有机化学 ›› 2012, Vol. 32 ›› Issue (11): 2129-2133.DOI: 10.6023/cjoc201205016 上一篇    下一篇

研究论文

2-(1H-苯并咪唑-2-基)-5-取代-1,3,4-噁二唑化合物的合成及抑菌活性

纪增臣a, 刘峰a, 张泽远b, 李付博a, 姜林b   

  1. a 山东农业大学植物保护学院 泰安 271018;
    b 山东农业大学化学与材料科学学院 泰安 271018
  • 收稿日期:2012-05-12 修回日期:2012-07-05 发布日期:2012-07-09
  • 通讯作者: 姜林 E-mail:jiangl@sdau.edu.cn
  • 基金资助:

    山东省自然科学基金(No. ZR2009BM044)资助项目.

Synthesis and Antifungal Activity of Novel 2-(1H-Benzimidazol-2-yl)-5-substituted-1,3,4-oxadiazole Derivatives

Ji Zengchena, Liu Fenga, Zhang Zeyuanb, Li Fuboa, Jiang Linb   

  1. a College of Plant Protection, Shandong Agricultural University, Taian 271018;
    b College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018
  • Received:2012-05-12 Revised:2012-07-05 Published:2012-07-09
  • Supported by:

    Project supported by the Natural Science Foundation of Shandong Province (No. ZR2009BM044).

以苯并咪唑-2-甲酸、水合肼、取代苯基异硫氰酸酯和取代苯甲酸等为原料, 经多步反应合成了16种2-(苯并咪唑-2-基)-5-取代苯基-1,3,4-噁二唑和2-(苯并咪唑-2-基)-5-取代苯胺基-1,3,4-噁二唑新化合物, 并考察了微波辐射对反应的影响. 产物结构利用IR, 1H NMR, 13C NMR和元素分析确证. 用生长速率法测试了目标化合物对番茄灰霉病菌和小麦菌核病菌的离体抑制活性, 结果表明3种化合物对番茄灰霉病菌有很高的抑制活性, 其EC50分别为2.55, 6.34和5.12 μg/mL, 活性高于对照药剂多菌灵(EC50 =7.40 μg/mL).

关键词: 苯并咪唑, 1,3,4-噁二唑, 合成, 抑菌活性

Sixteen novel 2-(1H-benzimidazol-2-yl)-5-substituted phenyl-1,3,4-oxadiazoles and 2-(1H-benzimidazol-2-yl)-5-substituted phenylamino-1,3,4-oxadiazoles were synthesized from benzimidazole-2-carboxylic acid, hydrazine hydrate, substituted phenyl isothiocyanate and substituted benzoic acid by multi-step reactions. The target compounds were evaluated for their antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum, and the results indicated that three target compounds displayed excellent antifungal activities against Botrytis cinerea, with EC50 values of 2.55, 6.34 and 5.12 μg/mL, respectively, even higher than that of carbendazim.

Key words: benzimidazole, 1,3,4-oxadiazole, synthesis, antifungal activity