5-乙氧羰基甲硫基-1,2,4-三唑席夫碱的合成及杀菌活性

doi:10.3724/SP.J.1095.2014.30488

摘要/Abstract

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

Abstract: Nine Shiff bases 3-methyl-4-(X-substituted-benzylideneamino)-5-ethoxycarbonyl methylsulfanyl-1,2,4-triazole a～i were 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 f against Gibberlla saubinetii and Fusarium oxysporium f.s.p. niveum indicate that their antifungal activities are better than that of triadimefon.

Key words: Schiff base, methyl-amino-ethoxycarbonylmethylsulfanyl-triazole, synthesis, antifungal activity

中图分类号:

O622.6

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, DOI: 10.3724/SP.J.1095.2014.30488.

YANG Qingcui1,2, SUN Xiaohong1,3*, LIU Yuanfa4, CHEN Bang4, SHEN Shengqiang3. Synthesis and Antifungal Activity of Schiff Bases of 5-Ethoxycarbonylmethylsulfanyl-1,2,4-triazole[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30488.

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