Peach Leafminer Moth Sex Pheromone And Its Synthetic Intermediates

With people's universal concern of health and ecological environment, synthesis of efficient, safe, and environmentally compatible green pesticide has become the focus of the pesticide research fields. Green pesticide is called pollution-free pesticide or environmentally friendly pesticide, which can be easily decomposed with low-residue or no residues, efficient to bacteria or pests, and no dangerous to human being and livestock. Insect pheromone is one of the animal biochemical green pesticides. In accordance with the provisions of"Green food-Pesticide application guideline", promulgated by China Ministry of Agriculture, we can only use animal biochemical pesticides (insect pheromone) in the grade AA, grade A green food production.The peach leafminer moth, Lyonetia clerkella Linnaeus (Lepidoptera: Lyonetiidae) is distributed in China and Japan. Because larval damage occurs within the leaves and the larvae are not exposed to the usual contact sprays, this leafminer is a major pest insect in peach orchards. It causes heavy defoliation prior to harvest. With the peach leafminer moth's degree of damage Increasing and the occurrence area expanding, the research for the peach leafminer moth has grown from 1991.Semiochemical is trace chemicals that the organisms secrete in vitro and can affect other organisms'physiological and behavioral responses, including pheromone and allelochemical. The sex pheromone of the peach leafminer moth is a kind of pheromone, which is a special odour substance the peach leafminer female moth secreted and released in vitro after the sexual maturity. It is a promising green pesticide because of having a chemical communication function and luring male moths to mate. SATO et al. (1986) reported that the (S)-14-methyl-1-octadecene showed strong biological activity, which is the long-chain compound with a chiral centre at the carbon-14 position. Therefore, the synthesis is usually divided into two steps: the first step is the synthesis of long-chain with a terminal olefin and the second step is the synthesis of the short-chain part with a chiral center. Then the two parts were coupled together to yield (S)-14-Methyl-1-octadecene.The studies of this paper include:1. Designing the reasonable synthesis route of (S)-14-Methyl-1-octadecene;2. Finding efficient and reasonable green catalyst for monobromination of 1,6-hexandiol ;3. Synthesizing acetic acid 6-bromo-hexyl ester. Because of pollution-free and environment-friendly, non-corrosive, 1,6-hexandiol is known as a piece of new cornerstone in the organic synthesistoday.In the issue, we chose 1,6-hexandiol as starting materials.Chosing mocular iodine as catalyst is a innovative research in the 1,6-hexandiol single-bromination reaction.The practical significance of every processing is to meet the requirements of environmental protection.Through single-factor experiments and orthogonal experiments in the processing of monobromination of 1,6-hexandiol catalysed by iodine, we found the optimal reaction conditions are as following: the amount of catalyst is 0.048 g, the optimal molar ratio of 1,6-hexandiol to hydrogen bromine is 1:2, the reaction optimal temperature is 90℃, refluxing for 6 h.In the synthesis processing of acetic acid 6-bromo-hexyl ester by 6-bromo-1-hexanol and acetic acid, we replace conventional catalyst H2SO4 with CaCl2, because of it's quickly, high efficient, low pollution and simply to operation & post-processing, the synthesis processing fully complied with green chemistry.