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

Abstract

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

The application of “plug-in molecules” method in novel strobilurin fungicides screening

“…The synthetic route of targeted compounds 5 from commercially available starting materials is outlined in Scheme 2. As reported in the literature, 24,25 precursor 4 was prepared from methyl (E)-2-(2-(bromomethyl)phenyl)-2-(methoxyimine)acetate and N-hydroxyphthalimide by nucleophilic substitution and hydrazidation. The condensation reaction of compounds 3 and 4 formed a carbon-nitrogen double bond; however, due to the steric hindrance, the products were mainly in trans conguration.…”

“…Steric map indicating areas where steric bulk is predicted to increase (green) or decrease (yellow) activity. 25 Compound 5-06 with the highest activity was selected to explain the contour map. The introduction of a big steric substituent at the 3position and 4-position (green) and a small steric substituent at the 2-position (yellow) of the benzene ring was conducive to fungicidal activity ( Fig.…”