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Pyrethroid compound

A technology for pyrethroids and compounds, which is applied in the field of pyrethroid compounds, and can solve problems such as the difficulty of costing new pyrethroid compounds

Inactive Publication Date: 2018-07-06
JIANGSU YANGNONG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, it is becoming more and more difficult to obtain new pyrethroid compounds that can surpass the old varieties in terms of efficacy, toxicity, cost, etc.

Method used

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Examples

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Embodiment 1

[0043] Example 1: Compound A1 of the present invention: 2,3,5,6-tetrafluorobenzyl-2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxy Synthesis of esters

[0044] In a 200ml four-neck bottle, put 10.0g (0.05mol) of 2,3,5,6-tetrafluorobenzyl alcohol, 5.0g of pyridine, dissolve in 60ml of toluene, stir after throwing in, add dropwise at 0~5℃ 9.73 g (0.05 mol) of 2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylic acid chloride was added dropwise to 20°C for 4 hours. Wash with 400ml of 5% hydrochloric acid, and then with 400ml of 5% NaHCO3, separate the oil layer and heat it to 85°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluorobenzyl-2,2 -Dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylate, column chromatography treatment, weight 15.1g light brown oily liquid, content is 97.7%, yield 86%. The molecular formula of the compound: C 15 h 12 f 6 o 2Molecular weight: 338.24 Optical...

Embodiment 2

[0045] Example 2: Compound A2 of the present invention 2,3,5,6-tetrafluoro-4-methylbenzyl-2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl ) Synthesis of cyclopropane carboxylate

[0046] In a 200ml four-necked bottle, put 10.7g (0.05mol) of 2,3,5,6-tetrafluoro-p-methylbenzyl alcohol, 5.0g of pyridine, dissolve in 60ml of toluene, and stir after the addition, at 0 to 5°C 9.73 g (0.05 mol) of 2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylic acid chloride was added dropwise, and the temperature was raised to 18° C. to react for 4 hours. Wash with 400ml of 5% hydrochloric acid, then wash with 400ml of 5% NaHCO3, separate the oil layer and heat it to 85°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methylbenzyl Base-2,2-dimethyl-1R-trans-3-(2,2-difluorovinyl)cyclopropanecarboxylate, treated by column chromatography, the yield was 15.3g light brown oily liquid, and the content was 97.9%, yield 85%. Mol...

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Abstract

The invention discloses a pyrethroid compound. The structural formula of the compound is represented by formula A; the chrysanthemic acid part of the compound is a 1R, trans single optical isomer, wherein R is a H atom or a methyl group. The compound in the invention has a better insecticidal effect on certain target pests than compounds in the prior art.

Description

technical field [0001] The invention relates to a pyrethroid compound, in particular to a class of pyrethroid compounds with a specific three-dimensional configuration, a preparation method thereof and an application in pest control. Background technique [0002] Pyrethroid compounds are a class of biomimetic synthetic insecticides that can be used for a variety of pests and have high insecticidal activity. Pyrethroid compounds have the characteristics of high efficiency, low toxicity, low residue and good environmental compatibility, and have been widely used in the field of pest control. [0003] The prior art discloses a variety of pyrethroid compounds, such as pyrethrin, fenvalerate, etc. Although these compounds have good insecticidal activity, with long-term continuous single use, pests have developed resistance to pesticides. Therefore, new compounds need to be developed. [0004] On the other hand, as people's requirements for environmental protection are getting h...

Claims

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Application Information

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IPC IPC(8): C07C69/747C07C67/14A01N53/06A01P7/02A01P7/04
CPCC07C69/747A01N53/00C07C67/14
Inventor 周其奎沈阳黄成美吕杨贾炜
Owner JIANGSU YANGNONG CHEM
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