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

作　　者：游江 高亚强 周蒲 郭倩男 徐志红[1,2] YOU Jiang;GAO Yaqiang;ZHOU Pu;GUO Qiannan;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》2022年第4期723-731,共9页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31772170).

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^(1)H NMR、^(13)C NMR和高分辨质谱(HRMS)的确证。抑菌活性测定结果显示:在100μmol/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EC_(50)值为7.1μmol/L,抑菌活性高于对照药剂烯唑醇(EC_(50)值9.1μmol/L)。杀螨活性测定结果显示,在150μmol/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。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 ^(1)H NMR,^(13)C 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 100μmol/L with a inhibition rate of more than 50%.The EC_(50) value of compound 6p against Sclerotinia sclerotiorum was 7.1μmol/L,the fungicidal activity was higher than that of the control compound diniconazole(EC_(50) value was 9.1μmol/L).The results of acaricidal activity showed that at 150μmol/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.

关 键 词：1 2 4-三唑 氨基甲酸酯 杀菌活性 杀螨活性 

分 类 号：O626.2[理学—有机化学] TQ450.11[理学—化学]