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Pyrethroid compounds, preparation and use thereof

A compound and mixture technology, applied in the field of sanitary pest control, can solve the problems of increasing production cost, increasing environmental burden, increasing the amount of pyrethroid raw materials, etc., and achieves the effect of quickly killing pests

Active Publication Date: 2009-07-29
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But along with the growth of use time, mosquitoes and flies have produced certain resistance (Gao Xiwu etc., Chinese Journal of Vector Biology and Control, 2004, 15 (2), 105), in order to achieve the same control effect as before, the amount of pyrethroids added to products such as mosquito coils or aerosols has greatly increased
This not only increases the production cost, but also increases the burden on the environment.

Method used

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  • Pyrethroid compounds, preparation and use thereof
  • Pyrethroid compounds, preparation and use thereof
  • Pyrethroid compounds, preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0047] Preparation Example 1: Compound (1) α-cyano-3-phenoxy-4-fluoro-benzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxy Synthesis of esters

[0048] In a 200ml four-necked bottle, put 10.8g (0.05mol) of 4-fluoro-3-phenoxybenzaldehyde, 5g of pyridine, dissolve in 80ml of cyclohexane, dropwise add 2.45g (0.05mol) of NaCN Saturated aqueous solution, stirring for 10 minutes after throwing in, slowly adding 2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylic acid chloride 13.6g (0.06mol ), the dropwise temperature rises to 30°C for 4 hours of reaction. The organic phase was successively washed once with 50ml 5% sodium hydroxide solution, 5% hydrochloric acid and saturated brine, and the oil layer was separated and heated to 100°C under a negative pressure of 10mmHg to remove the solvent to obtain the compound α-cyano-3-phenoxy Dimethyl-4-fluoro-benzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylate 20.2, content 94.3%, yield 88.1% (calcula...

preparation Embodiment 2

[0049] Preparation Example 2: Synthesis of Compound (2) α-cyano-3-phenoxybenzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylate

[0050] In a 200ml four-necked bottle, drop 9.9g (0.05mol) of 3-phenoxybenzaldehyde, 5g of pyridine, be dissolved in 80ml cyclohexane, add dropwise the saturated aqueous solution containing 2.45g (0.05mol) NaCN, and then Add 0.5g of tetrabutylammonium bromide, stir for 10min after throwing in, slowly add 2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylate dropwise within 2 hours at 10-20°C 13.6 g (0.06 mol) of acid chloride was added dropwise to 30°C for 4 hours. The organic phase was successively washed once with 50ml 5% sodium hydroxide solution, 5% hydrochloric acid and saturated brine, and the oil layer was separated and heated to 100°C under a negative pressure of 10mmHg to remove the solvent to obtain the compound α-cyano-3-phenoxy 19.85% benzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylate, content 9...

preparation Embodiment 3

[0051] Preparation Example 3: Synthesis of Compound (3) 3-phenoxy-4-fluoro-benzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylate

[0052] In a 200ml four-necked bottle, put 10.9g (0.05mol) of 4-fluoro-3-phenoxybenzyl alcohol, 5g of pyridine, dissolve in 80ml of toluene, stir after throwing in, and slow down within 2 hours at 10-20°C. 13.6 g (0.06 mol) of 2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropanecarboxylic acid chloride was slowly added dropwise, and the temperature was raised to 30° C. for 4 hours after the dropwise reaction. The organic phase was successively washed once with 50ml of 5% sodium hydroxide solution, 5% hydrochloric acid and saturated brine, and the separated oil layer was heated to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain the compound 3-phenoxy-4- Fluoro-benzyl-2,2-dimethyl-3-(2-trifluoromethylvinyl)cyclopropane carboxylate 18.82, content 96.9%, yield 89.9% (calculated as aldehyde). The molecula...

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Abstract

The invention relates to pyrethroid compounds with general formula of (A), or stereochemical isomers thereof, or a mixture of the stereochemical isomers and a preparation method of the compounds and the application thereof in hygiene insecticidal products. In the formula (A), R refers to F atom or H atom, and Z is cyano (-CN) or H atom. Experiments show that the compounds have good effects on preventing sanitary insect pests of mosquitoes, flies, German cockroaches, etc.

Description

technical field [0001] The present invention relates to pyrethroid compounds, in particular to a compound conforming to the following formula (A), or its stereochemical isomers, or a mixture of these stereoisomers, its preparation method and its application in the field of sanitation pest control. [0002] [0003] (In the formula: R is an F atom or an H atom, and Z is a cyano group (-CN) or an H atom.) Background technique [0004] It is widely known that pyrethroids can be used to control mosquitoes and have high insecticidal activity. Because of its high efficiency, low toxicity, low residue and good environmental compatibility, it has been widely used in the field of sanitary pest control. But along with the growth of use time, mosquitoes and flies have produced certain resistance (Gao Xiwu etc., Chinese Journal of Vector Biology and Control, 2004, 15 (2), 105), in order to achieve the same control effect as before, the amount of pyrethroid added to products such as...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/39C07C69/747C07C253/00C07C67/14A01N53/08A01P7/04A01P7/00
Inventor 戚明珠周景梅姜友法朱萍王东朝杨建文孙鹏
Owner JIANGSU YANGNONG CHEM
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