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5-乙氧羰基甲硫基-1,2,4-三唑席夫碱的合成及杀菌活性
引用本文:杨清翠,孙晓红,刘源发,陈邦,沈生强. 5-乙氧羰基甲硫基-1,2,4-三唑席夫碱的合成及杀菌活性[J]. 应用化学, 2014, 31(7): 788-792. DOI: 10.3724/SP.J.1095.2014.30488
作者姓名:杨清翠  孙晓红  刘源发  陈邦  沈生强
作者单位:(1.西北大学化工学院 西安 710069;2.西安建筑科技大学理学院 西安 710055;3.西北大学化工学院化学研究所 西安 710069;4.西北大学化学与材料科学学院 西安 710069)
基金项目:国家自然科学基金资助项目(21073141);陕西省教育厅自然科学专项基金资助项目(2013JK0666)~~
摘    要:以3-甲基-4-氨基-5-乙氧羰基甲硫基-1,2,4-三唑为原料,与取代芳醛合成9种3-甲基-4-(X-取代基苯亚甲基氨基)-5-乙氧羰基甲硫基-1,2,4-三唑席夫碱化合物a~i。 产物结构经1H NMR、IR和MS等技术手段确证。 其中化合物3-甲基-4-(4-羟基苯亚甲基氨基)-5-乙氧羰基甲硫基-1,2,4-三唑h进一步经X射线单晶衍射得到其晶体结构(CCDC:910927):C14H16N4O3S,Mr=320.37,Orthorhombic,P2(1)2(1)2(1)/n,a=0.9220(10) nm,b=1.5823(17) nm,c=2.1667(2) nm,V=3.161(6) nm3,Z=8,F(000)=1344。 化合物对4种植物病原菌的初步生物活性测试结果(EC95值)表明,化合物d、e、f对供试菌种西瓜枯萎病和小麦赤霉病的抑菌活性优于对照原药三唑酮。

关 键 词:席夫碱  甲基氨基乙氧羰基甲硫基三唑  合成  杀菌活性  
收稿时间:2013-09-26
修稿时间:2013-12-31

Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole
YANG Qingcui,SUN Xiaohong,LIU Yuanfa,CHEN Bang,SHEN Shengqiang. Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole[J]. Chinese Journal of Applied Chemistry, 2014, 31(7): 788-792. DOI: 10.3724/SP.J.1095.2014.30488
Authors:YANG Qingcui  SUN Xiaohong  LIU Yuanfa  CHEN Bang  SHEN Shengqiang
Affiliation:(1.College of Chemical Engineering,Northwest University,Xi′an 710069,China;2.School of Science,Xi′an University of Architecture and Technology,Xi′an 710055,China;3.Chemical Research Institute,College of Chemical Engineering,Northwest University,Xi′an 710069,China;4.College of Chemistry and Materials Science,Northwest University,Xi′an 710069,China)
Abstract:Nine Shiff bases 3-methyl-4-(X-substituted-benzylideneamino)-5-ethoxycarbonyl methylsulfanyl-1,2,4-triazole a~iwere synthesized from 3-methyl-4-amino-5-ethoxycarbonylmethyl sulfanyl-1,2,4-triazole and substituted aromatic aldehydes. The structures of synthetic compounds were confirmed by 1H NMR, IR, MS analyses.The crystal structure of 3-methyl-4-(4-hydroxybenzylideneamino)-5-ethoxycarbonylmethylsulfanyl-1,2,4-triazole h(CCDC:910927) was determined by X-ray diffraction as:C14H16N4O3S, Mr=320.37, Orthorhombic, P2(1)2(1)2(1)/n, a=0.9220(10) nm, b=1.5823(17) nm, c=2.1667(2) nm, V=3.161(6) nm3, Z=8, F(000)=1344. The antifungal activities of the new Schiff bases against four vegetable pathogens have been tested. The EC95 values of compounds d, e and fagainst Gibberlla saubinetii and Fusarium oxysporium f.s.p. niveum indicate that their antifungal activities are better than that of triadimefon.
Keywords:Schiff base  methyl-amino-ethoxycarbonylmethylsulfanyl-triazole  synthesis  antifungal activity
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