有机化学 ›› 2014, Vol. 34 ›› Issue (11): 2272-2278.DOI: 10.6023/cjoc201406021 上一篇    下一篇

研究论文

2-(2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-(1,2,4-三唑-1-甲基)-1,3-二氧戊环的合成与杀菌活性

李婉a, 唐建刚a, 胡艾希a, 叶姣a, 杨子辉a, 欧晓明b   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 湖南化工研究院 长沙 410007
  • 收稿日期:2014-06-15 修回日期:2014-07-07 出版日期:2014-11-25 发布日期:2014-07-15
  • 通讯作者: 胡艾希,axhu@hnu.edu.cn E-mail:axhu@hnu.edu.cn
  • 基金资助:

    国家科技部科技支撑计划(No.2011BAE06B01)资助项目.

Synthesis and Fungicidal Activity of 2-(2,2-Dimethyl-2,3-dihydro-benzofuran-5-yl)-2-(1,2,4-triazole-1-methyl)-1,3-dioxolane

Li Wana, Tang Jianganga, Hu Aixia, Ye Jiaoa, Yang Zihuia, Ou Xiaomingb   

  1. a Colleage of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Hunan Research Institute of Chemical Industry, Changsha 410007
  • Received:2014-06-15 Revised:2014-07-07 Online:2014-11-25 Published:2014-07-15
  • Supported by:

    Project supported by the State Commission of Science Technology of China (No.2011BAE06B01).

以对羟基苯乙酮为原料, 经醚化、Claisen重排、环合得2,2-二甲基-5-乙酰基-2,3-二氢苯并呋喃(4a). 2,2-二甲基- 5-乙酰基-2,3-二氢苯并呋喃(4a~4c)经卤代、缩酮化、取代反应得12种2-(2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-(1,2,4-三唑-1-甲基)-1,3-二氧戊环(1a~1l). 化合物经NMR, 元素分析等确证结构, 并测试了其对7种植物病菌的抑制活性, 结果显示化合物1a, 1b, 1e, 1f, 1g1l对油菜菌核病菌的抑制率均大于70% (25 mg/L), 化合物1a1b对小麦白粉病菌杀灭活性较好, 抑制率均为80.0% (500 mg/L).

关键词: 1,3-二氧戊环, 2,2-二甲基-2,3-二氢苯并呋喃, 1,2,4-三唑, 杀菌活性

Benzofuran and 1,2,4-triazole have been rewarded with much priority for their broad spectrum of biological activities, especially in the agricultural field. In this specific domain, they have always been used as fungicides, pesticide and plant growth regulators etc. Consequently, a series of new compounds containing 1,2,4-triazole, 1,3-dioxolane and benzofuran moieties were designed and synthesized. 1-(2,2-Dimethyl-2,3-dihydrobenzofuran-5-yl)ethanone (4a) were prepared from 1-(4-hydroxyphenyl)ethanone in three steps. Subsequently, 2-(2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-(1,2,4-triazol-1-methyl)-1,3-dioxolane (1a~1l) were synthesized from compounds 4a~4c. All compounds were verified by NMR and elemental analysis. Additionally, their fungicidal activities were evaluated against 7 kinds of crop fungus. The compounds 1a, 1b, 1e, 1f, 1g and 1l had relatively good inhibitory activity against Sclerotonia sclerotiorum, and the inhibitory rate were above 70% at 25 mg/L. Meanwhile, compounds 1a and 1b possessed potent inhibitory activity (80%) against Blumeria graminis at 500 mg/L.

Key words: 1,3-dioxolane, 2,2-dimethyl-2,3-dihydrobenzofuran, 1,2,4-triazole, fungicidal activity