4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones : Biological Isostere to 4-Chloro-2-carbamoyl-4-isoxazolin-3-ones

4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones : Biological Isostere to 4-Chloro-2-carbamoyl-4-isoxazolin-3-ones

4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones (4) were designed on the basis of biological isosterism and prepared in four steps. Some of these compounds showed sufficient pre-emergent herbicidal activities against various kinds of weeds. Among the synthesized compounds, 2-(N-(4-chlorophenyl)-N-isoprop...

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Veröffentlicht in:Chemical & pharmaceutical bulletin 2000/04/01, Vol.48(4), pp.509-515
Hauptverfasser: KUDO, Noriaki, YONEDA, akamitsu, SATO, Kazuo, HONMA, Toyokuni, SUGAI, Soji
Format: Artikel
Sprache:eng
Schlagworte:
2-sulfenyl-β-ketoester
3-hydroxyisoxazole
4-isoxazolin-3-one
biological isostere
Carbamates - chemical synthesis
Carbamates - pharmacology
cyclization
herbicide
Herbicides - chemical synthesis
Herbicides - pharmacology
Magnetic Resonance Spectroscopy
Models, Chemical
Oxazoles - chemical synthesis
Oxazoles - pharmacology
Plants - drug effects
Simazine - chemistry
Simazine - pharmacology
Sulfides - chemical synthesis
Sulfides - pharmacology
Triazines - chemistry
Triazines - pharmacology
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Zusammenfassung:4-Sulfenyl-2-carbamoyl-4-isoxazolin-3-ones (4) were designed on the basis of biological isosterism and prepared in four steps. Some of these compounds showed sufficient pre-emergent herbicidal activities against various kinds of weeds. Among the synthesized compounds, 2-(N-(4-chlorophenyl)-N-isopropylcarbamoyl)-4-ethyl-thio-5-methyl-4-isoxazolin-3-one (4cd) exhibited the most promising activity.
ISSN:0009-2363
1347-5223
DOI:10.1248/cpb.48.509