桃小食心虫性信息素的合成
Synthesis of the sex pheromone of the peach fruit moth,Carposina sasakii Matsumura
王颎琳 1孙效 1吴建伟 1边庆花 1王敏 1钟江春1
作者信息
- 1. 中国农业大学理学院应用化学系农药创新研究中心,北京 100193
- 折叠
摘要
桃小食心虫是我国最严重的蛀果害虫之一,利用其性信息素进行防控,具有高效、环保及不易产生抗性等优点.天然桃小食心虫性信息素(Z)-12-十九碳烯-9-酮与(Z)-13-二十碳烯-10-酮在昆虫体内含量极低,通过人工提取无法满足大规模防治需求.本研究以 3-溴-1-丙醇为原料,经四氢吡喃基(THP)保护、亲核取代、Brown P2-Ni还原(Ni(OAc)2 与NaBH4 催化氢化)、格氏试剂加成与重铬酸吡啶鎓(PDC)氧化等 7 步反应,构建了一种高效合成桃小食心虫性信息素的方法;并首次将Brown P2-Ni还原用于桃小食心虫性信息素顺式碳碳双键的构建,总收率为 5%.所构建的桃小食心虫性信息素合成方法操作简便,产品具有高度的区域选择性(Z:E>99:1),适用于桃小食心虫的绿色防控.
Abstract
The peach fruit moth(Carposina sasakii Matsumura)is one of China's most serious fruit-boring pests.Sex pheromone-based pest control has the advantages of being highly efficient,environmentally benign and rarely inducing pest resistance.However,the sex pheromone of the peach fruit moth,(Z)-12-decadecadecene-9-one and(Z)-13-decadecene-10-one,is extremely low in the pest.Therefore,it is insufficient for large-scale pest control via artificial extraction.An efficient synthesis of the sex pheromone has been developed via 7 steps including tetrahydro-2H-pyran-2-yl(THP)protection,nucleophilic substitution,Brown P2-Ni reduction,the addition of Grignard reagent and the oxidation with pyridinium dichromate(PDC)from 3-bromopropan-1-ol.Notably,Brown P2-Ni reduction was firstly used to construct a carbon-carbon double bond of the sex pheromone.The total yield was 5%.Our study has the advantages of simple operation and target pheromone with high regional selectivity(Z:E>99:1),which could be used for the green control of the peach fruit moth.
关键词
桃小食心虫/性信息素/合成/Brown/P2-Ni还原Key words
the peach fruit moth/sex pheromone/synthesis/Brown P2-Ni reduction引用本文复制引用
基金项目
国家重点研发计划(2017YFD0201404)
出版年
2024
国家科技期刊平台
NSTL
维普
万方数据