Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 396-403.DOI: 10.6023/cjoc201409031 Previous Articles     Next Articles



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 发布日期:2014-11-18
  • 通讯作者: 叶姣, 胡艾希;
  • 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 Published:2014-11-18
  • Supported by:

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

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