2,6-Diphenylpyridines: a new class of herbicides

Synthesis and herbicidal activity of 2-acylimino-3-phenyl-1,3-thiazolines—A new family of bleaching herbicides—

“…[7][8][9][10] As a starting point for structural optimization of the new lead, we divided the core structure into two subsections, the thiazoline nucleus (R 1 and R 2 ) and the imino group (X), while keeping the 3-trifluoromethylphenyl moiety at 3-position on the 1,3-thiazoline ring (Fig.1).…”

“…[2][3][4][5][6] Until now, this method has served as a rich lead source to find a number of various heterocycles with bleaching herbicidal activity. [7][8][9][10] While exploring the synthetic development of N,S-heterocycles using heterocumlenes, 11) such as acyl isothiocyanates, 12) we discovered novel cyclization reactions affording 2-(N-acylimino)-5-methylene-1,3-thiazolidines (V; R 3 ϭH). Compounds V thus obtained can be easily interconverted to 2-(N-acylimino)-5-methyl-1,3-thiazolines (VI; R 3 ϭH).…”

Bleaching Herbicides: Action Mechanism in Carotenoid Biosynthesis, Structural Requirements and Engineering of Resistance

“…Since then, novel compounds have been identified as phytoene desaturase inhibitors. Among them are 2,6-diphenylpyridines (Kawamura et al 1991;Babczinski et al 1992), diarylpyrimidines (Kawamura et al 1993), tetrahydropyrimidinones (Babczinski et al 1995a), I,l'-biphenyl derivatives (Laber et al 1999), phenylpyrimidinones (Burdge 2000) and diphenylpyrrolidinones (Ogawa et al 2001). Typical and efficient bleaching compounds possess a central five-or sixmembered heterocycle carrying one or two substituted phenyl rings.…”

Inhibition of carotenoid biosynthesis by interaction of 2,6-diphenylpyridine derivatives with phytoene desaturation

“…Herbicidal inhibitors exhibiting this mode of action are, e.g., the phenylpyridazinone norflurazon , the phenylfuranone flurtamone , or tetrahydropyrimidinones (Babczinski et al, 1990). For a new class of herbicidal compounds, the 4-substituted-2,6-diphenylpyridines, bleaching activity was recently proposed (Kawamura et al, 1991).…”