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Novel pyrethroid compounds derived from tefluthrin

A technology for pyrethroids and compounds, applied in the field of pyrethroids, can solve the problems of high toxicity and insecticidal efficacy, restricted use, long residual effect and the like

Inactive Publication Date: 2010-02-03
杨泽华
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, tefluthrin is the first pyrethroid insecticide used in soil, which can maintain a long residual effect on soil pests without causing long-term residual danger, but the disadvantage is relatively high toxicity and insecticidal effect Still relatively not high enough, limiting its use in household sanitation insecticides

Method used

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  • Novel pyrethroid compounds derived from tefluthrin
  • Novel pyrethroid compounds derived from tefluthrin
  • Novel pyrethroid compounds derived from tefluthrin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 compound (1)

[0026] 23.2 g of 3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added to the dropping funnel, and 110 g of toluene, Pyridine 9.5g, 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl alcohol 22.9g, stir to dissolve completely, drop 3-(3,3,3- Trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid chloride, add dropwise for 1 hr, end the heat preservation and continue stirring for 0.5-1 hr. Add 5% hydrochloric acid solution for pickling, separate the water phase, and wash the oil layer with 5% NaHCO 3 The solution was washed with alkali, and then the oil layer was washed twice with deionized water. The washed oil layer removes toluene to obtain compound (1): 3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid-2,3,5,6 -Tetrafluoro-4-methoxymethylbenzyl ester, the weight is 41.5g, the content is 95.2%, and the yield is 95.4%.

Embodiment 2

[0027] The synthesis of embodiment 2 compound (2)

[0028] 23.2 g of 3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added to the dropping funnel, and 110 g of toluene, Pyridine 9.5g, 2,3,5,6-tetrafluoro-4-methoxybenzyl alcohol 21.4g, stir to dissolve completely, drop 3-(3,3,3-tris Fluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic acid chloride, add dropwise for 1 hr, end the heat preservation and continue stirring for 0.5-1 hr. Add 5% hydrochloric acid solution for pickling, separate the water phase, and wash the oil layer with 5% NaHCO 3 The solution was washed with alkali, and then the oil layer was washed twice with deionized water. The washed oil layer removes toluene to obtain compound (1): 3-(3,3,3-trifluoro-1-propenyl)-2,-dimethylcyclopropanecarboxylic acid-2,3,5,6- Tetrafluoro-4-methoxybenzyl ester has a weight of 39.9 g, a content of 95.5%, and a yield of 95.2%.

Embodiment 3

[0029] The synthesis of embodiment 3 compound (3)

[0030] 23.2 g of 3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride was added to the dropping funnel, and 110 g of toluene, Pyridine 9.5g, 2,3,5,6-tetrafluoro-4-methylbenzyl alcohol 19.8g, stir to dissolve completely, drop 3-(3,3,3-trifluoro - 1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride, add dropwise for 1 hr, end the heat preservation and continue stirring for 0.5-1 hr. Add 5% hydrochloric acid solution for pickling, separate the water phase, and wash the oil layer with 5% NaHCO 3 The solution was washed with alkali, and then the oil layer was washed twice with deionized water. The washed oil layer removes toluene to obtain compound (1): 3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid-2,3,5,6 -Tetrafluoro-4-methylbenzyl ester, the weight is 38.2g, the content is 96.1%, and the yield is 95.6%.

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Abstract

The invention relates to novel pyrethroid compounds shown in a general formula (I), which have good insect expelling, killing and preventing activity, and can be used surely. In the formula, when X is-H group, R can be -H, -CH3, -OCH3 and -CH2OCH3 group; and when the X is -Cl group, the R can be -H, -OCH3, -CH2OCH3 group.

Description

technical field [0001] The present invention relates to some new pyrethroid compounds and their preparation methods. Background technique [0002] Pyrethroids are a class of artificially synthesized insecticides that mimic the structure of natural pyrethrins. With their high efficiency, low toxicity, easy degradation, and good environmental compatibility, they basically occupy the household hygiene insecticide market and some pesticide markets. Among them, tefluthrin is the first pyrethroid insecticide used in soil, which can maintain a long residual effect on soil pests without causing long-term residual danger, but the disadvantage is relatively high toxicity and insecticidal effect Still relatively not high enough, limiting its use in household sanitation insecticides. [0003] The applicant synthesized some new compounds by comparing the configuration, efficacy, vapor pressure, etc. of tefluthrin with some new pyrethroid compounds recently developed. The preliminary eff...

Claims

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Application Information

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IPC IPC(8): C07C69/747C07C69/757A01P7/00
Inventor 杨泽华陈虎彪徐永晨
Owner 杨泽华
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