Synthesis and fungicidal activities of positional isomers of the N-thienylcarboxamide |
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| Authors: | Hiroyuki Katsuta Tomomi Shirakawa Miyuki Kawashima Shinichi Banba |
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| Institution: | 1.Corporate Planning Department, Mitsui Chemicals Agro, Inc., Nihonbashi Dia Building, 1-19-1 Nihonbashi, Chuo-ku, Tokyo 103-0027, Japan;2.Research and Development Division, Agrochemicals Research Center, Mitsui Chemicals Agro, Inc., 1358 Ichimiyake, Yasu, Shiga 520-2362, Japan;3.Research and Development Division, Agrochemicals Research Center, Mitsui Chemicals Agro, Inc., 1144 Togo, Mobara, Chiba 297-0017, Japan |
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| 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. |
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| Keywords: | penthiopyrad thiophene positional isomers bioisostere succinate dehydrogenase inhibitor (SDHI) |
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