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New pyrethroid compound and preparation method and application

A technology of pyrethroids and compounds, applied in the field of pyrethroids, can solve the problems of high lethality and fast knockdown, etc.

Active Publication Date: 2010-03-10
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Preliminary drug efficacy tests of these compounds have shown that they have good insecticidal activity, fast knockdown and high lethality

Method used

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  • New pyrethroid compound and preparation method and application
  • New pyrethroid compound and preparation method and application
  • New pyrethroid compound and preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0023] Synthesis of 1R-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid with 1:1 ratio of cis to trans

[0024] In a 250ml four-necked bottle, 15.6g (0.1mol) of methyl 1R-3-formyl-2,2-dimethylcyclopropanecarboxylate, 50ml anhydrous tetrahydrofuran, was dropped into with a cis-to-trans ratio of 1:1, Then add 0.5g potassium tert-butoxide, and add 34.5g (0.1mol) (C 6 h 5 ) 3 P + -CH 2 CF 3 - Dissolve the suspension in 80ml tetrahydrofuran, drop it within 2 hours, then raise the temperature to 20°C for 8 hours reaction. Remove tetrahydrofuran under 50mmHg negative pressure, add 100ml of toluene, wash twice with 200ml of water respectively, separate the toluene layer and add 100g of 10% sodium hydroxide solution, heat to 80°C under stirring for 2 hours, cool to room temperature, separate Remove the toluene layer. Transfer the water layer to a 250ml three-neck flask, add 100g of 30% sulfuric acid solution dropwise in an ice-water bath, keep the temperat...

preparation Embodiment 2

[0026] Preparation of 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid with a cis-trans ratio of 1:1

[0027]In a 100ml beaker, 16.4g (92.3 %), then add 1:1 weight ratio of methanol-water solution 30g, stir at 40°C for 30 minutes, filter, and the gained solid is stirred in 15g of 1:2 weight ratio of methanol-water solution for 30 minutes at 30°C, and again After filtration, the resulting solid was washed once with 5ml of water, and air-dried to obtain 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2 with a cis-to-trans ratio of 1:1. - 5.8 g of dimethylcyclopropanecarboxylic acid, content 98.7%. Combine the mother liquors filtered twice, concentrate on a thin-film evaporator at 40°C and 100mmHg negative pressure until solids are precipitated, take back the concentrated solution and cool to 5°C, some solids precipitate again, filter, and air-dry to obtain a cis-trans ratio of 1 : 4.2 g of 1R-(E)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbo...

preparation Embodiment 3

[0029] 2,3,5,6-tetrafluoro-4-methoxybenzyl-1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)- 2, the preparation of 2-dimethyl cyclopropane carboxylate (compound 1)

[0030] In a 500ml flask, the 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2 -20.8g (0.1mol) of dimethylcyclopropanecarboxylic acid, 2,3,5,21.0g (0.1mol) of 6-tetrafluoro-4-methoxybenzyl alcohol, 180ml toluene, install the water trap, and Add 0.1g of p-toluenesulfonic acid, heat to reflux, react with water for 6 hours, add 20ml of toluene in the middle, cool to room temperature after the reaction, wash once with 100g water, wash once with 100g 5% dilute hydrochloric acid, wash once with 100g 5% dilute hydrochloric acid Wash once with sodium bicarbonate solution, and finally wash once again with 100g of water, collect the toluene layer and heat it to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain 2,3,5,6-tetrafluoro-4-methoxybenzyl- 1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanec...

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Abstract

The invention provides a pyrethroid compound which is a stereoisomer of 2,3,5,6-tetrafluoro-4-methoxybenzyl-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate. The compound is characterized in that the structure of the compound is shown in formula (A), wherein the carbon-carbon double bond in the carboxylic acid part of the formula (A) is Z configuration, the absolute configuration of the 1-site of cyclopropane is R configuration; the compound is 2,3,5,6-tetrafluoro-4-methoxybenzyl-1R-(Z)-3-(3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylate. The pyrethroid compound has high activity and significant effect for controlling the pestiferous pests. The invention also provides a preparation method and an application of the pyrethroid compound.

Description

technical field [0001] The invention relates to a pyrethroid compound, a preparation method thereof and an application for preventing and controlling 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. In CN101381306A, we have formed a series of novel fluorine-containing pyrethroid compounds by modifying the structure of traditional pyrethroid acids and alcohols. Preliminary drug efficacy tests of these compounds have shown that they have good insecticidal activity, fast knockdown and high lethality. However, these new pyrethroid compounds still have some defects in the basic insecticidal activity or vapor pressure. We continued to study on the basis of previous work and found that 2,3,5,6-tetrafluoro- 4-methoxybenzy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/743C07C67/08A01N53/06A01P7/04A01N25/18A01N25/20A01N25/34
Inventor 戚明珠周景梅姜友法贺书泽王东朝何红军
Owner JIANGSU YANGNONG CHEM
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