2,6-Dichlorobenzamide

Chemical properties

white to brown-grey crystalline powder

The Uses of 2,6-Dichlorobenzamide

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

Definition

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

Metabolic pathway

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).