| Atrijuglans hetaohei Yang is a kind of boring pest, which seriously affects the productionand quantity of walnuts. It is difficult to monitor and control this pest due to its specialbiology and damage. Spraying insecticide can cause serious problems such as environmentalpollution, insect resistance and pesticide residues. In view of its serious harm to walnutindustrial and the lack of effective monitoring and control technology, a new controltechnology needs to be developed. Application of sex pheromone of insects for monitoringand controlling is one important strategy, which has many advantages such as high efficiencyand environmental protection. Application of this technology in the control of A. hetaohei isundoubtedly the best choice.On the basis of previous studies, this paper improves the synthesis method of A.hetaohei’s sex pheromone. Several candidate compounds of the sex pheromone of A. hetaoheihave been synthesized by Coupling with Grignard reagent. Through extraction experiment,several possible active compounds of A. hetaohei’s sex pheromone have been found.Attractant activities of some sex pheromone candidate compounds of A. hetaohei have beenstudied. The main results are as follows:1. Seven kinds of16carbon enol or ester sex pheromone candidate compounds weresynthesized by Coupling reaction. Taking the cheap1,5-Pentanediol and(E,E)-2,4-Hexadien-1-ol as raw materials, make1,5-Pentanediol to region-selectivelybrominate, hydroxyl protect and react with Magnesium to get BrMg(CH2)5OTHP, followingCoupling reaction with Li2CuCl4catalyst and hydrolysis reaction to get (E)-7-pentadecen-1-ol.Using similar methods, use1,6-Hexanediol and E-2-Decen-1-ol as raw materials to get(E)-hexadec-8-en-1-ol, use1,7-Heptanediol and E-2-Decen-1-ol as raw materials to get(E)-hexadec-9-en-1-ol,use1,7-Heptanediol and (2E,4E)-2,4-Nonadien-1-ol as raw materialsto get E9,E11-16carbon diene-1-ol. After end-product structure confirmation with GC-MS,compounds are in more than95%purity. The advantages of optimized Coupling jointdiagnosis are product good stereo selectivity, less by-products and raw materials easy to get.2. Optimized the route of coupling of synthetic. Different solvents, catalysts and the amount of hydrobromic affect the productivity of the mono-brominated and the production ofby-products. The comparative experiment result indicates that under the iodine catalyst, withbenzene solvents, glycol and40%hydrobromic acid mole ratio of1:1.5,16hours of reaction,the monobromination reaction exhibited best selectivity and higher productivity; Usingmethyl iodide as the initiator can significantly improve the success rate of the preparation ofgrignard reagent(BrMg(CH2)nOTHP).3. Optimized indoor adult breeding conditions and found the phenomenon of adultsmate behavior. We extracted sex pheromone from the sex gland of A. hetaohei indoors.Analyzing these extracts with GC-MS indicated that the main compositions could be mixtureswhich include hexadecenol including a carbon-carbon double bond, palmitoleyl acetateincluding a carbon-carbon double bond and palmitoleyl including two carbon-carbon doublebonds.4. Preliminarily analyzed the activity of candidate sex pheromone components of A.hetaohei. Electroantennogram(EAG), Y-tube experiments and outdoor trapping experimentsindicated that in all the selected compounds, Z-9-16:OH, Z-9-16:OAc and Z-11-16:OAcshowed EAG activity indoors but no attractant activity in the fields.This paper optimized the route of coupling compositions, efficiently and simplycompounded some sex pheromone candidate compounds of A. hetaohei which provides ascientific basis and reference for the composition of unsaturated aliphatic enol sex pheromonecompounds. Through analyzing the extracts form the sexual glands of A. hetaohei by GC-MS,possible structure of sex pheromone has been gained. The activity experiment furthernarrowed the range of compounds. All these results laid a theoretical foundation for theresearch of A. hetaohei’s sex pheromone. |
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