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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。
The soybean pod borer Leguminivora glycinivorella sex pheromone was synthesized by coupling coupling reaction of 1,6-hexanediol and E, E-2,4-hexadienol under the reaction of dilithium tetrachlorocuprate (Li2CuCl4) The main components E, E-8, 10-dodecadienyl acetate (Ⅰ), the total yield of 30%; Ⅰ under the similar conditions were synthesized Ⅰ Ⅱ ~ Ⅷ. The structures of all products were confirmed by 1H NMR, 13C NMR and GC-MS. The synthesis method has the advantages of cheap raw materials, less by-products and high stereoselectivity. The results of field experiments showed that the entrapping effect on the fruit flies was better than that of the control when the entrainer contained 0.1 mg of the compound I, 0.01 mg II, and 0.1 or 0.5 mg IV, respectively. M (IV) = 10: 1, m (I): m (Ⅶ) = 1: 5 and m At 1.0 mg, its lure activity is comparable to standard lure.