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Synthesis, Herbicidal Activity and Thermal Stability of N-(2-Phenyloxiran-2-ylmethyl) benzenesulfonamide Derivatives
Akemi HOSOKAWA, Masahiro YAMADA, Seiichi SUZUKI, Osamu IKEDA, Koichi YONEYAMA and Tetsuo JIKIHARA
J. Pestic. Sci.
26, 1-8 (2001)
In the course of studies on novel sulfonamide derivatives, we found that 4,N-dimethyl-N-(2-phenyloxiran-2-ylmethyl) benzenesulfonamide was herbicidally active. In spite of its high activity, the compound did not have enough stability for practical use. To improve the stability and herbicidal activity by molecular modification, a series of sulfonamide derivatives with phenyl substituted oxirane moiety were prepared. Among them, N-[2-(3-chlorophenyl)oxiran-2-ylmethyl]-4-cyano-N-methylbenzenesulfonamide possessed the highest herbicidal activity with enough thermal stability. Halohydrin derivatives were also prepared as an alternative solution for the stability. Among them, N-(3-bromo-2-hydroxy-2-phenypropyl)-4-chloro-N-difluoromethyl-3-methylbenzensulfonamide was the most favorable for herbicide. Both compounds showed excellent herbicidal activity against grass weeds and some of broad leaf weeds in paddy condition with selectivity to transplanted rice.
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