大豆食心虫性信息素及其类似物的简易合成及田间引诱活性

Convenient synthesis and field evaluation of the sex pheromone of Leguminivora glycinivorella and its analogues

以1,6-己二醇和E,E-2,4-己二烯醇为原料,在四氯合铜酸二锂(Li2CuCl4)催化下通过Coupling偶联反应合成出大豆食心虫Leguminivora glycinivorella性信息素的主要组分E,E-8,10-十二碳二烯醇乙酸酯(Ⅰ),总收率30%;在相近条件下合成了Ⅰ的类似物Ⅱ～Ⅷ。所有产物的结构均经1H NMR、13C NMR和GC-MS确证。该合成方法原料廉价易得,副产物少,产物立体选择性高。田间试验结果表明:当每诱芯含0.1 mg化合物Ⅰ、0.01 mgⅡ、和0.1或0.5 mgⅣ时对大豆食心虫具有较好的引诱效果;混配结果显示,当诱芯质量比分别为m(Ⅰ)∶m(Ⅳ)=10∶1、m(Ⅰ)∶m(Ⅶ)=1∶5及m(Ⅰ)∶m(Ⅷ)=1∶5或1∶1,且每诱芯混剂含量为1.0 mg时,其引诱活性与标准诱芯相当。

（E,E）-8,10-Dodecadienyl acetate（Ⅰ）,the main component of the sex pheromone of Leguminivora glycinivorella,was synthesized via coupling reactions catalysed by Li2CuCl4 starting from 1,6-hexanediol and（E,E）-2,4-hexadienol in a total yield of 30%.Its analogue compounds Ⅱ-Ⅷ were synthesized in the similar procedures.The structures of the synthetic compounds were confirmed by GC-MS,1H NMR and 13C NMR.Compounds Ⅰ to Ⅷ were efficiently synthesized starting from cheap raw materials with less by-products and high streoselectivities.Field tests showed that the single component of Ⅰ（0.1 mg）,Ⅱ（0.01 mg）,and Ⅳ（0.1 mg or 0.5 mg） was attractive to L.glycinivorella males,and the attractiveness of binary mixture of m（Ⅰ）∶m（Ⅳ）=10∶1,m（Ⅰ）∶m（Ⅶ）=1∶5 and m（Ⅰ）∶m（Ⅷ）=1∶5 or 1∶1 at 1.0 mg/trap was equal to the standard lures.