2008-58-4

white to brown-grey crystalline powder

2,6-Dichlorobenzamide is the persistent metabolite of herbicide 2,6-Dichlorobenzonitrile (D431945).

ChEBI: A member of the class of benzamides that is benzamide substituted by chloro groups at positions 2 and 6.

Including 2,6-dichlorobenzamide was prepared as follows: in a 500 ml reaction flask, add 2,6-dichlorobenzonitrile 51.6 g (0.3 mol), 41.6 g of water, 0.6 g of 30% sodium hydroxide solution, warming to 35 ° C., drop 55.65 g (0.45 mol) of 27.5% hydrogen pero

Oral doses of DCB are excreted by rats as DCB, two monohydroxy-DCBs, 2-chloro-5-hydroxy-6- (methylthio)benzamide, and 2-chloro-5-hydroxy-6-[S- (N-acetyl)-cysteinyl]benzamide. Biliary excretion (33% of the dose), enterohepatic circulation, and intestinal microfloral metabolism are involved in the formation of 2-chloro-5-hydroxy-6-(methylthio)benzamide. The major route for the metabolism of DCB is the conjugation with glutathione in a process involving phenyl ring hydroxylation at the ortho position to the S-glutathionyl moiety. Two mechanisms can be processed for the formation of hydroxylated metabolites resulting from the epoxidation at the 2- and 3-positions of the phenyl ring (for the proposed mechanisms: see the text).