1,2,4-二唑类衍生物的设计、合成及抗菌活性  

Design,synthesis and anti-fungal activity of 1,2,4-oxadiazole derivatives

作　　者：王锋 陈钰[2] 裴鸿艳 刘东东 张静 张立新[1,2] WANG Feng;CHEN Yu;PEI Hongyan;LIU Dongdong;ZHANG Jing;ZHANG Lixin(College of Chemical Engineering,University of Science and Technology Liaoning,Anshan 114051,Liaoning,China;Institute of Functional Molecules,Shenyang University of Chemical Technology,Shenyang 110142,Liaoning,China)

机构地区：[1]辽宁科技大学化学工程学院,辽宁鞍山114051 [2]沈阳化工大学功能分子研究所,辽宁沈阳110142

出　　处：《化工学报》2023年第3期1390-1398,共9页CIESC Journal

基　　金：南宁市科技研究与技术开发计划项目重大科技专项(20201043);南宁市创新创业领军人才“邕江计划”创业项目(2020002-1)。

摘　　要：大豆锈病是危害大豆生产的主要真菌病害。为了研发新型高效的杀菌剂,以N-(4-(5-(三氟甲基)-1,2,4-二唑-3-基)苯基)环丙甲酰胺为先导化合物,采用结构修饰的方法,引入新的取代基,以此设计了12个新型1,2,4-二唑类衍生物,通过肟化、合环、还原及缩合反应,合成得到,经1H NMR和ESI-MS确证化学结构。测试了它们对大豆锈病的抗菌活性:当质量浓度为3.125 mg/L时,化合物5b、5d、6a、6e和6g对大豆锈病的抑制率分别为60%、65%、100%、98%和95%,优于对照药剂苯醚甲环唑(50%);化合物6a抗菌活性优异,当质量浓度为0.39125 mg/L时,对大豆锈病仍有90%抑制率。分子对接的结果说明,化合物6a与组蛋白去乙酰化酶4(HDAC 4)和组蛋白去乙酰化酶7(HDAC 7)有着多种相互作用。Soybean rust is one of the main fungal diseases affecting soybean production.To develop novel and highly effective fungicide,N-(4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl)cyclopropanecarboxamide was used as the lead compound.Using the method of structural modification and introducing new substituents,12 new 1,2,4-oxadiazole derivatives were designed,synthesized through oximation,ring closure,reduction and condensation reactions.Their chemical structures were characterized by 1H NMR and ESI-MS.The bioassay results showed that the inhibition rates of compounds 5b,5d,6a,6e and 6g against soybean rust at the concentration of 3.125 mg/L were 60%,65%,100%,98%and 95%,respectively.The activities were all better than that of control agent difenoconazole(50%).Compound 6a displayed prominent anti-fungal activity.When the mass concentration was 0.39125 mg/L,it still had 90%inhibition rate against soybean rust.The molecular docking results showed that compound 6a had various interactions with histone deacetylase 4(HDAC4)and histone deacetylase 7(HDAC7).

关 键 词：大豆锈病 1 2 4-二唑 设计 反应 合成 抗菌活性 分子对接 

分 类 号：TQ455.4[化学工程—农药化工]