有机化学 ›› 2014, Vol. 34 ›› Issue (10): 2057-2062.DOI: 10.6023/cjoc201404008 上一篇    下一篇

研究论文

新型吡唑联吡咯类杂环化合物的合成及杀菌活性

王子时a, 叶汉韬a, 肖丹a, 马东升a, 高金胜a,b, 于颖慧a, 侯广峰b, 闫鹏飞a   

  1. a. 黑龙江大学化学化工与材料学院 哈尔滨 150080;
    b. 黑龙江大学农药工程中心 哈尔滨 150080
  • 收稿日期:2014-04-03 修回日期:2014-05-07 发布日期:2014-06-09
  • 通讯作者: 马东升, 侯广峰 E-mail:hougf@hlju.edu.cn
  • 基金资助:

    国家自然科学基金(Nos. 21371052,21272061)及黑龙江省教育厅科学研究基金(No. 12531512)资助项目.

Synthesis and Fungicidal Activity of New Pyrrolpyrazole Compounds

Wang Zishia, Ye Hantaoa, Xiao Dana, Ma Dongshenga, Gao Jinshenga,b, Yu Yinghuia, Hou Guangfengb, Yan Pengfeia   

  1. a. School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080;
    b. Engineering Research Center of Pesticide of Heilongjiang University, Heilongjiang University, Harbin 150080
  • Received:2014-04-03 Revised:2014-05-07 Published:2014-06-09
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21371052 and 21272061) and the Scientific Research Fund of Heilongjiang Provincial Education Department (No. 12531512).

为寻找具有更高生物活性、更环保的新农药杀菌剂,基于杀菌剂氟咯菌腈设计并合成了10个新型吡唑联吡咯类杂环化合物,以吡唑环代替氟咯菌腈上原有的苯环,以期提高其杀菌活性. 采用1H NMR,FTIR,单晶X射线衍射、元素分析和熔点测定等测试手段对目标化合物及其中间体的结构进行了表征与确认,并通过挥发法培养得到了6个目标化合物的单晶. 还对其中6个化合物进行了生物活性测试,测试结果表明各化合物对水稻纹枯病、黄瓜灰霉病、黄瓜霜霉病均表现出一定的抑菌效果,可作为先导化合物对其结构进行深入的研究,为新农药杀菌剂的开发提供了理论支持.

关键词: 氟咯菌腈, 吡唑联吡咯类化合物, 合成, 反应条件, 生物活性测试

With the aim of obtaining new potential fungicide candidates with higher biological activities and environmental safety, ten new pyrrolpyrazole compounds based on the structures of fludioxonil were designed and synthesized. The benzene ring in original fludioxonil structure is replaced by pyrazole ring to improve its bactericidal activity. All the structures of target products and their intermediates are characterized and confirmed by 1H NMR, FTIR, single crystal diffraction, HPLC, elemental analysis and melting point determination. Six single crystals of final products are also achieved by volatilization under room temperature. Biological activity tests are conducted for six compounds. The results show that each compound exhibits certain antibacterial activity toward rhizoctonia, botrytis cinerea and cucumber downy mildew, which provides valuable information for further development of new pesticides fungicides.

Key words: fludioxonil, pyrrolpyrazole compound, synthesis, reaction condition, biological activity test