| Lepidopteran insect sex pheromones have a wide range of applications in agriculture as green biorational pesticides due to their high efficiency and specificity without toxicity,pollution and harm to beneficial insects.This paper mainly studies the synthesis of two kinds of insect sex pheromone(E/Z)-8-dodecenyl acetate,(E/Z)-9-tridecene acetate and their analogues.1,8-octanediol,1,9-nonanediol symmetric glycol and symmetrical 10-hydroxydecanoic acid adopted as starting materials,9 target compounds are synthesized through a three step reaction such as single esterification,oxidation and Wittig reaction.Among these 9 compounds,(E/Z)8-dodecenyl acetate and(E/Z)9-tetradecyl acetate are known insect sex pheromones,based on which,other 7analogues are designed and synthesized:(E/Z)8-tridecenyl acetate,and(E/Z)-8-tetradecenyl acetate,(E/Z)9-tridecenyl acetate,(E/Z)9-petadecenyl acetate,(E/Z)methyl 10-tetradecenoate,(E/Z)methyl 10-petadecenoate and(E/Z)methyl10-hexadecenate.These 7 compounds are expected to be potential novel insect sex pheromones with good physiological activities.At the same time,the influences of different alkali on Wittig reactions are also investigated to get optimum technological conditions.Finally,the purity and structure of the above compounds and their intermediates are all confirmed by NMR,MS,IR,GC and HPLC. |
