| Title: | "Modular synthesis of the pheromone (2S,7S)-2,7-nonanediyl dibutyrate and its racemate and their field efficacy to control orange wheat blossom midge, Sitodiplosis mosellana (Gehin) (Diptera: Cecidomyiidae)" |
| Author(s): | Li C; Wu Y; Yin X; Gong Z; Xing H; Miao J; Wang S; Liu J; Na R; Li QX; |
| Address: | "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. Seed Control Station of Agriculture and Rural Bureau, Handan, China. Institute of Plant Protection, Luoyang Academy of Agriculture and Forestry Sciences, Luoyang, China. Department of Molecular Biosciences and Bioengineering, University of Hawaii at Manoa, Honolulu, HI, USA" |
| ISSN/ISBN: | 1526-4998 (Electronic) 1526-498X (Linking) |
| Abstract: | "BACKGROUND: Sudden outbreaks of the orange wheat blossom midge, Sitodiplosis mosellana (Gehin) 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. RESULTS: 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). CONCLUSION: 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. (c) 2022 Society of Chemical Industry" |
| Keywords: | "Animals *Diptera Pheromones/pharmacology *Sex Attractants/pharmacology *Citrus sinensis (2S, 7S)-2, 7-Nonanediyl dibutyrate Sitodiplosis mosellana integrated pest management olfactometer orange wheat blossom midge sex pheromone;" |
| Notes: | "MedlineLi, Changkai Wu, Yuqing Yin, Xinming Gong, Zhongjun Xing, Hongxia Miao, Jin Wang, Shuzhi Liu, Jia Na, Risong Li, Qing X eng U1904111/Earmarked Fund for China Agriculture Research System/ U.S. Department of Agriculture/ National Natural Science Foundation of China/ England 2022/09/11 Pest Manag Sci. 2023 Jan; 79(1):97-104. doi: 10.1002/ps.7177. Epub 2022 Sep 22" |
