Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives

doi:10.6023/cjoc201409031

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

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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

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 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 Jiao^a, Yan Xiaowei^a, Zhang Cuiyang^a, Hu Aixi^a, Ou Xiaoming^b

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).

1. Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives.PDF(1779KB)

Abstract

A novel series of cycloproply derris dihydrazone derivatives 3a～3p 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

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Ye Jiao, Yan Xiaowei, Zhang Cuiyang, Hu Aixi, Ou Xiaoming. Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives[J]. Chin. J. Org. Chem., 2015, 35(2): 396-403.

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环丙鱼藤双腙的合成与抑菌活性

Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives

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