Sitodiplosis mosellana Gehin sex pheromone precursor and sitodiplosis mosellana Gehin sex pheromone

Abstract

The invention relates to a sitodiplosis mosellana Gehin sex pheromone precursor compound as well as a synthesis method and an application of sitodiplosis mosellana Gehin sex pheromone. According to the synthesis method of the sitodiplosis mosellana Gehin sex pheromone precursor compound, CuCl and hydroxylamine hydrochloride are added to a Schlenk tube equipped with a magnetic stirrer under the protection of nitrogen gas, the tube is put in an ice bath to be cooled, 70% of a n-butylamine aqueous solution in percentage by mass is injected, chiral alkynol II is added, bromo-chiral alkynol III is slowly added, a reaction liquid reacts at the low temperature, a product is extracted with ethyl ether after the reaction ends, washed with a saturated sodium chloride aqueous solution and dried, a coarse product is obtained after pressure reduction, and chiral alkynol IV is obtained through purification with column chromatography. The prepared sitodiplosis mosellana Gehin sex pheromone has high optical activity; besides, the synthetic route is simple, the cost is low, and the sitodiplosis mosellana Gehin sex pheromone has commercial application value.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and provides a method for synthesizing the sex pheromone precursor of the red midge and the sex pheromone of the red midge. Background technique [0002] The red midge is widely distributed in Asia, North America and Europe, causing huge economic losses all over the world. Wheat midge is one of the three major pests of wheat in China. It broke out twice in the 1950s and 1980s in my country, which seriously affected the wheat production and people's life in the Huanghuai River Basin. Wheat midges cause damage by sucking the juice of wheat grains being filled by larvae during the wheat grain filling stage, resulting in shrunken grains or empty shells. In the main wheat producing areas of my country, the yield is usually reduced by 10%-20%, and in severe cases, the yield is reduced by 80%-90%. . [0003] The wheat red midge is small in size, reproduces quickly, and is very harmful. It is difficult ...

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Problems solved by technology

2. The enantiomers of pheromone molecules are synthesized by Grignard reagents and chiral oxirane or other chiral source compounds. This method has certain restrictions on the synthesis of some specific target compounds, and the synthesis process is relatively complicated and cumbersome ( JChemEcol 2005, 31, (8), 1807–1828)

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