N-((5-烷硫基-1,3,4-噁二唑)-2-基)甲基溴代吡咯腈的合成及生物活性  

Synthesis and biological activity of N-((5-alkylthio-1,3,4-oxadiazole)-2-ylmethyl)tralopyril

作　　者：周蒲 黄俊杰 何昌文 郭倩男 游江 刘一凡 徐志红[1] ZHOU Pu;HUANG Junjie;HE Changwen;GUO Qiannan;YOU Jiang;LIU Yifan;XU Zhihong(School of Agriculture,Yangtze University,Jingzhou 434025,Hubei Province,China;Jingzhou Forest Protection Station,Jingzhou 434025,Hubei Province,China)

机构地区：[1]长江大学农学院,湖北荆州434025 [2]荆州市森林保护站,湖北荆州434025

出　　处：《农药学学报》2022年第6期1367-1376,共10页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31772170).

摘　　要：为了发现农药活性的新化合物,以溴代吡咯腈为原料,通过亲核取代、肼解和成环等反应,设计合成了一系列N-((5-烷硫基-1,3,4-噁二唑)-2-基)甲基溴代吡咯腈目标化合物(5a~5t),所有化合物的结构均得到核磁共振氢谱和高分辨质谱确证。杀菌活性测定结果显示:在浓度为0.20 mmol/L时,大部分目标化合物具有一定的抑菌活性,其中化合物5h对水稻稻瘟病菌Magnaporthe oryzae的抑制率为60.07%,优于对照药剂咯菌腈(58.21%)。杀虫与杀螨活性测定结果显示:在浓度为0.20 mmol/L时,大部分目标化合物对斜纹夜蛾Spodoptera litura和朱砂叶螨Tetranychus cinnabarinus雌成螨具有一定的杀虫和杀螨活性,但均低于对照药剂虫螨腈(100%)。杀线虫生物测定结果显示:在浓度为0.20 mmol/L时,大部分目标化合物表现出优异的杀线虫活性,其中化合物5k、5r和5s对秀丽隐杆线虫Caenorhabditis elegans的LC_(50)值分别为0.0918、0.0733和0.0810 mmol/L,优于对照药剂噻唑膦(0.2798 mmol/L)。本研究所合成的目标化合物具有一定的杀菌、杀虫、杀螨和杀线虫活性,可为溴代吡咯腈衍生物的设计和合成提供参考。In order to find new compounds with pesticide activity,a series of N-((5-alkylthio-1,3,4-oxadiazole)-2-methyl)tralopyril were designed and synthesized from tralopyril by nucleophilic substitution,hydrazinolysis and cyclization.The structures of these derivatives were confirmed by 1H NMR and HRMS.The test against 5 pathogenic fungi showed that most of the target compounds had certain fungicidal activity at the concentration of 0.20 mmol/L,and the inhibitory rate of compound 5h against Magnaporthe oryzae was 60.07%,which was better than that of the control agent fludioxonil(58.21%).The results of insecticidal and acaricidal activities showed that at the concentration of 0.20 mmol/L,some of the target compounds had certain insecticidal and acaricidal activities against Spodoptera litura and adult mite of Tetranychus cinnabarinus,while all were lower than the control agent chlorfenapyr(100%).The results of nematicidal activity showed that most of the compounds exhibited excellent nematicidal activity at the concentration of 0.20 mmol/L.The LC_(50) values of compounds 5k,5r and 5s against Caenorhabditis elegans were 0.0918,0.0733,0.0810 mmol/L respectively,which were better than the control agent fosthiazate(0.2798 mmol/L).The target compounds synthesized in this study have certain fungicidal,insecticidal,acaricidal and nematicidal activities,which can provide a reference for the design and synthesis of tralopyril derivatives.

关 键 词：溴代吡咯腈 1 3 4-噁二唑 硫醚 合成 生物活性 

分 类 号：O626.27[理学—有机化学] TQ450.11[理学—化学]