有机化学 ›› 2015, Vol. 35 ›› Issue (10): 2229-2233.DOI: 10.6023/cjoc201504018 上一篇    下一篇

研究简报

含吗啉环的2-苯并咪唑基氰基甲酮肟醚的合成及杀菌活性

曲智强, 李付博, 邢程远, 姜林   

  1. 山东农业大学化学与材料科学学院 泰安 271018
  • 收稿日期:2015-04-13 修回日期:2015-05-29 发布日期:2015-06-04
  • 通讯作者: 姜林 E-mail:jiangl@sdau.edu.cn
  • 基金资助:

    山东省科技发展计划(No. 2013GZX20109)资助项目.

Synthesis and Antifungal Activity of Novel Benzimidazol-2-ylcyanoketone Oxime Ethers Containing Morpholine Moiety

Qu Zhiqiang, Li Fubo, Xing Chengyuan, Jiang Lin   

  1. College of Chemistry and Material Science, Shandong Agricultural University, Taian 271018
  • Received:2015-04-13 Revised:2015-05-29 Published:2015-06-04
  • Supported by:

    Project supported by the Science and Technology Development Plan of Shandong Province (No. ZR2013GZX20109).

利用活性结构拼接原理, 以2-苯并咪唑乙腈、亚硝酸钠、氯乙酰吗啉、卤代烃等为原料, 经过肟化、取代和醚化等三步反应合成了一系列新型的[1-(4-吗啉基)羰基亚甲基苯并咪唑-2-基]氰基甲酮肟醚(4a4h), 其结构经IR, NMR, MS和元素分析确认. 初步生物活性测试结果表明, 部分化合物对生菜灰霉菌和番茄菌核菌有较高的抑制活性, 与对照药剂多菌灵相比, 含4-氟苄基或4-氯苄基的化合物4e, 4f活性优异.

关键词: 肟醚, 苯并咪唑, 吗啉, 杀菌活性

A series of benzimidazol-2-ylcyanoketone oxime ethers containing morpholine moiety (4a4h) were synthesized from 2-benzimidazolyl acetonitrile, sodium nitrite, chloroacetyl morpholine and haloalkane/benzyl chloride via sequential reactions of oximation, substitution and etherification. The structures of the target compounds were elucidated by IR, NMR, MS, and elemental analysis. All the target compounds were tested for in vitro antifungal activities against Botrytis cinerea and Sclerotinia sclerotiorum by the mycelium growth rate test, and the results indicated that some compounds displayed higher antifungal activity as compared to carbendazim, among which the compounds containing 4-fluorobenzyl or 4-chlorobenzyl moiety (4e, 4f) have excellent activity.

Key words: oxime ether, benzimidazole, morpholine, antifungal activity