory experiments. Example 6. Object - rice weevil. The insecticidal activity of compounds is studied by treating Petri dishes with acetone solutions of new substances at a fluid flow rate of 0.5 ml / dm. After evaporation of the solvent, 25 weevils are placed in the cups, and the food for them in the form of five wheat grains is placed for them. The cups are closed with gauze and kept in a thermostat at an air temperature of 21-22 ° C and a relative humidity of 70-80%. The repetition of the experience is threefold. Standard - chlorophos. The activity of the compounds is determined a day after setting the experiment, the data of which are presented below. SCBO,%: Compounds Chlorophos (standard) 0.27 The data obtained indicate a high activity of the proposed compounds in relation to the rice weevil, which in action approximates or exceeds the standard by more than 2 to 3 times. Example 7. Object - indoor flies (imago). The insecticidal effect of the new compounds is studied on houseflies aged 5 days according to the procedure described for testing substances in the rice weevil. Chlorophos serves as the standard in experiments, and the variant without insecticides is used as a control. The results of the experiments are presented below. Compounds of CKso,%: 1.0.09 20.11 30.10 Chlorophos. (standard) 0.11 From the obtained data, it is clear that the new compounds have a high activity with respect to indoor flies and in effect are not inferior or somewhat superior to the reference preparation, chlorophos. Example 8. Object - indoor flies (larvae). Insecticidal activity of the compounds is studied by the above method on the larvae of 3-4 days old laboratory culture of indoor flies. The effect of the compounds is determined 48 hours after the test, the results of which are presented below. Compounds CKso,% 10.25 50.40 Chlorophos (reference) 0.31. From the obtained data it is clear that the new compounds are highly active in relation to the larvae of house flies and in action approach or exceed the standard of chlorophos. Example 9. Object - cereal tl. To study the insecticidal activity of vepdids, female aphids, whose culture develops year-round in greenhouse conditions on young wheat plants, are used in experiments. The experiments were carried out according to the method described for the study of the insecticidal state of rice weevil. The results of the experiments are presented below. Compounds of CKso,%: 10,009 20,036 30,007 40,007 50,009. Chlorophos (standard) 0.030 As can be seen from the obtained data, all the proposed compounds do not yield or exceed the standard (chlorophos) by 3-4 times. Field experiments Studying the effectiveness of the compound, ethyl- (2-chlorocyclohexene-1-yl) dimethylamidothiophosphate, in the control of cereal aphids on winter wheat crops.

Crops are treated with manual hydraulic control with a flow rate of working fluid of 400 l / ha.

The effectiveness of insecticides is determined by reducing the population of plants by aphids per

The obtained data testifies to the high efficiency of compound 3 in the fight against cereal aphids, which, by its insecticidal effect, approaches the BI-58 standard.

The proposed compounds have low toxicity to warm-blooded animals. When administered intramuscularly to white mice, it is 1000 mg / kg of live weight.

Thus, the proposed compounds, along with high insecticidal activity, have low toxicity to warm-blooded animals.

Claims (3)

1.Melnikov NI. Chemistry and pesticide technology. M., “Himi, 1975, p.598. 2. In the same place 542. 3.F. W. Lichtenthaler, Chem. Rev. “The Chemistry and Properties of Enol phosplates, (1961), 61.607.