高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (5): 892-901.doi: 10.7503/cjcu20160065

• 有机化学 • 上一篇    下一篇

1H-1,2,4-三唑-5-氨基甲酸酯类化合物的合成、 结构表征及杀虫、 抑菌活性

贾长青1, 杨冬燕1, 车传亮1, 马永强1, 芮昌辉2, 闫晓静2, 覃兆海1()   

  1. 1. 中国农业大学理学院, 北京 100193
    2. 中国农业科学院植物保护研究所, 北京 100193
  • 收稿日期:2016-01-26 出版日期:2016-05-10 发布日期:2016-04-18
  • 作者简介:联系人简介: 覃兆海, 男, 博士, 教授, 博士生导师, 主要从事新农药创制研究. E-mail:qinzhaohai@263.net
  • 基金资助:
    国家自然科学基金(批准号: 31272076)资助

Synthesis, Structural Characterization, Insecticidal and Fungicidal Activity of (1H-1,2,4-Triazol-5-yl)carbamates

JIA Changqing1, YANG Dongyan1, CHE Chuanliang1, MA Yongqiang1, RUI Changhui2, YAN Xiaojing2, QIN Zhaohai1,*()   

  1. 1. College of Science, China Agricultural University, Beijing 100193, China
    2. Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China
  • Received:2016-01-26 Online:2016-05-10 Published:2016-04-18
  • Contact: QIN Zhaohai E-mail:qinzhaohai@263.net
  • Supported by:
    † Supported by the National Natural Science Foundation of China(No.31272076)

摘要:

通过活性基团拼接的方法, 将氨基甲酸酯结构和1H-1,2,4-三唑-5-胺有机结合, 设计合成了一系列结构新颖的多取代1H-1,2,4-三唑-5-氨基甲酸酯类化合物(5和6), 所有化合物的结构经核磁共振(NMR), 红外光谱(IR), 高分辨质谱(HRMS)及元素分析等方法确证.初步杀虫活性测定结果表明, 大部分化合物对桃蚜[Myzus persicae(Sulzer)]具有良好的杀虫活性, 致死率大于90%. 精密毒力测试结果表明, 化合物5b的半致死浓度(LC50)为9.49 μg/mL, 具有进一步研究开发的价值.抑菌活性初步测试结果表明该类化合物的抑菌活性一般, 在50 μg/mL浓度下少数化合物也表现出一定的离体抑菌活性. 对此类化合物的构效关系进行了讨论.

关键词: 1H-1,2,4-三唑-5-胺, 氨基甲酸酯, 杀虫活性, 抑菌活性

Abstract:

A series of novel (1H-1,2,4-triazol-5-yl)carbamates(5 and 6) was synthesized via the method of combining the crucial sub-structures of carbamates and 1H-1,2,4-triazole-5-amines in one molecules. Their structures were characterized by nuclear magnetic resonance(NMR), infrared(IR) spectrometry, high resolution mass spectrometry(HRMS) and elemental analysis. The preliminary insecticidal activity assays indicated that the lethal rates of target compounds to Myzus persicae were good at the concentration of 500 μg/mL. And the lethal rate of several compounds was more than 90%. Further research of these compounds against Myzus persicae indicated that compound 5b showed considerably high activity with a LC50 of 9.49 μg/mL, which confirmed that these compounds are valuable for further study. The preliminary fungicidal activity assays indicated that these compounds exhibited low fungicidal activity against tested fugi in vitro. At a dose of 50 μg/mL, only a few of compounds gave limited inhibition on mycelium growth. In addition, the structure-activity relationship was also discussed.

Key words: 1H-1,2,4-triazole-5-amine, Carbamate, Insecticidal activity, Fungicidal activity

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