Metabolism of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane in the mouse

The metabolites of 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethane (DDT) and 1,1-dichloro-2,2-bis(p-chlorophenyl)ethane (DDD) found in the urine of female Swiss mice are reported. The metabolites of DDT are DDD, 1-chloro-2,2-bis(p-chlorophenyl)ethene (DDMU), 1,1-dichloro-2,2-bis(p-chlorophenyl)ethene (DDE), 2,2-bis(p-chlorophenyl)acetic acid (DDA), 2-hydroxy-2,2-bis(p-chlorophenyl)acetic acid (αOH-DDA) and 2,2-bis(p-chlorophenyl)ethanol (DDOH), while DDD afforded DDMU, DDE, DDA, αOH-DDA and DDOH. The relative excreted levels of DDA and DDOH and the absence of 2,2-bis(p-chlorophenyl)acetaldehyde (DDCHO) are not consistent with the generally accepted path way for DDA formation, which involves sequential metabolism of DDT and DDD via DDOH to afford DDA. The quantitative results are interpreted to mean that DDA is formed by hydroxylation at the chlorinated sp³-side chain carbon of DDD to give 2,2-bis(p-chlorophenyl)acetyl chloride (DDA-Cl), which in turn is hydrolyzed to DDA. The excretion of αOH-DDA from both DDT- and DDD-treated mice has never been previously observed. It is suggested that this metabolite arises from the initial epoxidation of DDMU, a metabolite of DDT and DDD, to yield 1,2-epoxy-1-chloro-2,2-bis(p-chlorophenyl)ethane (DDMU-epoxide). This chloroepoxide is then hydrolyzed and oxidized to produce the αOH-DDA.     

Metabolism of DDT and Kelthane in cell suspension cultures of parsley (Petroselinum hortense,Hoffm.) and soybean (Glycine max L.)

Cell suspension cultures of parsley and soybean were incubated for 44 to 48 h with¹⁴C-labeled DDT or Kelthane; autoclaved cultures were used as controls. Most of the radioactivity became associated with the cells, and metabolites were isolated by a sequential extraction procedure. The metabolites amounted to 0.6 to 2.2% of the applied pesticide. Relatively non-polar metabolites were identified as DDE in the case of DDT, and remained unidentified in the case of Kelthane. Polar metabolites were also isolated and are as yet unidentified. They were chromatographically different from the known and less polar metabolites of DDT and Kelthane reported from animal and insect studies. [DDT-1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)-ethane; Kelthane=(1,1-bis-(4-chlorophenyl)-2,2,2-trichloro-ethanol; DDE=1,1-Dichloro-2,2-bis-(4-chlorophenyl)-ethylene.]Abbreviations DDT 1,1,1-Trichloro-2,2-bis-(4-chlorophenyl)-ethane - Kelthane (1,1-bis-(4-chlorophenyl)-2,2,2-trichloro-ethanol - DDE 1,1-Dichloro-2,2-bis-(4-chlorophenyl)-ethylene - DDA 2,2-bis-(4-chlorophenyl)-acetic acid - DDOH 2,2-bis-(4-chlorophenyl)-ethanol - DDD 1,1-Dichloro-2,2-bis-(4-chlorophenyl)-ethane - DBP 4,4-Dichloro-benzophenone - DDMU 1-Chloro-2,2-bis-(4-chlorophenyl)-ethylene - DDM Bis-(4-chlorophenyl)-methane - FW-152 1,1-Bis-(4-chlorophenyl)-2,2-dichloro-ethanol - SDS sodium dodecylsulphate