Molecular and crystal structures of N-phenylsuccinimides, and their fungicidal activities

Abstract

The crystal structures of seven N-phenylsuccinimides have been determined: N-phenyl-(I), N-(2-fluorophenyl)-(II), N-(2-bromophenyl)-(III), N-(3-fluorophenyl)-(IV), N-(3-bromophenyl)-(V), N-(4-fluorophenyl)-(VI), and N-(4-bromophenyl)-(VII). The molecules showed marked twisting around the C(6)-N(7) bond: The torsion angle between the least-squares planes of the benzene and succinimide rings was never 0°, being 59.6°[for (I)], 63.5°(II), 69.8°(III), 54.5°(IV), 59.8°(V), 55.9°(VI), or 62.2°(VII). The relation of torsion angle to fungicidal activity against Botrytis cinerea is discussed.