Inhibition ofNarcissus pseudonarcissusPhytoene Desaturase by Herbicidal 3-Trifluoromethyl-1,1′-biphenyl Derivatives

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...

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Bibliographic Details
Published in:Pesticide biochemistry and physiology 1999-03, Vol.63 (3), p.173-184
Main Authors: Laber, Bernd, Usunow, Gerlinde, Wiecko, Elzbieta, Franke, Wilfried, Franke, Heinrich, Köhn, Arnim
Format: Article
Language:English
Subjects:
bleaching herbicides
carotenoid biosynthesis
daffodil chromoplasts
Narcissus pseudonarcissus
norflurazon
phytoene desaturase
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Summary: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. IC;i5;i0 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 IC50values for inhibition of phytoene desaturase with the biological activity in preemergence upland tests in the greenhouse.
ISSN:0048-3575
1095-9939
DOI:10.1006/pest.1999.2401