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2-（1,3,4-噻二唑胺甲基）苯酚的合成及其杀菌活性

唐子龙1,2*,常书红2,3,颜林2,刘汉文1,2   

  1. (1.湖南科技大学，理论化学与分子模拟省部共建教育部重点实验室 湘潭 411201；
    2.湖南科技大学化学化工学院 湘潭 411201；3.江西东邦药业有限公司 奉新 330700)
  • 收稿日期:2011-09-13 修回日期:2011-11-27 出版日期:2012-08-10 发布日期:2012-08-10
  • 通讯作者: 唐子龙，副教授; Tel:0731-58290187; Fax:0731-58290509; E-mail:zltang67@yahoo.com.cn; 研究方向：有机合成，药物化学
  • 基金资助:
    国家自然科学基金（21042011）资助项目；湖南省教育厅重点项目（10A034）；湖南省博士后基金课题（2010RS4033）

Synthesis and Fungicidal Activity of 2-(1,3,4-Thiadiazolylaminomethyl)phenols

TANG Zilong1,2*, CHANG Shuhong2,3, YAN Lin2, LIU Hanwen1,2   

  1. (1.Key Laboratory of Theoretical Chemistry and Molecular Simulation of
    Ministry of Education,Hunan University of Science and Technology,Xiangtan 411201,China;
    2.School of Chemistry and Chemical Engineering,Hunan University of Science and Technology，
    Hunan University of Science and Technology,Xiangtan 411201,China;
    3.Jiangxi Dongbang Pharmaceutical Co. Ltd.,Fengxin 330700,China)
  • Received:2011-09-13 Revised:2011-11-27 Published:2012-08-10 Online:2012-08-10

PDF

1083

被引次数

3

摘要： 以2-氨基-5-烃基-1,3,4-噻二唑和水杨醛为原料，分别用“分步法”和“一锅法”经还原中间产物Schiff碱的C=N双键合成了一系列2-（（1,3,4-噻二唑基）胺甲基）苯酚类新化合物，“一锅法”的产率较高，为56%~80%。 产物的结构用IR、1H NMR、13C NMR和MS进行了表征。 初步测试了目标化合物的杀菌活性，证明化合物对赤星病菌具有较好的抑菌活性，当浓度为25 mg/L时，化合物3i的抑制率为76%，化合物3f、3h、3k和3l的为70%。

关键词: 噻二唑胺甲基苯酚, 合成, 杀菌活性

Abstract: A series of 2-(1,3,4-thiadiazolylaminomethyl)phenols was synthesized by reducing the C=N double bond of the intermediate Schiff bases prepared from the reaction of 2-amino-5-alkyl(aryl)-1,3,4-thiadiazoles and salicylaldehyde via either fractional step method or one-pot process. The yields of the products obtained from one-pot synthesis were higher and in the range of 56%~80%. The structures of the products were characterized by means of IR, 1H NMR, 13C NMR and MS. The fungicidal activity of the title compounds was evaluated preliminarily, some of which exhibited moderate activity against Alternaria alternata. The inhibitory rate of compound 3i was 76% at the concentration of 25 mg/L, and 70% for compounds 3f, 3h, 3k and 3l.

Key words: thiadiazolylaminomethylphenol, synthesis, fungicidal activity

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