松香基二萜类手性昆虫拒食剂的合成及定量构效关系研究

项目名称： 松香基二萜类手性昆虫拒食剂的合成及定量构效关系研究

项目编号： No.31470596

项目类型： 面上项目

立项/批准年度： 2015

项目学科： 农业科学

项目作者： 饶小平

作者单位： 中国林业科学研究院林产化学工业研究所

项目金额： 80万元

中文摘要： 昆虫拒食剂因为具有使用效果好、对环境友好、不易产生抗性等优点，成为无公害农药中的重要品种。本项目针对松香三环二萜及多个手性中心的结构特点，采用催化异构、D-A 加成等手段分离纯化松香树脂酸及衍生物单体，并对树脂酸及衍生物进行结构修饰，合成一系列结构新颖的手性松香基醇、醚、酯、含氟、杂环等二萜衍生物，对衍生物进行IR,NMR,MS 等结构鉴定及X衍射结构解析。采用叶蝶法，研究其对蚜虫、斜纹夜蛾等昆虫的拒食活性，筛选具有较强开发价值的新型昆虫拒食剂。用AMPAC软件计算松香衍生物的量子化学参数及结构描述符，并用CODESSA软件对结构参数与拒食活性进行线性回归，建立定量构效关系QSAR模型，根据QSAR模型指导高活性化合物的合成及活性研究。探索结构类型、取代基、立体空间构型等结构对昆虫拒食活性的影响，总结结构与性能的关系。为创新生物农药的开发提供理论指导，为松香的高值化利用开辟新的途径。

中文关键词： 松香；二萜；手性；拒食剂；定量构效关系

英文摘要： Insect antifeedant has the advantages of good effect, environment friendly, not easy to produce resistance, so they have become an important variety of enviroment friendly pesticides. According to the unique structure of tricyclohydrophenanthrene and multi chiral center of rosin. This project aim to isolate dehydroabietic acid, acrylpimaric acid and their derivatives through catalytic isomerization reaction, D-A addition reactrions. chemical modification of rosin acids and their derivatives, synthesis of a series of novel chiral diterpenoid abietyl alcohol, ether, ester, fluorinated heterocyclic antifeedant, using IR, NMR, MS and X-ray structure analysis to determine their stereo structures. And study their antifeedant activity to insects, such as Aphids and Spodoptera litura by leaf disc method. Calculate the quantum chemical data and structure descriptors of rosin derivatives by AMPAC software and correlate their structure activity relationship by CODESSA through linear regression, set up a QSAR model and direct the synthesis and activity of high activity compounds. Exploring the influence of structure, substitute group and configuration of structure on their antifeedant activity. Exploring their structure and activity relationship. This study can provide theoretical guidance for the development and innovation of biological pesticide, and to open up a new way for the high value utilization of rosin.

英文关键词： rosin;diterpenoid;chiral;antifeedant;quantitative structure activity relationship