吡啶环修饰的昆虫激肽模拟物的合成及杀蚜活性

    Synthesis and aphicidal activity of insect kinin analogs modified with pyridine

    • 摘要: 为寻找新型杀蚜化合物,为农业生产提供更有效的虫害治理方案,本研究以课题组前期发现的高活性昆虫激肽模拟物Ⅳ-3为先导化合物,通过活性亚结构拼接,用吡啶环取代Ⅳ-3 N 端肉桂酰基团的苯乙烯部分,并保持其余四肽结构不变,设计并采用Fmoc固相合成法获得了12个未见文献报道的目标化合物,结构均通过 1H NMR、HRMS 确证。生物活性测试结果表明:目标化合物对大豆蚜均具有杀蚜活性,其中-10 (LC50 = 4.5 µmol/L) 的活性优于先导化合物 Ⅳ-3 (LC50 = 16.63 µmol/L) 和商品化杀蚜剂吡蚜酮 (LC50 = 19.75 µmol/L)。初步构效关系分析表明,杀蚜活性受吡啶环上取代基的位置和种类影响:当取代基相同时,4-位取代活性最佳;当取代基位置相同时,则以CF3 取代活性最佳;吡啶环与羰基之间的碳链长度对活性无明显影响。研究结果对新型小肽类杀蚜剂的创制具有参考价值。

       

      Abstract: To discover novel aphicidal compounds and provide more effective pest management solutions for agricultural production, the highly active insect kinin mimic Ⅳ-3, previously discovered by our research group, was selected as a lead compound. A total of 12 novel target analogs were designed by replacing the styrene moiety of the cinnamoyl group at the N-terminus with a pyridine ring fragment through active substructure stitching while maintaining the tetrapeptide structure, and prepared using the Fmoc solid-phase synthesis method. Their structures were confirmed by HRMS and 1H NMR. The bioassay results showed that all the target compounds had aphicidal activity against A. glycines. The activity of Ⅱ-10 (LC50 = 4.5 µmol/L) was superior to that of the lead compound Ⅳ-3 (LC50 = 16.63 µmol/L) and the commercially available pymetrozine (LC50 = 19.75 µmol/L). Preliminary structure-activity relationship analysis suggested that aphicidal efficacy is influenced by both the position and the type of substituents on the pyridine ring, with the 4-position substitution and CF3 substituent proving most effective. This study provides valuable insights for the development of novel insect kinin-based aphicides.

       

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