王颎琳, 孙效, 吴建伟, 边庆花, 王敏, 钟江春. 桃小食心虫性信息素的合成[J]. 农药学学报, 2024, 26(2): 402-407. DOI: 10.16801/j.issn.1008-7303.2024.0015
    引用本文: 王颎琳, 孙效, 吴建伟, 边庆花, 王敏, 钟江春. 桃小食心虫性信息素的合成[J]. 农药学学报, 2024, 26(2): 402-407. DOI: 10.16801/j.issn.1008-7303.2024.0015
    WANG Jionglin, SUN Xiao, WU Jianwei, BIAN Qinghua, WANG Min, ZHONG Jiangchun. Synthesis of the sex pheromone of the peach fruit moth, Carposina sasakii Matsumura[J]. Chinese Journal of Pesticide Science, 2024, 26(2): 402-407. DOI: 10.16801/j.issn.1008-7303.2024.0015
    Citation: WANG Jionglin, SUN Xiao, WU Jianwei, BIAN Qinghua, WANG Min, ZHONG Jiangchun. Synthesis of the sex pheromone of the peach fruit moth, Carposina sasakii Matsumura[J]. Chinese Journal of Pesticide Science, 2024, 26(2): 402-407. DOI: 10.16801/j.issn.1008-7303.2024.0015

    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

    • 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.

       

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