A novel series of substituted 2,4-diarylpyrimidines was synthesized and found to possess bleaching herbicidal activity. These diarylpyrimidines, which incorporate a pyrimidine nucleus substituted by two aryl moieties, are new chemical families of bleaching herbicides. The structure-activity relationships were probed by substitution of the pyrimidine and/or aryl groups. Highest activity was seen with compounds that contain three substituents: a trifluoromethyl group at a meta position of an aryl moiety at the pyrimidine 4-position, a fluorine or trifluoromethyl group at the para position of the other at the 2-position, and a methoxy group at the 5-position.
A novel series of 4-substituted 2,6-diphenylpyridines was synthesized and found to possess bleaching herbicidal activity. These diphenylpyridines, which incorporate a pyridine nucleus substituted by two phenyl moieties, are new chemical families of bleaching herbicides. The structure-activity relationships indicated very specific structure requirements for herbicidal activity. In general, herbicidal activity was the highest in compounds that contain three substituents: a CF 3 at the 2-or 3-position of one phenyl ring, a CF 3 group at the 4-position of the other, and a methoxy, ethoxy, or methylthio group at the pyridine 4-position. Physiological and biochemical properties of diphenylpyridines have been also investigated. Their primary mode of action is direct inhibition of phytoene desaturase which results in decreased biosynthesis of colored carotenoides and subsequent photooxidation of chlorophyll in the light.A variety of pyridines are known to possess herbicidal activity. However, only a few heterocycles with a pyridine nucleus have been reported as bleaching herbicides (7-2). Recently, a series of herbicidal pyridine derivatives was disclosed (3). In our continuous effort to find a new class of bleaching herbicides, we discovered that 2,6-diphenylpyridines (General Structure 1) showed bleaching herbicidal activity. In general, diphenylpyridines exhibit moderate preemergent herbicidal activity and good postemergent herbicidal activity on broadleaf weeds. At postemergent application, the chlorotic symptoms can not be observed in primary leaves, only secondary and later leaves become chlorotic, 2-3 days after application. The bleaching symptoms observed resulted in sever necrosis, leading to plant death after 25-30 days. From the symptoms and structural similarity to other well known bleaching herbicides, like fluridone and flurtamone, the compound was expected to inhibit carotenoid biosynthesis. Our interest in the structure and herbicidal activity of this novel heterocyclic compound prompted us to examine a systematic screening study on diphenylpyridine herbicides. Here, we now report the syntheses, structure-activity relationships, and mode of action of diphenylpyridines.
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