Synthesis of spirothiohydantoin analogues of hydantocidin

Tetrahedron
1995.0

Abstract

Synthesis of spiothiohydantoin derivatives of hydantocidin is described. The key feature of the synthesis was spirothiohydantoin ring formation through an iminophosphorane intermediate. Spirothiohydantoin derivative 2 maintained comparable herbicidal activity to that of the natural compound except against fall panicum, when applied through a foliage of weeds at 1000 ppm. Surprisingly, its epimer 15 also demonstrated good herbicidal activity under the same condition, while 5-epi-hydantocidin 16 displayed fair activity.

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