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致倦库蚊(Culexpipiensquinquefasciatus)产生的引诱产卵的信息素被鉴定为赤式-6-乙酰氧基-5-十六碳内酯。用环戊酮和十一碳醛经醇醛缩合产生2-(1-羟基十一烷基-1-)环戊酮,再通过拜尔-维利格反应和乙酰化作用合成了这种内酯的赤式和苏式异构体的混合物。合成产物由等比例的四种异构体组成,包括具有活性的赤式-(5R,6S)和它的对映异构体,以及另外两个苏式异构体。用合成的信息素对四种(亚种)蚊虫做了引诱产卵的生物测定,发现该产物对同种不同亚种的淡色库蚊(Cx.pipienspallens)和致倦库蚊均有引诱雌蚊产卵的活性,且对前者的引诱力更强,并能保持至少10天以上;而对同属不同种的三带喙库蚊(Cx.tritaeniorhynchus)和另一个属的埃及伊蚊(Aedesaegypti)则无活性,表明该信息素具有种的(而非属的)特异性。
Pheromone induced by Culex pipiens quinquefasciatus was identified as erythro-6-acetoxy-5-hexadecanolide. The synthesis of 2- (1-hydroxyundecyl-1-) cyclopentanone from aldol with cyclopentanone and undecylenaldehyde followed by Bayer-Willigel reaction and acetylation Mixtures of erythro and threo isomers of esters. The synthetic product consists of four isomers in equal proportions, including the active erythro- (5R, 6S) and its enantiomers, as well as the other two threo isomers. The biosynthesis of four kinds of (subspecies) mosquitoes was induced by the synthetic pheromone. The results showed that all the three species of Cx.pipienspallens and Culex quinquefasciatus could attract female mosquitoes Spawning activity, and more attractive to the former, and can be maintained for at least 10 days or more; and for the same species of Culex tritaeniorhynchus (Cx.tritaeniorhynchus) and another genus Aedes aegypti Inactive, indicating that the pheromone has a species-specific (but not genus-specific) identity.