A Concise Li/liq. NH3 Mediated Synthesis of (4E,10Z)-Tetradeca-4,10-dienyl Acetate: The Major Sex Pheromone of Apple Leafminer Moth, Phyllonorycter ringoniella

摘要

Apple, originated from central Asia and Europe, is one of the widely cultivated tree fruit around the world that has become very important in both human diet and health aspects due to its exceptional nutrition and biological significance. The commercial outcome of apple orchards is greatly affected by various insect pests like tufted apple bud moth (Platynota idaeusalis (Walker)), codling moth (Cydia pomonella) and light brown apple moth (Epiphyas postvittana) to name a few around the world. Even though, pesticides show efficient results in controlling these pests, they are having disadvantages owing to less nutrition and thus pheromones come in to more attention. Pheromones are chemical substances that secreted or excreted to elicit social response among the members of same species with opposite sex. To discover appropriate methods for the accurate estimation of insect numbers, development timing and control, the sex attractants have already been studied by several research groups. The apple leafminer moth, Phyllonorycter ringoniella (or Litho-colletis ringoniella), is a serious insect pest on apple trees with four to five generations a year in Korea, Japan and China. The two components (4E,10Z)-tetradeca-4,10-dienyl acetate (E4, Z10-14:Ac; 1) and (Z)-tetradec-10-enyl acetate (Z10-14:Ac; 1a) are identified in the female sex pheromone of apple leafminer moth (Figure 1). Major component in the blend of these two has found to be 1, in examining male response (taxis, approach, and landing) of P. ringoniella that were observed in Korea, Japan and China.