Design, synthesis, crystal structure and fungicidal activity of (E)-5-(methoxyimino)-3, 5-dihydrobenzo[e][1, 2]oxazepin-4(1H)-one analogues12. Issue 5 (21st March 2017)

• Record Type: Journal Article
• Authors: Yang, Dongyan; Wan, Chuan; He, MengMeng; Che, Chuanliang; Xiao, Yumei; Fu, Bin; Qin, Zhaohai
• Is Part Of: MedChemComm. Volume 8:Issue 5(2017)
• Page Start: 1007
• Page End: 1014
• Publication Date: 2017-03-21
• Subjects: Pharmaceutical chemistry -- Periodicals; 615.19
• DOI: 10.1039/c7md00025a
• Languages: English
• ISSNs: 2040-2503

Abstract

Abstract : It is the first reported the synthesis of 1, 2-benzoxazepinone. These compounds showed excellent fungicidal activity. Abstract : A practical method of four-step synthesis towards novel ( E )-5-(methoxyimino)-3, 5-dihydrobenzo[ e ][1, 2]oxazepin-4(1 H )-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 1 H NMR, 13 C 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 compounds5-03 and5-09 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(1 H )-one analogues could be considered as potential fungicidal candidates for crop protection.