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Biodegradability Prediction NATO ASI Series Advanced Science Institutes Series A Series presenting the results of activities sponsored by the NA TO Science Committee, which aims at the dissemination of advanced scientific and technological knowledge, with a view to strengthening links between scientific communities. The Series is published by an international board of publishers in conjunction with the NATO Scientific Affairs Division A Life Sciences Plenum Publishing Corporation B Physics London and New York C Mathematical and Physical Sciences Kluwer Academic Publishers D Behavioural and Social Sciences Dordrecht, Boston and London E Applied Sciences F Computer and Systems Sciences Springer-Verlag G Ecological Sciences Berlin, Heidelberg, New York, London, H Cell Biology Paris and Tokyo I Global Environmental Change PARTNERSHIP SUB-SERIES 1. Disarmament Technologies Kluwer Academic Publishers 2. Environment Springer-Verlag / Kluwer Academic Publishers 3. High Technology Kluwer Academic Publishers 4. Science and Technology Policy Kluwer Academic Publishers 5. Computer Networking Kluwer Academic Publishers The Partnership Sub-Series incorporates activities undertaken in collaboration with NA TO's Cooperation Partners, the countries of the CIS and Central and Eastern Europe, in Priority Areas of concern to those countries. NATo-PCO-DATA BASE The electronic index to the NATO ASI Series provides full bibliographical references (with keywords and/or abstracts) to more than 50000 contributions from international scientists published in all sections of the NATO ASI Series. Access to the NATO-PCO-DATA BASE is possible in two ways: - via online FILE 128 (NATO-PCO-DATA BASE) hosted by ESRIN, Via Galileo Galilei, 1-00044 Frascati, Italy. - via CD-ROM "NATO-PCO-DATA BASE" with user-friendly retrieval software in English, French and German (© WTV GmbH and DATAWARE Technologies Inc. 1989). The CD-ROM can be ordered through any member of the Board of Publishers or through NATO PCO, Overijse, Belgium. Series 2: Environment - Vol. 23 Biodegradability Prediction edited by Willie J. G. M. Peijnenburg National Institute of Public Health and the Environment, Bilthoven, The Netherlands and Jirl Damborsky Department of Microbiology, Faculty of Science, Masaryk University, Brno, Czech Republic .... " Springer-Science+Business Media, B.V. Proceedfngs of the NATO Advanced Research Workshop on QSAR Biodegradation 11: QSARs for Biotransformation & Biodegradation Luhai!ovice, Czech Republic May 2-3, 1996 A CJ.P. Catalogue record for this book is available from the Library of Congress ISBN 978-94-010-6398-2 ISBN 978-94-011-5686-8 (eBook) DOI 10.1007/978-94-011-5686-8 Printed on acid-free paper All Rights Reserved @ 1996 Springer Science+Business Media Dordrecht Originally published by Kluwer Academic Publishers in 1996 Softcover reprint of the hardcover 1s t edition 1996 No part of the material protected by this copyright notice may be r~produced or utilized in any form or by any means, electronic or mechanical, including photo copying, recording or by any information storage and retrieval system, without written permission from the copyright owner. TABLE OF CONTENTS Preface vii Acknowledgement ix Introduction Introduction, Main Conclusions and Recommendations of the Workshop "QSAR Biodegradation II" W.1. G. M. Peijnenburg, J. Damborsky Part I. Biodegradability (foundations, testing) Biodegradability of Xenobiotic Organic Compounds Depends on their Chemical Structure and Efficiently Controlled, and Productive Biochemical Reaction Mechanisms R.-M. Wittich 7 Biodegradability Testing of Xenobiotics P. Pitter, V. Sykora 17 Part II. Biodegradability Modelling (trends, methods) The META-CASETOX System for the Prediction of the Toxic Hazard of Chemicals Deposited in the Environment G. Klopman 27 Application of Artificial Intelligence in Biodegradation Modelling D. Gamberger, S. Sekusak, Z. Medven, A. Sabljic 41 Polychlorinated Dibenzo-p-Dioxins in Anaerobic Soils and Sediments. A Quest for Dechlorination Pattern-Microbial Community Relationships P. Adriaens, A.L. Barkovskii, M. Lynam, J. Damborsky, M. Kuty 51 A Biodegradability Evaluation and Simulation System (BESS) Based on Knowledge of Biodegradation Pathways B. Punch, A. Patton, K. Wight, R. J. Larson, P.H. Masscheleyn, L. Forney 65 A Mechanistic Approach to Deriving Quantitative Structure Biodegradability Relationships. A Case Study: Dehalogenation of Haloaliphatic Compounds J. Damborsky, K. Manova, M. Kuty 75 Part III. Biodegradability Prediction (applications) Quantitative Structure-Biodegradability Studies: An Investigation of the MITI Aromatic Compound Data-Base J. Dearden, M. T. D. Cronin 93 VI Prediction of Biodegradability from Chemical Structure: Use of MITI Data, Structural Fragments and Multivariate Analysis for the Estimation of Ready and Not Ready Biodegradability H. Loonen, F. Lindgren, B. Hansen, W. Karcher 105 Development of Structure-Biodegradability Relationships (SBRs) for Estimating Half-Lifes of Organic Contaminants in Soil Systems R. Govind, L. Lei, H. Tabak 115 Subject Index 139 Author Index 143 PREFACE Large numbers of hazardous organic chemicals are emitted into the environment from anthropogenic and natural sources. Assessment of the ecological impact of the emissions related to the production and use of chemicals, requires to have available simple, and above all, reliable models that can be used to both qualitatively and quantitatively describe the fate and behaviour of these compounds in the environment. Up till now several of the transport and transformation processes that may contribute significantly to the removal of xenobiotics from distinct environmental compartments have been studied in detail and various models and process descriptions are available. Several reaction paths have been investigated intensively and an increasing number of reaction rate constants can now be estimated quite accurately using a variety of Quantitative Structure Activity Relationships (QSARs). For most organic chemicals, biodegradation is the dominant transformation pathway, contributing significantly to the attenuation of their environmental concentrations. Presumably due to the complexity of the biodegradative pathways, at the moment it only to a limited extent is possible to extrapolate results of biodegradation tests obtained in the laboratory, to realistic environmental field conditions; methods for predicting rates of biodegradation in the field seem to be lacking completely. Thus, to understand the fate of a substance and to predict exposure concentrations for risk assessment, information on the biodegradability of a substance is critical to the assessment. Currently, however, QSARs for estimating the biodegradability of a substance are not only limited in number, but their validity is being questioned. These observations prompted us to organise a first workshop on QSARs for Biodegradation in September 1994 (as a satellite workshop to the 6th International Work shop on QSAR in Environmental Sciences, organised in Belgirate [Italy] by dr. W. Karcher -European Chemicals Bureau, Joint Research Centre of the European Communi ties, Ispra [Italy D. Although one of the main conclusions was that there still is insufficient knowledge of the basic processes that take place during biodegradation, at the same time the meeting revealed that a broad range of molecular descriptors is available with high potency to be the relevant parameters for description of the structural features connected with the ability of a compound to be converted by the action of living organisms [1]. Also, highly sophisticated statistical and computational methods are available, like multivariate statistics, neural networks, genetic algorithms, to explore and find structure-activity relationships. It was revealed that it is the biodegradation data entering in the analysis and probably also the whole philosophy used for biodegradation modelling which can not be considered as being satisfactory at present. There is no doubt, that the biodegradability of a particular organic compound in the environment is not dependent only on its structure, but also on factors related to the environmental conditions the chemical resides in. The latter factors were in the past completely neglected in Quantitative Structure-Biodegradabiliy Relationship (QSBR) models. In other words, it was concluded that up till now insufficient attention has been paid to the "biological" and "ecological" part of the biodegradation process in structure-biodegradability models. vii viii Considering the long history of the investigations into the processes of biodegradation of organic compounds by living organisms, we believe that there exists far more knowledge about these processes than has been incorporated into the structure-bio degradability models to date. We therefore decided to organise the second workshop on QSARs for biodegradation. In co-operation with the NATO Scientific Affairs Division, this workshop was held in May 1996 in Luhacovice (Czech Republic). One of the ideas standing behind the meeting in Luhacovice was to bring together experts working on biodegradation problems and those working on the development and the analysis of Quantitative Structure-Biodegradability Relationships, and initiate a public discussion on 'bringing the knowledge on biological aspects of biodegradation into QSBR models'. As the QSAR analysis has always been considered to be a interdisciplinary area, we believe that this discussion could be successful. In these proceedings, participants of the "NATO Advanced Research Workshop on QSAR Biodegradation II" report on the present state of art with regard to QSBRs and on the main findings of the deliberations. The contributions may be classified into three distinct categories: (i) The main characteristics and foundations of biodegradation. This section includes on the one hand overviews of the microbial aspects of biodegradation, whereas on the other hand the methods that are available for testing the biodegradability of chemical substances are reviewed. (ii) Trends and methods in biodegradation modelling. In this section amongst others, several computerised systems for the prediction of the biodegradability of chemicals deposited in the environment are highlighted. (iii)The application of predictive methods for biodegradation: the application and validation of some newly developed predictive models for biodegradation of organic compounds in both the aquatic and the terrestrial compartment is highlighted in this section. W.J.G.M. Peijnenburg, J. Damborsky, Editors REFERENCE 1. Peijnenburg, W.J.G.M. and Karcher, W. (eds.), Proceedings of the Workshop "Quantitative Structure Activity Relationships for Biodegradation ", National Institute of Public Health and Environmental Protection (RIYM), Bilthoven, The Netherlands, Report no. 719101021. ACKNOWLEDGEMENT On behalf of all participants to the Workshop "QSAR Biodegradation II: QSARs for Biotransformation & Biodegradation", we gratefully acknowledge all support obtained from the NATO Scientific Affairs Division. Special thanks are due to dr. L. Veiga da Cunha, Director Priority Area on Environmental Security, for his active support in the organisational aspects of the meeting. Also we wish to acknowledge the organisers of TOCOEN '96, and especially prof. I. Holoubek, for kindly providing all logistic and technical facilities during the workshop. Part of the preparation of the workshop report was carried out under the framework of the project "Fate and Activity Modelling of Environmental Pollutants Using Structure Activity Relationships", financially supported by the Environmental Technologies RTD Programme (DG XIIID-I) of the Commission of the European Communities under contract number ENV4 -CT96-0221. Additional funding was obtained in the framework of the EU Programme on Science and Technology Co-operation with Central and Eastern European countries under the supplementary agreement number CIPD-CT93- 0042. Financial support from the European Union is gratefully acknowledged. W.J.G.M. Peijnenburg J. Damborsky ix INTRODUCTION, MAIN CONCLUSIONS AND RECOMMENDATIONS OF THE WORKSHOP "QSAR BIODEGRADATION II" W.J.G.M. PEIJNENBURG National Institute of Public Health and the Environment, Laboratory for Ecotoxicology, P.O. Box I, 3720 BA Bilthoven, THE NETHERLANDS and J. DAMBORSKY Faculty of Science, Masaryk University Kotlarska 2, 61 I 37 Brno, CZECH REPUBLIC 1. Introduction For most organic chemicals, biodegradation is the dominant transformation pathway, contributing significantly to the attenuation of their environmental concentrations. When biodegradation is complete and mineralisation to carbon dioxide or methane occurs, organic carbon and other elements from the substance, like for instance nitrogen and sulphur, are released and reassimilated into natural elemental cycles. To understand the fate of a chemical and to assess its ecological impact, information on the biodegra dability is critical. Basically two types of biodegradation data are required. The first type of information is on whether the substance is completely biodegradable or if persistent metabolites are formed. In the case of formation of persistent metabolites an additional impact assessment will need to be conducted for them and the long-term potential for impacts due to accumulation evaluated. The second type of data is on the rate of biodegradation in relevant environmental compartments. This information is used to predict the concentrations to which organisms will be exposed in the environment. The rate data can also be used to assess the potential for accumulation. The question whether a chemical is completely biodegradable is usually answered by looking at the results of a standard biodegradation test. There are several ways to estimate the rate of biodegradation in the environmental compartment in which the chemical will reside. The most straight forward method is to measure the rate in the environmental media of interest. However, these type of biodegradation tests are complicated and thus data are limited. An alternative approach is to measure the rate in a screening test or to assume some rate for substances that "pass" the test and apply a scaling factor to convert that rate to one that is applicable to the environmental compartment of interest. In case of substances that are to be considered readily biode- 1 W. J. G. M. Peijnenburg andJ. DamborskY (eds.), Biodegradability Prediction, 1-5. © 1996 Kluwer Academic Publishers.
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