Pyrethroid compound, preparation method and application thereof

A technology of pyrethroids and compounds, which is applied in the field of pyrethroid compounds to achieve the effect of quickly killing pests

Active Publication Date: 2009-11-18
JIANGSU YANGNONG CHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, studies on the pharmacodynamics of the different optical isomers of the compound have not been reported.

Method used

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  • Pyrethroid compound, preparation method and application thereof
  • Pyrethroid compound, preparation method and application thereof
  • Pyrethroid compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0042] 2,3,5,6-Tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (Compound I) Synthesis:

[0043] In a 2000ml four-necked bottle, put 112.0g of tetrafluoro-p-methoxymethylbenzyl alcohol and 38.0g of pyridine, dissolve in 800ml of toluene, stir after throwing in, and add (R)-2,2 - 114.0 g of dimethyl-3-trans-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride was added dropwise to 20°C for 4 hours. Wash with 400ml 5% hydrochloric acid, then wash with 400ml 5% NaHCO 3 After washing, the oil layer was heated to 100°C under a negative pressure of 10mmHg to remove the solvent toluene to obtain the compound 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2,2 -dichlorovinyl)-2,2-dimethylcyclopropane carboxylate as light yellow solid, weight 203.3g, content 97.8%, yield 95.8%. The molecular formula of the compound: C 17 h 17 Cl 2 f 4 0 3 ; Molecular weight: 416.2; Optical rotation [α] = -9.32; Soluble in organic solven...

preparation Embodiment 2

[0045] 2,3,5,6-Tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate Synthesis of (Compound II):

[0046] Put 56.0g of tetrafluoro-p-methoxymethylbenzyl alcohol, 25g of pyridine, and 400ml of toluene into a 1000ml four-necked bottle, stir for 15 minutes at room temperature, and drop (R)-2,2-dimethyl at 0-5°C Base-3-trans-(2,2-dibromovinyl)cyclopropanecarboxylic acid chloride 79.4g, after dripping, keep warm at 10°C for 1 hour, wash the oil layer with 150ml 5% hydrochloric acid, and then wash with 100ml 5% NaHCO 3 Wash, then wash until neutral. The oil layer was detoluene under negative pressure, the final temperature was 100°C, and the absolute pressure was 10mmHg to obtain the compound 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2,2-di Bromovinyl)-2,2-dimethylcyclopropanecarboxylate is an off-white solid with a weight of 125.1 g, a content of 97.1%, and a yield of 96.2%.

preparation Embodiment 3

[0048] 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2-chloro-2-bromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Synthesis of ester (compound III):

[0049] Put 112.0g of tetrafluoro-p-methoxymethylbenzyl alcohol, 50.0g of pyridine, and 800ml of toluene into a 2000ml four-neck flask, stir to dissolve, and drop (R)-2-chloro-2-bromo- 136.2g of 3-trans-(2,2-dichlorovinyl)cyclopropanecarboxylic acid chloride, after the dropwise addition, keep the reaction at 10°C for 4 hours, pickle with 5% hydrochloric acid, and wash with 5% NaHCO 3 The solution was washed with alkali, and then the oil layer was washed twice with 200 ml of deionized water. The oil layer was detoluene under negative pressure, the final temperature was 100°C, and the absolute pressure was 10mmHg to obtain the compound 2,3,5,6-tetrafluoro-4-methoxymethylbenzyl (1R,3S)-3-(2-chloro 2- Bromovinyl)-2,2-dimethylcyclopropanecarboxylate is an off-white solid with a weight of 229.8g, a content of 98.2%, and a yi...

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Abstract

The invention provides a pyrethroid compound A which has a structural formula on the right, wherein R1 and R2 are respectively the same or different halogens, and the pyrethroid compound is a d-trans single optical active isomer. The pyrethroid compound has more obvious effect of desinsection compared with a racemic compound or other compounds of the same class of the prior art. The invention also provides a preparation method and application in sanitary insecticidal products of the pyrethroid compound A.

Description

technical field [0001] The invention relates to a pyrethroid compound, in particular to a single optically active pyrethroid compound, a preparation method and application thereof. 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] and R 1 and R 2 It is the racemic compound of chlorine at the same time, and the Chinese patents whose publication numbers are CN1669429 and CN1669419 once mentioned that the racemic compound can be used to control hygienic pests. However, there is no report on the pharmacodynamic studies of the different optical isomer components of the compound. As people's requirements for environmental protection are getting higher and higher, the high biological activity of pesticides has attracted more and more attenti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/743C07C67/14A01N53/06A01P7/00
Inventor 董兆云赵建伟姜友法王怀明陈月华
Owner JIANGSU YANGNONG CHEM
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