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To investigate the effects of bioisosteric replacement of the phenyl group with the thienyl group, N -phenylcarboxamide and three regioisomers of N -(substituted-thienyl)carboxamide were synthesized. The inhibitory activity on the succinate dehydrogenase prepared from the gray mold Botrytis cinerea as well as the fungicidal activity against B. cinerea were evaluated. Two isomers, N -(2-substituted-3-thienyl)carboxamide and N -(4-substituted-3-thienyl)carboxamide exhibited the same level of activity as the phenyl derivative, whereas N -(3-substituted-2-thienyl)carboxamide exhibited lower activity than the phenyl derivative, suggesting that the 2-substituted-3-thienyl and 4-substituted-3-thienyl groups functioned as bioisosteres of the phenyl group in N -phenylcarboxamide, but the other did not.

Synthesis and fungicidal activities of positional isomers of the <i>N</i>-thienylcarboxamide