环丙鱼藤双腙的合成与抑菌活性
收稿日期: 2014-09-19
修回日期: 2014-11-03
网络出版日期: 2014-11-18
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
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).
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3a～3p, 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3d和3o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, 3h和3k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, 3i和3l在500 mg/L浓度下对小麦白粉病菌的防治率为80.0%～90.0%.
叶姣 , 颜晓维 , 张翠央 , 胡艾希 , 欧晓明 . 环丙鱼藤双腙的合成与抑菌活性[J]. 有机化学, 2015 , 35(2) : 396 -403 . DOI: 10.6023/cjoc201409031
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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