Study On Total Synthesis And Biological Activity Of Sex Pheromone Of Lyonetia Clerkella

Traditional pesticides can ensure the yield of crops,while also cause residues and pollutions with the development of society.People pay more attention to environment and bio-pesticides&green pesticides are getting more and more attraction.New bio-pesticides have advantages such as high selectivity,low toxicity,none-target harmless,easy degradation,etc.Insect pheromones are one type of the biological pesticides that are often used for monitoring and trapping pests,by efficiency specificity,and no pollution.Peach leafminer moth Lyonetia clerkella?Linnaeus?is a common pest of Lepidoptera?Lyonetiidae?.It mainly harms the leaves of Rosaceae fruit trees,and the larvae infiltrate into the leaves to feed and form curved channels,causing the leaves to fall off and affecting the growth of the tree.In this paper,Peach leafminer moth synthetic sex pheromone for the study,based on the total synthesis of its sex pheromone.We have designed a cheap,simple,and highly effective synthetic route and conducted insect sex pheromone bioactivity experiments.The research content and results are as follows:1.The sex pheromones of Peach leafminer moth have been accomplished in this thesis.The syntheses of 15 compounds were completed,of which 7 compounds are new ones.All these compounds were characterized by ¹H NMR and ¹³C NMR,the chirality of 9 chiral compounds were measured by polarimeter.Some important intermediates and all the target molecules were characterized by HRMS.2.The construction of C-C skeleton was furnished throug Wittig olefination;Evans asymmetric alkylation was adopted for the structure of chiral center.The syntheses of one routes of the sex pheromone of?S?-14-methyl-1-octadecene peach leafminer moth synthesis route were completed.The route of the sex pheromone of peach leafminer moth was completed in 17.5%overall yield?12steps?from cheap?-butyrolactone.The C-C skeleton was constructed by using Wittig olefination and the chiral center was built by Evans asymmetric alkylation.3.In the syntheses of insect pheromones,the wittig olefination was used many times.Although,it generally gave Z/E mixture,these results didn't affect target molecule.Because the double bond of the target compound is at the end group.4.Using the synthesized target compound?S?-14-methyl-1-octadecene as a Y-tube olfactory detection test,the attraction rate of male moths was 51%,which was very significantly correlated?p=0.003?,indicating that The synthesized target product has a strong attraction to the leaf moth.5.The EAG test results showed that when the stimulating concentrations were 0.01?g/?L,0.1?g/?L,and 1?g/?L,the antennae of?S?-14-methyl-1-octadecene The potential response was significantly higher than that of female moths?p<0.05?,which further indicated that the sex pheromone synthesized by the Peach leaf moth had a significant attracting effect on the male moth.