1,3-二取代-1<i>H</i>-1,2,4-三唑-5-胺类化合物的合成、结构表征及抑菌活性

引用本文: 贾长青, 苏旺苍, 徐彦军, 刘吉平, 覃兆海. 1,3-二取代-1H-1,2,4-三唑-5-胺类化合物的合成、结构表征及抑菌活性[J]. 有机化学, 2016, 36(4): 830-837. doi: 10.6023/cjoc201510021 shu

Citation: Jia Changqing, Su Wangcang, Xu Yanjun, Liu Jiping, Qin Zhaohai. Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-triazole-5-amines[J]. Chinese Journal of Organic Chemistry, 2016, 36(4): 830-837. doi: 10.6023/cjoc201510021 shu

1,3-二取代-1H-1,2,4-三唑-5-胺类化合物的合成、结构表征及抑菌活性

贾长青 ^a, ,
苏旺苍 ^b, ,
徐彦军 ^a, ,
刘吉平 ^a, ,
覃兆海 ^{a,
,}

a.
a. 中国农业大学理学院北京 100193;
b.
b. 河南农业科学院郑州 450002

通讯作者: 覃兆海

基金项目:
国家自然科学基金(No.31272076) (No.31272076)

农业部行业专项基金(No.2011BAE06B05-5)资助项目. (No.2011BAE06B05-5)

摘要: 以硝基胍、醛和卤代烷烃为原料,通过肼解、缩合、烷基化和酸催化分子内环化等反应,合成了一系列结构新颖的1,3-二取代-1H-1,2,4-三唑-5-胺类化合物,其结构经¹H NMR、¹³C NMR、IR以及HRMS等方法确证.初步离体抑菌活性测定表明,在50mg/L药剂浓度下,大部分化合物均具有一定的抑菌活性.相对于其他目标化合物,1-正丁基-3-(4-氯苯基)-1H-1,2,4-三唑-5-胺(6y)表现出较广谱的抑菌活性,对五种病原菌的抑菌活性均在53%以上.该类化合物合成简单,易于衍生化,可作为抑菌先导化合物进行优化.

关键词:

English

Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-triazole-5-amines

a.
a. College of Sciences, China. Agricultural University, Beijing 100193;
b.
b. Henan Academy of Agricultural Sciences, Zhengzhou 450002

Corresponding author: 覃兆海

Received Date: 19 October 2015
Available Online: 10 December 2015
Fund Project:
国家自然科学基金(No.31272076)

农业部行业专项基金(No.2011BAE06B05-5)资助项目.

Abstract: A novel series of 1,3-disubstituted-1H-1,2,4-triazole-5-amines were synthesized via hydrazinolysis, condensation, alkylation and acid-catalyzed intramolecular cyclization starting from nitroguanidine 1. Their structures were characterized by IR, ¹H NMR, ¹³C NMR and HRMS analysis. The preliminary bioassay indicated that most of them showed certain extent of growth inhibition in vitro against six phytopathogen fungi. Compared with other target compounds, 1-(n-butyl)-3- (4-chlorophenyl)-1H-1,2,4-triazole-5-amine (6y) was found to have high activity and the widest fungicidal spectrum. Its inhibition rates to five pathogens were all above 53%. This kind of compounds could be synthesized and derived easily, and were valuable as lead structure for future developing novel fungicides.

Key words:

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

1,3-二取代-1H-1,2,4-三唑-5-胺类化合物的合成、结构表征及抑菌活性

通讯作者: 覃兆海

English

Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-triazole-5-amines

Corresponding author: 覃兆海

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

1,3-二取代-1H-1,2,4-三唑-5-胺类化合物的合成、结构表征及抑菌活性

通讯作者: 覃兆海

English

Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-triazole-5-amines

Corresponding author: 覃兆海

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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