The metabolism of the soil fumigant 1,2-dibromo-3-chloropropane in the rat.
The soil fumigant 1,2-dibromo-3-chloropropane (I) undergoes hydrolysis in the rat to a series of epoxide metabolites. Alkylation of glutathione by these epoxides produces 2 urinary metabolites identified as the mercapturic acids VI (R=COCH3) and VII (R-COCH3). Hydrolysis of the epoxides produces the male antifertility agents alpha-chlorohydrin (IX, X-Cl) and alpha-bromohydrin (IX, X-Br) which are oxidatively metabolized to oxalic acid (XII), thus causing renal damage. These metabolic pathways can explain the toxic nature of the fumigant as a carcinogen, a male chemosterilant and as an agent causing kidney damage.
D000818:Animals; D004852:Epoxy Compounds / Q000378:metabolism; D006846:Hydrocarbons, Halogenated / Q000378:metabolism* / Q000494:pharmacology; D006868:Hydrolysis; D007668:Kidney / Q000187:drug effects; D008297:Male; D009929:Organ Size / Q000187:drug effects; D011407:Propane / Q000031:analogs & derivatives* / Q000378:metabolism / Q000494:pharmacology; D051381:Rats; D013737:Testis / Q000187:drug effects
D004852:Epoxy Compounds; D006846:Hydrocarbons, Halogenated; C007318:1,2-dibromo-3-chloropropane; D011407:Propane