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第 36 卷第 5 期 精 细 化 工 Vol.36, No.5
201 9 年 5 月 FINE CHEMICALS May 2019

医药与日化原料
2-取代-4-氯-5-芳基-2H-1,2,3-三唑类

化合物的合成及生物活性

*
李孙勇，博 瑞，李元祥
（怀化学院 化学与材料工程学院，有机合成研究所，湖南 怀化 418008）

摘要：以芳醛、硝基甲烷及叠氮化钠为起始原料，经环化、氯化、烃化反应，以收率 53%~94%合成了 15 个 2-
取代-4-氯-5-芳基- 2H-1,2,3-三唑类化合物（Ⅳa~o），经核磁共振波谱、质谱和元素分析对目标化合物的结构进
行确证。采用菌丝生长速率测定法，在质量浓度 25 mg/L 下，目标化合物对小麦赤霉病菌、辣椒疫霉病菌、烟
草赤星病菌、黄瓜灰霉病菌、水稻纹枯病菌及油菜菌核病菌 6 种作物病菌进行离体抑菌活性实验。初步的抑菌
活性测试结果表明：化合物Ⅳd 对小麦赤霉病菌、黄瓜灰霉病菌及油菜菌核病菌的抑制率分别为 70.4%、74.1%
和 72.9%，化合物Ⅳk 对黄瓜灰霉病菌及油菜菌核病菌的抑制率分别为 87.0%及 84.7%。Ⅳd 对辣椒疫霉病菌的
抑制率为 61.4%，高于商品化品种苯醚甲环唑的 42.5%。
关键词：1,2,3-三唑；氯化；烃化；结构表征；杀菌活性
中图分类号：O622.6 文献标识码：A 文章编号：1003-5214 (2019) 05-0951-06

Synthesis and Biological Activity of 2-Substituted-4-chloro-
5-aryl-2H-1,2,3-triazole Derivatives

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LI Sun-yong, BO Rui, LI Yuan-xiang
（College of Chemistry and Materials Engineering, Institute of Organic Synthesis, Huaihua University, Huaihua
418008, Hunan, China）

Abstract: Fifteen 2-substituted-4-chloro-5-aryl-2H-1,2,3-triazole derivatives(Ⅳa~o) were synthesized using
aryl aldehyde, nitromethane and sodium azide as starting materials by cyclization, chlorination and
1
alkylation reactions with the yield of 53%~94%. The structures of title compounds were confirmed by HNMR,
13
CNMR, mass spectra and elemental analysis techniques. Their antifungal activities were evaluated in vitro
against six phytopathogenic fungi (Gibberella zeae, Phytophythora capsici, Alternaria alternate, Botrytis
cinerea, Rhizoctonia solani and Sclerotonia sclerotiorum) using mycelium growth rate method at 25 mg/L.
The results of bioassay showed that some compounds exhibited excellent fungicidal activities. For example,
the inhibition rates of compound Ⅳd against Gibberella zeae, Botrytis cinerea and Sclerotonia sclerotiorum
were 70.4%, 74.1% and 72.9%, respectively. The inhibition rates of compound Ⅳk against Botrytis cinerea
and Sclerotonia sclerotiorum were 87.0% and 84.7%, respectively. The inhibition rate of Ⅳd against
Phytophythora capsici was 61.4%, which was higher than that of commercial difenoconazole 42.5%.
Key words: 1,2,3-triazole; chlorination; alkylation; structural characterization; fungicidal activity
Foundation items: Natural Science Foundation of Hunan Province (2016JJ4072); Scientific Research Fund
of Hunan Provincial Education Department (16A165); Constructing Program of the Key Discipline Finance
in Huaihua University

[1]
三唑富氮化合物通常具有含氮量高、密度大、 分子间易形成氢键等特点 。三唑环是酰胺键的电

收稿日期：2018-09-18; 定用日期：2019-01-10; DOI: 10.13550/j.jxhg.20180697
基金项目：湖南省自然科学基金项目（2016JJ4072）；湖南省教育厅科学研究重点项目（16A165）；怀化学院重点学科资助课题
作者简介：李孙勇（1995—），男，硕士生。联系人：李元祥（1968—），男，博士，教授，E-mail：hhxyliyuanjun@163.com。