A review of structure-based biodegradation estimation methods.

Biodegradation, being the principal abatement process in the environment, is the most important parameter influencing the toxicity, persistence, and ultimate fate in aquatic and terrestrial ecosystems. Biodegradation of an organic chemical in natural systems may be classified as primary (alteration of molecular integrity), ultimate (complete mineralization; i.e. conversion to inorganic compounds and/or normal metabolic processes), or acceptable (toxicity ameliorated). Most of the biodegradation correlations presented in the literature focus on the characterization of primary or ultimate, aerobic degradation. The US Environmental Protection Agency (USEPA) is charged with determining the risks associated with the thousands of chemicals employed in commerce, an effort that is being facilitated through much research aimed at reliable structure-activity relationships (SAR) to predict biodegradation of chemicals in natural systems. To this end, models are needed to understand the mechanisms of biodegradation, to classify chemicals according to relative biodegradability, and to develop reliable biodegradation estimation methods for new chemicals. Frequently, published correlations associating molecular structure to biodegradation will attempt to quantify the degradability of a limited set of homologous chemicals. These correlations have been dubbed quantitative structure biodegradability relationships (QSBRs). More scarce and valuable to researchers are those models that predict the biodegradability of compounds possessing a wide variety of chemical structures. The latter may use any of several techniques and molecular descriptors to correlate biodegradability: QSBRs, pattern recognition, discriminant analysis, and principle component analysis (PCA), to name several. Generally, models either predict the propensity of a chemical to biodegrade using Boolean-type logic (i.e. whether a chemical will "readily biodegrade" or not), or else they quantify the degree of biodegradation by providing information such as rate constants. Such quantitative predictions of biodegradability come in a diversity of parameters, including half-lives, various biodegradation rates and rates constants, theoretical oxygen demand (ThOD), biological oxygen demand (BOD), and others. In this paper, after describing the advantages and disadvantages of the various biodegradation estimation methods found in the literature, the best models are compared to conclude which provide the greatest utility for determining the biodegradability of chemicals with widely varying structures. The group contribution technique presented by Boethling et al. [Environmen. Sci. Technol. 28 (1994) 459] appears to be the most advantageous for use in broad screening for tendency to biodegrade. The model is simple to use, calculating a probability of biodegrading ranging from 0 (none) to 1 (certain), and has proven to be accurate for a wide range of chemical structures, as established by the large, high-quality data set (BIODEG evaluated biodegradation database, Syracuse Research Corporation, Merrill Lane, Syracuse, NY 13210) used to develop this correlation. The authors, therefore, recommend the method of Boethling et al. [Environ. Sci. Technol. 28 (1994) 459] for the initial screening of chemicals to aid in determining whether additional information is necessary to establish relative biodegradability. For readers with applications requiring more quantitative results, such as biodegradation rate constants, enough model details are presented in this paper to allow the reader to pick a suitable correlation, although the reader is cautioned to consult the original, primary reference for the complete method description, equations, and limitations.