有机化学 ›› 2015, Vol. 35 ›› Issue (2): 396-403.DOI: 10.6023/cjoc201409031 上一篇    下一篇

研究论文

环丙鱼藤双腙的合成与抑菌活性

叶姣a, 颜晓维a, 张翠央a, 胡艾希a, 欧晓明b   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 国家农药创制工程技术研究中心 长沙 410007
  • 收稿日期:2014-09-19 修回日期:2014-11-03 出版日期:2015-02-25 发布日期:2014-11-18
  • 通讯作者: 叶姣, 胡艾希 E-mail:yejiao@hnu.edu.cn;axhu@hnu.edu.cn
  • 基金资助:

    湖南省自然科学基金(No. 12jj3012)资助项目.

Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives

Ye Jiaoa, Yan Xiaoweia, Zhang Cuiyanga, Hu Aixia, Ou Xiaomingb   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b National Engineering and Technology Center for Pesticide Research and Development, Changsha 410007
  • Received:2014-09-19 Revised:2014-11-03 Online:2015-02-25 Published:2014-11-18
  • Supported by:

    Project supported by the Natural Science Foundation of Hunan Province (No. 12jj3012).

以鱼藤酮为原料, 经氧硫叶立德开环、环合, 再与水合肼缩合制备关键中间体(2R)-5-[5',6'-二甲氧基-1',1'a,2',7'b-四氢环丙并[c]苯并吡喃-7'b-基)(亚联氨基)甲基]-2-(丙烯-2"-基)-2,3-二氢苯并呋喃-4-酚(2), 2与多种醛/酮反应, 合成16个结构新颖的环丙鱼藤双腙化合物3a3p, 结构经1H NMR和LRMS确证. 初步抑菌活性测试表明, 鱼藤双腙化合物对稻纹枯病菌、油菜菌核病菌和小麦白粉病菌的抑制率/防治率较高. 其中化合物3d3o在500 mg/L浓度下对稻纹枯病菌的防治率分别为55.1%和55.5%; 化合物3a, 3c, 3e, 3h3k在25 mg/L浓度下对油菜菌核病菌的抑制率分别为76.8%, 87.0%, 70.6%, 72.5%和65.2%; 化合物3a, 3c, 3g, 3i3l在500 mg/L浓度下对小麦白粉病菌的防治率为80.0%~90.0%.

关键词: 鱼藤酮, 双腙, 合成, 抑菌活性

A novel series of cycloproply derris dihydrazone derivatives 3a3p were designed and synthesized by reacting substituted aldehydes/ketones with intermediate (2R)-5-[(5',6'-dimethoxy-1',1'a,2',7'b-tetrahydrocyclopro-pa[c]chromen-7'b- yl)(hydrazono)methyl]-2-(prop-1"-en-2"-yl)-2,3-dihydrobenzofuran-4-ol (2), which was synthesized via the reactions of the rotenone, dimethyloxosulphonium methylide and hydrazine hydrate. Their structures were characterized by 1H NMR and LRMS. The results of bioassay indicated that the title compounds exhibited potent fungicidal activity against Rhizoctonia solani, Sclerotonia sclerotiorum and Blumeria graminis. Compounds 3d and 3o showed 55.1% and 55.5% control rates against Rhizoctonia solani at 500 mg/L, respectively, compounds 3a, 3c, 3e, 3h and 3k showed 76.8%, 87.0%, 70.6%, 72.5% and 65.2% inhibition rates against Sclerotonia sclerotiorum at 25 mg/L, respectively, and compounds 3a, 3c, 3g, 3i and 3l showed 80.0%~90.0% control rate against Blumeria graminis at 500 mg/L.

Key words: rotenone, dihydrazone, synthesis, fungicidal activity