Synthesis and Fungicidal Activity of 2-Alkylaminosulfonyl-5,6-dihydro-dibenzo[b,e]azephine-6,11-dione
文献类型: 外文期刊
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关键词: 5,6-dihydro-dibenzo[b,e]azephine-6,11-dione;2-(alkylaminosulfonyl)-5,6-dihydro-dibenzo[b,e]azephine-6,11-dione;synthesis;fungicidal activity
期刊名称:CHINESE JOURNAL OF ORGANIC CHEMISTRY ( 影响因子:1.652; 五年影响因子:1.2 )
ISSN: 0253-2786
年卷期: 2014 年 34 卷 12 期
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收录情况: SCI
摘要: A series of novel 2-(alkylaminosulfonyl)-5,6-dihydro-dibenzo[b,e]azephine-6,11-dione derivatives were synthesized starting from anthraquinone by Schmidt rearrangement to 5,6-dihydro-dibenzo[b,e]azephine-6,11-dione, followed by chlorosulfonylation and amination. Their structures were confirmed by H-1 NMR, C-13 NMR and high-resolution mass spectrometry (HRMS). The preliminary bioassay showed that compounds have some fungicidal activity against Rhizoctonia solani, Sclerotinia sclerotiorum and Phomopsis asparagi. Among them, 2-(3-trifluoromethyl-4-bromophenylaminosulfonyl)-5,6-dihydro-dibenzo[b,e]azepine-6,11-dione (4u) has good fungicidal activity against Phomopsis asparagi and the inhibition rate reached 96.3% at 50 mu g/mL, and is comparable with commercial fungicide chlorothalonil. The preliminary structure-activity relationship analysis indicated that introduction of fluorine is favorable to the increase of the activity.
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