游江, 高亚强, 周蒲, 郭倩男, 徐志红. N-取代苯基-1-(2,4-二氟苯基)-2-(1H-1,2,4-三唑-1-基)乙基氨基甲酸酯的合成及生物活性[J]. 农药学学报, 2022, 24(4): 723-731. DOI: 10.16801/j.issn.1008-7303.2022.0016
    引用本文: 游江, 高亚强, 周蒲, 郭倩男, 徐志红. N-取代苯基-1-(2,4-二氟苯基)-2-(1H-1,2,4-三唑-1-基)乙基氨基甲酸酯的合成及生物活性[J]. 农药学学报, 2022, 24(4): 723-731. DOI: 10.16801/j.issn.1008-7303.2022.0016
    YOU Jiang, GAO Yaqiang, ZHOU Pu, GUO Qiannan, XU Zhihong. Synthesis and biological activity of N-substituted phenyl-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylcarbamate[J]. Chinese Journal of Pesticide Science, 2022, 24(4): 723-731. DOI: 10.16801/j.issn.1008-7303.2022.0016
    Citation: YOU Jiang, GAO Yaqiang, ZHOU Pu, GUO Qiannan, XU Zhihong. Synthesis and biological activity of N-substituted phenyl-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylcarbamate[J]. Chinese Journal of Pesticide Science, 2022, 24(4): 723-731. DOI: 10.16801/j.issn.1008-7303.2022.0016

    N-取代苯基-1-(2,4-二氟苯基)-2-(1H-1,2,4-三唑-1-基)乙基氨基甲酸酯的合成及生物活性

    Synthesis and biological activity of N-substituted phenyl-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethylcarbamate

    • 摘要: 为了寻找高活性的三唑类苯基氨基甲酸酯衍生物,以 1,2,4-三氮唑、2-氯-2,4-二氟苯乙酮为原料,采用活性亚结构拼接的策略,设计并合成了18个未见文献报道的N-取代苯基-1-(2,4-二氟苯基)-2-(1H-1,2,4-三唑-1-基)乙基氨基甲酸酯衍生物 6a ~ 6r 。其结构均通过 1H NMR、13C NMR和高分辨质谱(HRMS)的确证。抑菌活性测定结果显示:在100 μmol/L下,化合物 6m 对6种供试真菌具有良好的抑制作用,抑制率均达到50%以上。化合物 6p 对油菜菌核病菌Sclerotinia sclerotiorum的EC50值为7.1 μmol/L,抑菌活性高于对照药剂烯唑醇(EC50值9.1 μmol/L)。杀螨活性测定结果显示,在150 μmol/L时,化合物 6h6k6o 在48 h时对朱砂叶螨Tetranychus cinnabarinus的致死率分别为67.7%、74.9%和57.5%,杀螨活性低于对照药剂阿维菌素B1a(致死率100%)。本研究所合成的化合物 6o 兼具一定杀菌和杀螨活性,可为新型三唑类杀菌杀螨化合物的设计与研究提供参考。

       

      Abstract: In order to find highly active triazole phenyl carbamate derivatives, 1,2,4-triazole and 2-chloro-2,4-difluoroacetophenone were used as raw materials, and the strategy of active substructure splicing was adopted, eighteen N-substituted phenyl-1-(2,4-difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethyl carbamate derivatives 6a-6r were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR and high resolution mass spectrometry (HRMS). The results of fungicidal activity assay showed that compound 6m had a good inhibitory effect on the 6 tested fungi at 100 μmol/L with a inhibition rate of more than 50%. The EC50 value of compound 6p against Sclerotinia sclerotiorum was 7.1 μmol/L, the fungicidal activity was higher than that of the control compound diniconazole (EC50 value was 9.1 μmol/L). The results of acaricidal activity showed that at 150 μmol/L, the lethal rates of compounds 6h , 6k and 6o were 67.7%, 74.9% and 57.5% for Tetranychus cinnabarinus at 48 h, respectively, and the acaricidal activity was lower than that of the control compound abamectin B1a (100%). The compound 6o synthesized in this study has both fungicidal and acaricidal activities, which can provide a reference for the design and research of novel fungicidal and acaricidal triazole compounds.

       

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