Li Changkai, Wu Yuqing, Yin Xinming, Gong Zhongjun, Xing Hongxia, Miao Jin, Wang Shuzhi, Liu Jia, Na Risong, Li Qing X
Collaborative Innovation Center of Henan Grain Crops, National Key Laboratory of Wheat and Maize Crop Science, College of Plant Protection, Henan Agricultural University, Zhengzhou, China.
Institute of Plant Protection, Henan Academy of Agricultural Sciences, Zhengzhou, China.
Pest Manag Sci. 2023 Jan;79(1):97-104. doi: 10.1002/ps.7177. Epub 2022 Sep 22.
Sudden outbreaks of the orange wheat blossom midge, Sitodiplosis mosellana (Géhin) cause huge wheat yield losses. Use of sex pheromones is more efficient than laborious egg counting to monitor these hidden-concealed insects. Quick synthesis of the sex pheromones is therefore required to meet the sudden outbreak needs.
A synthetic approach of stereospecific and racemic S. mosellana pheromones was presented. This method afforded the stereospecific and racemic S. mosellana pheromones in three steps and high enantioselectivity (> 98% ee for (2S,7S)-2,7-nonanediyl dibutyrate) in less than 1 day with 74% and 73% overall yields, respectively, whereas most conventional methods require longer synthesis time with less than 40% yield. The synthesis routes could quickly and economically afford the pheromones, starting from synthon (S)-but-3-yn-2-ol (1a) or but-3-yn-2-ol (1b), through the same three-step processes of coupling, reduction, and esterification. The Y-tube olfactometer results showed significant attractiveness of the synthetic stereospecific and racemic sex pheromones to S. mosellana males relative to the blank control (P < 0.001). Field trials also demonstrated significant attractiveness of the synthetic stereospecific and racemic sex pheromones relative to the blank control (P < 0.001).
This modular approach is conducive to the deployment of field traps and timely responses to S. mosellana outbreaks and can be a time-saving and cost-effective tool to manage S. mosellana. © 2022 Society of Chemical Industry.
小麦吸浆虫（Sitodiplosis mosellana (Géhin)）的突然爆发会导致小麦产量大幅损失。利用性信息素监测这些隐蔽性害虫比费力的虫卵计数更有效。因此，需要快速合成性信息素以满足突发虫害的需求。
提出了一种立体特异性和外消旋性小麦吸浆虫性信息素的合成方法。该方法通过三步反应，以高对映选择性（(2S,7S)-2,7-壬二醇二丁酸酯的对映体过量值>98% ee）在不到1天的时间内分别以74%和73%的总收率得到立体特异性和外消旋性小麦吸浆虫性信息素，而大多数传统方法需要更长的合成时间且收率低于40%。该合成路线从合成子(S)-3-丁炔-2-醇(1a)或3-丁炔-2-醇(1b)开始，通过相同的偶联、还原和酯化三步过程，能够快速且经济地得到性信息素。Y型嗅觉仪结果显示，合成的立体特异性和外消旋性性信息素对小麦吸浆虫雄虫的吸引力相对于空白对照具有显著差异（P<0.001）。田间试验也表明合成的立体特异性和外消旋性性信息素相对于空白对照具有显著吸引力（P<0.001）。
这种模块化方法有利于田间诱捕器的部署以及对小麦吸浆虫爆发的及时应对，并且可以成为一种节省时间和成本效益高的小麦吸浆虫防治工具。© 2022化学工业协会。
