草地贪夜蛾性信息素的合成

Synthesis of the sex pheromones of Spodoptera frugiperda(J.E,Smith)

草地贪夜蛾性信息素具有不伤害天敌、不产生抗药性、对环境安全等优点。其主要活性成分为:(Z)-7-十二碳烯-1-醇乙酸酯、(Z)-9-十二碳烯-1-醇乙酸酯、(Z)-9-十四碳烯-1-醇乙酸酯、(Z)-11-十六碳烯-1-醇乙酸酯、(E)-7-十二碳烯-1-醇乙酸酯和(9Z, 12E)-9,12-十四碳二烯-1-醇乙酸酯。本文研究了一种高效、简捷的合成草地贪夜蛾性信息素的新方法,其关键步骤包括:醛与官能团化鏻盐的Wittig偶联、炔的烷基化以及丙二酸与丙醛的Knoevenagel缩合等反应。其中醛与羟基鏻盐的Wittig反应及Knoevenagel缩合反应首次用于草地贪夜蛾性信息素的合成。

The sex pheromone of Spodoptera frugiperda(J.E,Smith),has the advantages of the safety to the environment and the natural enemies,and without insecticides resistance.Its active components included(Z)-dodec-7-en-1-yl acetate,(Z)-dodec-9-en-1-yl acetate,(Z)-tetradec-9-en-1-yl acetate,(Z)-hexadec-11-en-1-yl acetate,(E)-dodec-7-en-1-yl acetate and(9Z,12E)-tetradeca-9,12-dien-1-yl acetate.The novel,efficient and concise synthesis of S.frugiperda(J.E,Smith)sex pheromones has been achieved.The key steps of this synthetic approach involved Wittig coupling of aldehyde with functionalized phosphomium salt,the alkylation of alkynes,and Knoevenagel condensation reaction of malonic acid with propionic aldehyde.Furthermore,the Wittig reaction of hydroxy-bearing phosphomium salt and Knoevenagel condensation reaction were firstly applied to the synthesis of S.frugiperda(J.E,Smith)sex pheromones.