Method for synthesizing tetradecene alcohol acetic ester in ostrinia nubilalis sex pheromone

Abstract

The invention discloses a method for synthesizing tetradecene alcohol acetic ester in ostrinia nubilalis sex pheromone, which takes ethyltriphenylphosphonium bromide and 1, 12-codlemone as starting materials. The method comprises the following steps: the 1, 12-codlemone is subjected to a unilateral transesterification reaction to obtain 12-hydroxy dodecanol acetic ester, and then subjected to an oxidation reaction to obtain 12-oxo dodecanol acetic ester which is in a Wittig reaction with the ethyltriphenylphosphonium bromide to obtain (Z / E)-12 tetradecenoic alcohol acetic ester of high cis-trans ratio in Asian ostrinia nubilalis sex pheromone. The invention has the advantages of simple and reasonable synthesis route, convenient and safe operation, high usage ratio of raw materials, short synthesis time and the like.

Description

technical field [0001] The invention relates to a chemical synthesis method of the main component compound (Z / E)-12-tetradecenol acetate of the sex pheromone of the Asian corn borer. Background technique [0002] The Asian corn borer (Ostrinia furnacalis Guenee) is a major pest that harms high-stalk crops such as corn and sorghum in the Far East, and it is widely distributed in my country. Corn is one of the most important crops widely planted in my country, and the Asian corn borer has seriously harmed the yield and quality of corn in my country. The corn borer has a very mixed feeding habit and is the main pest of corn. When the pest occurs, it will damage all parts of the corn plant except the root, making the damaged part lose its function and greatly reducing the corn kernels. In general occurrence years, corn production can be reduced by 10%, and in major occurrence years, corn production reduction can even exceed 30%. Corn borer damages corn stalks with larvae that ...

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Problems solved by technology

There are reports at home and abroad on the synthesis method of the compound (Z / E)-12-tetradecenyl acetate in the sex pheromone of the Asian corn borer: Klun ① 、Ando ② Du Jiawei ③ etc. with long-chain acetylenic alcohols as intermediates, Li Zhengming ④ etc. used organoboron reagents to complete the synthesis of the sex pheromone (respectively see ①, Klun J A, Bierl-Leonhardt B A, Schwarz M, et al.SexPheromone of the Asian Corn Borer Moth[J].Life Science, 1980, 27 (17): 1603-1606.; ②, Ando T, Saito C, Arai K, et al. (Z)-and (E)-12-Tetradecenyl Acetates: Sex Pheromone of Oriental Corn Borer (Lepidoptera: Pyralidae)[J] .Agric Biol Chem, 1980, 44(11): 2643-2649.; ③, Zhu Yuxin, Wang Meizhen, Du Jiawei. Improved synthesis of sex pheromone from the Asian corn borer, Entomological Research Collection [C]. Seventh episode, Shanghai: Shanghai Science and Technology Press, 1987, 13-17.), the above methods have problems such as expensive raw materials, harsh reaction conditions, and long steps; Chen Jiawei ⑤ , Liu Fuchu ⑥ , Li Jiuming ⑦ etc. take 1,12-dodecanediol and 10-undecenol or Z-15-tetradecenoic acid or 10-hydroxydecanoic acid as starting materials, and obtain the pheromone through a multi-step reaction (respectively See ⑤, Chen Jiawei, Jiang Jilong, Lu Jun. Improved Synthesis of Sex Pheromone in Ostrinia oleatus [J]. Organic Chemistry, 1989, 9: 80-83.; Synthesis [J]. Organic Chemistry, 1995, 15: 546-549.; ⑦, Li Jiuming, Huang Guozheng, Yong Jianping. A new method for the synthesis of sex pheromone from the Asian corn borer [J]. Pesticides, 2007, 46 (6 ): 388-389.), the above methods all have problems such as lengthy experimental steps and inconvenient operation

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