Chinese Journal of Organic Chemistry >
Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives
Received date: 2014-09-19
Revised date: 2014-11-03
Online 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 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
Ye Jiao , Yan Xiaowei , Zhang Cuiyang , Hu Aixi , Ou Xiaoming . Synthesis and Fungicidal Activity of the Cycloproply Derris Dihydrazone Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(2) : 396 -403 . DOI: 10.6023/cjoc201409031
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