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

作　　者：张馨元 李欣潞[1] 张怡萌 陈黛妮 孙文玉 钟震宇 杨新玲[1] ZHANG Xinyuan;LI Xinlu;ZHANG Yimeng;CHANDNI Iqbal;SUN Wenyu;ZHONG Zhenyu;YANG Xinling(Innovation Center of Pesticide Research,Department of Applied Chemistry,College of Science,China Agricultural University,Beijing 100193,China)

机构地区：[1]中国农业大学理学院应用化学系农药创新中心,北京100193

出　　处：《农药学学报》2025年第1期33-39,共7页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(No.21877126).

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Ⅱ-10(LC_(50)=4.5μmol/L)的活性优于先导化合物Ⅳ-3(LC_(50)=16.63μmol/L)和商品化杀蚜剂吡蚜酮(LC_(50)=19.75μmol/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。To discover novel aphicidal compounds and provide more effective pest management solutions for agricultural production,the highly active insect kinin mimicⅣ-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 ofⅡ-10(LC_(50)=4.5μmol/L)was superior to that of the lead compoundⅣ-3(LC_(50)=16.63μmol/L)and the commercially available pymetrozine(LC_(50)=19.75μmol/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.

关 键 词：昆虫激肽模拟物 吡啶 合成 杀蚜活性 构效关系 

分 类 号：TQ450.1[化学工程—农药化工] S482.3[农业科学—农药学]