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Optically active pyrethroid and preparation method and application thereof

A technology for pyrethroids and compounds, which is applied in the field of preparation of pyrethroid compounds, and can solve problems such as rising production costs

Active Publication Date: 2013-05-29
CHINA CATALYST HLDG CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This not only leads to increased production costs, but also seriously ignores that when an optically active pyrethroid compound contains a certain proportion of cis-dex-isomers and trans-dex-isomers at the same time, its insecticidal activity is much higher than either Insecticidal activity effect of a single optical isomer

Method used

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  • Optically active pyrethroid and preparation method and application thereof
  • Optically active pyrethroid and preparation method and application thereof
  • Optically active pyrethroid and preparation method and application thereof

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Experimental program
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Effect test

preparation Embodiment 1

[0068] A kind of preparation of chiral cyclopropane catalyst (chiral Cu(II) catalyst) of the present invention

[0069] Under the protection of argon, 0.30g (0.50mmol) (R)-1,1-bis[(2-n-octyloxy-5-tert-butyl)phenyl]-2-amino-1-propanol , 0.12g (0.50mmol) 2-bromo-4-nitrosalicylaldehyde, 0.11g (0.52mmol) copper acetate monohydrate were added to 10mL anhydrous methanol in sequence, after stirring at room temperature for half an hour, 0.0416g solid NaOH was added (1.04mmol), stirred overnight, evaporated the solvent, added 20mL water to the residue, extracted three times with 30mL benzene, and dried the organic phase with anhydrous potassium carbonate. The solvent was distilled off under reduced pressure to obtain 0.38 g of a chiral cyclopropane catalyst of the present invention——Cu(II) / Schiff base catalyst.

preparation Embodiment 2

[0071] Synthesis of compound I(a) (trans:compound I with a cis ratio of 60:40)

[0072] 1) Synthesis of cis and trans dextrorotatory 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxyethyl ester

[0073]In a 50ml four-neck flask, add 0.01mmol of the chiral cyclopropane catalyst prepared according to the method of Preparation Example 1, 1mmol of 2-methyl-5,5-dichloro-2,4-pentadiene and 2ml dichloroethane solvent, preheat to 80°C, slowly add 1.2mmol ethyl diazoacetate to the above reactant, specifically, a few drops can be added first to initiate the reaction, and the temperature is lowered to 75°C under the protection of argon. Then within 3 hours, use a syringe pump to add the remaining ethyl diazoacetate solution at a constant speed, continue to stir for 2 hours, and the reaction is over. The reaction solution is directly separated from 15 grams of silica gel to remove the cyclopropanation catalyst, and then washed with 20ml of dichloromethane. Silica gel was concentrated...

preparation Embodiment 3

[0077] Synthesis of Compound II

[0078] 1) Resolution of trans-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid

[0079] In a 1000ml four-necked bottle, put 90.0 g of trans-2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropanecarboxylic acid and 80.0 g of d-chloramphenicol, dissolve Add 500ml of toluene, stir after throwing in, heat up to 110°C and reflux for 1 hour, then cool to 40°C within 3 hours, keep warm for 1 hour, then cool to 10°C within 2 hours, keep warm for 0.5 hours, there are a lot of crystals at this time Precipitate. Filter, add 100g of 10% hydrochloric acid to the obtained mother liquor to acidify to PH=2-3, separate layers, wash the oil layer with water to near neutrality, heat to 100°C under 10mmHg negative pressure to remove solvent toluene, and obtain trans dextrorotary ( 1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 40.5g, dextrorotatory active body ee value 96%.

[0080] 2) Resolution of cis 2,2-dimethyl-3-(2-methy...

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Abstract

The invention provides a synthetic pyrethroid compound; the structure of the compound is shown by the formula A and comprises two cistron dextroisomers containing a formula B and a formula C; the molar ratio of the anti-form dextroisomer and the cis-form dextroisomer is 0.1:1-10:1, wherein R1 and R2 are halogen, halohydrocarbon, aliphatic hydrocarbon, aliphatic ether, alkoxy or hydrogen atom; X is aliphatic hydrocarbon of 1-3 carbon atoms, aliphatic ether, alkoxy, alkyne or nitrile grouping; compared with the prior art, the synthetic pyrethroid compound has high insecticidal activity; the invention further provides a preparation method of the synthetic pyrethroid compound and the application of preventing sanitary insect pests.

Description

technical field [0001] The invention relates to a pyrethroid compound, especially a preparation method and application of a pyrethroid compound comprising a pair of cis-trans dextrorotatory optically active isomers. Background technique [0002] It is well known that pyrethroids can be used to control mosquitoes and have high insecticidal activity. It is known from the specification disclosed by EP-31199A that some fluorine-substituted benzyl esters of haloalkenyl cyclopropanecarboxylic acids have insecticidal activity, and in these compounds, the 1-position and 3 Isomers in which the substituents at the - position are in the cis configuration are more active than those in which the substituents at the 1- and 3-positions of the cyclopropane ring are in the trans configuration. U.S. Patent No. 4,370,346 introduces R in compounds of general formula A and B 1 and R 2 The racemic compound when it is chlorine at the same time can be used as a class of insecticide control agent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/747C07C67/03A01N53/06A01P7/04
Inventor 李进刘颐静
Owner CHINA CATALYST HLDG CO LTD
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