邓珅钏, 李旭军, 朱祥, 杜晓英, 李俊凯, 徐志红. 新型三唑哌嗪类衍生物的合成及生物活性[J]. 农药学学报, 2021, 23(2): 269-278. DOI: 10.16801/j.issn.1008-7303.2021.0009
    引用本文: 邓珅钏, 李旭军, 朱祥, 杜晓英, 李俊凯, 徐志红. 新型三唑哌嗪类衍生物的合成及生物活性[J]. 农药学学报, 2021, 23(2): 269-278. DOI: 10.16801/j.issn.1008-7303.2021.0009
    DENG Shenchuan, LI Xujun, ZHU Xiang, DU Xiaoying, LI Junkai, XU Zhihong. Synthesis and biological activities of novel triazole piperzazine derivatives[J]. Chinese Journal of Pesticide Science, 2021, 23(2): 269-278. DOI: 10.16801/j.issn.1008-7303.2021.0009
    Citation: DENG Shenchuan, LI Xujun, ZHU Xiang, DU Xiaoying, LI Junkai, XU Zhihong. Synthesis and biological activities of novel triazole piperzazine derivatives[J]. Chinese Journal of Pesticide Science, 2021, 23(2): 269-278. DOI: 10.16801/j.issn.1008-7303.2021.0009

    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

    • 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1H NMR、13C 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200 μmol/L下,化合物 7n7r7s 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49.49 μmol/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。

       

      Abstract: 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 1H NMR, 13C 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.

       

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