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

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 6h 、 6k 和 6o 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。

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

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.