有机化学 ›› 2015, Vol. 35 ›› Issue (5): 1166-1172.DOI: 10.6023/cjoc201410041 上一篇    下一篇

研究简报

新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮的合成及杀菌活性

阮铃莉a, 范人杰a, 刘幸海a, 陈杰b, 翁建全a   

  1. a 浙江工业大学化学工程学院 杭州 310032;
    b 国家南方农药创制中心浙江基地生测部 杭州 310023
  • 收稿日期:2014-10-31 修回日期:2014-12-14 发布日期:2015-01-07
  • 通讯作者: 翁建全 E-mail:jqweng@zjut.edu.cn
  • 基金资助:

    国家自然科学基金(No.30900959)和浙江省公益性(No.2014C31127)资助项目.

Synthesis and Antifungal Activity of Novel 3-[(5-Benzylthio- 1,3,4-oxadiazol-2-yl)methyl]benzo[d]thiazol- (oxazol)-2(3H)-ones

Ruan Linglia, Fan Renjiea, Liu Xinghaia, Chen Jieb, Weng Jianquana   

  1. a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032;
    b Bioassay Department, Zhejiang Branch of National Southern Pesticide Research Centre, Hangzhou 310023
  • Received:2014-10-31 Revised:2014-12-14 Published:2015-01-07
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.30900959) and Public Project of Zhejiang Province (No.2014C31127).

为寻找新型高效杂环农药先导化合物, 以取代苯并噻(噁)唑酮为原料, 经取代、肼化、环化、苄基化反应合成了21个新型取代3-[(5-苄硫-1,3,4-噁二唑-2-基)甲基]苯并[d]噻(噁)唑-2(3H)-酮类化合物, 并利用1H NMR, IR, EI-MS及元素分析对其结构进行表征. 初步生物活性试验结果表明, 在50 mg/L浓度下, 大部分化合物对黄瓜炭疽病菌(Colletotrichum orbiculare), 灰葡萄孢菌(Botrytis cinerea)和水稻纹枯病菌(Rhizoctonia solani)具有中等杀菌活性, 其中化合物5b对灰葡萄胞菌和水稻纹枯病菌的抑制率均达到了85%以上.

关键词: 苯并噻(噁)唑酮, 硫醚, 1,3,4-噁二唑, 微波合成, 杀菌活性

In order to find novel biologically active pesticide lead compounds, twenty-one novel 3-[(5-benzylthio-1,3,4- oxadiazol-2-yl)methyl]benzo[d]thiazol(oxazol)-2(3H)-ones were synthesized by 2-benzothiazolinone/benzoxazolone as starting materials via substitution, hydrazine, cyclization and the last benzylation reaction. The structures of the title compounds were characterized by 1H NMR, IR, EI-MS and elemental analysis. The preliminary bioassay results indicated that most of them showed moderate inhibition activity against Colletotrichum orbiculare, Botrytis cinerea and Rhizoctonia solani at 50 mg/L, and the inhibition rate of compound 5b against Botrytis cinerea and Rhizoctonia solani reached above 85%.

Key words: 2-benzothiazolinone/benzoxazolone, thioether, 1,3,4-oxadiazole, microwave synthesis, antifungal activity