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

doi:10.6023/cjoc201510021

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (4): 830-837.DOI: 10.6023/cjoc201510021 Previous Articles Next Articles

ARTICLE

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

收稿日期:2015-10-19 修回日期:2015-11-19 发布日期:2015-12-10
通讯作者: 覃兆海 E-mail:qinzhaohai@263.net
基金资助:
国家自然科学基金(No.31272076)和农业部行业专项基金(No.2011BAE06B05-5)资助项目.

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

Jia Changqing^a, Su Wangcang^b, Xu Yanjun^a, Liu Jiping^a, Qin Zhaohai^a

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

Received:2015-10-19 Revised:2015-11-19 Published:2015-12-10
Supported by:
Project supported by the National Natural Science Foundation of China (No. 31272076) and the National Scientific and Technology Supporting Program of China (No. 2011BAE06B05-5).

1. Synthesis, Structure Characterization and Fungicidal Activity of 1,3-Disubstituted-1H-1,2,4-triazole-5-amines.PDF(5315KB)

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: 1H-1,2,4-triazole-5-amine, synthesis, intramolecular cyclization, fungicidal activity

Cite this article

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]. Chin. J. Org. Chem., 2016, 36(4): 830-837.

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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

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

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