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; Chuan Wan; MengMeng He; Chuanliang Che; Yumei Xiao; Bin Fu; Zhaohai Qin

doi:10.1039/c7md00025a

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

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

Authors

Dongyan Yang¹, Chuan Wan¹, MengMeng He¹, Chuanliang Che¹, Yumei Xiao¹, Bin Fu¹, Zhaohai Qin¹

Affiliation

¹ College of Science , China Agricultural University , Beijing 100193 , China . Email: qinzhaohai@263.net ; ; Tel: +86 (0)10 62732958.

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.