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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 problems such as no compound research reports, and achieve the effect of quickly killing pests

Active Publication Date: 2009-01-21
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Among them, there are compounds where R1 is CF3 and R2 is Cl. In the report at that time, this type of compound was used to control pests in the form of a mixture of various isomers, but no further research reports on this compound have been seen since then.

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
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Effect test

preparation Embodiment 1

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

[0044] In a 1000ml four-necked bottle, drop into trans 2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid 100.0g, d-chloramphenicol 100.0 g, dissolved in 500ml of toluene, stirred after throwing in, heated to 110°C for reflux reaction for 1 hour, then cooled to 40°C within 3 hours, kept for 1 hour, then cooled to 10°C within 2 hours, kept for 0.5 hours, at this time A large number of crystals were precipitated. Filter, add 100g of 10% hydrochloric acid to the mother liquor obtained to acidify to pH 2-3, separate layers, wash the oil layer to near neutrality, heat to 100°C under 10mmHg negative pressure to remove the solvent toluene, and obtain the dextrorotatory trans ( 1R,3S)-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 trans-2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid

[0046] In a 1000ml four-necked bottle, put 100.0g of trans-2,2-dimethyl-3-(2-chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic acid, dextrorotatory PTE ((+ ) β-p-methylphenyl-α-phenylethylamine) 125.0g, dissolved in 400ml toluene, stirred after throwing in, heated to 110°C for reflux reaction for 1 hour, then cooled to 60°C within 3 hours, and kept for 1 hour, Cool to 20°C within 2 hours and keep warm for 1 hour. At this time, a large amount of crystals precipitated, and the crystals were obtained by filtration, acidified to pH 2 by adding 200g of 5% hydrochloric acid, and extracted by adding 400ml of toluene at the same time. Toluene is removed by heating to 100°C under negative pressure of 10mmHg to obtain dextrorotatory trans (1R,3S)-2,2-dimethyl 3-(2-chloro-2-trifluoromethylvinyl) ) Cyclopropanecarboxylic acid 45.2g, dextrorotatory effective b...

preparation Embodiment 3

[0047] Preparative Example 3: Acid Chlorination of (1R,3S)-2,2-Dimethyl 3-(2-Chloro-2-trifluoromethylvinyl)cyclopropanecarboxylic Acid

[0048] In a 1000ml four-necked bottle, drop (1R, 3S)-2,2-dimethyl 3-(2-chloro-2-trifluoromethylvinyl) cyclopropanecarboxylic acid obtained in Preparation Example 1 242.5g (1mol ee value 95%), dissolved in 600ml toluene, stirred after throwing in, warming up to 50°C, adding 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,3S)-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 with the following structural formula (X), a preparation method thereof and application of the compound in health disinsection products. The R in the formula is methoxymethyl (-CH2OCH3) or H atom. Tests show that the compound shown in the formula (X) has excellent control effect against pests such as mosquitoes, flies and Blattella germanica; and particularly, the dextral trans-form single optical isomer of the compound has better disinsection activity compared with corresponding racemate.

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] It is widely known that pyrethroid compounds can be used to control mosquitoes and have high insecticidal activity. US Patent No. 4,370,346 discloses such compounds conforming to the following structural formula for the first time. [0003] [0004] Among them, there are compounds in which R1 is CF3 and R2 is Cl. In the report at that time, this type of compound was used to control pests in the form of a mixture of various isomers, but there has been no further research report on this compound since then. On the other hand, it is generally believed that 2-chloro-2-trifluoromethylvinyl-2,2-dimethylcyclopropanecarboxylic acid is used as the acid part structure in pyrethroids, and its cis isomer is better ( US4512931). We have carried out in-depth research on t...

Claims

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Application Information

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IPC IPC(8): C07C69/747A01N53/08A01P7/00A01P17/00
Inventor 戚明珠周景梅姜友法朱萍赵建伟
Owner JIANGSU YANGNONG CHEM
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