Inhibition of Narcissus pseudonarcissus phytoene desaturase by herbicidal 3-trifluoromethyl-1,1'-biphenyl derivatives
1999
Laber, B. | Usunow, G. | Wiecko, E. | Franke, H. | Kohn, A.
A synthesis program directed to the discovery of novel bleaching herbicides led to the preparation of substituted 3-trifluoromethyl-1,1'-benzoxazoles and 3-trifluoromethyl-1,1'-biphenyls with thiazole-, thiadiazole-, and benzthiazole substituents. Herein, we show that these compounds interfere with the biosynthesis of colored carotenoids by inhibiting the enzyme phytoene desaturase IC50 values for inhibition of phytoene desaturase have been determined for 62 derivatives. Several new compounds were found that inhibited phytoene desaturase up to 400-fold more potently than the commercial bleaching herbicide norflurazon. The derived relationships between chemical structure and enzyme inhibition were used to generate a model of the proposed herbicide binding site. The implication that phytoene desaturase is the target site for the substituted 3-trifluoromethyl-1,1'-benzoxazole and biphenyl classes of herbicides is supported by a significant correlation of the IC50, values for inhibition of phytoene desaturase with the biological activity in preemergence upland tests in the greenhouse.
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