Microorganisms in soils and waters convert many synthetic organic chemicals to inorganic products. Other compounds are transformed only by cometabolism. These microbial processes may lead to environmental detoxication, the formation of new toxicants, or the biosynthesis of persistent products. Type reactions are proposed for major categories of enzymatic transformation of synthetic chemicals in soils, natural waters, and sewage. Some organic molecules are resistant to microbial attack, and explanations for the persistence of such compounds are suggested.

https://science.sciencemag.org/content/sci/211/4478/132.full.pdf

Biodegradation of Chemicals of Environmental Concern

Considerable progress has been made in the last few years in understanding the mechanisms of microbial degradation of halogenated aromatic compounds. Much is already known about the degradation mechanisms under aerobic conditions, and metabolism under anaerobiosis has lately received increasing attention. The removal of the halogen substituent is a key step in degradation of halogenated aromatics. This may occur as an initial step via reductive, hydrolytic or oxygenolytic mechanisms, or after cleavage of the aromatic ring at a later stage of metabolism. In addition to degradation, several biotransformation reactions, such as methylation and polymerization, may take place and produce more toxic or recalcitrant metabolites. Studies with pure bacterial and fungal cultures have given detailed information on the biodegradation pathways of several halogenated aromatic compounds. Several of the key enzymes have been purified or studied in cell extracts, and there is an increasing understanding of the organization and regulation of the genes involved in haloaromatic degradation. This review will focus on the biodegradation and biotransformation pathways that have been established for halogenated phenols, phenoxyalkanoic acids, benzoic acids, benzenes, anilines and structurally related halogenated aromatic pesticides. There is a growing interest in developing microbiological methods for clean-up of soil and water contaminated with halogenated aromatic compounds.

Microbial breakdown of halogenated aromatic pesticides and related compounds

(1980). Chlorinated Phenols: Occurrence, Toxicity, Metabolism, And Environmental Impact. CRC Critical Reviews in Toxicology: Vol. 7, No. 1, pp. 1-35.

Chlorinated Phenols: Occurrence, Toxicity, Metabolism, And Environmental Impact

The ability of two white rot fungi to deplete pentachlorophenol (PCP) from soil, which was contaminated with a commercial wood preservative, was examined in a field study. Inoculation of soil containing 250 to 400 μg of PCP g−1 with either Phanerochaete chrysosporium or P. sordida resulted in an overall decrease of 88 to 91% of PCP in the soil in 6.5 weeks. This decrease was achieved under suboptimal temperatures for the growth and activity of these fungi, and without the addition of inorganic nutrients. Since the soil had a very low organic matter content, peat was included as a source of organic carbon for fungal growth and activity. A small percentage (8 to 13%) of the decrease in the amount of PCP was a result of fungal methylation to pentachloroanisole. Gas chromatographic analysis of sample extracts did not reveal the presence of extractable transformation products other than pentachloroanisole. Thus, when losses of PCP via mineralization and volatilization were negligible, as they were in laboratory-scale studies (R. T. Lamar, J. A. Glaser, and T. K. Kirk, Soil Biol. Biochem. 22:433-440, 1990), most of the PCP was converted to nonextractable soil-bound products. The nature, stability, and toxicity of soil-bound transformation products, under a variety of conditions, must be elucidated before use of these fungi in soil remediation efforts can be considered a viable treatment method.

https://www.fpl.fs.fed.us/documnts/pdf1990/lamar90c.pdf

In situ depletion of pentachlorophenol from contaminated soil by Phanerochaete spp.

The degradation products of diuron (photoproducts and metabolites), already described in the literature, were synthesized in order to carry out further investigations. Their ecotoxicity was determined using the standardized Microtox® test, and most of the derivatives presented a nontarget toxicity higher than that of diuron. Therefore, the biotransformation of these compounds was tested with four fungal strains and a bacterial strain, which were known to be efficient for diuron transformation. With the exception of the 3,4-dichlorophenylurea, all the degradation products underwent other transformations with most of the strains tested, but no mineralization was observed. For many of them, the biodegradation compound for which the toxicity was important was 3,4-dichlorophenylurea. This study underlines the importance of knowing the nature of the degradation products, which has to be kept in mind while analyzing natural water samples or soil samples.

Degradation products of a phenylurea herbicide, diuron: synthesis, ecotoxicity, and biotransformation.

The formation of pentachloroanisole by methylation from pentachlorophenol by Trichoderma virgatum in liquid cultures was detected using gas chromatography and confirmed by melting point determinati...

E. L. Johnson

Papers

Methylation of pentachlorophenol by Trichoderma virgatum.