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Chlorinated Insecticides
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G.T Brooks
ISBN 978-1-138-50533-9
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www.crcpress.com
Chlorinated
Insecticides
V olume II
Biological and
Environmental Aspects
Author:
G. T. Brooks
The University of Sussex
Brighton, Sussex
England
First published 1974 by CRC Press
Taylor & Francis Group
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Reissued 2018 by CRC Press
© 1974 by Taylor & Francis
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PESTICIDE CHEMISTRY SERIES - PREFACE
The literature on pesticides is voluminous, but scattered among dozens of journals and
texts written or edited by experts. Until now, with the publication of Chlorinated
Insecticides by G. T. Brooks, there has been no attempt to produce a single,
comprehensive series on the chemistry of pesticides. CRC Press should be commended for
having undertaken this Herculean task.
When asked by the publisher to serve as editor of the Pesticide Chemistry Series, I
discussed the idea with some of my colleagues at the International Pesticide Congress in
Tel Aviv in 1971. At that time, Dr. Brooks enthusiastically agreed to become the author
of the treatise on chlorinated insecticides, which became such a comprehensive work that
it is being published in two volumes.
As editor of this series, my goal has been choosing experts in their respective fields
who would be willing to write single-authored books, thus assuring uniformity of style
and thought for the individual text as well as the entire series. I would like to express my
deep appreciation to each author for having undertaken the large task of writing in such a
comprehensive manner without the aid of contributors or an editorial board.
Chlorinated Insecticides is the first contribution to this series; subsequent volumes
under preparation will appear in the near future under titles such as Organophosphate
Pesticides; Herbicides; and Fungicides. Looking into the future, we plan to include books
on the chemistry of juvenile hormones and pheromones. Suggestions on other titles and
possible authors are invited from the reader.
Gunter Zweig
Editor
Pesticide Chemistry Series
THE AUTHOR
Gerald T. Brooks was formerly in the Biochemistry Department of the Agricul
tural Research Council’s Pest Infestation Laboratory (now the Pest Infestation
Control Laboratory of the Ministry of Agriculture, Fisheries, and Food) at Slough,
England. He is currently Senior Principal Scientific Officer in the Agricultural Re
search Council Unit of Invertebrate Chemistry and Physiology at the University of
Sussex, Brighton, England. He holds B.Sc. and Ph.D. degrees of the University of
London, and is a Fellow of The Royal Institute of Chemistry. His field of work is
the chemistry, biochemistry, and toxicology of insecticides and hormones.
To Ann, my wife and former colleague, and my many friends in Insecticide Toxicology
whose work is referred to in these pages.
TABLE OF CONTENTS
Chapter 1
Introduction...........................................................................................................................................................1
Chapter 2
Insect Resistance to Chlorinated Insecticides ................................................................................................3
A. Resistance and Its Measurement ..............................................................................................................3
B. Inheritance and Biochemical Genetics of Resistance..............................................................................8
1. Mode of Inheritance...........................................................................................................................8
2. Biochemical Genetics ................................................................................................................10
a. Houseflies .............................................................................................................................10
b. Mosquitoes.............................................................................................................................18
c. Other Species........................................................................................................................23
3. Postadaption and Resistance ........................................................................................................24
C. Development of Resistance in the Field .................................................................................................29
1. Background ................................................................................................................................29
2. Species of Public Health or Veterinary Importance................................................................31
a. Houseflies ............................................................................................................................31
b. Other Noxious D iptera........................................................................................................35
c. Mosquitoes............................................................................................................................37
d. Lice, Fleas, Bedbugs, Reduviid Bugs, and Cockroaches....................................................43
e. Acarina (Ticks and M ites)....................................................................................................46
3. Species of Agricultural Importance ............................................................................................48
a. Impact of Resistance in Agricultural Insects ....................................................................48
b. Resistance in Soil Insects ....................................................................................................55
c. Resistance in Stored Product Insects .............................................................................57
4. Stability of Resistance....................................................................................................................58
Chapter 3
Action of Chlorinated Insecticides...................................................................... 63
A. Introduction ............................................................................................................................................63
B. Environmental Behavior and Metabolism................................................................................................65
1. Biodynamics....................................................................................................................................66
a. Insects....................................................................................................................................66
b. In Soil, Plants, and Microorganisms....................................................................................67
c. In Vertebrates........................................................................................................................73
2. Nature of the Transformation Products........................................................................................77
a. DDT Group............................................................................................................................77
b. Lindane (7-HCH) 80
c. Heptachlor, Chlordane, Isobenzan, and Endosulfan .........................................................84
d. Aldrin and Dieldrin ............................................................................................................89
e. Isodrin and Endrin................................................................................................................94
3. Biochemical Aspects........................................................................................................................97
a. General Mechanisms of Organochlorine Insecticide Metabolism ......................................97
b. Enzymatic Detoxication and Insect Resistance..............................................................101
c. Interactions with Microsomal Enzymes ............................................................................105
C. Toxicity ...................................................................................................................................................110
1. Toxicity to Insects and Structure-Activity Relations ...............................................................110
a. DDT Group...........................................................................................................................110
b. Cyclodiene Insecticides.......................................................................................................115
c. Hexachlorocyclohexane and Toxaphene..........................................................................121
2. Toxicity to Vertebrates and Other Nontarget Organisms..........................................................123
a. DDT Group..........................................................................................................................123
b. Cyclodiene Insecticides......................................................................................................127
c. Hexachlorocyclohexane and Toxaphene..........................................................................129
D. Mode and Mechanism of Action ..........................................................................................................130
1. DDT ..............................................................................................................................................130
2. Lindane and the Cyclodiene Insecticides ..................................................................................136
a. Lindane ..............................................................................................................................136
b. Cyclodiene Insecticides......................................................................................................138
E. An Addendum on Mirex ............................................... 143
Chapter 4
Residues and Prospects......................................................................................................................................145
References..........................................................................................................................................................153
Systematic Names Index...................................................................................................................................177
General Index ...................................................................................................................................................181
