Abstract
N-(3, 5-dichlorophenyl)-N′-methoxyformamidine (DPMF) with specific fungicidal activity against a benzimidazole-resistant isolate of Botrytis cinerea was synthesized and its fungitoxic properties were studied. DPMF had fungicidal effects similar to those of methyl N-(3, 5-dichlorophenyl)carbamate (MDPC) in terms of negatively correlated cross-resistance to benzimidazole fungicides. In microscopic observation DPMF nearly equaled MDPC in the morphological effect on B. cinerea. Based on the fungicidal properties, structural similarity of DPMF and MDPC was studied by computational techniques in order to rationalize their bioisosterism. The results suggested that their functional groups were similar in terms of molecular shape and electrostatic potential distributions when they are compared in one of the energy-minimum conformations.
