新型三唑哌嗪类衍生物的合成及生物活性  

Synthesis and biological activities of novel triazole piperzazine derivatives

作　　者：邓珅钏 李旭军 朱祥[1] 杜晓英[1,2] 李俊凯[1,2] 徐志红[1,2] DENG Shenchuan;LI Xujun;ZHU Xiang;DU Xiaoying;LI Junkai;XU Zhihong(School of Agriculture,Yangtze University,Jingzhou 434025,Hubei Province,China;Institute of Pesticides,Yangtze University,Jingzhou 434025,Hubei Province,China)

机构地区：[1]长江大学农学院,湖北荆州434025 [2]长江大学农药研究所,湖北荆州434025

出　　处：《农药学学报》2021年第2期269-278,共10页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31772170)。

摘　　要：以1,2,4-三唑、2-氯-2,4-二氟苯乙酮和哌嗪为原料,通过活性亚结构拼接合成了一个系列20个新型三唑哌嗪类衍生物7a~7t,其结构均经过了^(1)H NMR、^(13)C NMR和高分辨质谱确证。分别采用菌丝生长速率法和触杀法测定了目标化合物的杀菌活性和杀虫活性。杀菌活性测定结果显示:大部分化合物对小麦赤霉病菌、水稻纹枯病菌和水稻稻瘟病菌具有良好的抑制作用,在200μmol/L下,化合物7n、7r和7s对小麦赤霉病菌的抑制率分别为60.19%、62.27%和50.00%,与对照药剂三唑酮抑菌效果相当;化合物7r对水稻纹枯病菌的EC50值为49.49μmol/L。杀虫活性测定结果显示,在100 mg/L时,化合物7o对斜纹夜蛾幼虫的致死率为40.00%,略低于对照药剂氰氟虫腙(46.67%)。本研究所合成的新化合物兼具杀菌和杀虫活性,可为新型三唑哌嗪类衍生物的生物活性研究提供参考。Twenty novel triazole piperzazine derivatives 7a-7t were synthesized using 1,2,4-triazol,2-chloro-1-(2,4-difluorophenyl) ethanone and piperzazine compounds as the starting materials, through the combination of active substructures. All target compounds were characterized by ^(1)H NMR, ^(13)C NMR and HRMS. The fungicidal activities and insecticide activities of compounds were evaluated by the hyphal growth rate method and the drop method. The results showed that most of those compounds exhibited high inhibitory effects against Rhizoctonia solani, Fusarium graminearum and Magnaporthe oryzae. Compounds 7n, 7r and 7s exhibited good fungicidal activities with the inhibition rate of 60.19%, 62.27% and 50.00% against F. graminearum at the concentration of 200 μmol/L,resepectively. They were equal to triadimenol. And the EC50 value of compound 7r was 49.49 μmol/L against R. solani. Moreover, The results indicated that compound 7o showed 40.00% mortality rate against Spodoptera litura larva at 100 mg/L, which was slightly lower than that of the commercial insecticide cyhalothrin(46.67%). The compounds with good fungicidal activities and insecticidal activities were synthesized in this work, which provided a reference for the activity study for novel triazole piperzazine derivatives.

关 键 词：三唑化合物 哌嗪 活性亚结构 杀菌活性 杀虫活性 

分 类 号：O626.26[理学—有机化学] TQ450.11[理学—化学]