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Synthesis and fungicidal activities of positional isomers of the N-thienylcarboxamide.

ABSTRACT: 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.

SUBMITTER: Katsuta H

PROVIDER: S-EPMC8175219 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Synthesis and fungicidal activities of positional isomers of the N-thienylcarboxamide.

Katsuta Hiroyuki H Shirakawa Tomomi T Kawashima Miyuki M Banba Shinichi S

Journal of pesticide science 20210501 2

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)carboxa ...[more]

PMID: 34135685

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