Synthesis of optically active N-(2-pyridyloxiran-2-ylmethyl) benzenesulfonamide derivatives and their herbicidal activity

Article abstract of DOI:10.1271/bbb.65.1482

Novel herbicidally active sulfonamide compounds having a 2-arylsubstituted oxiranylmethyl structure are racemates due to a chiral carbon in the oxirane moiety. To clarify the stereochemical structure-activity relationship, we synthesized each enantiomer of 4-chloro-N-[2-(6-chloropyridin-2-yl)-2-oxiran-2-ylmethyl]-3,N- dimethylbenzenesulfonamide and N-[2-(6-chloropyridin-2-yl)-2-oxiran-2-ylmethyl]-N-methyl-5,6,7,8- tetrahydronaphthalene-2-sulfonamide by chemical methods including Sharpless asymmetric chlorohydroxylation. The results of herbicidal tests indicated that the (S)-isomers were the active forms.

Full text of DOI:10.1271/bbb.65.1482

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Synthesis of Optically Active N-(2-Pyridyloxiran-2-
ylmethyl) benzenesulfonamide Derivatives and Their
Herbicidal Activity
Akemi HOSOKAWAa, Manabu KATSURADAa, Osamu IKEDAa, Noriko MINAMIa & Tetsuo
JIKIHARAa
a Agricultural Chemicals Laboratory, Yokohama Research Center, Mitsubishi Chemical Co.
Ltd.
Published online: 22 May 2014.
To cite this article: Akemi HOSOKAWA, Manabu KATSURADA, Osamu IKEDA, Noriko MINAMI & Tetsuo JIKIHARA (2001)
Synthesis of Optically Active N-(2-Pyridyloxiran-2-ylmethyl) benzenesulfonamide Derivatives and Their Herbicidal Activity,
Bioscience, Biotechnology, and Biochemistry, 65:7, 1482-1488, DOI: 10.1271/bbb.65.1482
To link to this article: http://dx.doi.org/10.1271/bbb.65.1482
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