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Design, synthesis, crystal structure and fungicidal activity of (E)-5-(methoxyimino)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one analogues

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Abstract

A practical method of four-step synthesis towards novel (E)-5-(methoxyimino)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one antifungals is presented, where a commercially available pesticide and pharmacology intermediate, (E)-methyl 2-(2-(bromomethyl)phenyl)-2-(methoxyimino)acetate (1), was used as starting material. These compounds were confirmed by 1H NMR, 13C NMR, high-resolution mass spectroscopy and X-ray crystal structure. Via in vitro fungicidal evaluation, the moderate to high activities of several compounds against eight phytopathogenic fungi were demonstrated. Especially, the fungicidal activities of compounds 5-03 and 5-09 were comparable to those of the controls azoxystrobin and trifloxystrobin in precise virulence measurements for four fungi. These results suggested that dihydrobenzo[e][1,2]oxazepin-4(1H)-one analogues could be considered as potential fungicidal candidates for crop protection.

Graphical abstract: Design, synthesis, crystal structure and fungicidal activity of (E)-5-(methoxyimino)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one analogues

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Publication details

The article was received on 15 Jan 2017, accepted on 01 Mar 2017 and first published on 08 Mar 2017


Article type: Research Article
DOI: 10.1039/C7MD00025A
Citation: Med. Chem. Commun., 2017, Advance Article
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    Design, synthesis, crystal structure and fungicidal activity of (E)-5-(methoxyimino)-3,5-dihydrobenzo[e][1,2]oxazepin-4(1H)-one analogues

    D. Yang, C. Wan, M. He, C. Che, Y. Xiao, B. Fu and Z. Qin, Med. Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7MD00025A

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