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. 2017 Mar 8;8(5):1007-1014.
doi: 10.1039/c7md00025a. eCollection 2017 May 1.

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

Dongyan Yang  1 , Chuan Wan  1 , MengMeng He  1 , Chuanliang Che  1 , Yumei Xiao  1 , Bin Fu  1 , Zhaohai Qin  1
Affiliations

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

Dongyan Yang et al. Medchemcomm. .

Erratum in

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.

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Figures

Fig. 1
Fig. 1. Biologically active compounds containing benzoxazepinone moiety.
Scheme 1
Scheme 1. Strategies for the target compound design.
Scheme 2
Scheme 2. Preparation of title compounds.
Fig. 2
Fig. 2. X-ray crystal structure of 5-09 (CCDC-; 1518111).
Fig. 3
Fig. 3. Inhibitory rates of selected compounds against PI, ST and PG.
Fig. 4
Fig. 4. Topomer CoMFA contour maps of compound 5-09. (a) Steric field around benzoxazepinone moiety. (b) Electrostatic field around benzoxazepinone moiety. (c) Steric field around R group (4-ClC6H4CH2). (d) Electrostatic field around R group (4-ClC6H4CH2).
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