Table Of ContentaSARin
Environmental Toxicology
QSAR in
Environmental Toxicology
Proceedings of the Workshop on Quantitative Structure-Activity
Relationships (QSAR) in Environmental Toxicology
held at McMaster University, Hamilton, Ontario, Canada,
August 16-18, 1983.
Edited by
Klaus L. E. Kaiser
National Water Research Institute,
Canada Center for Inland Waters, Burlington, Ontario, Canada
D. Reidel Publishing Company
A MEMBER OF THE KLUWER ACADEMIC PUBLISHERS GROUP
Dordrecht / Boston / Lancaster
library of Congress Cataloging in Publication Data
Workshop on quantitative structure-activity relationships
(QSAR) in Environmental Toxicology (1983: McMaster University)
Quantitative Structure-Activity Relations in Environmental Toxicology
Bibliography: p.
Includes index.
1. Pollutants-structure-activity relationships-Congresses. 2. Pollutants-
toxicology-Congresses. I. Kaiser, Klaus L. E., 1941- II. Title.
QH545.AIW67 1983 574.2'4 84-9820
ISBN -13: 978-94-009-6417-4 e-ISBN -13: 978-94-009-6415-0
DOl: 10.1007/978-94-009-6415-0
Published by D. Reidel Publishing Company
P.O. Box 17,3300 AA Dordrecht, Holland
Sold and distributed in the U.S.A. and Canada
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© 1984 by D. Reidel Publishing Company, Dordrecht, Holland
Softcover reprint of the hardcover 1st edition 1984
No part of the material protected by this copyright notice may be reproduced or utilized
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TABLE OF CONTENTS
Preface ix
List of Contributors and Participants Xl
Foreword 1
A.M. Bobra. W. Y. Shiu and D. Mackay / Structure-activity
relationships for toxicity of hydrocarbons,
chlorinated hydrocarbons and oils to Daphnia magna 3
I. Chu. D.C. Villeneuve and V.K. Valli / Comparative toxi
city and metabolism of tetrachlorobenzene isomers 17
J.M. Cullen and KoL.K. Kaiser / An examination of the role
of rotational barriers in the toxicology of PCB's 39
I
D.G. Dixon, P.V. Hodson and KoL.K. Kaiser The use of rapid
biochemical indicators of toxicant stress to
generate biological data bases for QSAR 67
W.J. Dunn III, D. L. Stalling and S. Wold / The use of SIMCA
pattern recognition in the analysis of complex
chromatographic data 75
K. Enslein, M.K. Tomb and T.R. Lander / Structure-activity
models of biological oxygen demand 89
D. Freitag, J.P. Lay and F. Korte / Environmental hazard
profile - test results as related to structures
and translation into the environment III
vi TABLE OF CONTENTS
E. Halfon / Predicting the environmental fate of toxic
contaminants in large lakes: data requirements
for mathematical models 137
D.J. Hallett / The need and requirements for quantitative
structure-activity relations (QSAR) in the Great
Lakes Water Quality Program 153
D.R. Hart / Assessment of mutagenic effects in amphibian
embryos 167
P.V. Hodson. D.G. Dixon and LL.E. Kaiser / Lethal dose
versus lethal concentration as indicator of
contaminant toxicity to fish 179
K.L.E. Kaiser. D.G. Dixon and P.V. Hodson / QSAR studies on
chlorophenols, chlorobenzenes and para-substituted
phenols 189
R. Koch / Quantitative structure-activity relationships in
ecotoxicology: possibilities and limits 207
K. Kwasniewska and LL.E. Kaiser / Toxicities of selected
chloroanilines to four strains of yeast 223
G.A. leBlanc / Comparative structure-toxicity relationships
between acute and chronic effects to aquatic
organisms 235
D. Mackay and W. Y. Shiu / Relationships between physical-
chemical and environmental partitioning
coefficients 261
L.D. Newsome. R.L. Lipnick and D.E. Johnson / Validation of
fish toxicity QSARs for certain non-reactive,
non-electrolyte organic compounds 279
B.G. Oliver / The relationship between bioconcentration
factor in rainbow trout and physical-chemical
properties for some halogenated compounds 301
TABLE OF CONTENTS
V1.1.
J.lt. Ribo and LL.B. Kaiser / Toxicities of chloroanilines
to Photobacterium phosphoreum and their correla
tions with effects on other organisms and
structural parameters 319
T.W. Schultz and B.A. Moulton / Structure-activity correla
tions of selected azaarenes, aromatic amines, and
nitroaromatics 337
v. Zitko / Data evaluation in the development of QSAR 359
General Discussion 369
Author Index 379
Formula Index 385
Subject Index 396
PREFACE
Ever since Rachel Carson's Silent Spring, we have generally
become aware of environmental contaminants and their effects on the
ecosystem. The findin~ of PCB's in fish by Soren Jensen in Sweden,
the recognition of mirex as contaminant in fish from Lake Ontario, and
the discoveries of contaminant laden leachates from dumpsites such as
the Love Canal have become milestones in the search for and charac
terization of contaminants in our environment.
At this time, the problem no longer is so much the identifi
cation of contaminants and their sources. Rather, we are now faced
with solving questions on the fates and effects of such compounds.
This includes the search for mechanisms to deal effectively with the
large number of chemicals already found in water, air and biota. One
of such time and cost saving scientific avenues is the field of
quantitative structure-activity correlations for the prediction of the
environmental behavior and effects of compounds.
This volume presents the papers and ensuing discussions at
the Workshop on Quantitative Structure-Activity Relations in Environ
mental Toxicology at McM~ster University, Hamilton, Ontario, August 16
to 18, 1983. In contrast to other conferences on QSAR which generally
emphasize QSAR as a tool for the development of new drugs, biocides
and so forth, this workshop addressed specifically the environmental
implications of existing chemicals. Therefore, one of its primary
objectives was to stimulate collaboration and discussion between
biologists, chemists, physicists, and engineers, and between experi
mentalists and modellers. Consequently, not every paper in this
volume is dealing with structure-activity correlations in the
classical sense. However, the solution of environmental contamination
problems is neither restricted to the application of anyone scienti
fic discipline nor the prerogative of anyone jurisdiction. To the
ix
x PREFACE
contrary, timely and cost-effective solutions must be based on the
collaborative expertise of many scientific disciplines as well as on
the cooperation of industry, academia and public agencies. In summary
then, the results presented here help to set the stage for further
research on environmental contamination, a problem which is faced by
most nations.
Both the workshop and these proceedings would not have been
possible without the acitve support of many colleagues, for which I
thank deeply. In particular, I wish to acknowledge Dr. Rod J. Allan,
Chief of the Environmental Contaminants Division, National Water
Research Institute, for his encouragement and support, Dr. Peter V.
Hodson, Great Lakes Fisheries Research Branch, Department of Fisheries
and Oceans, and Dr. D. George Dixon, Department of Biology, University
of Waterloo for their help in planning and organizing the workshop,
Messrs. Howard Hunter and Brandon Hickie for their assistance in
running the workshop, Mrs. Gaye Scott for the preparation of the
discussion transcripts, and her valuable assistance in editing, proof
reading, and indexing of the manuscripts, and Mrs. Dianne Crabtree for
her skill and patience in the typing and pagination of this volume.
Finally, I thank all authors, speakers, session chairmen and reviewers
whose participation and efforts are greatly appreciated. I hope this
volume proves beneficial to all readers, freshman or specialist alike.
February 1984 Klaus L.E. Kaiser
LIST OF CONTRIBUTORS AND PARTICIPANTS
R.J. Allan, Environmental Contaminants Division, National Water
Research Institute, Burlington, Ontario L7R 4A6, Canada.
R. Bisson, Environmental Protection Service, Environment Canada,
Ottawa, Ontario KIA lC8, Canada.
A. Bobra, Institute for Environmental Studies, University of Toronto,
Toronto, Ontario M5S lA4, Canada.
S.A. Boliska, Department of Biology, University of Waterloo,
Waterloo, Ontario N2L 3Gl, Canada.
N.C. BoIs, Department of Psychiatry, Uni versi ty of California, La
Jolla, California 92093, U.S.A.
I. Chu, Environmental and Occupational Toxicology Division, Health
and Welfare Canada, Ottawa, Ontario KIA OL2, Canada.
G. Craig, Toxicity Unit, Ontario Ministry of the Environment,
Rexdale, Ontario M4V IP5, Canada.
P. Craig, Health Designs, Inc., Rochester, New York 14604, U.S.A.
J.M. Cullen, Department of Chemistry, Harvard University, Cambridge,
Massachusetts 02138, U.S.A.
D.G. Dixon, Department of Biology, University of Waterloo, Waterloo,
Ontario N2L 3Gl, Canada.
W.J. Dunn, III, Department of Medicinal Chemistry & Pharmacognosy,
University. of Illinois, Chicago, Illinois 60680, U.S.A.
xi
xii LIST OF CONTRIBUTORS AND PARTICIPANTS
K. Enslein, Health Designs, Inc., Rochester, New York 14604, U.S.A.
D. Freitag, GSF, Institute for Ecological Chemistry, D-8042
Neuherberg, Federal Republic of Germany.
D.F. Hagen, 3M Central Research Laboratories, St. Paul, Minnesota
55133, U.S.A.
E. Halfon, Aquatic Physics and System Division, National Water
Research Institute, Burlington, Ontario L7R 4A6, Canada.
D.J. Hallett, Environment Canada, Toronto, Ontario M4T 1M2, Canada.
D.R. Hart, IEC Beak Consultants Ltd., Mississauga, Ontario L4V IPl,
Canada.
P.v. Hodson, Great Lakes Fisheries Research Branch, Department of
Fisheries and Oceans, Burlington, Ontario L7R 4A6, Canada.
D.E. Johnson, Office of Toxic Substances, U. S. Environmental
Protection Agency, Washington, DC 20460, U.S.A.
K.L.E. Kaiser, Environmental Contaminants Division, National Water
Research Institute, Burlington, Ontario L7R 4A6, Canada.
R. Koch, Department of Toxicology, Institute of Hygiene, DDR-6500
Gera, German Democratic Republic.
F. Korte, Institute for Chemistry, Technical University Munich,
D-8050 Freising-Weihenstephan, Federal Republic of Germany.
K. Kwasniewska, Environmental Contaminants Division, National Water
Research Institute, Burlington, Ontario L7R 4A6, Canada.
s.s. Lande, 3M Environmental Laboratory, St. Paul, Minnesota 55133,
U.S.A.
T.R. Lander, Health Designs Inc., Rochester, New York 14604, U.S.A.
J.P. Lay, GSF, Institute for Ecological Chemistry, D-8042 Neuherberg,
Federal Republic of Germany.
