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Pyrethroid compound and application thereof

A technology for pyrethroids and compounds, applied in the field of pyrethroid compounds, which can solve the problems of increasing environmental burden, increasing the amount of pyrethroid raw materials, and increasing production costs

Active Publication Date: 2013-06-05
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 compound and application thereof
  • Pyrethroid compound and application thereof
  • Pyrethroid compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0064] Preparation Example 1: 2,3,5,6-tetrafluoro-α-cyanobenzyl-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate compound Synthesis of 1

[0065] In a 200ml four-necked bottle, put 8.9g (0.05mol) of 2,3,5,6-tetrafluorobenzaldehyde, 5g of pyridine, dissolve in 80ml of cyclohexane, dropwise add 2.45g (0.05mol) of NaCN Saturated aqueous solution of 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid chloride 11.2g ( 0.06mol), the dropwise temperature rises 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 separated oil layer was heated to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain compound 2,3,5,6- Tetrafluoro-α-cyanobenzyl-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate, content 94.8%, yield 91.1% (calculated as aldehyde) . The molecular formula of the compound: C 18 h 15 f 4 NO 2 , molecular...

preparation Embodiment 2

[0066] Preparation Example 2: 2,3,5,6-Tetrafluoro-α-cyanobenzyl-2,2-dimethyl-3-(2,2-difluoro-1-vinyl)cyclopropanecarboxylic acid Synthesis of ester compound 2

[0067] In a 200ml four-necked bottle, put 8.9g (0.05mol) of 2,3,5,6-tetrafluorobenzaldehyde, 5g of pyridine, dissolve in 80ml of cyclohexane, dropwise add 2.45g (0.05mol) of NaCN 2,2-dimethyl-3-(2,2-difluoro-1-vinyl)cyclopropanecarboxylic acid chloride 11.67 g (0.06mol), dropwise and rise 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 separated oil layer was heated to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain compound 2,3,5,6- Tetrafluoro-α-cyanobenzyl-2,2-dimethyl-3-(2,2-difluoro-1-vinyl) cyclopropane carboxylate, content 95.4%, yield 92.5% (with aldehyde count). The molecular formula of the compound: C 16 h 9 f 6 NO 2 , molecular weight: 361.3, nuclear magnetic...

preparation Embodiment 3

[0069] Preparation Example 3: 2,3,5,6-Tetrafluoro-α-cyanobenzyl-2,2-dimethyl-3-(2,2-dichloro-1-vinyl)cyclopropanecarboxylic acid Synthesis of ester compound 3

[0070] In a 200ml four-necked bottle, put 8.9g (0.05mol) of 2,3,5,6-tetrafluorobenzaldehyde, 5g of pyridine, dissolve in 80ml of cyclohexane, dropwise add 2.45g (0.05mol) of NaCN 2,2-dimethyl-3-(2,2-dichloro-1-vinyl)cyclopropanecarboxylic acid chloride 13.65 g (0.06mol), dropwise and rise to 30°C for 4 hours. 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 compound 2,3,5,6-tetra Fluoro-α-cyanobenzyl-2,2-dimethyl-3-(2,2-dichloro-1-vinyl)cyclopropane carboxylate, content 95.1%, yield 91.7% (calculated as aldehyde ). The molecular formula of the compound: C 16 h 9 Cl 2 f 4 NO 2 , molecular weight: 394.1, nucl...

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Abstract

The invention relates to pyrethroid compound, the preparation method thereof and the application thereof to the prevention and treatment of sanitary insects such as mosquitoes, flies, or cockroaches. The pyrethroid compound has the general formula of (A), wherein R is H atom, methyl or methoxymethyl (-CH2OCH3), X1 and X2 are same methyls, F atoms, Cl atoms or Br atoms, or X1 is trifluoromethyl-CF3 and X2 is F atom, Cl atom, Br atom or H atom. Experiments show that the pyrethroid compound which has the general formula of (A) has the good effect of preventing and treating the sanitary insects such as the mosquitoes, the flies, or the German cockroaches.

Description

technical field [0001] The invention relates to a pyrethroid compound, a preparation method and its application in preventing and controlling mosquitoes, flies, cockroaches and other hygienic pests. Background technique [0002] 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 mosquito coils or aerosols has greatly increased. This not only increases the production cost, but also increases the burden on the environment. [0003] The inventors have formed a series of novel fluorine-co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/39C07C253/30A01N53/06A01P7/00
Inventor 戚明珠姜友法王东朝吕杨周景梅杨建文孙鹏
Owner JIANGSU YANGNONG CHEM