Synthesis and herbicidal activities of novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl carboxamides and thiocarboxamides.

A series of novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl carboxamides and thiocarboxamides were synthesized as potential lead compounds of inhibitors targeting D1 protease in plants. These compounds were designed on the basis of a D1 protease inhibitor hit structure identified by homology modeling and virtual screening. The syntheses of these compounds were accomplished via a four-step procedure including the isoxazole ring formation, alpha-bromination of acetyl group, thiazole ring formation, and carboxamide/thiocarboxamide attachment.

N-Phenyl-4-(8-phenyl-4,5-dihydro-1,2-benzoxazolo[4,5-d]thia-zol-2-yl)piperidine-1-carboxamide.

In the title molecule, C(26)H(24)N(4)O(2)S, the dihedral angle between the isoxazole ring and the adjoining benzene ring is 21.4 (5)°, and between the isoxazole ring and the thia-zole ring is 14.3 (4)°.