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Synthesis Of The Bioactive Sex Pheromone Of Pink Bollworm

Posted on:2021-01-13Degree:MasterType:Thesis
Country:ChinaCandidate:M TangFull Text:PDF
GTID:2393330620972909Subject:Chemical Biology
Abstract/Summary:PDF Full Text Request
Cotton is one of the most important economic crops in China.The pink bollworm,pestinophora gossypiella(Saunders),is one of the main pests of cotton.The sex pheromone structure of pink bollworm was a mixture of(Z,Z)-7,11-hexadecanenyl acetate(Z7,Z11-16: OAc)(1a)and(Z,E)-7,11-hexadecanenyl acetate(Z7,E11-16: OAc)(1b).When the two structures are mixed in the ratio of 1:1,they have the highest EAG response value.In this study,"C5 + C4 + C7" carbon skeleton construction strategy was adopted.Two isomers of sex pheromone of pink bollworm were synthesized by 7 steps of Julia-kocienski reaction and Wittig reaction with cheap raw materials such as 1,4-butanediol,n-pentanol and heptanic acid.The ratio of the two isomers was approximately 1:1,and the total yield was 9.1%.After preliminary estimation,the cost price was ? 256 / g.A new,simple and cheap synthetic method for sex pheromone of pink bollworm was proposed.It provides theoretical basis and material basis for the Stereosynthesis of insect sex pheromone,production and application of attractant.It provides a new idea for the synthesis of other straight chain pheromones with two double bonds.The related activity test and process optimization are still in progress.The advantage of this synthetic route is that the Z/E ratio of C11 carbon double bond is close to the Z/E ratio of natural pink bollworm pheromone by using cheap raw materials and simple methods.GC-MS was used to detect the Z/E ratio of C9 fragments,so as to control the ratio of the final target product(1a / 1b)to 1:1.This proportion of products can be used for the control of pink bollworm without the separation of stereoisomers.
Keywords/Search Tags:Sex Pheromone of Pectinophora gossypiella, Wittig reaction, Julia-Kocienski reaction, Sex pheromone components proportion control
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