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Pyrethroid compounds, preparation and use thereof

A technology of pyrethroids and compounds, which is applied in the field of pyrethroid compounds, can solve the problems of unseen commercialization of hygienic insecticide products, and achieve the effect of quickly killing pests

Active Publication Date: 2008-12-17
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] When R 1 is chlorine, R 2 When it is trifluoromethyl, it is the racemate of compound A in the present invention, but there has been no report that this type of compound is applied to the commercialization of hygienic insecticide products

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

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preparation Embodiment 1

[0043] Preparation Example 1: Resolution of cis 2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid (cis chrysanthemic acid)

[0044] In a 1000ml four-necked bottle, put 100.0g of cis-kungfu chrysanthemic acid and 100.0g of dextrochloramphenicol, dissolve in 500ml of toluene, stir after throwing in, heat up to 110°C for reflux reaction for 1 hour, and then within 3 hours Cool to 40°C, keep warm for 1 hour, then cool to 10°C within 2 hours, keep warm for 0.5 hour, at this time, a large amount of crystals are precipitated. Filtrate, add 100g 10% hydrochloric acid in the obtained mother liquor to acidify to pH 2-3, separate layers, wash the oil layer to near neutrality, heat to 100 ℃ under 10mmHg negative pressure to remove solvent toluene, obtain dextrorotary cis ( 1R,3R)-2,2-Dimethyl 3-(2-chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid 45.5g, dextrorotatory active body ee value 95%.

preparation Embodiment 2

[0045] Preparation Example 2: Resolution of cis-kung fu chrysanthemic acid

[0046] In a 1000ml four-necked bottle, put 100.0g of cis-kung fu chrysanthemic acid, 125.0g of dextrorotatory PTE, dissolve in 400ml of toluene, stir after throwing in, heat up to 110°C for reflux reaction for 1 hour, and then cool to within 3 hours. 60°C, keep warm for 1 hour, then cool to 20°C within 2 hours, keep warm for 1 hour, at this time, a large number of crystals precipitate, filter to get crystals, add 200g of 5% hydrochloric acid to acidify, add 400ml of toluene to extract at the same time, separate layers, and oil layer Wash with water until nearly neutral, and heat to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain dextrocis (1R,3R)-2,2-dimethyl 3-(2-chloro-2-trifluoromethane Base vinyl) cyclopropane carboxylic acid 45.2g, dextral effective body ee value 94%.

preparation Embodiment 3

[0047] Preparation Example 3: Acid Chlorination of (1R, 3R)-2,2-Dimethyl 3-(2-Chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic Acid (dextrorotary cis-Kongfu Chrysanthemum Acid)

[0048] In a 1000ml four-necked bottle, put 242.5g (1 molee value 95%) of D-cis chrysanthemic acid obtained in Preparation Example 1 into 600ml of toluene, stir after throwing in, heat up to 50°C, and add SOCl dropwise 2 142g (1.2mol), dropwise completed within 2 hours, then heated up to 60°C, and kept warm for reaction. After completion of the reaction, heat to 80°C under 30mmHg negative pressure to remove solvent toluene, then rectify under 10mmHg negative pressure, and collect 60°C-75°C fractions to obtain (1R,3R)-2,2-dimethyl-3-( 2-Chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid chloride 249.6.1g, yield 94.3%, dextrorotatory active body ee value 95%.

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Abstract

The invention provides a novel pyrethroid compound having the following structural formula (X), a preparation method of the compound and application thereof in sanitary desinsection products. In the formula, R is methoxymethyl (-CH2OCH3) or an H atom. Experiments show that the compound of the formula (X) has very good control efficiency on sanitary insect pests such as mosquito, fly, and blattella germanica, etc. In addition, the advantage which is especially worth being noticed is that the single optical isomer of the dextral cis form of the compound has better desinsection activity compared with corresponding despinner.

Description

technical field [0001] The invention relates to a pyrethroid compound, in particular to a single optically active pyrethroid compound, as well as its preparation method and application. Background technique [0002] Pyrethroid compounds can be used to control mosquitoes and have high insecticidal activity, which has been widely known. US Patent No. 4,370,346 disclosed for the first time that this type of compound meets the following structural formula, [0003] [0004] When R 1 is chlorine, R 2 When it is a trifluoromethyl group, it is the racemate of compound A in the present invention, but there has been no report on the application of this type of compound to the commercialization of hygienic insecticide products. We have conducted in-depth research on the insecticidal activity of these compounds and found that compound A has excellent insecticidal activity, and its efficacy is about 40 times that of traditional Es-allethrin, and it also exceeds the current commerci...

Claims

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Application Information

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IPC IPC(8): C07C69/747A01N53/08A01P7/00
Inventor 戚明珠周景梅姜友法朱萍赵建伟徐海鹏孙鹏
Owner JIANGSU YANGNONG CHEM
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