Bioavailability of chlorocatechols in naturally contaminated sediment samples and of chloroguaiacols covalently bound to C2-guaiacyl residues

Bacteria in anaerobic enrichment cultures that dechlorinated a range of chlorocatechols were used to examine the stability of endogenous chlorocatechols in a contaminated sediment sample and in interstitial water prepared from it. During incubation of the sediment sample for 450 days with or without added cells, there was a decrease in the concentration of solvent-extractable chlorocatechols but not in that of the total chlorocatechols, including sediment-associated components. In the presence of azide, the decrease in the concentrations of the former was eliminated or substantially decreased. Control experiments in which 3,4,5-trichlorocatechol was added to the sediment suspensions after 130 days showed that its dechlorination was accomplished not only by the added cells but also by the endemic microbial flora. It was concluded that the endogenous chlorocatechols in the sediment were not accessible to microorganisms with dechlorinating activity. On the other hand, microorganisms were apparently responsible for decreasing the solvent extractability of the chlorocatechols, and this effect decreased with increasing length of exposure time. Similar experiments carried out for 70 days with the sediment interstitial water showed that the chlorocatechols that were known to be associated with organic matter were also inaccessible to microbial dechlorination. Experiments with model compounds in which 4,5,6-trichloroguaiacol and tetrachloroguaiacol were covalently linked to C2-guaiacyl residues showed that these compounds were resistant to O demethylation or dechlorination during incubation with a culture having these activities. The only effect of microbial action was the quantitative reduction in 12 days of the C'1 keto group to an alcohol which was stable against further transformation for up to 65 days. The results of these experiments are consistent with the existence of chlorocatechols and chloroguaiacols in contaminated sediments and illustrate the cardinal sig