H. Mcfadden, J. Huppatz, C. Kennard
Apr 1, 1993
Citations
0
Influential Citations
2
Citations
Journal
Zeitschrift für Naturforschung C
Abstract
Several acrylic acid derivatives incorporating elements of sulfonylurea structure around a central vinylogous core were synthesized and found to be moderate inhibitors of the enzyme, acetohydroxyacid synthase (AHAS). Some com pounds showed post-emergence herbicidal activity against mustard. Biological activity was found to be markedly influenced by the nature of the 2-arylcarbamoyl group. When this group contained a phenyl ring the compounds were inactive. A 4,6-dim ethoxypyrimidin-2-ylcarbamoyl function resulted in the best activity but this activity was highly dependent on the nature of the 4,6-substituents on the pyrimidine ring, with 4,6-dim ethylpyrimidines showing very little activity. The structures of the most active compound, ethyl 3-(2-chlorophenyl)sulfonylamino-3-m ethylthio-2-[(4,6-dimethoxypyrimidin- 2-yl)carbam oyl]acrylate, and an inactive analogue, 4,6-dimethylpyrimidin-2-yl-3-(2-chlorophenyl) sulfonylamino-3-methylthio-2-cyanoacrylate, were determined by X -ray crystallography. The resulting structures showed several conformational differences which may play an important role in inhibitor binding to AHAS and the resultant herbicidal activity.