| Identification | More | [Name]
2,6-Dichlorobenzamide | [CAS]
2008-58-4 | [Synonyms]
2,6-DICHLOROBENZAMIDE
LABOTEST-BB LT00455181
TIMTEC-BB SBB008056
ALDRIN PESTANAL (1,2,3,4,10,10-HEXA-CHLO
2,6-DICHLORBENZAMIDE
BENZAMIDE,2,6-DICHLORO-
2,6-BAM | [EINECS(EC#)]
217-918-4 | [Molecular Formula]
C7H5Cl2NO | [MDL Number]
MFCD00007975 | [Molecular Weight]
190.03 | [MOL File]
2008-58-4.mol |
| Hazard Information | Back Directory | [Chemical Properties]
white to brown-grey crystalline powder | [Uses]
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. | [Synthesis]
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 | [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). |
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