高等学校化学学报 ›› 2015, Vol. 36 ›› Issue (12): 2415-2420.doi: 10.7503/cjcu20150508

• 有机化学 • 上一篇    下一篇

二芳基肟苄醚类化合物的合成及杀菌活性

李秀云1, 万川1, 杜士杰1, 李红1, 袁会珠2, 蒋家珍1, 肖玉梅1, 覃兆海1()   

  1. 1. 中国农业大学理学院, 北京 100193
    2. 中国农业科学院植物保护研究所, 北京 100193
  • 收稿日期:2015-06-30 出版日期:2015-12-10 发布日期:2015-11-19
  • 作者简介:联系人简介: 覃兆海, 男, 博士, 教授, 博士生导师, 主要从事新农药创制研究. E-mail:qinzhaohai@263.net
  • 基金资助:
    国家“十二五”科技支撑计划项目(批准号: 2015BAK45B01)资助

Synthesis and Fungicidal Activities of Biaryl Methanone O-Benzyl Oximes

LI Xiuyun1, WAN Chuan1, DU Shijie1, LI Hong1, YUAN Huizhu2, JIANG Jiazhen1, XIAO Yumei1, QIN Zhaohai1,*()   

  1. 1. College of Science, China Agricultural University, Beijing 100193, China
    2. Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, China
  • Received:2015-06-30 Online:2015-12-10 Published:2015-11-19
  • Contact: QIN Zhaohai E-mail:qinzhaohai@263.net
  • Supported by:
    † Supported by the "12th Five Year" National Science and Technology Support Program of China(No. 2015BAK45B01).

摘要:

以吡啶芳酮为原料, 合成了11个含二芳基肟醚结构单元的甲氧丙烯酸酯类化合物, 通过氢核磁共振谱(1H NMR)、 碳核磁共振谱(13C NMR)和高分辨质谱(HRMS)等方法对其结构进行了确证. 离体杀菌活性测定结果表明, 该类化合物对供试的7种植物病原菌普遍表现出较高的抑制活性, 其中化合物5d和5g的活性与对照药剂嘧菌酯和肟菌酯相当. 进一步活体盆栽验证实验结果表明, 在400 mg/L浓度下, 部分化合物表现出很好的防治效果, 如化合物5h对小麦白粉病和黄瓜炭疽病的防治效果达100%. 另外, 该类化合物对稻梨孢的孢子萌发具有强烈的抑制作用, 在25 mg/L浓度下, 绝大多数化合物的抑制率达到100%, 但对灰葡萄孢的孢子萌发普遍无效. 研究结果显示该类化合物具有进一步开发的价值.

关键词: 甲氧丙烯酸酯, 吡啶苯基肟, 苄基醚, 杀菌活性

Abstract:

To discover new strobilurin analogs with high pesticidal activity, 11 novel methoxy acrylates bearing biaryl methanone oxime ether moieties were synthesized from aroyl pyridines, and characterized by 1H and 13C NMR and HRMS. In vitro fungicidal evaluation indicated that all of the target compounds exhibited excellent activities against tested seven phytopathogenic fungi, and compounds 5d and 5g displayed comparable overall activities to azoxystrobin and trifloxystrobin. Some of the target compounds also exhibited excellent in vivo control effects at 400 mg/L, for example, compound 5h could 100% control wheat powdery mildew and cucumber anthracnose. Furthermore, at 25 mg/L, these compounds, including control agents, completely inhibited spores germination of rice blast, but no effect at all for cucumber gray mold. These results suggested that this class of compounds might deserve to be developed as new potential agricultural fungicides.

Key words: Methoxy acrylate, Pyridinyl phenyl metnanone oxime, Benzyl ether, Fungicidal activity

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