CRC REVIVALS CRC REVIVALS

G.T Brooks
Chlorinated Insecticides
Chlorinated Insecticides
Volume I
Technology and Application

G.T Brooks

ISBN 978-1-138-55045-2

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www.crcpress.com
 Chlorinated
Insecticides
Volume I
Technology and Application

Author:

G. T. Brooks
The University of Sussex
Brighton, Sussex
England
First published 1974 by CRC Press
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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.
 CHLORINATED INSECTICIDES
TECHNOLOGY AND APPLICATIONS

TABLE OF CONTENTS

Chapter 1
I n tr o d u c tio n ....................................................................................................................................................... 4

Chapter 2
Chlorinated Insecticides of the DDT Group ....................................................................................................7
A. History and D e v elo p m e n t.......................................................................................................................... 7
1. Origins and Applications in World War II ........................................................................................7
2. Development of Application Methods ........................................................................................ 18
a. As Sprays, Dusts, Emulsions, etc.............................................................................................18
b. More Durable F o rm u la tio n s................................................................................................22
3. Applications in Pest Control ........................................................................................................26
a. Toxicity to Plants and Beneficial I n s e c ts ............................................................................26
b. Agricultural A p p lic a tio n s....................................................................................................28
c. Public Health, Veterinary, and Other Applications ........................................................ 35
d. Current Status of D D T ........................................................................................................39
B. Synthesis, Physical, and Chemical P r o p e r tie s ........................................................................................46
1. General Synthetic Routes ............................................................................................................. 46
2. Technical Materials and Physical P r o p e r tie s ................................................................................52
3. Constitution and C hem istry............................................................................................................59
C. Principles of A n a ly sis................................................................................................................................68
L Gravimetric, Total Chlorine, Colorimetric A n a ly s is ..................................................................... 68
2. Spectrophotometry, Polarography, Isotope T e c h n iq u e s ............................................................ 73
3. Analysis and Structure Determination of Organochlorines by Chromatography, NMR, and Mass
Spectrometry...................................................................................................................................... 77
a. Column, Paper, Thin-layer, and Gas-liquid Chromatography ........................................ 77
b. Modern Physical M e th o d s ....................................................................................................82
4. B io a ssa y ............................................................................................................................................ 83

Chapter 3
Insecticides of the Diene-organochlorine Group ........................................................................................85
A. Introduction ........................................................................................................................................... 85
1. The Diels-Alder R e a c tio n ................................................................................................................85
2. The Nomenclature of Cyclodiene In se c tic id e s............................................................................ 87
B. Synthesis and Chemistry ....................................................................................................................... 99
1. Hexachlorocyclopentadiene and Its Self-condensation products; Chlordecone (Kepone®),
Despirol®, Mirex, and P e n t a c ® ....................................................................................................99
2. The Diels-Alder Reaction with Hexachlorocyclopentadiene and Its R e la tiv e s ...................... 105
a. Alodan®, Endosulfan, Isobenzan, Heptachlor, Chlordane, and A n a lo g u e s.................. 105
b. Aldrin, Dieldrin, Isodrin, Endrin, and Related C o m p o u n d s .......................................... 113
3. Synthesis of Radiolabeled C y c lo d ie n e s............................ 117
4. Constitution and Chemical Reactions of C y c lo d ie n e s.............................................................. 123
a. Configuration of the Ring S y s t e m s .................................................................................. 123
b. Heptachlor, Chlordane, and Related Compounds .......................................................... 124
c. Isobenzan and E n dosulfan.................................................................................................. 131
d. Aldrin and Dieldrin .......................................................................................................... 132
e. Isodrin and E n d r i n ..............................................................................................................136
C. History and Development of the Commercial Cyclodiene Insecticides............................................. 140
1. Chlordane and Heptachlor .......................................................................................................... 140
a. Origins, Physical Properties, and Formulations ...............................................................141
b. Applications in Agriculture and PublicHealth ................................................................ 151
c. Principles of A n a y lsis...........................................................................................................155
2. Endosulfan and Isobenzan .......................................................................................................... 158
a. Origins and Physical P ro p e rtie s.................................................................... 158
b. Applications of Endosulfan .............................................................................................. 159
c. Analysis of E n d o s u lfa n ...................................................................................................... 160
3. Aldrin, Dieldrin, Isodrin, and E n d r i n ...........................................................................................161
a. Origins and Physical P ro p e rtie s.......................................................................................... 161
b. Formulations and Early E v a lu a tio n .................................................................................. 166
c. Applications in Agriculture and Against Pests Affecting Man and A n im a ls .................. 171
d. Principles of A n a ly sis...........................................................................................................176
e. Current Status of Aldrin, Dieldrin andEndrin ................................................................ 178
4. Applications of Chlordecone (Kepone), Mirex,and P e n t a c ........................................................ 182

Chapter 4
Gamma-l,2,3,4,5,6,-Hexachlorocyclohexane ............................................................................................ 185
A. Origins, Preparation and PhysicalProperties ......................................................................................185
1. Applications in Agriculture and Against Pests AffectingMan and Animals ............................ 192
2. Stereochemistry, Constitution and R e a c tio n ...............................................................................196
3. A n a ly s is .......................................................................................................................................... 202

Chapter 5
Polychloroterpene Insecticides [Toxaphene] .............................................................................................. 205
A. Origins, Preparation, Physical P ro p e r tie s .............................................................................................. 205
B. Applications in Agricultural and Against Insects Affecting Man and A n im a ls................................ 207
C. Analysis ....................................... 210

R efe ren c es.................................................................................................... - ................................................211

Systematic Names I n d e x ................................................................................................................................ 233
General Index ................................................................................................................................................ 237
 FOREWORD

This definitive and most detailed work ever to (along with some of their metabolic products),
have been published, devoted exclusively to the they appear to have endangered the survival of
chemistry and biology of chlorinated insecticides, certain species of predatory birds whose diets are
comes from the authoritative pen of a leading restricted to animals which store the chlorinated
investigator in this field. It should serve for many insecticides of their derivatives in their tissues.
years to come as the prime reference source both Such findings, along with some oncological studies
for instructional and research purposes, for it not of more or less questionable applicability to
only delineates that which is known about this humans, have prompted official departments of
valuable class of compounds, but also emphasizes public health in some countries to proscribe the
those important biological and ecological areas in chlorinated insecticides for all uses. In this
which our knowledge is still much too sketchy and situation, it behooves investigators to keep the
in which further investigation may be expected to shelves of their stockrooms well filled with
uncover facts of great interest and wide supplies of these compounds for possible experi­
applicability. mental use, against the day when some of them
In a way, it is ironic that this excellent treatise may no longer be available on the market.
should appear at a time that seems to mark the The extension of programs currently required
twilight of the various uses of the chlorinated for the biological screening of new insecticide
insecticides. It is not that they have been super­ candidates has made this sort of research so
seded by some other class or classes of chemicals expensive that even the wealthiest manufacturers
that have proved themselves cheaper or more are now seriously considering abandoning the
effective. Quite the contrary; the cost effectiveness search for new insecticides as economically un­
of the chlorinated insecticides has remained un­ rewarding. Further advances in the field of pest
equaled since their introduction some three control in agriculture and public health will then
decades ago. Neither is it because the amounts of depend, to an even greater extent, upon the
insecticide required are, from an agricultural or interest of governmental agencies and upon univer­
public health standpoint, so very great. Indeed, the sity laboratories. These, however, must consider
very hallmark of the chlorinated insecticides, the shrinking purchasing power of their budgets
which characterized them originally as wonder and the concomitant inevitable expansion of their
chemicals, was the unbelievably small amounts involvement in other interests. The upshot is that
needed over a given area to effect complete the outlook at the moment for effective insect
control of insect pests. It is the very persistence of pest control is bleak. Thus, once again, shallow, if
trace quantities of this class of chemicals that has well-intentioned clamor threatens to do great harm
been seized upon by some environmentalists as to national economies and to impressive public
ammunition in their war to eliminate totally, for health advances.
whatever use, all chlorinated insecticides, which, Yet, despite the gloomy picture of the moment,
but a comparatively few years ago, were lauded as a more balanced attitude toward the chlorinated
the saviors of a hungry and disease-ridden insecticides may eventually prevail. Meanwhile, it
humanity. Participants in these activities should should be of benefit to the chemist and biologist
observe the impact of the current world grain to keep up-to-date on all that has been done (and
shortage on food prices and consider the vital role omitted) in this field. For, once the mode of
of well-proven control chemicals for cereal pests in biological activity of these compounds is more
balancing an increasingly precarious food supply in fully elucidated, it would seem quite likely that
our favor. new types of chlorinated insecticides and, indeed,
By and large, the chlorinated insecticides have related structural types lacking chlorine may be
not been shown to have produced any symptoms devised, which will combine price effectiveness
of chronic toxicity in the general public. However with environmental acceptability.

Julius Hyman
Berkeley, California

1
 PREFACE

It is now nearly 23 years since the publication since resistance represents a failure of applications.
of the second and revised edition of the book by Accordingly, it is emphasized that the division is
West and Campbell entitled DDT: The Synthetic merely one of convenience and the two parts are
Insecticide. Since then, although numerous texts to be regarded as a single entity dealing with the
have included sections on various aspects of science of chlorinated insecticides.
chlorinated insecticide technology and biology, While the chemistry of DDT analogues is
there has been no publication that has attempted reasonably straightforward, that of the cyclodiene
to treat the subject as a whole, in spite of all that insecticides is unfortunately more complicated and
has been achieved by the use of these compounds a different order of presentation has been adopted
and all that has been said about them in the for them. Thus, sections on the stereochemistry of
controversial atmosphere of recent years. This the Diels-Alder reaction and on the nomenclature
two-volume book makes some attempt to fill the of cyclodienes have been included in Volume I in
gap, although it does not deal with the chlorinated an attempt to clarify some of the more difficult
hydrocarbons used as fumigants. points, this and other basic information being
The task of writing about chlorinated insec­ presented before the history and use aspects.
ticides is a truly formidable one, since the amount
The development of insect resistance to organo-
of literature on the chemistry of these compounds
and their effects, real or imaginary, on living chl orine insecticides is an interesting and
organisms has grown phenomenally in recent important part of their history and accordingly has
years. While there is a clear need to present the been discussed in some detail in Volume II. All
rem aining aspects of their environmental
complicated science of these chemicals in an
behaviour are conveniently treated in Volume II
understandable fashion, attempts to do so usually
under “action,” dealing with topics ranging from
result in misleading and dangerous oversimplifica­
biodynamics, through biochemical interactions, to
tions and generalizations. Thus, a statement such
mechanism of action. A final short section in that
as “ this chlorinated insecticide fed to rats in the
volume deals with some general matters, including
diet produces liver damage” is totally meaningless
current arrangements for regulating pesticide
without details of the level and duration of the
residues in food.
feeding. Likewise, a text without adequate
references is of little value because the reader is Since the combined volumes are intended to be
often unable to properly distinguish between what of use to those whose interests are historical or in
is actually in the scientific literature and what is applications, as well as to chemists, toxicologists,
the opinion of the author. This area above all is and resistance geneticists, some parts are inevitably
one in which those who are interested should, if more readable than others. If readers from any one
they wish, have access to the original work in of these areas are so much as tempted to examine
order to make their own judgments. Accordingly, one or more of the others, then the book will have
the levels of treatments have been included when­ served a useful purpose.
ever possible, and the text is as fully referenced as The provision of copies of their books by Dr. T.
is feasible. F. West and Professor A. W. A. Brown is gratefully
The subject falls conveniently into one volume acknowledged, as also various items of information
dealing with chemistry and applications (techno­ furnished by Mr. J. A. Smith, Dr. R. F. Glasser,
logical aspects) and a second (biological and and colleagues of the Shell International Chemical
environmental aspects) which considers their inter­ Company, by Dr. P. B. Polen of the Velsicol
actions with living systems. However, rigid division Chemical Corporation, and by Dr. A. Calderbank
is neither easy nor entirely desirable, and there is of Jealott’s Hill Research Station, Imperial
inevitably some degree of overlapping between Chemical Industries, Plant Protection Limited. It is
those parts of the subject that can be treated from a pleasure to thank Dr. J. Robinson of Shell
several points of view. Thus, there is a relationship Research Limited, Tunstall laboratory and
between “ applications” in Volume I and “ develop­ Professor J. R. Busvine o f the London School of
ment of resistance in the field,” in Volume II, Hygiene, who kindly read various parts of the

2 Chlorinated Insecticides
manuscript, and Dr. C. T. Bedford, also of the Views or opinions expressed herein should not
Tunstall laboratory, for valuable discussions be taken to represent those of any official source,
relating to cyclodiene insecticide nomenclature. unless references are given.

G. T. Brooks
Brighton, England

3
 Chapter 1

INTRODUCTION

There is a natural, but unfounded tendency to The origin of chemical insect control seems to
regard human life as being different from other be lost in antiquity. According to one source,1
forms in its degree of subjection to natural laws. It pyrethrum was introduced into Europe from the
is, of course, true that because of his varied skills, Far East by Marco Polo, and another authority
man is probably better able than many other states that the use of pyrethrum as an insecticide
species to survive in a hostile environment, but by certain Caucasian tribes was observed in the
beyond this, it needs to be pointed out rather early 19th century.2 Extracts of roots of plants of
forcibly that human life, like other forms, is a the Derris species have long been used by primitive
com plex equilibrium between processes of peoples as fish poisons, and it was suggested in
chemical synthesis and degradation that is 1848 that such extracts might be insecticidal.
supported by the continual intake of gaseous, Preparations from the plant sab adilla contain
liquid, and solid chemicals of all kinds from the veratrine alkaloids, and for centuries have been
external environment. There is no doubt that some used as insecticides by South American natives,
of these chemicals from natural sources (in the while the application of tobacco extracts (nicotine
food) have deleterious effects on life in the long alkaloids) as insecticides dates from the mid-18th
term and this is undoubtedly one reason why century.1 The general toxicity of alkaloids from
man’s allotted lifespan is 70 years rather than the South American plant Ryania speciosa has also
some much higher figure. been known for some time, but the insecticidal
To the scientist who, by his training, has properties were first reported in 1945. Various oils
become accustomed to thinking in chemical terms such as petroleum, kerosene, creosote, and
and whose work brings him into daily contact with turpentine came into use in the 18th Century, but
chemicals, the realization that members of the their use was limited due to phytotoxicity and
general p u b lic apparently have scarcely they were succeeded by highly refined oils for­
appreciated the extent of their dependence on mulated as emulsions of low phytotoxicity.
chemistry for actual existence as well as for Several elements and their salts have had
comfortable survival comes as a considerable longstanding use as insecticides. Plinius is said to
shock. Viewed against the inevitability of human have recommended arsenic for this purpose in 70
involvement with chemicals, the popular objection A.D., and arsenic sulfide was used by the Chinese
to one particular group of toxic substances from in the 16th Century.3 Paris Green (a complex of
among the immense number to which humans and copper arsenite and copper acetate), calcium
other living organisms have undoubtedly been arsenate, and lead arsenate came into use in the
exposed over a long period of time seems almost 19th Century and a use was found for various salts
irrelevant. Nevertheless, the controversy surround­ of copper, zinc, thallium, chromium, lead,
ing the chlorinated insecticides has served to mercury and selenium, and cryolite (sodium
stimulate renewed interest in the relationship fluoaluminate). Some of these compounds are
between man and his environment. Furthermore, highly persistent and give rise to considerable
the ability to detect minute quantities of these residue hazards. Hydrogen cyanide was used
compounds has given warning of the way in which against scale insects by the year 1886 and dinitro-
stable, man-made materials can become distributed phenols as insecticides as early as 1892. Methyl
far beyond the spheres in which their use was bromide and carbon disulfide have been used for
originally intended. Since the effects of such many years and the use of naphthalene and
distributions cannot readily be predicted, it is p-dichlorobenzene dates from the beginning of the
clearly prudent to use materials having these 20th Century.1
properties with as much restraint as possible, but A few additional potential insecticides were
bearing in mind the benefits that accrue from their recognized in the 1930’s, but there seem to have
use in relation to the actual hazards so far been few developments of importance before the
established. appearance of DDT. World food supply comes

4 Chlorinated Insecticides
largely from cereal crops that require for their depending upon the number of difficulties en­
protection chemicals having a significant degree of countered in the process.
persistence if economy in rates and frequency of It is sobering to read that in 1967 the ten best
application are to be achieved. Therefore, it seems selling insecticides had been introduced, on
a remarkable stroke of good fortune that within average, 17 years before and none of them within
little more than 10 years after 1939, a whole series the previous 10 years.6 In view of the hazards, it is
of chlorinated insecticides was discovered, and not surprising that manufacturers of insecticide
that several of them had the requisite properties chemicals, faced with the possibility that insect
for the efficient and economic protection of resistance to a successful new compound may
cereals, as well as collectively exhibiting an develop within a short time, are becoming increas­
astonishing range of activity towards insect pests ingly reluctant to invest in this area. Yet chemical
of other crops and insect vectors of disease. pest control continues to play a vital role in the
Whether discoveries of this magnitude and value modern agricultural practices that nowadays
will occur again is open to speculation. In the produce crop yields unheard of 30 years ago. High
decade prior to 1967, the total pesticide industry yields are now quite vital for survival and there
research budget probably increased up to three will be a requirement for chemical agents in one
times over that in 1957, but fewer insecticides form or another for the foreseeable future.
were introduced than during the preceding decade.
With the ever-increasing restrictions placed upon While the object of progress is doubtless that
new compounds on environmental and other modern, comfortable man should have leisure to
grounds, the chances of achieving major sales and contemplate his situation and to devise even better
profits become much more difficult. This last and safer ways to maintain it, great care must be
factor can hardly be ignored, since research funds taken to ensure that short-sighted action does not
must be derived from the sale of previously nullify the benefits already won, especially if there
successful compounds. Figures published in 1969 is the added risk of destroying the machinery that
indicate that the average total investment in a created them in the first place and might
compound that finally reaches the market conceivably repeat the process. Thus, it is to be
(excluding the cost of developing manufacturing hoped that man will shortly come to terms with
processes, marketing, advertising, etc.) rose from his chemical origins so that some middle way can
$1,196,000 in 1956 to nearly $3 million in 1964, be found through the controversy that currently
and $4 million in 1969. The overall survival rate of surrounds the use of chemicals of all kinds.
compounds entering the complex evaluation pro­ The use of chlorinated insecticides should be
cedure fell correspondingly from 1 in 1,800 to 1 in viewed against this background. Whatever their
3,600 and finally to 1 in 5,040.4 Other figures shortcomings, and it is unlikely that any device
indicate even longer odds of 7,000—10,000:1.5 created by man will be perfect, the story of their
The time now required to bring a new compound discovery and development is one of outstanding
into commercial use is estimated at 5 to 7 years, achievement which deserves due recognition.

5
 REFERENCES
1. Department of Health, Education, and Welfare, Report of the Secretary’s Commission on Pesticides and Their
Relationship to Environmental Health, Parts I and II, U.S. Govt. Print. Off., Washington, D.C., 1969,44.
2. O’Brien, R. D Insecticides, Action and Metabolism, Academic Press, New York, 1967, 165.
3. Perkow, W^ Die Insektizide, Huther Verlag, Heidelberg, 1956, 360.
4. von Rumker, R., Guest, H. R., and Upholt, W. M., The search for safer, more selective and less persistent pesticides,
Bioscience, 20, 1004, 1970.
5. Agrochemical Industry in Japan, published by Japan Agricultural Chemicals Overseas Development Commission
(JACODEC), Tokyo, 1971.
6. Pesticides and Health, Royal Dutch Shell Group Briefing Service, February, 1967.
7. Lauger, P., Martin, H., and Muller, P., Uber Konstitution und toxische Wirkung von natürlichen und neuen
synthetischen insektentotenden stoffen, Helv. Chim. Acta, 27, 892, 1944.
8. Zeidler, O., Verbindungen von chloral mit brom-und chlorbenzol, Chem. Ber., 7, 1180, 1874.
9. Lauger, P., Uber neue, sulfogruppenhaltige mottenschutzmittel, Helv. Chim. Acta, 27, 71, 1944.
10. Chattaway, F. D. and Muir, R. J. K., The formation o f carbinols in the condensation of aldehydes with
hydrocarbons,/. Chem. Soc. (Lond.), 701, 1934.
11. Muller, P., Uber zusammenhange zwischen konstitution und Insektizider Wirkung I, Helv. Chim. Acta, 29, 1560,
1946.
12. West, T. F. and Campbell, G. A., DDT and Newer Persistent Insecticides, revised 2nd ed., Chapman and Hall,
London, 1950.
13. Busvine, J. R., New synthetic contact insecticides, Nature (Lond.), 158, 22, 1946.
14. Barlsch, E., Eberle, D., Ramsteiner, K., Tomann, A., and Spindler, M., The carbinole acaricides: Chlorobenzilate and
chloropropylate, Residue Rev., 39, 1 , 1971.
15. Martin, H., Há., Pesticide Manual, 2nd ed. British Crop Protection Council, 1971, 495.
16. Busvine, J. R., Mechanism of resistance to insecticides in house flies, Nature (Lond.), 168, 193, 1951.
17. Miles, J. W., Goette, M. B., and Pearce, G. W., A new high temperature test for predicting the storage stability of
DDT water-dispersible powders, Bull. W.H.O., 27, 309, 1962.
18. Hadaway, A. B. and Barlow, F., Some physical factors affecting the efficiency of insecticides, Trans. R. Soc. Trop.
Med. Hyg., 46, 236, 1952.
19. van Tiel, N., On ‘Supona’, a new type of DDT suspension, Bull. Entomol. Res., 43, 187, 1952.
20. Philips, N. V., Gloeilampen fabricken (Stabiliser for aqueous pesticide emulsions), Netherland Patent 6809975, June
1970.
21. Wiesmann, R., cited in DDT, the Insecticide Dichlorodiphenyltrichloroethane and its significance, Muller, P., Ed.,
Birkhauser Verlag, Basel, 1955, 14.
22. van Tiel, N., Influence of Resins on Crystal Size and Toxicity o f Insecticidal Residues, Ph.D. Thesis, University of
Leyden, 1955.
23. Hayhurst, H., The action on certain insects of fabrics impregnated with DDT, J. Soc. Chem. Ind., 64, 296, 1945.
24. Brown, A. W. A., Insect Control by Chemicals, John Wiley, New York, 1951.
25. Carruth, L. A. and Howe, M. L., Chlorinated hydrocarbons and cucurbit foliage, J. Econ. Entomol., 4 1 ,3 5 2 , 1948.
26. Cullinan, F. P., Effect of DDT on plants, Agrie. Chem., 2, 18, 1947.
27. Wilson, J. K. and Choudhri, R. S., DDT and soil microflora, J. Econ. Entomol., 39, 537, 1946.
28. Edwards, C. A., Soil pollutants and soil animals, Sci. Am., 220, 8 8 , 1969.
29. Linsley, E. G. and MacSwain, J. W., DDT dusts in alfalfa, and bees, J. Econ. Entom ol, 40, 358, 1947.
30. Stahl, C. F., Relative susceptibility of Protoparce sexta and P. quinquemaculata, J. Econ. Entomol., 39, 610, 1946.
31. Dowden, P. B., DDT to control Lymantria dispar, cited in Brown, A. W. A., Insect Control by Chemicals, John
Wiley, New York, 1951, 603.
32. Hofmaster, R. N. and Greenwood, D. E., Organic insecticides for fall armyworm, J. Econ. E ntom ol, 42, 502, 1949.
33. Blanchard, R. A. and Chamberlin, T. R., Insecticides for corn earworm and armyworm, J. Econ. Entom ol, 41, 928,
1948.
34. Bishopp, F. C., New insecticides to date, J. Econ. Entom ol, 39, 449, 1946.
35. Weinman, C. J., Chlorinated hydrocarbons for codling moth control, J. Econ. Entomol., 40, 567, 1947.
36. Sun, Y-P., Rawlins, W. A., and Norton, L. B., Toxicity of chlordane, BHC and DDT, J. Econ. Entom ol, 41, 91,
1948.
37. Plumb, G. H., DDT sprays against Dutch elm disease, J. Econ. Entom ol, 43, 110, 1950.
38. Kapoor, 1. P., Metcalf, R. L., Nystrom, R. F., and Sangha, G. K., Comparative metabolism o f methoxychlor,
methiochlor and DDT in mouse, insects, and in a model ecosystem, J. Agrie. Food Chem., 18, 1145, 1970.
39. E.I. du Pont de Nemours & Co., Industrial and Biochemicals Department, Technical Data Sheets, 1969, etc.
40. Martin, H., Eá.yPesticide Manual, 2nd ed., British Crop Protection Council, 1971,428.
41. Metcalf, R. L., Organic Insecticides, John Wiley (Interscience) New York, 1955.
42. Brown, A. W. A., Insect resistance in arthropods, W.H.O. Monogr. Ser., No. 38, 1958.

21
 43. Brown, A. W. A. and Pal, R., Insect Resistance in Arthropods, 2nd ed., W.H.O., Geneva, 1971.
44. Insecticide resistance and vector control, W.H.O. Monogr: Ser., No. 443, 1970.
45. Niswander, R. E. and Davidson, R. H., Chlordane and lindane versus DDT for roaches, /. Econ. Entomol., 41,6 5 2 ,
1948.
46. Busvine, J. R., DDT and analogues for Pediculus and Cimex, Nature (Lond.), 156, 169,1945.
47. Busvine, J. R., Review o f lousicides, Br. Med. Bull, 3, 215, 1945.
48. Busvine, J. R. and Pal, R., The impact of insecticide-resistance on control of vectors and vector-borne diseases, Bull
W.H.O., 40,7 3 1 , 1969.
49. Busvine, J. R., DDT and BHC for the bedbug and louse, A««. A p p i Biol, 33, 271, 1946.
50. Pampana, E., A Textbook o f Malaria Eradication, 2nd ed., Oxford University Press, 1969.
51. Peffly, R. L. and Gahan, J. B., Residual toxicity of DDT analogues, J. Econ. Entom ol, 42, 113, 1949.
52. Metcalf, R. L., Kapoor, I. P., and Hirwe, A. S., Biodegradable analogues of DDT, Bull W.H.O., 44, 363, 1971.
53. Bruce, W. N. and Decker, G. C., Chlordane, DDD and DDT for fly control, J. Econ. Entom ol, 40, 530, 1947.
54. Brooks, G. T., Pesticides in Britain, in Environmental Toxicology o f Pesticides, Matsumura, F., Boush, G. M.,and
Misato, T., Eds., Academic Press, New York and London, 1972, 61.
55. The place of DDT in operations against malaria and other vector-borne diseases, Off Ree. W.H.O., No. 190, 1971,
176.
56. Food and Agriculture Organization, F.A.O. Production Year Book, 1969, 23, 496.
56a. Carson, R., Silent Spring, Houghton-Mifflin Co., Boston, 1962, 368.
57. Department of Health, Education, and Welfare, Report o f the Secretary's Commission on Pesticides and Their
Relationship to Environmental Health, Pts. I and II, U.S. Govt. Print. Off., Washington, D.C., 1969.
58. Matsumura, F., Current pesticide situation in the United States, in Environmental Toxicology o f Pesticides,
Matsumura, F., Boush, G. M., and Misato, T., Eds., Academic Press, New York and London, 1972, 33.
59. Edwards, C. A., CRC Uniscience Series, Persistent Pesticides in the Environment, Butterworths, London, 1970.
60. Department of Education and Science, Further review of certain persistent organochlorine pesticides used in Great
Britain, Report by the Advisory Committee on Pesticides and Other Toxic Chemicals, HMSO London, 1969.
61. Muller, P., Physike und Chemie des DDT-insektizides, in DDT, the Insecticide Dichlorodiphenyltrichloroethane and
its Significance, Muller, P., Ed., Birkhauser Verlag, Basel, 1955.
62. Haller, H. L., The chemical composition of technical DDT, J. Am. Chem. Soc., 67, 1591, 1945.
63. Forrest, J., Stephenson, O., and Waters, W. A., Chemical investigations of the insecticide ‘DDT and its analogues, J.
Chem. Soc. (Lond.), 333,1946.
64. Cochrane, W. P. and Chau, A. S. Y., Chemical derivatization techniques for confirmation of organochlorine residue
identity, in Pesticides Identification at the Residue Level, Adv. Chem. Ser., No. 104, 11, 1971.
65. Rogers, E. F., Brown, H. D., Rasmussen, I. M., and Heal, R. E., The structure and toxicity of DDT insecticides, J.
Am. Chem. Soc., 75, 2991, 1953.
6 6 . Skerrett, E. J. and Woodcock, D., Insecticidal activity and chemical composition. II. Synthesis of some analogues of
DDT,/. Chem. Soc. (Lond.), 2718, 1950.
67. Metcalf, R. L. and Fukuto, T. R., The comparative toxicity o f DDT and analogues to susceptible and resistant
houseflies and mosquitos, Bull. W.H.O., 38, 633, 1968.
6 8 . Holán, G., l,l-Bis(p-ethoxyphenyl) dimethylalkane Insecticides, German patent 1,936,494, 1970; C.A., 72,90045,
1970.
69. Kaluszyner, A., Reuter, S., and Bergmann, E. D., Synthesis and biological properties of diaryl (trifluoromethyl)
carbinols, / Am. Chem. Soc., 77, 4165, 1955.
70. Wiles, R. A. (to Allied Chemical Corporation), U.S. patent 3,285,811, 1966; C.A., 60, 18572, 1967.
71. Holán, G., Diphenyldichlorocyclopropane Insecticides, Australian patent 283,356, 1968; C.A., 71, 12815, 1969.
72. Muller, P. (to Geigy AG), Insecticidal Compounds, U.S. patent 2,397,802; C.A., 40, 3849, 1946.
73. Haas, H. B., Neher, M. B., and Blickenstaff, R. T .,In d Eng. Chem., 43, 2875, 1951.
74. Holán, G., l,l-Bis(p-Ethoxyphenyl)dimethylalkane Insecticides, German patent 1,936,495, 1970; C.A., 72,
100259, 1970.
75. Grommiti, O., Buck, A. C., and Becker, E. I., l,l-Di(p-chlorophenyl)ethane, / Am. Chem. Soc., 67, 2265, 1945.
76. Bergmann, E. D. and Kaluszyner, A., Di(p-chlorophenyl)trichloromethylcarbinol and related compounds, J. Org.
Chem., 23, 1306, 1958.
77. Hinsberg, O., Uber die bildung von saureestern und saure amiden bei gegenwart von wasser und alkali, Chem. Ber.,
23, 2962, 1890.
78. Huisman, H. O., Uhlenbroek, J. H., and Meitzer, J., Preparation and acaricidal properties of substituted
diphenylsulfones, diphenylsufides and diphenylsulfoxides, R eel Trav. Pays-Bas Belg., 77, 103, 1958.
79. Monroe, E. and Hand, C. R., Some bis-(aryloxy)methanes, J. Am. Chem. Soc., 72, 5345, 1950.
80. Hilton, B. D. and O’Brien, R. D., A simple technique for tritiation of aromatic insecticides, / Agrie. Food Chem.,
12, 236, 1964.
80a. Kapoor, I. P., Metcalf, R. L., Hirwe, A. S., Coats, J. R., and Khalsa, M. S., Structure activity correlations of
biodegradability of DDT analogs,/ Agrie. Food Chem., 21, 310, 1973.

212 Chlorinated Insecticides

81. Fields, M., Gibbs, J., and Walz, D. E., The synthesis of l,l,l-trichloro-2,2-bis(4'-chlorophenyl-4'-C 1 4) ethane,
Science, 112, 591, 1950.
82. Dachauer, A. C., Cocheo, B., Solomon, M. G., and Hennessy, D. J., The synthesis of tertiary carbon deuterated DDT
and DDT analogs,/. Agrie. Food Chem., 11, 47, 1963.
83. Sumerford, W. T., A synthesis of DDT, J. A m Pharm Assoc.,34, 259, 1945.
84. Rueggeberg, W. H. C. and Torrans, D. J., Production of DDT, Ind. Eng. Chem, 38, 211, 1946.
85. Mosher, S. H., Cannon, M. R., Conroy, E. A., Van Strien, R. E., and Spalding, D. P., Preparation of technical DDT,
Ind. Eng. Chem, 38, 916, 1946.
86. Specifications for Pesticides used in Public Health, 3rd ed., W.H.O., Geneva, 1967
87. Gunther, F. A., cited in West, T. F. and Campbell, G. A., DDT and Newer Persistent Insecticides, 2nd ed., Chapman
and Hall, London, 1950, 43.
88. Gooden, E. L., Optical crystallographic properties o f DDT, J. Am. Chem. Soc., 67, 1616, 1945.
89. Wild, H. and Brandenberger, E., Zur krystallstruktur des p,p'-dichlorodiphenyl trichlorathan, Helv. Chim. Acta, 28,
1692, 1945.
90. Balsón, E. W., Vapour pressures of DDT, BHC, and DNOC, Trans. Faraday Soc., 43, 54, 1947.
90a. Spencer, W. F. and Claith, M. M., Volatility of DDT and related compounds, J. Agrie. Food Chem, 20, 645, 1972.
90b. Claith, M. M. and Spencer, W. F., Dissipation of pesticides from soil by vola talization of degradation products. I.
Lindane and DDT, Environ. Sci. Technol, 6 ,9 1 0 , 1972.
91. Kenaga, E. E., Factors related to bioconcentration of pesticides, in Environmental Toxicology o f Pesticides,
Matsumura, F., Boush, G. M., and Misato, T., Eds., Academic Press, New York and London, 1972, 193.
92. Riemschneider, R., Chemical structure and activity of DDT analogues with special consideration of their spatial
structures, Adv. Pest. Control Res., 2, 307, 1958.
93. Bradlow, H. and Van der Werf, C., Composition of Gix, J. Am. Chem. Soc., 69, 662, 1947.
94. Schneller, G. H. and Smith, G. B. L-, 1-Trichloro -2,2-bis(p-methoxyphenyl)ethane (methoxychlor), Ind. Eng.
Chem., 41, 1027, 1949.
95. Harris, L. W., Condensation of aldehydes, U.S. patent 2,572,131; C.A., 46, 5088, 1952.
96. Adams, C. E., British patent 709,564; C.A., 49, 10376, 1955.
97. Grummitt, O., Di (p-chlorophenyl) methylcarbinol, a new miticide, Science, 111, 361, 1950.
98. Barker, J. S. and Maughan, F. R., Acaricidal properties of Rohm and HaasFW-293, J. Econ. E ntom ol, 49, 458,
1956.
99. Gatzi, K. and Stammbach, W., Liber die natur der nebenprodukte in technischen p,p'- dichlorodiphenyl-trichlor-
athan, Helv. Chim. Acta, 29,563, 1946.
100. Schechter, M. S. and Haller, H. L., Colorimetric tests for DDT, and related compounds, J. Am. Chem. Soc., 6 6 ,
2129,1944.
101. Balaban, I. E. and Sutcliffe, F. K., Thermal stability of DDT, Nature (Lond.), 155, 755, 1945.
102. Scholefield, P. G., Bowden, S. T., and Jones, W. J., The thermal decomposition of l,l,l-trichloro-2,2-bis-(p-chloro-
phenyl)ethane (DDT) and some of its phase equilibria, /. Soc. Chem. Ind., 65, 354, 1946.
103. Fleck, E. E. and Haller, H. L., Catalytic removal of hydrogen chloride from some substituted a- trichloroethanes,/.
Am. Chem. Soc., 6 6 , 2095, 1944.
104. Gunther, F. A., Blinn, R. C., and Kohn, G. K., Labile organo-halogen compounds and their gas chromatographic
detection and determination in biological media, Nature (Lond.), 193, 537, 1962.
105. Fleck, E. E., Preston, R. K., and Haller, H. L., Sym-tetraphenylethane from DDT and related compounds, J. Am.
Chem. Soc., 67, 1419,1945.
106. Cristol, S. J., Kinetic study of the dehydrochlorination of substituted 2,2-diphenylchloroethanes related to D DT,/.
Am. Chem. Soc., 67, 1494, 1945.
107. England, B. D. and McLennan, D. J., Kinetics and mechanism o f the reaction of DDT with sodium benzenethiolate
and other nucleophiles, J. Chem. Soc. (Lond.), B7, 696, 1966.
108. Cristol, S. J. and Haller, H. L., Dehydrochlorination of l-trichloro-2-o-chlorophenyl-2-p-chlorophenylethane
(o,p'-DDT isomer),/. Am. Chem. Soc., 67, 2222, 1945.
109. McKinney, J. D., Boozer, E. L., Hopkins, H. P., and Suggs, J. E., Synthesis and reactions o f a proposed DDT
metabolite, 2,2-bis(p-chlorophenyl) acetaldehyde, Experientia, 25, 897, 1969.
110. Plimmer, J. R., Klingebiel, U. I., and Hummer, B. E., Photooxidation of DDT and DDE, Science, 167, 67, 1970.
111. Institut für ökologische Chemie, Jahresbericht 1970, Klein, W., Weisgerber, I., and Bieniek, D., Eds., Gesellschaft für
Strahlen und Umweltforschung mbH, München, 1971,48.
112. McKinney, J. D. and Fishbein, L., DDE formation, dehydrochlorination or dehypochlorination, Chemosphere, [2 ],
67, 1972.
113. Zweig, G., Ed., Analytical Methods for Pesticides, Plant Growth Regulators and Food Additives, Vols. I—V,
Academic Press, New York and London, 1963, et seq.
114. Gunther, F. A., Ed., Residue Reviews, Springer-Verlag, New York.
115. Raw, G. R., Ed., CIPAC Handbook, Vol. I, Analysis o f Technical and Formulated Pesticides, Collaborative
International Pesticides Analytical Council Ltd., Harpenden, U. K., 1970.
116. Shell Chemical Corporation, Handbook o f Aldrin, Dieldrin and Endrin Formulations, 2nd ed., Agricultural
Chemicals Division, New York, 1959, et seq.

213
117. Castillo, J. C. and Stiff, H. A., Application of the xanthydrol-KOH-pyridine method to the determination o f 2,2-
bis(p-chlorophenyl)-l,l,l-trichloroethane (DDT) in water, Mil. Surg., 97, 500, 1945; C.A., 2561, 1946.
118. Claborn, H. V., Determination of DDT in the presence of DDD (l,l-dichloro-2,2-bis(p-chlorophenyl)ethaqe (also
called TDE), /. Assoc. Offic. Agrie. Chem., 29, 330,1946.
119. Bradbury, F. R., Higgons, D. J., and Stoneman, J. P., Colorimetric method for the estimation of 2,2-bis(p-chloro-
phenyl)-l,l,l-trichloroethane (DDT),/. Soc. Chem. Ind., 66, 65, 1947.
120. Miskus, R., Analytical methods for DDT, in Analytical Methods for Pesticides, Plant Growth Regulators and Food
Additives, Vol. II, Zweig, G., Ed., Academic Press, New York and London, 1964, 97.
121. Claborn, H. V. and Beckman, H. F., Determination of l,l,l-trichloro-2,2-bis(p-methoxyphenyl) ethane in milk and
fatty materials, Anal. Chem., 24, 220, 1952.
122. Gillett, J. W., Van der Geest, L. P. S., and Miskus, R. P., Column partition chromatography of DDT and related
compounds, Anal. Biochem., 8, 200, 1964.
123. Jones, L. R. and Riddick, J. A., Colorimetric determination of 2-nitro-l,l-bis(p-chlorophenyl)alkanes, Anal Chem.,
23,349,1951.
124. Blinn, R. C. and Gunther, F. A., The utilisation of infrared and ultra violet spectrophotometric procedures for assay
of pesticide residues, Residue Rev., 2, 99, 1963.
125. Gilbert, G. G. and Sader, M. H., Fluorimetrie determination of pesticides, Anal. Chem., 41, 366, 1969.
126. Allen, P. T., Polarographie methods for pesticides and additives, in Analytical Methods for Pesticides, Plant Growth
Regulators and Food Additives, Vol. V, Zweig, G., Ed., Academic Press, New York, 1966, 67.
127. Gajan, R. J., Analysis of pesticide residues by polarography, /. Assoc. Offic. Agrie. Chem, 4 8,1027, 1965.
128. Gajan, R. J. and Link, J., An investigation of the oscillography of DDT and certain analogues, J. Assoc. Offic. Agrie.
Chem., 47, 1118, 1964.
129. Cisak, A., Study of the electroreduction mechanism of halogen derivatives of cyclohexane, Rocz. Chem., 37, 1025,
1963.
130. Cisak, A., Polarographie properties of aldrin, isodrin, a-chlordane, 0-chlordane, dieldrin and endrin, Rocz. Chem.,
40, 1717, 1966.
131. Gajan, R. J., Applications of polarography for the detection and determination of pesticides and their residues,
Residue Rev., 5, 80, 1964.
132. Gajan, R. J., Recent developments in the detection and determination of pesticides and their residues by
oscillographic polarography, Residue Rev., 6, 75, 1964.
133. Casida, J. E., Radiotracer studies on metabolism, degradation, and mode of action of insecticide chemicals, Residue
Rev., 25, 149, 1969.
134. Gorsuch, T. T., Radioactive Isotope Dilution Analysis, Review No. 2, The Radiochemical Centre, Amersham, U.K.
135. Goodwin, E. S., Goulden, R., Richardson, A., and Reynolds, J. G., The analysis of crop extracts for traces of
chlorinated pesticides by gas-liquid partition chromatography, Chem. Ind. (Lond.J, 1220, 1960.
136. Goodwin, E. S., Goulden, R., and Reynolds, J. G., Rapid identification and determination of residues o f chlorinated
pesticides in crops by gas-liquid chromatography, Analyst, 86, 697, 1961.
137. Widmark, G., Modern trends of analytical chemistry as regards environmental chemicals, in Environmental Quality
and Safety; Chemistry, Toxicology and Technology, Voi. I, Coulston, F. and Körte, F., Eds., Georg Thieme Verlag,
Stuttgart, Academic Press, New York, 1972, 78.
138. Mitchell, L. C , Separation and identification of chlorinated organic pesticides by paper chromatography,/. Assoc.
Offic. Agrie. Chem., 41, 781, 1958.
139. McKinley, W. P., Paper chromatography, in Analytical Methods for Pesticides, Plant Growth Regulators and Food
Additives, Voi. I, Zweig, G., Ed., Academic Press, New York, 1963, 227.
140. Winteringham, F. P. W., Harrison, A., and Bridges, R. G., Radioactive tracer-paper chromatography techniques,
Analyst, 77, 19, 1952.
141. Abbott, D. C. and Thomson, J., The application of thin-layer chromatographic techniques to the analysis of
pesticide residues, Residue Rev., 11, 1, 1965.
142. Mangold, H. K., Isotope technique, in Thin Layer Chromatography, a Laboratory Handbook, 2nd ed., Stahl, E., Ed.,
Allen and Unwin, London, 1969.
143. Burchfield, H. P. and Storrs, E. E., Biochemical Applications o f Gas Chromatography, Academic Press, New York
and London, 1962.
144. Coulson, D. M. Cavanagh, L. A., de Vries, J. E., and Walther, B., Microcoulometric gas chromatography of
pesticides,/. Agrie. Food Chem., 8, 399, 1960.
145. Cassil, C. C., Pesticide residue analysis by microcoulometric gas chromatography, Residue Rev., 1, 37, 1962.
146. Lovelock, J. E. and Lipsky, S. R., Electron affinity spectroscopy — a new method for the identification of
functional groups in chemical compounds separated by gas chromatography, / Am. Chem. Soc., 82, 431, 1960.
147. de Faubert Maunder, M. J., Egan, H., and Robum, J., Some practical aspects of the determination of chlorinated
pesticides by electron-capture gas chromatography, Analyst, 89, 157, 1964.
148. Clark, S. J., Quantitative determination of pesticide residues by electron absorption chromatography: characteristics
of the detector, Residue Rev., 5, 33, 1964.

214 Chlorinated Insecticides

149. Burke, J. A. and Holswade, W., A gas chromatographic column for pesticide residue analysis: retention times and
response data,/. A ssoc. Offic. Agrie. Chem ., 49, 374, 1966.
150. Ott, D. E. and Gunther, F. A., DDD as a decomposition product o f DDT, R esidu e R ev., 10, 70, 1965.
151. Robinson, J., Organochlorine compounds in man and his environment, Chem. Br., 7, 472, 1971.
152. Bowman, M. C. and Beroza, M., Extraction p values of pesticides and related compounds in six binary solvent
systems,/. A ssoc. Offic. Agrie. Chem ., 48, 943, 1965.
153. Bache,tC. A. and Lisk, D. J., Selective emission spectrometric determination of nanogram quantities of organic
bromine, chlorine, iodine, phosphorus and sulfur compounds in a helium plasma, Anal. Chem ., 39, 787, 1967.
154. Keith, L. H., Alford, A. L., and Garrison, A. W., The high resolution NMR spectra of pesticides II; DDT-type
compounds,/. A ssoc. Offic. Agrie. Chem ., 52, 1074,1969.
155. Baldwin, M. K., Robinson, J., and Carrington, R. A. G., Metabolism of HEOD (dieldrin) in the rat: examination of
the major faecal metabolite, Chem. Ind. (L on d.), 595, 1970.
156. Cochrane, W. P., Forbes, M., and Chau, A. S. Y., Cyclodiene chemistry. IV. Assignment of configuration of two
nonachlors via synthesis and derivatisation,/ . A ssoc. Offic. Agrie. Chem ., 53, 769, 1970.
157. Mackenzie, K. and Lay, W. P., Fragmentation o f tetrahydromethanonaphthalenes and their diaza- and
benzo-analogues, T etrahedron L e tt., No. 37, 3241, 1970.
158. McKinney, J. D., Keith, L. H., Alford, A., and Fletcher, C. E., The proton magnetic resonance spectra of some
chlorinated polycyclodiene pesticide metabolites, rapid assessment of stereochemistry, Can. J. Chem ., 49, 1993,
1971.
159. Keith, L. H. and Alford, A. L., Long-range couplings in the chlorinated poly cyclodiene pesticides, Tetrahedron
L e tt., 2489,1970.
160. Nagl, H. G., Klein, W., and Korte, F., Uber das reaküons verhalten von dieldrin in losung und in der gasphase,
Tetrahedron, 26, 5319, 1970.
161. Roll, D. B. and Biros, F. J., Nuclear quadrupole resonance spectrometry of some chlorinated pesticides, A n a l
Chem ., 41,407, 1969.
162. Damico, J. N., Barron, R. P., and Ruth, J. M., The mass spectra of some chlorinated pesticidal compounds, Org.
Mass S p ectr., 1, 331, 1968.
163. Scopes, N. E. A. and Lichtenstein, E. P., The use of F olsom ia fim etaria and D rosophila m elanogaster as test insects
for the detection of insecticide residues, /. Econ. E n tom ol., 60, 1539, 1967.
164. Sun, Y-P., Bioassay-insects, in A n a lytica l M eth ods fo r P esticides, Plan t G row th R egulators a n d F o o d A d d itiv es, Voi.
I, Zweig, G., Ed., Academic Press, New York and London, 1963, 399.
165. Alder, K. and Stein, G., The course of the diene synthesis, A n g ew Chem ., 50, 510, 1937.
166. Bergmann, F. and Eschinazi, H. E., Sterical course and the mechanism of the diene reactions, /. A m . Chem. Soc.,
65, 1405, 1943.
166a. Gill, G. B., The application o f the Woodward-Hoffman orbital symmetry rules to concerted organic reactions, Q.
R ev. Chem. Soc. (L o n d ), 22, 338, 1968.
167. Buchel, K. H., Ginsberg, A. E., Fischer, R., and Korte, F., /3-Dihydroheptachlor, ein insektizid mit sehr niedriger
warmblüter-toxizitat, T etrahedron L ett., No. 33, 2267, 1964.
168. Soloway, S. B., Stereochemistry of Bridged Polycyclic Compounds, Ph.D. Thesis, University of Colorado, 1955.
169. Benson, W. R., Note on nomenclature of dieldrin and related compounds, /. A ssoc. Offic. A grie., Chem ., 52, 1109,
1969.
169a. Bedford, C. T., Von Baeyer - IUPAC Names and Recommended Trivial Names of Dieldrin, Endrin, and 24
Related Compounds, Shell Research Ltd., Tunstall Laboratory Research Report, November 1972.
170. Bird, C. W., Cookson, R. C., Crundweü, E., Cyclisations and rearrangements in the isodrin-aldrin series, J. Chem.
Soc. (L o n d .), 4809, 1961.
171. Parsons, A. M. and Moore, D. J., Some reactions of dieldrin and the proton magnetic resonance spectra of the
products,/. Chem. Soc. (L on d.), C., 2026, 1966.
172. Eckroth, D. R., A method for manual generation of correct von Baeyer names of polycyclic hydrocarbons, /. Org.
Chem ., 32,3362, 1967.
172a. International Union of Pure and Applied Chemistry, IU PA C N om en clatu re o f Organic C h em istry, 3rd ed.,
Butterworth, London, 1971.
173. Straus, F., Kollek, L., and Heyn, W., Uber den ersatz positiven Wasserstoffs durch halogen, Chem. B er., 63B, 1868,
1930.
174. Kleiman, M., Chlorination of cyclopentadiene, U.S. patent 2,658,085, 1953; C.A., 48, 12798, 1954.
175. Lidov, R. E., Hyman, J., and Segel, E., Diels-Alder adducts of hexahalocyclopentadiene with quiñones, U.S. patent
2,584,139, 1952; C .A ., 46, 9591, 1952.
176. Frensch, H., Entwicklung und Chemie der dien-gruppe, einer neuen klasse biozider Wirkstoffe, M e d Chem ., 6 , 556,
1957.
177. Ungnade, H. E. and McBee, E. T., The chemistry of perchlorocyclopentenes and cyclopentadienes, Chem. R ev., 58,
249,1958.
178. Gilbert, E. E. and Giolito, S. L., Pesticides, U.S. patent 2,616, 928; C.A., 47, 2424, 1953.
179. McBee, E. T., Roberts, C. W., Idol, J. D., and Earle, R. H., An investigation of the chlorocarbon, Cj 0 G , 2, mp485°
and the ketone, Ct qCIj o, mp349°, /. A m . Chem. Soc., 78, 1511, 1956.

215
180. Gilbert, E. E., Lombardo, P., Rumanowski, E. J., and Walker, G. L., Preparation and insecticidal evaluation of
alcoholic analogs of kepone, /. Agrie. F o o d Chem ., 14,111 ,1 9 6 6 .
181. Allen, W. W., The effectiveness of various pesticides against resistant two-spotted spider mites on green house roses,
J. E con. E n to m o l. , 5 7 ,1 8 7 ,1 9 6 4 .
182. McBee, E. T. and Smith, D. K., The reduction of hexachlorocyclopentadiene, 1,2,3,4,5-pentachlorocyclopentadiene,
J. A m . Chem . Soc., 77, 389,1955.
183. McBee, E. T., Meyers, R. K., and Baranauckas, C. F., 1,2,3,4-Tetracyclopentadiene. 1. The preparation of the diene
and its reaction with aromatics and dienophiles, J. A m . Chem. Soc., 77, 8 6 , 1955.
184. Soloway, S. B., Correlation between biological activity and molecular structure of the cyclodiene insecticides, A dv.
P est C o n tro l R es., 6 , 85,1965.
185. Volodkovich, S. D., Melnikov, N. N., Plate, A. F., and Prianishnikova, M. A., Reaction of 1,1-difluorotetrachloro-
cyclopentadiene with some unsaturated compounds, / Gen. Chem. (U .S .S .R .), 28, 3153, 1958.
186. Riemschneider, R. and Kuhnl, A., Zur chemie von poly halo cyclopentadienen und verwandten Verbindungen,
M onatsh. Chem ., 8 6 , 879,1953.
187. Banks, R. E., Harrison, A. C., Haszeldine, R. N., and Orrell, K. G., Diels-Alder reactions involving perfluorocyclo-
pentadiene, Chem . C om m un., 3 ,4 1 ,1 9 6 5 .
188. Riemschneider, R., The chemistry of the insecticides of the diene group, World Rev. P est C ontrol, 2, 29, 1963.
189. Riemschneider, R. and Nehring, R., Ein Thiodan-Analoges aus trimethyltrichlorocyclopentadienen, Z. N aturforsch.
T e il.B ., 17b, 524,1962.
190. Bluestone, H., l,2,3,4,10,10-Hexachloro-6,7-Epoxy-l,4,4a,5,6,7,8,8a-Octahydro-l,4,5,8- Dimethanonaphthalene
and Insecticidal Compositions Thereof, U.S. patent 2,676,132,1954; C.A., 48, 8474, 1954.
191. Mackenzie, K., The reaction of hexachlorobicyclo [2,2,1] heptadiene with potassium ethoxide, J. Chem. Soc.
(L o n d .), 86,457,196 2 .
192. Brooks, G. T. and Harrison, A., The effect of pyrethrin synergists, especially sesamex, on the insecticidal potency of
hexachlorocyclopentadiene derivatives (‘cyclodiene’ insecticides) in the adult housefly, M usca dom estica, L.,
B ioch em . P harm acol. , 13, 827, 1964.
193. Riemschneider, R., Gallert, H., and Andres, P., Uber der herstellung von 1,4,5,6 ,7,7-hexachlorobicyclo [2.2.1]
hepten-5-bishydroxymethylen-2,3, Afora/s/z. Chem ., 9 2 ,1 0 7 5 ,1 9 6 1 .
194. Riemschneider, R. and Kotzsch, H. J., Hexachlorocyclopentadiene and allylglykolather, M onatsh. C hem ., 91, 41,
1960.
195. Riemschneider, R., Herzel, F., and Koetsch, H. J., 2-Methylen-l,4,5,6,7,7-hexachlorbicyclo [2.2.1] hepten-(5),
M onatsh. Chem ., 92, 1070, 1961.
196. Riemschneider, R., Penta- und hexachlorocyclopentadien als philodiene komponenten, B otyu -K agaku , 28, 83,
1965.
197. Forman, S. E., Durbetaki, A. J., Cohen, M. V., and Olofson, R. A., Conformational equilibria in cyclic sulfites and
sulfates. The configurations and conformations of the two isomeric thiodans, /. Org. Chem ., 30, 169,1965.
198. Feichtinger, H. and Linden, H. W., Telodrin, its synthesis and derivatives, Chem. Ind. (L on d.), 1938, 1965.
199. Gross, H., Darstellung und reaktionen des 2,5-dichlor-tetrahydrofurans, Chem. Ber., 95, 83, 1962.
200. Hyman, J., Improvements In or Relating to a Method of Forming Halogenated Organic Compounds and the
Products Resulting Therefrom, British patent 618,432, 1949.
201. Herzfeld, S. H. and Ordas, E. P., l-Hydroxy-4, 7-methano-3a,4,7,7a-tetrahydro-4, 5,6,7,8,8-hexachloroindene and
method of preparing same, U.S. patent 2,528,656, 1950.
202. Goldman, A., Kleiman, M., and Fechter, H. G., Production of Halogenated Polycyclic Alcohols, U.S. patent
2,750,397, 1956.
203. Arvey Corporation, Improvements in or Relating to Halogenated Dicyclopentadiene Epoxides, British patent
714,869,1954.
204. Buchel, K. H., Ginsberg, A. E., and Fischer, R., Isomierung und Chlorierung von dihydroheptachlor, Chem. Ber., 99,
416.1966.
205. Buchel, K. H., Ginsberg, A. E., and Fischer, R., Synthese und Struktur von heptachlor-methano-tetrahydroindanen,
Chem. B èr., 9 9 ,405, 1966.
206. Buchel, K. H., Ginsberg, A. E., and Fischer, R., Synthese und Struktur von isomeren des chlordans, Chem . Ber., 99,
421.1966.
207. March, R. B., The resolution and chemical and biological characterisation of some constituents of technical
chlordane, /. E con . E n to m o l., 45, 452, 1952.
208. Cochrane, W. P., Forbes, M., and Chau, A. S. Y., Assignment of configuration of two nonachlors via synthesis and
derivatisation,/. A ssoc. Offic. Agrie. Chem ., 53, 769, 1970.
209. Hyman, J., Freireich, E., and Lidov, R. E., Bicyclo-heptadienes and process of preparing the same, British patent
701,211,1953.
210. Plate, A. F. and Pryanishnikova, M. A., Preparation of bicyclo [2.2.1] hepta-2,5-diene by the condensation of
cyclopentadiene with acetylene, Izvest. A kad. N au k SSSR ., O td e l K him . N auk, 741,1956.
211. Lidov, R. E. and Soloway, S. B., Improvements In or Relating to Methods of Preparing Insecticidal Compounds and
the Insecticidal Compounds Resulting From Said Methods, British patent 692,546, 1953.

216 Chlorinated Insecticides

212. Lidov, R. E. and Soloway, S. B., Process of Preparing Polycyclic Compounds and Insecticidal Compositions
Containing the Same, British patent 692,547, 1953.
213. Winteringham, F. P. W. and Harrison, A., Mechanisms o f resistance of adult houseflies to the insecticide dieldrin,
Nature, (L o n d ), 184, 608, 1959.
214. Kudema, J. G., Sims, J. W., Wilkstrom, J. R., and Solo way, S. B., The preparation of some insecticidal chlorinated
bridged phthalazines, J. A m . Chem. Soc., 81, 382,1959.
215. Kleiman, M., Pesticidal Compounds, U.S. patent 2,655,513,1953.
216. Beilin, R. H., Endrin Stabilization Using Inorganic and Organic Nitrite Salts, U.S. patent 2,768,178, 1956.
217. Nagl, H. G., Klein, W., and Körte, F., Uber das reaktionsverhalten von dieldrin in losung und in der gasphase,
T etrah edron, 26, 5319, 1970.
218. Busvine, J. R., The insecticidal potency o f 7 -BHC and the chlorinated cyclodiene compounds and the significance of
resistance to them, Bull. E n tom ol. R es., 55, 271,1964.
219. Adams, C. H. M. and Mackenzie, K., Dehalogenation of isodrin and aldrin with alkoxide base, J. Chem . Soc.
( L o n d ) , C, 480,1969.
220. Bienieck, D., Moza, P. N., Klein, W. and Körte, F., Reduktive dehalogenierung von chlorierten cyclischen kohlen
Wasserstoffen, Tetrahedron L e tt., 4055, 1970.
221. Volodkovich, S. D., Vol’Fson, L. G., Kuznetsova, K. V., and Mel’nikov, N. N., Synthesis of a-oxides by the
oxidation of polycyclic haloderivajives with, hydrogen peroxide, J. Gen. Chem. ( U .S.S.R . ), 29, 2797, 1959.
222. Brooks, G. T., The synthesis of 1 4 C-labelledl :2 :4:10:10-hexachloro-6:7 -epoxy-1 :4:4a:5:6:7:8:8a-octahydro-exo-
l:4-exo-5:8-dimethanonaphthalene,/. Chem. Soc. (L on d.), 3693, 1958.
223. Körte, F., Metabolism of Chlorinated Insecticides, Paper Presented to the Joint FAO/IAEA Division o f Atomic
Energy in Agriculture, Panel on the uses of Radioisotopes in the detection of Pesticide Residues, Vienna, April
1965.
224. Körte, F. and Rechmeier, G., Mikrosynthese von Aldrin-14C und Dieldrin- 1 4 C, Justu s L iebigs A nn . Chem ., 656,
131, 1962.
225. McKinney, R. M. and Pearce, G. W., Synthesis of carbon-14-labeled aldrin and dieldrin, J. Agrie. F o o d Chem ., 8 ,
457, 1960.
226. Thomas, D. J. and Kilner, A. E., The synthesis of the insecticides aldrin and dieldrin labelled with carbon-14 at high
specific activity, in R a d io iso to p e s in th e Physical Sciences an d In du stry, International Atomic Energy Agency,
Vienna 1962.
227. Körte, F. and Stiasni, M., Mikrosynthese von 14 C-markiertem Telodrin, Justus Liebigs A nn. Chem ., 656, 140, 1962.
228. Black, A. and Morgan, A., Herstellung einiger Cl-38-markierten chlorierten Kohlen Wasserstoffe durch neutro-
nenbestrahlung und gaschromatographie, Int. J. A p p i. R adiat, h o t ., 21, 5, 1970.
229. Dailey, R. E., Walton, M. S., Beck, V., Leavens, C. L., and Klein, A. K., Excretion, distribution, and tissue storage of
a 1 4 C-labeled photoconversion product of 14 C-dieldrin, J. Agrie. F o o d Chem ., 18, 443, 1970.
230. Riemschneider, R., Zur Chemie von polyhalocyclopentadienen und verwandten Verbindungen, IV. Thermische
Spaltung und oxydation des adduktes C10 H6 Cl6, Chem. Ber., 89, 2697, 1956.
231. Lidov, R. E. and Bluestone, H., Cyclobutano-compounds, U.S. patent 2,714,617; C .A ., 50, 5756, 1956.
232. Cochrane, W. P. and Forbes, M. A., Practical Applications of Chromous Chloride to the Confirmation of
Organochlorine Pesticide Residue Identity, Paper presented at the 2nd International Congress of Pesticide
Chemistry, Tel Aviv, Israel, 1971.
233. Davidow, B. and Radomski, J. L., Isolation of an epoxide metabolite from fat tissues of dogs fed heptachlor, J.
Pharm acol. Exp. Ther., 107, 259, 1953.
234. Brooks, G. T. and Harrison, A., The toxicity of a-DHC and related compounds to the housefly (M. d o m estic a ) and
their metabolism by housefly and pig liver microsomes, L ife Sci., (Oxford), 6 , 1439, 1967.
235. Brooks, G. T., unpublished results.
236. Chau, A. S. Y. and Cochrane, W. P., Cyclodiene chemistry. I. Derivative formation for the identification of
heptachlor, heptachlor epoxide, cis-chlordane, trans-chlordane and aldrin pesticide residues by gas chromatography,
J. A ssoc. Offic. Agrie. Chem ., 52, 1092, 1969.
237. Cochrane, W. P., Cyclodiene chemistry II. Identification of the derivatives employed in the confirmation of the
heptachlor, heptachlor epoxide, cis-chlordane, and trans-chlordane residues, J. A ssoc. Offic. Agrie. C hem ., 52, 1100,
1969.
238. Chau, A. S. Y. and Cochrane, W. P., Cyclodiene chemistry III. Derivative formation for the identification of
heptachlor, heptachlor epoxide, cis-chlordane, trans-chlordane, dieldrin, and endrin pesticide residues by gas
chromatography, / A ssoc. O ffic. Agrie. Chem ., 52, 1220, 1969.
239. Cochrane, W. P. and Forbes, M. A., Isomerisation of l-exo-4,5,6,7,8,8-heptachloro-2,3-endo-epoxy-3a,4,7,7a-
tetrahydro-4,7-methanoindane with base, Can. J. Chem ., 49, 3569,1971.
240. Polen, P. B., personal communication, 1970.

217
241. Rosen, J. D., Conversion of pesticides under environmental conditions, in Environmental Quality and Safety, Vol. 1,
Coulston, F. and Korte, F., Eds., Georg Thieme Verlag, Stuttgart; Academic Press, New York, 1972.
242. McGuire, R. R., Zabik, M. J., Schuetz, R. D., and Flotard, R. D», Photolysis of l,4,5,6,7,8,8-heptachloro-3a,4,7,7a-
tetrahydro-4,7-methanoindene (cage formation vs. photodechlorination), / Agrie. Food Chem., 18, 319, 1970.
243. Brooks, G. T. and Harrison, A., Structure-activity relationships among insecticidal compounds derived from
chlordene, Nature (Lond.J, 205, 1031, 1965.
244. Institut fur Ökologische Chemie, Jahresbericht 1969, Klein, W. and Drefahl, B., Eds., Gesellschaft für Strahlen und
Umweltforschung mbH, München, 1970.
244a. Ivie, G. W., Knox, J. R., Khalifa, S., Yamamoto, I., and Casida, J. E., Novel photoproducts of heptachlor epoxide,
tazrts-chlordane, and trans-nonachloi, Bull. Environ. Contam. Toxicol., 7, 376, 1972.
245. Vollner, L., Klein, W., and Körte, F., Photoumlagerung der komponenten des technischen chlordans, Tetrahedron
Lett., 2967, 1969.
246. Schwemmer, B., Cochrane, W. P., and Polen, P. B., Oxychlordane, animal metabolite of chlordane: isolation and
synthesis, Science, 169, 1087, 1970.
247. Polen, P. B., Hester, M., and Benziger, J., Characterisation of oxychlordane, animal metabolite of chlordane, Bull.
Environ. Contam. Toxicol, 5, 521, 1971.
248. Maier-Bode, H., Properties, effect, residues and analytics of the insecticide endosulfan, Residue Rev., 22, 1, 1968.
249. Chau, A. S. Y. and Cochrane, W. P., Cis-opening of the dieldrin oxirane ring, Chem. Ind. (Lond.J, 1568, 1970.
250. Adams, C. H. M. and Mackenzie, K., Dehalogenation of isodrin and aldrin with alkoxide base, /. Chem. Soc.
(Lond.J, C, 480, 1969.
251. Robinson, J., Richardson, A., Bush, B., and Elgar, K., A photoisomerisation product of dieldrin, Bull. Environ.
Contam. Toxicol, 1, 127, 1966.
252. Benson, W. R., Photolysis of solid and dissolved dieldrin, J. Agrie. Food Chem., 19, 66 , 1971.
253. Cookson, R. C. and Crundwell, E., Transannular reactions in the isodrin series, Chem Ind. (Lond.J, 703, 1959.
254. Soloway, S. B., Damiana, A. M., Sims, J. W., Bluestone, H., and Lidov, R. E., Skeletal rearrangements in reactions of
isodrin and endrin,/. Am. Chem. Soc., 82, 5377, 1960.
255. Weil, E. D., Colson, J. G., Hoch, P. E., and Gruber, R. H., Toxic chlorinated methanoisobenzofuran derivatives,/.
Heterocycl. Chem., 6 , 643, 1969.
256. Bruck, P., Thompson, B., and Winstein, S., Dechlorination of isodrin and related compounds, Chem Ind. (Lond.J,
405,1960.
257. Phillips, D. D., Pollard, G. E., and Soloway, S. B., Thermal isomerisation of endrin and its behaviour in gas
chromatography,/. Agrie. Food Chem., 10, 217, 1962.
258. Rosen, J. D., Sutherland, D. J., and Lipton, G. R., The photochemical isomerisation of dieldrin and endrin and
effects on toxicity, Bull. Environ. Contam. Toxicol, 1, 133, 1966.
259. Zabik, M. J., Schuetz, R. D., Burton, W. L., and Pape, B. E., Studies of a major photolytic product of endrin, /.
Agrie. Food Chem., 19, 308, 1971.
260. Brooks, G. T., Degradation of Organochlorine Insecticides, Problems and Possibilities, in Proceedings of the 2nd
International IUPAC Congress of Pesticide Chemistry 1971, Voi. 6 ; Fate o f Pesticides in Environment, Tahori, A. S.,
Ed., Gordon and Breach, London, 1972, 223.
261. Martin, H. and Wain, R. L., Insecticidal action of DDT, Nature (Lond.J, 154, 512, 1944.
262. Prill, E. A., Diels-Alder syntheses with hexachlorocyclopentadiene, /. Am. Chem. Soc., 69, 62, 1947.
263. Riemschneider, R., Neue kontakt-insetizide der halogenkohlen wasserstoffe-klasse (M410, M344), Mitt. Physiol.
Chem. Inst. Univ. Berlin, R8, March 1947; C.A., 48, 2973, 1954.
264. Riemschneider, R. and Kuhnl, A., Mitt. Physiol. Chem. Inst. Univ. Berlin, R .ll, October 1947 (see also reference
186).
265. Kearns, C. W., Ingle, L., and Metcalf, R. L., New chlorinated hydrocarbon insecticide, J. Econ. Entomol., 38, 661,
1945.
266. Hyman, J., personal communication, 1972.
267. Velsicol Corporation, Improvements in the Production of New Diels-Alder Adducts, British patent 614,931, 1948;
C.A., 43,4693, 1949.
268. Hyman, J., Improvements in or relating to method of forming halogenated organic compounds and the products
resulting therefrom, British patent 618,432, 1949; C.A., 43, 5796, 1949.
269. Ingle, L., A Monograph On Chlordane. Toxicological and Pharmacological Properties, University of Illinois, 1965.
270. Velsicol Chemical Corporation, Chlordane Formulation Guide, Bulletin No. 502-35R, 1970.
271. Velsicol Chemical Corporation, Standard for Technical Chlordane, August 1971.
272. Polen, P. B., Chlordane: Composition, Analytical Considerations and Terminal Residues, paper presented to a
meeting of the IUPAC Commission on Terminal Residues, Geneva, Switzerland, 1966.
273. Riemschneider, R. and Graviz, B. B., Uber den räumlichen Bau einiger Addukte aus hexachlorocyclopentadien und
ungesattigen Verbindungen (Dien-gruppe), Botyu-kagaku, 25, 123, 1960.
274. Vogelbach, C., Isolation of new crystalline substances from technical grade chlordan, Angew Chem., 63, 378, 1951.
275. Harris, C. R., Factors influencing the biological activity of technical chlordane and some related components in soil,
/. Econ. Entomol., 65, 343, 1972.

218 Chlorinated Insecticides

276. Saha, J. G. and Lee, Y. W., Isolation and identification of the components of a commercial chlordane formulation,
Bull. Environ. Contam. Toxicol., 4, 285, 1969.
277. Belt-plus Insecticide, Velsicol Chemical Corporation Development Bulletin no. 01-054-601, April 1971.
278. Freeman, S. M. D., cited in Ingle, L., A Monograph on Chlordane. Toxicological and Pharmacological Properties,
University of Illinois, 1965, 12.
279. Herzfeld, S. H. and Ordas, E., Improvements In or Relating To Processes For the Production of Derivatives of
Diels-Alder Adducts of Hexachlorocyclopentadiene and Cyclopentadiene, British patent 652,300, 1951.
280. Whaley, R.E., Heptachlor Insecticide, U.S. patent 3,541,163, 1970; C.A., 74,53177, 1971.
281. Velsicol Chemical Corporation, Heptachlor Formulation Guide, Bulletin no. 504-16, 1964.
282. Busvine, J. R., The newer insecticides in relation to pests of medical importance, in symposium on insecticides,
Trans. R. Soc. Trop. Med. Hyg., 46, 245, 1952.
283. Velsicol Chemical Corporation, Chlordane Federal Label Acceptances, Bulletin no. 502-32, March 1968.
284. Miles, J. R. W., Tu, C. M., and Harris, C. R., Metabolism of heptachlor and its degradation products by soil
microorganisms,/. Econ. Entomol., 62, 1334, 1969.
285. Carter, F. L., Stringer, C. A., and Heinzelman, D., 1-Hydroxy-2,3-epoxychlordene in Oregon soil previously treated
with technical heptachlor, Bull. Environ. Contam. Toxicol., 6 , 249, 1971.
286. Bonderman, D. P. and Slach, E., Appearance of 1-hydroxychlordene in soil, crops and fish, J. Agrie. Food Chem.,
20, 328, 1972.
287. Miles, J. R. W., Tu, C. M., and Harris, C. R., Degradation of heptachlor epoxide and heptachlor by a mixed culture
of soil microorganisms, J. Econ. Entomol., 64, 839, 1971.
288. Harris, C. R., personal communication, 1972.
289. Davidow, B., A spectrophotometric method for the quantitative estimation of technical chlordan, J. Assoc. Offic.
Agrie. Chem., 33, 886, 1950.
290. Ordas, E. P., Smith, V. C., and Meyer, C. F., Spectrophotometric determination of heptachlor and technical
chlordane on food and storage crops, J. Agrie. Food Chem., 4,444, 1956.
291. Velsicol Chemical Corporation, Evaluation of Technical Heptachlor Formulations, Bulletin No. 504-17, undated.
292. Dorn, W., Statement of the State Secretary on a request of MdB(MP) Prinz Zu Sayn Wittgenstein et al. regarding the
fish kill in the Rhine, given at 20.2. 1970 in the Deutsche Bundestag (Parliament), 1970. Cited in Pesticides in the
Modern World, Cooperative Programme of Agro-Allied Industries, with F AO and other U.N. Organisations at the
Newgate Press Ltd., London, 1972, 5.
293. Farbwerke Hoechst, AG, personal communications, 1972.
294. Feichtinger, H. and Tummes, H., Verfahren Zur Hestellung Von 4,5,6,7,10,10-Hexachlor^,7-Endomethylen-
4,7,8,9-Tetrahydrophthalan, German patent 960,284, 1957.
295. Whetstone, R, R., Chlorinated derivatives of cyclopentadiene, in Kirk-Othmer: Encyclopedia o f Chemical
Technology, Voi. 5, 2nd ed., McKetta, J. J. and Othmer, D. F., Eds., John Wiley (Interscience), 1964, 240.
296. Farbwerke Hoechst, AG, Thiodan and the Environment, technical bulletin translated by Hoechst U.K., 1971;
Thiodan, [an undated bulletin on formulations and applications of Thiodan], Farbwerke Hoechst AG, Frankfurt a.
Main.
297. Frensch, H., Goebel, H., and Czech, M., Agents for killing undesired fish, U.S. patent 2,799,685 ; C.A., 3852, 1962.
298. Gorbach, S. and Knauf, W., Endosulfane and the environment in Environmental Quality and Safety, Vol. I,
Coulston, F. and Körte, F., Eds., Georg Thieme Stuttgart, Academic Press, New York, 1972, 250.
299. Schoettger, R. A., Toxicology of Thiodan in several fish and aquatic invertebrates, Investigations in Fish Control 35,
United States Department of the Interior, Bureau of Sport Fisheries and Wildlife, U.S. Govt. Print. Off., Washington
D.C., 1970
300. Zweig, G. and Archer, T. E., Quantitative determination of Thiodan by gas chromatography,/. Agrie. Food Chem.,
8, 190, 1960.
301. Shell Research Ltd., cited in Phillips, F. T., The rates of loss of dieldrin and aldrin by volatilisation from glass
surfaces, Pestic. Sci., 2, 255, 1971.
302. Kearns, C. W., Weinman, C., and Decker, G. C., Insecticidal properties of some new chlorinated organic compounds,
J. Econ. Entomol., 42, 127, 1949.
303. Jager, K. W., Aldrin, Dieldrin, Endrin and Telodrin, an Epidemiological and Toxicological Study o f Long-term
Occupational Exposure, Elsevier, Amsterdam, 1970.
304. Park, K. S. and Bruce, W. N., The determination of water solubility of aldrin, dieldrin, heptachlor and heptachlor
epoxide, /. Econ. Entomol, 61, 770, 1968.
304a. Delacy, T. P. and Kennard, C. H. L., Crystal structures of endrin and aldrin,/. Chem. Soc. (Lond.), Perkin II, 2153,
1972.
305. Aldrin and Dieldrin, An Appraisal of Data Submitted to International Regulatory Agencies, Shell International
Chemical Company Ltd., Regulatory Affairs Division, January 1972.
306. Summary of Technical Information, Registered Label Uses and Label Uses Withdrawn Since 1964, in; Aldrin,
Dieldrin, Endrin, a Status Report, Shell Chemical Company, Agricultural Chemicals Division, September 1967.
307. Endrin, the Foliage Insecticide, Shell International Chemical Company Ltd., Bulletin, 1964.
308. The Safe Handling and Toxicology o f Endrin, Shell International Chemical Company Ltd., undated bulletin.

219
309. Skenett, E. J. and Baker, E. A., A new colour reaction for dieldrin and endrin, Chem. Ind. (L o n d .) , 539, 1959.
310. Third World Food Survey, Basic Study No. 11, Food and Agriculture Organisation, 1963.
311. Pesticides and Health, Shell briefing service, Royal Dutch Shell Group, February 1967.
312. The Use of Pesticides, President’s Scientific Advisory Committee Report, Weisner, J. B., Chairman, Govt. Print. Off.,
Washington, D.C., May 15, 1963.
313. Glasser, R. F., The actions taken by Shell in response to recommendations of advisory committees and regulatory
agencies, in Symposium on the Science and Technology of Residual Insecticides in Food Production with Special
Reference to Aldrin and Dieldrin, Shell Oil Company, 1968, 225.
314. Hardie, D. W. F., Benzene Hexachloride, in K irk -O th m er E n cyclo p ed ia o f C hem ical T ech n ology, Voi. 5, 2nd ed.,
McKetta, J. J. and Othmer, D. F., Eds., John Wiley (Interscience), 1964, 267.
315. Lambermont, F., L’Hexachlorcyclohexane et son isomère gamma, paper presented at the 8 th International Congress
on Agriculture, Brussels, July 12, 1950.
316. Van der Linden, T., Uber die benzol-hexachloride und ihren zerfall in trichlor-benzole, Chem. B er., 45, 231, 1912.
317. Bender, H., Chlorinating benzene, toluene, etc., U.S. patent 2,010,841; 1935. C .A ., 29, 6607, 1935.
318. Stephenson, H. P., Curtis, A. L., Grant, A. E., and Hardie, T., cited in Haller, H. L., and Bowen, C. V., Basic facts
about benzene hexachloride, Agrie. C hem ., 2 ,1 5 ,1 9 4 7 .
319. Dupire, A. and Raucourt, M., Un insecticide nouveau: l’hexachlorure de benzene, C. R . A cad. A grie. Fr., 29, 470,
1943.
320. Bourne, L. B., Hexachlorocyclohexane as an insecticide, N atu re (L on d.), 156, 85, 1945.
321. Slade, R. E., The 7 -isomer of hexachlorocyclohexane (gammexane), Hurter Memorial Lecture, Chem. Ind. (L ond.),
6 4 ,3 1 4 ,1 9 4 5 .
322. Holmes, E., Recent British developments in taint-free use of BHC,Agrie. Chem ., 6 ,[1 2 ], 31, 1951.
323. Ishikura, H., Impact of pesticide usage on the Japanese environment, in E n viron m en tal T o x ico lo g y o f Pesticides,
Matsumura, F., Boush, G. M., and Misato, T., Eds., Academic Press, New York and London, 1972, 1.
324. Kenaga, E. E. and Allison, W. E., Commercial and experimental organic insecticides (1971 revision), B u ll E ntom ol.
Soc. A m ., 16,68, 1970.
325. Ishii, K., Chlorinated pesticides, in Japan P esticide In form ation , No. 3, Japan Plant Protection Association, 1970,
11 .
326. Shindo, N., The present situation of agricultural chemicals in the chemical industry of Japan, in Japan P esticide
In fo rm a tio n , No. 7, Japan Plant Protection Association, 1971, 10.
327. Kurihara, N., Sanemitsu, Y., Kimura, T., Kobayashi, M., and Nakajima, M., Stepwise synthesis of 3 ,4 , 5 , 6 -tetrachlo-
rocyclohexene-1 (BTC) isomers, Agrie. Biol. Chem. (Tokyo), 34, 784, 1970.
328. Cited in Hardie, D. W. F., Benzene hexachloride, in K irk-O th m er E n cyclopedia o f Chem ical T echnology, Voi. 5, 2nd
ed., Mcketta, J. J. and Othmer, D. F., Eds., John Wiley (Interscience), 1964, 274.
329. Gunther, F. A., Chlorination of benzene, Chem. Ind. (L on d.), 399, 1946.
330. Melnikov, N. N., C h em istry o f P esticides, Gunther, F. A. and Gunther, J. D., Eds., R esidue R ev., Voi. 36,
Springer-Verlag, New York, 1971.
331. Cooke, W. H. and Smart, J. C., Insecticide, British patent 586,439, 1944; C .A ., 41, 7640, 1947.
332. Hay, J. K. and Webster, K. C., Insecticide, British patent 586,442, 1944; C.A., 7640, 1947.
333. Balsón, E. W., Studies in vapour pressure measurement, Trans. Faraday Soc., 43, 54, 1947.
334. Kanazawa, J., Yashima, T., and Kiritani, K., Contamination of ecosystem by pesticides II, Kagaku (S cien ce), 41,
383, 1971.
335. Fürst, H. and Praeger, K., Isolation of pure 7 -isomer from crude hexachlorocyclohexane mixtures, German patent
1,093,791, 1959; C.A., 55, 19124,1961.
336. Bishopp, F. C , The insecticide situation, J. Econ. E n to m o l., 39, 449, 1946.
337. Rohwer, S. A., Effect of individual BHC isomers on plants, Agrie. Chem ., 4, 75, 1949.
338. Burnett, G. F., Trials of residual insecticides against anophelines in African-type huts, Bull.E ntom ol. R es., 48, 631,
1957.
339. Hocking, K. S., Armstrong, J. A., and Downing, F. S., cited in Pampana E., A T e x tb o o k o f Malaria E radication, 2nd
ed., Oxford University Press, 1969, 133.
340. Cross, H. F. and Snyder, F. M., Imprégnants against chiggers, J. Econ. E n to m o l., 41, 936, 1948.
340a. Ulmann, E., Ed., Lindane, M onograph o f an In secticide, Verlag K. Schillinger, Freiburg im Breisgau, 1972.
341. Hassell, O., Stereochemistry of cyclohexane, Q. R ev. Chem. Soc. (L on d.), 7, 221, 1953.
342. Orloff, H. D., The stereoisomerism of cyclohexane derivatives, Chem. R ev., 54, 347, 1954.
343. Riemschneider, R., Spat, M., Rausch, W., Bottger, E., Zur Chemie von polyhalocyclohexanen XXIV. 1,2,3,4,5,6-
hexachlorocyclohexan von schmp. 88-89°,M o n a tsch . Chem ., 84, 1068, 1953.
344. Kauer, K., Du Vali, R., and Alquist, F., Epsilon isomer of 1,2,3,4,5,6-hexachlorocyclohexane, Ind. Eng. C hem ., Ind.
E d., 39, 1335, 1947.
345. Visweswariah, K. and Majumder, S. K., A new insecticidal isomer of hexachlorocyclohexane (BHC), Chem . Ind.
(L o n d .), 379,1969.
346. Cristol, S. J., The structure of a-benzene hexachloride, J. A m . Chem. Soc., 71, 1894, 1949.
347. Bastiansen, O., Ellefson, O., and Hassel, O., Structure of a, ß, 7, 6 , and e benzene hexachloride, R esearch, 2, 248,
1948.

220 Chlorinated Insecticides

348. Bastiansen, O., Ellefson, O., and Hassell, O., Electron diffraction investigation of a, /3, 7 , 6 and e benzene
hexachloride, A cta Chem. Scand., 3, 918, 1949.
349. Norman, N., The crystal structure of the epsilon isomer of 1,2,3,4,5,6-hexachlorocyclohexane, A c ta C hem . Scand.,
4, 251, 1950.
350. Hetland, E., Dipole moments of ot, 0 , 7 , and 6 hexachlorocyclohexane and tetrachlorocyclohexane (mp 174°), A eta
Chem. Scand., 2, 678, 1948.
351. Kolka, A., Orloff, H., and Griffing, M., Two new isomers of benzene hexachloride, J. A m . Chem. Soc., 76, 3940,
1954.
352. Whetstone, R. R., Davis, F., and Ballard, S., Interconversion of hexachlorocyclohexane isomers, J. A m . Chem. Soc.,
75,1768,1953.
353. Guilhon, M. J., The insecticidal and toxic properties of some sulfur derivatives of hexachlorocyclohexane, C. R.
A cad. Agrie. Fr., 23, 101, 1947; C.A., 41, 6363, 1947.
354. Cristol, S., The kinetics of the alkaline dehydrochlorination of the benzene hexachloride isomers. The mechanism of
second order elimination reactions, J. A m . Chem. Soc., 69, 338, 1947.
355. Gunther, F. and Blinn, R. C., Alkaline degradation of benzene hexachloride,/. A m . Chem. Soc., 69, 1215, 1947.
356. La Clair, J. B., Determination of BHC by hydrolysable chlorine method, Anal. Chem ., 20, 241, 1948.
357. Riemschneider, R., Konstitution und Wirkung von insektiziden. Mitt XVI, Z. A ngew . E nt., 48, 423, 1961.
358. Kurihara, N., BHC - its toxicity and its penetration, translocation and metabolism in insects and mammals, B ochu
Kagaku, 35(11), 56, 1970.
359. Riemschneider, R., Poly halo cyclohexanen und verwandten Verbindungen. Mitt XXX: Relativ konfigura?
tionsbestimmung. Konfigurations-bezeichnungen von polyhalocyclohexanen und cyclohexenen, Ö sterreichische
Chem iker-Zeitung, 55, 102, 1954.
360. Kurihara, N., Sanemitsu, Y., Tamura, Y., and Nakajima, M., Studies on BHC isomers and their related compounds.
Part II. Isomerisation of 3 ,4 ,5 ,6 -tetrachlorocyclohexene-l (BTC) isomers, Agrie. Biol. Chem. (T o k y o ), 34, 790,
1970.
361. Kurihara, N., Sanemitsu, Y., Nakajima, M., McCasland, G. E., and Johnson, L. F., Studies on BHC isomers and their
related compounds. III. Proton magnetic resonance studies at 220 MHz of two new iodopentachlorocyclohexanes
derived from tetrachlorocyclohexene (BTC), Agrie. Biol. Chem. (T o k y o ), 35, 71, 1971.
362. Bridges, R. G., Retention of 7 -benzene hexachloride by wheat and cheese, J. Sci. F o o d A grie., 431, 1958.
363. Schedi ter, M. S. and Hornstein, I., Colorimetric determination of benzene hexachloride, Anal. Chem ., 24, 544,
1952.
364. Physical and Chemical Properties of Hercules Toxaphene; Hercules Incorporated Agricultural Chemicals Technical
Data Bulletin AP-103A; various Hercules technical bulletins.
365. Klein, A. K. and Link, D. J., Field weathering of toxaphene and chlordan, J. A ssoc. Offic. Agrie. Chem ., 50, 586,
1967.
366. Desalbres, L. and Rache, J., Les terpènes polychlorés et leurs propriétés insecticides, Chim. Ind. (Paris), 59, 236,
1948.
367. Khanenia, F. S. and Zhuravlev, S. V., cited in Busvine, J. R., The insecticidal potency of 7 -BHC and the chlorinated
cyclodiene compounds and the significance of resistance to th em , Bull. E n tom ol. R es., 55, 271, 1964.
368. Weinman, C. and Decker, G. C., Chlorinated hydrocarbon insecticides used alone and in combinations for
grasshopper control,/. Econ. E n tom ol., 42, 135, 1949.
369. Schread, J. C , Persistence of DDT, parathion, etc., for P opillia japón ica control,/. Econ. E n to m o l, 42, 383, 1949.
370. The Use of Toxaphene Low Volume Formulations for Cotton Insect Control, Hercules Incorporated Bulletin,
Wilmington, Delaware, 1969, 24 pp.
371. Beckman, H. F., Ibert, E. R., Adams, B. B., Skoolin, D. O., Determination of total chlorine in pesticides by
reduction with a liquid anhydrous ammonia-sodium mixture, /. Agrie. F o o d Chem ., 6 , 104, 1958.
372. Graupner, A. J. and Dunn, C. L., Determination of toxaphene by a spectrophotometric diphenylamine procedure,/.
Agrie. F o o d Chem ., 8 , 286, 1960.
373. Brown, A. W. A., Insect resistance, Farm Chemicals, September 1969 et seq.
374. Brown, A. W. A. and Pal, R., In sect R esistan ce in A rth ro p o d s, 2nd ed., W.H.O., Geneva, 1971, 446.
375. Busvine, J. R., A C ritical R e view o f th e Techniques U sed f o r Testing In se cticid e s , 2nd ed., Commonwealth
Agricultural Bureaux, 1971.
376. Bliss, C. L, Calculation of dose/mortality curve, Ann. A p p i. B io l, 22, 134, 1935.
377. Dyte, C. E., Insecticide resistance in stored-product insects with special reference to Tribolium castaneum , Trop.
S to re d Prod. I n f , (20), 13, 1970.
378. Georghiou, G. P., Genetics of resistance to insecticides in houseflies and mosquitoes, Exp. P a ra sito l, 26, 224, 1969.
379. Davidson, G., Insecticide resistance in A n o p h eles gam biae Giles, a simple case of Mendelian inheritance, N a tu re
(L on d.), 178, 861, 1956.
380. Davidson, G., Studies on insecticide resistance in anopheline mosquitoes, Bull. W.H.O., 18, 579, 1958.
381. Guneidy, A. M. and Busvine, J. R., Genetical studies on dieldrin-resistance in Musca do m estica L. and Lucilia
cuprina (Wied.), Bull. E n tom ol. R es., 55, 499, 1964.
382. Georghiou, G. P., March, R. B., and Printy, G. E., A study of the genetics of dieldrin-resistance in the housefly
{Musca d o m estica L.),B u ll. W.H.O., 29, 155, 1963.

221
383. Tadano, T. and Brown, A. W. A., Genetical linkage relationships of DDT resistance and dieldrin-resistance in Culex
p ip ie m fatigan s Wiedemann, Bull. W.H.O., 36, 101, 1967.
384. Brown, A. W. A., Insecticide resistance-genetic implications and applications, World. R ev. P est C on trol , 6 , 104,
1967.
385. Busvine, J. R., Developments in pest control, P est A rticle s an d N e w s Sum m aries P .A .N .S., [A ], 14, 310, 1968.
386. Tsukamoto, M., Biochemical genetics of insecticide resistance in the housefly, R esidu e R ev., 25, 289, 1969.
387. Tsukamoto, M. and Suzuki, R., Genetic analysis of DDT-resistance in strains of the housefly Musca do m estica L.,
B otyu -K agaku, 29, 76, 1964.
388. Oppenoorth, F. J., Some Cases of Resistance Caused by the Alteration of Enzymes, Proc. 12th Int. Congr.
Entomol., London, July 1964, 240.
389. Grigolo, A. and Oppenoorth, F. J., The importance of DDT-dehydrochlorinase for the effect of the resistance gene
kdr in the housefly, Genetica, 37, 159, 1966.
390. Khan, M. A. Q. and Terriere, L. C., DDT-dehydrochlorinase activity in housefly strains resistant to various groups of
insecticides,/. Econ. E n to m o l, 61, 732, 1968.
391. Sawicki, R. M. and Farnham, A. W., Examination of the isolated autosomes of the SKA strain of house-flies (M usca
d o m estica L.) for resistance to several insecticides with and without pretreatment with sesamex and TBTP, Bull.
E n to m o l. R es., 59, 409, 1968.
392. Hoyer, R. F. and Plapp, F. W., Jr., A gross genetic analysis of two DDT-resistant housefly strains, J. Econ. E n to m o l,
59,495, 1966.
393. Plapp, F. W., Jr. and Hoyer, R. F., Possible pleiotropism of a gene conferring resistance to DDT, DDT analogs, and
pyrethrins in the House Fly and Culex tarsalis, J. Econ. E n to m o l, 61, 761, 1968.
394. Plapp, F. W., Jr. and Hoyer, R. F., Insecticide resistance in the housefly: decreased rate of absorption as the
mechanism of action of a gene that acts as an intensifier of resistance, /. Econ. E n to m o l, 61, 1298, 1968.
395. Sawicki, R. M. and Farnham, A. W., Genetics of resistance to insecticides of the SKA strain of Musca domestica, IH.
Location and isolation of the factors of resistance to dieldrin, E n tom ol. Exp. A p p i , 11, 133, 1968.
396. Perry, A. S., Hennessy, D. J., and Miles, J. W., Comparative toxicity and metabolism of p, p'-DDT and various
substituted DDT-derivatives by susceptible and resistant houseflies, /. Econ. E n to m o l, 60, 568, 1967.
397. Oppenoorth, F. J., DDT-resistance in the housefly dependent on different mechanisms and the action of synergists,
M eded. L andbouw hogesch . O pzoekingsstn. Staat. G ent., 30, 1390, 1965.
398. El Basheir, S., Causes of resistance to DDT in a diazinon-selected and a DDT-selected strain of house flies, E n to m o l
E xp. A p p i , 10, 111, 1967.
399. Milani, R., Genetical aspects of insecticide resistance, B u ll W.H.O., Supplement, 29, 77, 1963.
400. Oppenoorth, F. J. and Nasrat, G. E., Genetics of dieldrin and gamma-BHC (lindane) resistance in the housefly
CMusca d o m estica ), E n to m o l Exp. A p p i , 9, 223, 1966.
401. Davidson, G., Resistance to Chlorinated Insecticides in Anopheline Mosquitoes, Proc. 12th Int. Congr. Entomol.,
London, July 1964, 236.
402. Oonnithan, E. S. and Miskus, R., Metabolism of C14 -dieldrin-resistant Culex p ip ie m qu in qu e fascia tu s Mosquitoes, /.
Econ. E n to m o l, 5,425, 1964.
403. Tadano, T. and Brown, A. W. A., Development of resistance to various insecticides in Culex p ip ie m fatigan s
Wiedemann, Bull. W.H.O., 35, 189, 1966.
404. Plapp, F. W., Jr., Chapman, G. A., and Morgan, J. W.,/. Econ. E n to m o l, 58, 1064, 1965.
405. Klassen, W. and Brown, A. W. A., Genetics of insecticide-resistance and several visible mutants in A e d e s aeg yp ti,
Can. J. Genet. C y to l, 6 , 61, 1964.
406. Lockhart, W. L., Klassen, W., and Brown, A. W. A., Crossover values between dieldrin-resistance and DDT ; resistance
and linkage-group-2 genes in A e d e s aegypti, Can. J. Genet. C yto l., 12,407, 1970.
407. Kimura, T. and Brown, A. W. A., DDT-dehydrochlorinase in A e d e s a egypti, J. Econ. E n to m o l., 57, 710, 1964.
408. Inwang, E. E., Khan, M. A. Q., and Brown, A. W. A., DDT-resistance in West African and Asian strains of A e d e s
a e g y p ti (L), Bull. W.H.O., 36,409, 1967.
409. McDonald, 1. C., Ross, M. H., and Cochran, D. G., Genetics and linkage of aldrin resistance in the German
cockroach, B lattelia germ anica (L),B u ll. W.H.O., 40, 745, 1969.
410. Matsumura, F., Telford, J. N., and Hayashi, M., Effect of sesamex upon dieldrin resistance in the German
cockroach,/. Econ. E n to m o l, 60, 942, 1967.
411. Read, D. C. and Brown, A. W. A., Inheritance of dieldrin-resistance and adult longevity in the cabbage maggot,
H ylem ya brassicae (Bouche), Can. J. Genet. C y to l, 8 . 71, 1966.
412. Hooper, G. H. S. and Brown, A. W. A., Dieldrin-resistant and DDT-resistant strains of the spotted root maggot
apparently restricted to heterozygotes for resistance,/. Econ. E n to m o l, 58, 824, 1965.
413. Lineva, V. A. and Derbeneva-Uhova, V. P., cited in Zaghloul, T. M. A. and Brown, A. W. A., Effects of sublethal
doses of DDT on the reproduction and susceptibility of Culex p ip ie m L., Bull. W.H.O., 38, 459, 1968.
414. Zaghloul, T. M. A. and Brown, A. W. A., Effects of sublethal doses of DDT on the reproduction and susceptibility
of Culex p ip ie m b ., Bull. W.H.O., 38, 459, 1968.
415. Moriarty, F., The sublethal effects of synthetic insecticides on insects, B io l R ev., 44, 321, 1969.
416. Hadaway, A. B., Cumulative effect of sublethal doses of insecticides on houseflies, N a tu re (L o n d .), 178, 149, 1956.

222 Chlorinated Insecticides

417. Ahmad, N. and Brindley, W. A., Modification of parathion toxicity to wax moth larvae by chlorcyclizine,
aminopyrine or phénobarbital, T o x ic o l A p p i P h a rm a c o l , 15, 433, 1969.
418. Agosin, M., Aravena, L., and Neghme, A., Enhanced protein synthesis in T riatom a infestans treated with DDT, E x p .
P a ra sito l, 16, 318, 1965.
419. Plapp, F. W., Jr. and Casida, J. E., Induction by DDT and dieldrin of insecticide metabolism by house fly enzymes,
J. Econ. E n to m o l. , 63, 1091,1970.
420. Walker, C. R. and Terriere, L. C., Induction of microsomal oxidases by dieldrin in M usca dom estica, E n to m o l E xp.
A p p i , 13, 260,1970.
421. Yu, S. J. and Terriere, L. C., Induction of microsomal oxidases in the housefly and the action of inhibitors and
stress factors, Pestic. B ioch em . P h y s io l, 1, 173, 1971.
422. Melander, A. L., Strain of A sp id io tu s resistant to lime-sulfur, J. Econ. E n to m o l, 7, 167, 1914.
423. Brown, A. W. A., Insecticide resistance comes of age, Bull. E n tom ol. Soc. A m ., 14, 3, 1968.
424. Keiding, J., Persistence of resistant populations after the relaxation of the selection pressure, W orld R ev. P est
C ontrol, 6 , 115. 1967.
425. Busvine, J. R., Mechanism of resistance to insecticides in house-flies, N atu re (L on d.), 168, 193, 1951.
426. Missiroli, A., Resistenza alii insecticidi di alcuni razze di M usca dom estica, Riv. P a ra ssito l, 12, 5, 1951.
427. Gilbert, I. H., Couch, M. D., and McDuffie, W. C., Development of resistance to insecticides in natural populations
of house-flies,/. Econ. E n to m o l, 46, 48, 1953.
428. March, R. B. and Metcalf, R. L., Insecticide-resistant flies, Soap Sanit. Chem ., 26, 121, 1950.
429. March, R. B., Summary of Research on Insects Resistant to Insecticides, in National Research Council, Division of
Medical Sciences, C onference on R esistan ce an d In sect P h y sio lo g y , Washington, D.C., Dec. 8 -9 , 1951, 45 (National
Research Council Publication 219).
430. Metcalf, R. L., Physiological basis for insect resistance to insecticides, P h y sio l R ev., 35, 197, 1955.
431. Georgopoulos, G. D., Extension to chlordane of the resistance to DDT observed in A n o p h ele s sacharovi, Bull.
W.H.O., 11, 855, 1954.
432. Davidson, G., Insecticide resistance in A n o p h eles gam biae Giles, N atu re (L on d.) ,1 7 8 , 705, 1956.
433. Wright, J. W., Present status of mosquito control, Pestic. S e t, 3, 471, 1972.
434. Busvine, J. R., Insecticide-resistance in mosquitoes, Pestic. S e t, 3, 483, 1972.
435. Hawkins, W. B., Tests on the Resistance of Anopheles Larvae in the Region of the Tennessee Valley Authority, in
Seminar on the Susceptibility of Insects to Insecticides, Panama, 2 3 -2 8 June 1958, Pan American Sanitary Bureau,
W.H.O., Washington D.C., 1958.
436. Cova-Garcia, P., Manifestations of behaviouristic resistance in Venezuela, in Seminar on the Susceptibility of Insects
to Insecticides, Panama, 23, June 1958, Pan American Sanitary Bureau, W.H.O., Washington D.C., 1958.
437. Gjullin, C. M. and Peters, R. F., Recent studies of mosquito resistance to insecticides in California, M o squ ito N ew s,
12, 1, 1952.
438. Rachou, R. G., Some manifestations of behaviouristic resistance in Brazil, in Seminar on the Susceptibility of
Insects to Insecticides, Panama, 23, 1958, Pan American Sanitary Bureau, W.H.O., Washington D.C., 1958.
439. Wharton, R. H., The behaviour and mortality of A n o p h eles m acu latus and Culex fatigan s in experimental huts
treated with DDT and BHC, B u ll E n to m o l R es., 42, 1, 1950.
440. Mosna, E., Culex p ip ien s autogenicus DDT-resistenti e loro controllo con Octaklor e esachlorocicloesano, Riv.
P a ra ssito l, 9, 19, 1948.
441. Kerr, J. A., de Camargo, S., and Abedi, Z. H., cited in Busvine, J. R. and Pal, R., The impact of
insecticide-resistance on control of vectors and vector-borne diseases, B u ll W.H.O., 40, 731, 1969.
442. Fay, R. W., Insecticide resistance in A e d e s a e g y p ti , A m . J. Trop. M ed. H yg., 5, 378, 1956.
443. Wright, J. W. and Brown, A. W. A., Survey of possible insecticide resistance in body lice, B u ll W.H.O., 16, 9, 1957.
444. Wright» J. W. and Pal, R., Second survey of insecticide resistance in body-lice, 1958-63, Bull. W.H.O., 33, 485,
1965.
445. Grayson, J. M., Effects on the German cockroach of twelve generations of selection for survival to treatments with
DDT and benzene hexachloride, J. Econ. E n to m o l, 46, 124, 1953.
446. Grayson, J. M., Differences between a resistant and a non-resistant strain of the German cockroach, J. Econ.
E n to m o l, 47, 253, 1954.
447. Whitnall, A. B. M. and Bradford, B., An arsenic resistant tick and its control with gammexane dips, Bull. E n tom ol.
R es., 40, 207, 1949.
448. Whitnall, A. B. M., Thorburn, J. A., Mellardy, W. M., Whitehead, G. B., and Meerholz, F., A BHC-resistant tick, Bull.
E n to m o l R es., 43, 51, 1952.
449. Stone, B. F. and Meyers, R. A. J., Dieldrin-resistant cattleticks, B ooph ilu s m icroplu s (Canestrini) in Queenland,
A u si. J. Agrie. R es., 8 , 312, 1957.
450. Wharton, R. H. and Roulston, W. J., Resistance of ticks to chemicals, A nn. R ev. E n to m o l, 15, 381, 1970.
451. Adkisson, P. L., Development of resistance by the tobacco budworm to endrin and carbaryl,7. Econ. E n to m o l., 61,
37,1968.
452. Plapp, F. W., Jr., Insecticide resistance in H eliothis: tolerance in larvae of H. viriscens as compared with H. zea to
organophosphate insecticides, J. Econ. E n to m o l, 64, 999, 1971.

223
453. Ishikura, H., High yield rice cultivation and the use of pesticides, Japan P esticide In fo rm a tio n , No. 5, Japan Plant
Protection Association, October 1970, 5.
454. Fukaya, F., Insecticide resistance, detection methods and counter-measures, Japan P esticide In fo rm a tio n , No. 6 ,
Japan Plant Protection Association, January 1971, 25.
455. Vernon, A. J., Control of cocoa capsids in West Africa, Chem. Ind. (L o n d ), 1219, 1961.
456. Rushton, M. P., Cocoa capsid control in Sierra Leone, Span , 6 , 23, 1963.
457. Dunn, J. A., Insecticide resistance in the cocoa capsid, D istantiella th eobrom a, N atu re (L on d.), 199, 1207, 1963.
458. Harris, C. R., Mazurek, J. H., and Svec, H. J., Cross-resistance shown by aldrin-resistant seed maggot flies, H ylem ya
spp., to other cyclodiene insecticides and related materials, J. E con. E n tom ol., 57, 702, 1964.
459. McClanahan, R. J,, Harris, C. R., and Miller, L. A., Resistance to aldrin, dieldrin, and hep tachlor in the onion
maggot, H ylem ya an tiqu a (Meig.) in Ontario, R ep. E n to m o l Soc. Ont., 89, 55, 1958.
460. Harris, C. R., Manson, G. F., and Mazurek, J. H., Development of insecticidal resistance by soil insects in Canada, J.
Econ. E n to m o l, 55, 777, 1962.
461. Coaker, T. H., Mowat, D. J., and Wheatley, G. A., Insecticide resistance in the cabbage root fly in Britain, N ature
(L o n d .), 200,664, 1963.
462. Gostick, K. G. and Coaker, T. H., Monitoring for Insecticide Resistance in Root Flies, Proc. 5th Br. Insectic. Fungic.
C o n f, 1969, 89.
463. Kilpatrick, J. W. and Schoof, H. F., Interrelationship of water and H erm etia illucens breeding to Musca dom estica
production in human excrement, ,4m: J. Trop. Med. H yg., 8 , 103, 1959.
464. Knutson, H., Changes in reproductive potential in houseflies in response to dieldrin, Mise. P u b i E n to m o l Soc. A m .,
1, 27, 1959.
465. Parkin, E. A., The onset of insecticide resistance among field populations of stored-product insects, J. S to re d Prod.
R es., 1, 3, 1965.
466. Lindgren, D. L. and Vincent, L. E., The susceptibility of laboratory reared and field-collected cultures of T ribolium
con fu su m and T. castaneum , to ethylene dibromide, hydrocyanic acid and methyl bromide, J. Econ. E n to m o l, 58,
551, 1965.
467. Dyte, C. E. and Blackman, D. G., The spread of insecticide resistance in Tribolium castaneum (Herbst), J. S to re d
Prod. R es., 6 , 255, 1970.
468. Lloyd, C. J., Studies on the cross-tolerance to DDT-related compounds of a pyrethrin-resistant strain of Sitoph ilu s
granarius (L.), /. S to re d Prod. R es., 5, 337, 1969.
469. Abedi, Z. H. and Brown, A. W. A., Development and reversion of DDT-resistance in A e d es aeg yp ti, Can. J. Genet.
C y to l , 2, 252, 1960.
470. Georghiou, G. P., March, R. B., and Printy, G. E., Induced regression of dieldrin-resistance in the housefly (Musca
d o m estica L.), Bull. W.H.O., 29, 167, 1963.
471. Georghiou, G. P. and Metcalf, R. L., Dieldrin susceptibility: partial restoration in anopheles selected with a
carbamate, Science, 140, 301, 1963.
472. Georghiou, G. P. and Bowen, W. R., An analysis of housefly resistance to insecticides in California, J. Econ.
E n to m o l, 59, 204, 1966.
473. Stone, B. F., The inheritance of DDT-resistance in the cattle tick, Boophilus microplus, A u st. J. Agrie. R es., 13,
984, 1962.
474. Schnitzerling, H. J., Roulston, W. J., and Schuntner, C. A., The absorption and metabolism of [ 14 C] DDT in
DDT-resistant and susceptible strains of the cattle tick B ooph ilu s m icroplus, A u st. J. Biol. Sci., 23, 219, 1970.
475. Winteringham, F. P. W., Mechanisms of selective insecticidal action, A nn. Rev. E n to m o l, 14, 409, 1969.
476. Gerolt, P., Mode of entry of contact insecticides, J. In sect P h y sio l, 15, 563, 1969.
477. Moriarty, F. and French, M. C., The uptake of dieldrin from the cuticular surface of Periplaneta A m erican a , Pestic.
B ioch em . P hysiol., 1, 286, 1971.
478. Narahashi, T., Effects of insecticides on excitable tissues, in A dvan ces in In sect P h ysiology, Voi. 8 , Beament, J. W.
L., Treherne, J. E., and Wigglesworth, V. B., Eds., Academic Press, London and New York, 1971.
479. Winteringham, F. P. W. and Lewis, S. E., On the mode of action of insecticides, Ann. Rev. E n to m o l, 4, 303, 1959.
480. Soto, A. R. and Deichmann, W. B., Major metabolism and acute toxicity of aldrin, dieldrin and endrin, Environ.
R es., 1, 307, 1967.
481. Robinson, J., Persistent pesticides, Ann. R ev. P h arm acol, 10, 353, 1970.
482. Brooks, G. T., The metabolism of diene-organochlorine (cyclodiene) insecticides, R esidu e R ev., 27, 81, 1969.
483. Brooks, G. T., The fate of chlorinated hydrocarbons in living organisms, in P esticide Term inal R esidues, Invited
papers from the IUPAC International Symposium on Terminal Residues, Tel Aviv, 1971, Tahori, A. S., Ed.,
Butterworths, London, 1971, 111.
484. Brooks, G. T., Pathways o f enzymatic degradation of pesticides, in E n viron m en tal Q u ality a n d S afety, Vol. I,
Coulston, F. and Korte, F., Eds., Georg Thieme, Stuttgart, Academic Press, New York. 1972. 106.
485. Matsumura, F., Metabolism of Pesticides in Higher Plants, in E n viron m en tal Q u ality a n d S afety, Vol. I, Coulston, F.
and Korte, F., Eds., Georg Thieme, Stuttgart, Academic Press, New York, 1972, 106.
486. Klein, W., Metabolism of Insecticides in Microorganisms and Insects, in E n viron m en tal Q u ality and S a fety, Vol. I,
Coulston, F., Korte, F., Eds., George Thieme, Stuttgart, Academic Press, 1972, 1964.

224 Chlorinated Insecticides

 487. Schaefer, C. H. and Sun, Y. P., A study of dieldrin in the housefly central nervous system in relation to dieldrin
resistance,/. Econ. E n to m o l, 60, 1580, 1967.
488. Sellers, L. G. and Guthrie, F. E., Localisation of dieldrin in the housefly thoracic ganglion by electron microscopic
autoradiography,/. E con . E n to m o l , 64, 352, 1971.
489. Telford, J. N. and Matsumura, F., Dieldrin binding in subcellular nerve components of cockroaches. An electron
microscopic and autoradiographic study, J. Econ. E n to m o l, 63, 795, 1970.
490. Kurihara, N., Nakajima, E., and Shindo, H., Whole body autoradiographic studies on the distribution of BHC and
nicotine in the American cockraoch, in B ioch em ical T o xicology o f In secticides, O’Brien, R. D. and Yamamoto, I.,
Eds., Academic Press, New York, 1970, 41.
491. Sun, Y. P., Dynamics of insect toxicology - a mathematical and graphical evaluation of the relationship between
insect toxicity and rates of penetration and detoxication of insecticides, /. Econ. E n tom ol., 61, 949, 1968.
492. Glasstone, S., A T ex tb o o k o f Physical C hem istry, 2nd ed., MacMillan, London, 1948, 1075.
493. Hewlett, P. S., Interpretation of dosage-mortality data for DDT-resistant houseflies, Ann. A p p i B io l, 46, 37, 1958.
494. Menzie, C. M., Fate of pesticides in the environment, A nn. R ev. E n tom ol., 17, 199, 1972.
495. Hamaker, J. W., Mathematical prediction of cumulative levels of pesticides in soil, in Organic Pesticides in the
Environment, A m . Chem. Soc.tA dv. Chem. Ser., 60, 122, 1966.
496. Decker, G. C., Bruce, N. W., and Bigger, J. H., The accumulation and dissipation of residues resulting from the use
of aldrin in soils, J. Econ. E n to m o l, 58, 266, 1965.
497. Lichtenstein, E. P., Persistence and degradation of pesticides in the environment, in S cien tific A sp e c ts o f P est
Control, Publication 1402, National Academy of Sciences, National Research Council, Washington, D.C., 1966.
498. Harris, C. R., Factors influencing the effectiveness of soil insecticides, ,4«rc. R ev. E n tom ol., 17, 177, 1972.
499. Harris, C. R. and Sans, W. W., Behaviour of dieldrin in soil: microplot field studies on the influence of soil type on
biological activity and absorption by carrots, J. Econ. E n to m o l, 65, 333, 1972.
500. Harris, G R., Factors influencing the biological activity of technical chlordane and some related compounds in
soil,/. Econ. E ntom ol., 65, 341, 1972.
501. Strickland, A. H., Some estimates of insecticide and fungicide usage in agriculture and horticulture in England and
Wales 1960-64. Pesticides in the environment and their effects on wildlife, /. A p p i E c o l, 3[suppl.], 3, 1966.
502. Third R e p o rt o f th e Research C o m m itte e on T oxic Chemicals, Agricultural Research Council, HMSO London, 1970,
69.
503. Plapp, F. W., Jr., On the molecular biology of insecticide resistance, in B ioch em ical T o xicology o f In secticides,
O’Brien, R. D. and Yamamoto, I., Eds., Academic Press, New York, 1970, 179.
504. Lichtenstein, E. P. and Corbett, J. R., Enzymatic conversion of aldrin to dieldrin with subcellular components of
pea plants, /. Agrie. F o o d Chem., 17, 589, 1969.
505. Yu, S. J., Kiigemagi, U., and Terriere, L. G, Oxidative metabolism of aldrin and isodrin by bean root fractions,/.
Agrie. F o o d Chem., 19, 5, 1971.
506. Lyr, H. and Ritter, G., Zum Wirkungsmechanismus von Hexachlorocyclohexan - Isomeren in Hefezellen, Z. Allge.
M ikrobiol., 9, 545, 1969.
507. Tu, C. M., Miles, J. R. W., and Harris, G R., Soil microbial degradation of aldrin, L ife Sci., [Oxford] 7, 311, 1968.
508. Körte, F., Metabolism of 1 4 C-labelled insecticides in microorganisms, insects and mammals, B otyu -kagaku, 32, 46,
1967.
508a. Rice, C. P. and Sikka, H. G, Uptake and metabolism of DDT by six species of marine algae, /. Agrie. F o o d Chem.,
21, 148, 1973.
509. Robinson, J., The burden of chlorinated hydrocarbon pesticides in man, Can. Med. A ssoc. J., 100, 180, 1969.
510. Quaife, M. L., Winbush, J. S., and Fitzhugh, O. G. Survey of quantitative relationships between ingestion and
storage of aldrin and dieldrin in animals and man, F o o d Cosm et. T o x ic o l, 5, 39, 1967.
511. Department of Health, Education, and Welfare, Report of the Secretary’s Commission on Pesticides and their
Relationship to Environmental Health, Parts I and II, U.S. Govt. Print. Off., Washington, D.C., 1969, 263.
512. Bitman, J., Cecil, H. G, Harris, S. J., and Fries, G. F., Comparison of DDT effect on pentobarbital metabolism in
rats and quail, /. Agrie. F o o d Chem., 19, 333, 1971.
513. Robinson, J., Roberts, M., Baldwin, M., and Walker, A. I. T., The pharamacokinetics of HEOD [dieldrin] in the rat,
F o o d Cosm et. T o x ic o l, 7, 317, 1969.
514. Brown, V. K. H., Robinson, J., and Richardson, A., Preliminary studies on the acute and subacute toxicities o f a
photoisomerisation product of HEOD, F o o d Cosm et. T o x ic o l, 5, 771, 1967.
515. Robinson, J. and Richardson, A. R., personal communication.
516. Hunter, C. G. and Robinson, J., Pharmacodynamics of dieldrin [HEOD]. I. Ingestion by human subjects for 18
months, Arch. Environ. H ealth, 15,614, 1967.
517. Klein, W., Muller, W., and Korte, F., Ausscheidung, Verteilung und Stoffwechsel von endrin-14C in ratten, Justu s
L iebigs Ann. Chem., 713, 180, 1968.
518. Kaul, R., Klein, W., and Körte, F., Metabolismus und kinetic der Verteilung von 0-dihydroheptachlor-14 C in
männlichen ratten, Tetrahedron, 26, 99, 1970.
519. Robinson, J. and Roberts, M., Accumulation, distribution and elimination of organochlorine insecticides by
vertebrates, Soc. Chem. Ind. (Lond.J M onogr., No. 29, 106, 1968.

225
520. Abbott, D. C., Collins, G. B., and Goulding, R., Organochlorine pesticide residues in human fat in the United
Kingdom 1969—71, Br. M ed. J., 553, 1972.
521. Coulson, J. C., Deans, I. R., Potts, G. R., Robinson, J., and Crabtree, A. N., Changes in organochlorine
contamination of the marine environment of Eastern Britain monitored by Shag eggs, N atu re (L o n d .), 236, 454,
1972.
522. Harrison, H. L., Loucks, O. L., Mitchell, J. W., Parkhurst, D. F., Tracy, C. R., Watts, D. G., and Yannacone, Y. J.,
Jr., Systems studies of DDT transport, Science, 170, 503, 1970.
523. Woodwell, M., Craig, P. P., and Johnson, H. A., DDT in the biosphere: where does it go? Science, 174,1101,1971.
524. Kapoor, I. P., Metcalf, R. L., Hirwe, A. S., Po-Yung Lu, Coats, J. R., and Nystrom, R. F., Comparative metabolism
of DDT, methylchlor, and ethoxychlor in mouse, insects, and in a model ecosystem, J. A grie. F o o d C hem ., 2 0 ,1 ,
1972.
525. Ivie, G. W. and Casida, J. E., Enhancement of photoalteration of cyclodiene insecticide chemical residues by
ro tenone, Science, 167, 1620,1970.
526. Bailey, S., Bunyan, P. J., Rennison, B. D., and Taylor, A., The metabolism of l,l-di[p-chlorophenyl]-2,2-dichloro-
ethylene and l,l-di[p-chlorophenyl]-2-chloroethylene in the pigeon, T oxicol. A p p i. P harm acol., 14, 23,1969.
527. Bailey, S., Bunyan, P. J., and Taylor, A., The metabolism of p,p'-DDT in some avian species, in E n viron m en tal
Q u ality a n d S a fety, Voi. I, Coulston, F. and Körte, F., Eds., Georg Thieme, Stuttgart, Academic Press, New York,
1972, 244.
528. Datta, P. R., In vivo detoxication of p,p'-DDT via p,p'-DDE to p,p'-DDA in rats,/«d. M ed., 39, 49, 1970.
529. Peterson, J. E. and Robinson, W. H., Metabolic products of p,p'-DDT in the rat, Toxicol. A p p i. P harm acol., 6 , 321,
1964.
530. Morgan, D. P. and Roan, C. C., Absorption, storage and metabolic conversion of ingested DDT and DDT metabolites
in m an, A rch. Environ. H ealth, 22, 301,1971.
531. Agosin, M., Michaeli, D., Miskus, R., Nagasawa, S., and Hoskins, W. M., A new DDT metabolising enzyme in the
German cockroach, J. Econ. E n tom ol., 54, 340, 1961.
532. Rowlands, D. G. and Lloyd, C. J., DDT metabolism in susceptible and pyrethrin resistant S itoph ilu s granarius [L .],
/. S to re d Prod. R es., 5 ,4 1 3 , 1969.
533. Leeling, N. C., personal communication, 1972.
534. Oppenoorth, F. J. and Houx, N. W. H., DDT resistance in the housefly caused by microsomal degradation, E n tom ol.
Exp. A p p i., 11, 81,1968.
535. McKinney, J. D. and Fishbein, L., DDE formation; dehydrochlorination or dehypochlorination, C hem osph ere, No.
2 ,6 7 ,1 9 7 2 .
536. Hassall, K. A., Reductive dechlorination of DDT; the effect of some physical and chemical agents on DDD
production by pigeon liver preparations, P estic. B ioch em . P h ysiol., 1, 259,1971.
537. Hathway, D. E., Biotransformations, in Foreign C o m p o u n d M etabolism in M am m als, Hathway, D. E., Brown, S. S.,
Chasseaud, L. F., and Hutson, D. H., Reporters, S pecialist P eriodical R e p o r t o f th e Chem ical S o c ie ty , Voi. 1,
London, 1970, 295.
538. Wedemeyer, G., Dechlorination of l,l,l-trichloro-2,2-bis[p-chlorophenyl] ethane by A ero bacter aerogenes, A p p i.
M icrobiol., 15,569, 1967.
539. Alexander, M., Microbial degradation of pesticides, in E n viron m en tal T oxicology o f P esticides, Matsumura, F.,
Boush, G. M., and Misato, T., Eds., Academic Press, New York and London, 1972, 365.
539a. Pfaender, F. K. and Alexander, M., Extensive microbial degradation of DDT in vitro and DDT metabolism by
natural communities,/. Agrie. F o o d Chem ., 20, 842, 1972.
539b. Albone, E. S., Eglinton, G., Evans, N. C., and Rhead, M. M., Formation of bis(p-chlorophenyl) acetonitrile
(p,p'-DDCN) from p,p'-DDT in anaerobic sewage sludge, N atu re (L o n d .), 240, 420, 1972.
539c. Jensen, S., Gothe, R., and Kindstedt, M. O., Bis-(p-chlorophenyl)-acetonitrile (DDCN), a new DDT derivative
formed in anaerobic digested sewage sludge and lake sediment, N atu re (L o n d .), 240, 421, 1972.
540. Oppenoorth, F. J., Resistance to gamma-hexachlorocyclohexane in Musca d o m estica L .,A r c h . N eerl. Z o o i, 12, 1,
1956.
541. Reed, W. T. and Forgash, A. J., Lindane: metabolism to a new isomer of pentachlorocyclohexene, Scien ce, 160,
1232, 1968.
542. Reed, W. T. and Forgash, A. J., Metabolism of lindane to organic-soluble products by houseflies, J. A grie. F o o d
Chem ., 18,475, 1970.
543. Grover, P. L. and Sims, P., The metabolism of 7 -2 , 3 ,4 ,5 ,6 -pentachlorocyclohex-l-ene and 7 -hexachlorocyclohexane
in rats, B ioch em . J., 96, 521, 1965.
544. Saha, J., cited in Hurtig, H., Significance o f conversion products and metabolites of pesticides in the environment, in
E n viron m en tal Q u ality a n d S afety, Coulston, F. and Körte, F., Eds., Georg Thieme, Stuttgart and Academic Press,
New York, 1972, 67.
545. Duxbury, J. M., Tiedje, J. M., Alexander, M., and Dawson, J. E., 2,4-D metabolism; enzymatic conversion of
chloromaleylacetic acid to succinic acid,/. Agrie. F o o d Chem ., 18, 199, 1970.
546. Bowman, M. C., Aeree, F., Jr., Lofgren, C. S., and Beroza, M., Chlorinated insecticides; Fate in aqueous suspensions
containing mosquito larvae, Science, 146, 1480, 1964.

226 Chlorinated Insecticides

547. Brooks, G. T., Harrison, A., and Lewis, S. E., Cyclodiene epoxide ring hydration by microsomes from mammalian
liver and houseflies, B iochem . P h arm acol, 19, 255, 1970.
548. Kaul, R., Klein, W., and Körte, F., Verteilung, ausscheidung und metabolismus von Telodrin und heptachlor in
ratten und männlichen kaninchen, endprodukt des warmblutermetabolismus von heptachlor, T etrahedron, 26, 331,
1970.
549. Matsumura, F. and Nelson, J. O., Identification of the major metabolic product of heptachlor epoxide in rat faeces,
B u ll Environ. Contam . T o x ic o l, 5,489, 1971.
550. Schwemmer, B., Cochrane, W. P., and Polen, P. B., Oxychlordane, animal metabolite of chlordane: isolation and
synthesis, Science, 169, 1087, 1970.
551. Lawrence, J. H., Barron, R. P., Chen, J. Y. T., Lombardo, P., and Benson, W. R., Note on identification of a
chlordane metabolite found in milk and cheese, J. A ssoc. Offic. Agrie. Chem ., 53, 261, 1970.
552. Street, J. C. and Blau, S. E., Oxychlordane: accumulation in rat adipose tissue on feeding chlordane isomers or
technical chlordane, J. Agrie. F o o d Chem ., 20, 395, 1972.
553. Davidow, B., Hagan, E., and Radomski, J. L., A metabolite of chlordane in tissues of animals, Fed. Proc. A b str., 10,
291, 1951.
554. Georgacakis, E. and Khan, M. A. Q., Toxicity of the photoisomers of cyclodiene insecticides to freshwater animals,
N a tu re (L on d.), 233, 120, 1971.
555. Gorbach, S., Haaring, R., Knauf, W., and Werner, H. J., Residue analysis and biotests in rice fields of East Java
treated with Thiodan, B u ll Environ. Contam . Toxicol., 6 , 193, 1971.
556. Brooks, G. T., Perspectives of cyclodiene metabolism, in Proceedings of the Symposium on the Science and
Technology of Residual Insecticides in Food Production with Special Reference to Aldrin and Dieldrin, Shell
Chemical Co. New York, Library of Congress Cat. No. 68-27527, 1968, 89.
557. Wong, D. T. and Terriere, L. C., Epoxidation of aldrin, isodrin and heptachlor by rat liver microsomes, B iochem .
P h a rm a co l, 14,375, 1965.
558. Nakatsugawa, T., Ishida, M., and Dahm, P. A., Microsomal oxidation of cyclodiene insecticides, B iochem .
P h a rm a co l, 14, 1853, 1965.
559. Heath, D. F., 36 Cl-dieldrin in mice, in R a d io iso to p e s a n d R adiation in E n to m o lo g y, Proc. Bombay Symposium
1960, International Atomic Energy Agency, Vienna, 1962, 83.
560. Heath, D. F. and Vandekar, M., Toxicity and metabolism of dieldrin in rats, Br. J. Ind. M ed., 21, 269, 1964.
561. Körte, F. and Arent, H., Isolation and identification of dieldrin metabolites from urine of rabbits after oral
administration of dieldrin-14 C, L ife S c i, [Oxford], 4, 2017, 1965.
562. Richardson, A., Baldwin, M. K., and Robinson, J., Metabolites of dieldrin [HEOD] in the urine and faeces of rats,
Chem. Ind. (L o n d .), 588, 1968.
563. Klein, A. K., Link, J. D., and Ives, N. F., Isolation and purification of metabolites found in the urine of male rats
fed aldrin and dieldrin,/. A ssoc. Offic. Agrie. Chem ., 51, 895, 1968.
564. Feil, V. J., Hedde, R. D., Zaylskie, R. G., and Zachrison, C. H., Identification of ira«s-6 , 7 -dihydroxydihydroaldrin
and 9 -[s>7 î-epoxy]hydroxy-l,2 , 3 ,4 , 1 0 , 10 -hexachloro-6 , 7 -epoxy-l, 4 ,4 a, 5,6,7,8,8a-octahydro-l,4-endo-5,8 -exo-
dim ethanonaphthalene,./. Agric. F o o d Chem ., 18, 120, 1970.
564a. Bedford, C. T. and Harrod, R. K., Synthesis of 9-hydroxy-HEOD, a major mammalian metabolite of HEOD
(dieldrin), Chem. C om m un., 735, 1972.
565. Baldwin, M. K., The metabolism of the chlorinated insecticides aldrin, dieldrin, endrin and isodrin, Ph.D. Thesis,
University of Surrey, 1971.
565a. Richardson, A. and Robinson, J., Identification of a major metabolite of HEOD (dieldrin) in human faeces,
X en o b io tica , 1, 213, 1971.
566. Oda, J. and Muller, W., Identification of a mammalian breakdown product of dieldrin, in E n viron m en tal Q u ality a n d
S a fety, Vol. 1, Coulston, F. and Körte, F., Eds., George Thieme, Stuttgart, Academic Press, New York, 1972, 248.
567. McKinney, J. D., personal communication, June, 1972.
568. McKinney, J. D., Matthews, H. B., and Fishbein, L., Major faecal metabolite of dieldrin in rat, structure and
chemistry,/. Agrie. F o o d Chem ., 20, 597, 1972.
569. Rosen, J. D., Conversion of pesticides under environmental conditions, in E n viron m en tal Q u ality an d S a fety, Vol. I,
Coulston, F. and Korte, F., Eds., George Thieme, Stuttgart, Academic Press, New York, 1972, 85.
570. Matsumura, F., Patii, K. C., and Boush, G. M., Formation of photodieldrin by microorganisms, Science, 170, 1206,
1970.
571. Baldwin, M. K. and Robinson, J., Metabolism in the rat of the photoisomerisation product of dieldrin, N atu re
(L on d.), 224, 283, 1969.
572. Khan, M. A. Q., Sutherland, D. J., Rosen, J. D., and Carey, W. F., Effect of sesamex on the toxicity and metabolism
of cyclodienes and their photoisomers in the housefly, /. Econ. E n to m o l, 63, 470, 1970.
573. Matthews, H. B. and Matsumura, F., Metabolic fate of dieldrin in the rat, J. Agrie. F o o d Chem ., 17, 845, 1969.
574. Klein, A. K., Dailey, R. E., Walton, M. S., Beck, V., and Link, J. D., Metabolites isolated from urine of rats fed
14 C-photodieldrin, /. Agrie. F o o d Chem ., 18, 705, 1970.
575. Dailey, R. E., Klein, A. K., Brouwer, E., Link, J. D., and Braunberg, R. C , Effect of testosterone on metabolism of
1 4 C-photodieldrin in normal, castrated and oophorectomised rats, /. Agrie. F o o d Chem ., 20, 371, 1972.
576. El Zorgani, G. A., Walker, C. H., and Hassall, K. A., Species differences in the in vitro metabolism of HEOM, a
chlorinated cyclodiene epoxide, L ife S c i, [Oxford], 9, (Part II), 415, 1970.
227
577. Körte, F., Ludwig, G., and Vogel, J., Umwandlung voñ Aldrin-14C and Dieldrin-14C durch mikroOrganismen,
leberhomogenate und moskito-larven, Ju stu s L iebigs A n n Chenu, 656,135, 1962.
578. Matsumura, F., Boush, G. M., and Tai, A., Breakdown of dieldrin by a soil microorganism, N atu re (L on d.), 219,
965, 1968.
579. Mehendale, H. M., Skrentny, R. F., and Dorough, H. W., Oxidative metabolism of aldrin by subcellular root
fractions of several plant species, /. Agrie. F o o d Chem ., 20, 398, 1972.
580. Giannotti, O., Estudos sobre o mecanismo de acao do aldrin, dieldrin e endrin em Periplane ta am ericana [L .]. A rq.
Inst. B io l Sao Paulo, 25, 253,1958.
581. Brooks, G. T., Mechanisms of resistance of the adult housefly [Musca d o m estica] to ‘cyclodiene* insecticides,
N a tu re (L o n d ), 186, 96, 1960.
582. Richardson, A., Robinson, J., and Baldwin, M. K., Metabolism o f endrin in the rat, C h em Ind. (L on d.), 502, 1970.
583. Pimentel, D., E cological E ffects o f P esticides on N o n -target Species, Office of Science and Technology, U.S. Govt.
Print Off., Washington, D.C., June, 1972.
584. Brooks, G. T. and Harrison, A., Relations between structure, metabolism and toxicity of the cyclodiene insecticides,
N a tu re (L o n d ), 198, 1169, 1963.
585. Schupfan, L, Sajko, B., and Ballschmiter, K., The chemical and photochemical degradation of the cyclodiene
insecticides aldrin, dieldrin, endosulfan and other hexachloronorbornene derivatives, Z. N aturforsch. Teil B, 27b,
147, 1972.
586. Schupfan, I. and Ballschmiter, ¡C, Metabolism of polychlorinated norbornenes by C lostridiu m bu tyricu m , N atu re
(L o n d ), 237, 100 , 1972.
587. Parke, D. V., The B io ch em istry o f Foreign C om poun ds, Pergamon Press, Oxford, 1968.
588. Estabrook, R. W., Baron, J., and Hildebrandt, A., A new spectral species associated with cytochrome P4 50 in liver
microsomes, C hem .-B iol In teraction s, 3, 260, 1971.
589. Tsukamoto, M., Metabolic fate o f DDT in D rosoph ila m elanogaster; identification o f a non-DDE metabolite,
B otyu -kagaku , 24, 141, 1959.
590. Sun, Y. P. and Johnson, E. R., Synergistic and antagonistic actions o f insecticide-synergist conbinations and their
mode o f action, J. A grie. F o o d C h e m , 8 , 261, 1960.
591. Ray, J. W., Insect microsomal cytochromes, in P est In festation Research 1965, Agricultural Research Council,
H.M.S.O., London, 1966, 59.
592. Lewis, S. E., Effect o f carbon monoxide on metabolism of insecticides in vivo, N a tu re (L on d.), 215, 1408, 1967.
593. Hodgson, E. and Plapp, F. W., Jr., Biochemical characteristics o f insect microsomes, J. A g rie F o o d Chem ., 18,
1048, 1970.
594. Casida, J. E., Mixed-function oxidase involvement in the biochemistry of insecticide synergists, J. Agrie. F o o d
C h e m , 18,753, 1970.
595. Krieger, R. L and Wilkinson, C. F., Localisation and properties of an enzyme system effecting aldrin epoxidation in
larvae o f the southern armyworm [Prodenia eridania] ,B io c h e m P h arm acol, 18, 1403,1969.
596. Krieger, R. L, Feeny, P. P., and Wilkinson, C. F., Detoxication enzymes in the guts of caterpillars: an evolutionary
answer to plant defenses? Science, 172, 579, 1971.
597. Wilkinson, C. F. and Brattsten, L. B., Microsomal drug metabolizing enzymes in insects, D rug M etab. R ev., 1, 153,
172. 1972.
598. Evans, W. G , Smith, B. S. W., Moss, P., and Fernley, H. N., Bacterial metabolism o f 4-chlorophenoxyacetate,
B ioch em . J., 122, 509, 1971, et. seq.
599. Rowlands, D. G., The metabolism o f contact insecticides in stored grain, R esid u e R ev., 17, 105, 1967.
600. Glass, B. L., Relation between the degradation of DDT and the iron redox system in soils, J. Agrie. F o o d C h e m , 20,
324,1972.
601. Brooks, G. T., Progress in metabolic studies of the cyclodiene insecticides and its relevance to structure-activity
correlations, World R ev. P est C on trol, 5, 62, 1966.
602. Oesch, F., Jenna, D. M., and Daly, J. W., Substrate specificity of hepatic epoxide hydrase in microsomes and in a
purified preparation: evidence for homologous enzymes, A rch. B io ch em B ioph ys ., 144, 253, 1971.
603. Boyland, E., in S p ecial P ublication No. 5, Williams, R. T., Ed., The Biochemical Society, London, 1950, 40.
604. Oesch, F., Kaubisch, N., Jerina, D. M., and Daly, J. W., Hepatic epoxide hydrase. Structure-activity relationships for
substrates and inhibitors, B io ch em istry, 10, 4858, 1971.
605. Boyland, E. and Chasseaud, L. F., Glutathione S-aralkyltransferase, B iochem . J., 115, 985, 1969.
606. Schonbrod, R. D., Khan, M. A. Q., Terriere, L. C , and Plapp, F. W., Jr., Microsomal oxidases in the housefly: a
survey of fourteen strains, L ife S c i (Oxford), 7 (Part 1), 681, 1968.
607. Khan, M. A. Q., Some biochemical characteristics of the microsomal cyclodiene epoxidase system and its
inheritance in the housefly, J. Econ. E n to m o l. , 62, 388, 1969.
608. Matthews, H. B. and Casida, J. E., Properties o f housefly microsomal cytochromes in relation to sex, strain,
substrate specificity, and apparent inhibition and induction by synergist and insecticide chemicals, L ife Sci.
(Oxford), 9 (Part 1), 989, 1970.
609. Ishida, Mm Comparative studies on BHC metabolising enzymes, DDT dehydrochlorinase and glutathione
S-transferases, Agrie. B io l Chem. (T o k y o ), 32, 947, 1968.

228 Chlorinated Insecticides

610. Goodchild, B. and Smith, J. N.,.The separation of multiple forms of housefly 1 , 1, 1-tri chlor o-2,2-bis-(p-chloro-
phenyl)ethane (DDT) dehydrochlorinase from glutathione S-aryltransferase by electrofocusing and electrophoresis,
B io ch em J., 117, 1005, 1970.
611. Dinamarca, M. L., Levenbook, L., and Valdes, E., DDT-dehydrochlorinase II. Subunits, sulfhydryl groups, and
chemical composition, A r c h B ioch em . B ioph ys., 147, 374, 1971.
612. Sternbuig, J., Kearns, C. W., and Moorefield, H., DDT-dehydrochlorinase, an enzyme found in DDT-resistant flies, J.
Agrie. F o o d C h e m , 2, 1125, 1954.
613. Lipke, H. and Kearns, C. W., DDT-dehydrochlorinase, in A d van ces in P est C on trol Research, Voi. 3, Metcalf, R. L.,
Ed., Interscience, New York, 1960, 253.
614. Mullins, L. J., The structure of nerve cell membranes, in M olecu lar S tru ctu re an d F u n ction al A c tiv ity o f N erve Cells ,
Grenell, R. G. and Mullins, L. J., Eds., Publication No. 1, American Institute of Biological Sciences, Washington,
D.C., 1956.
615. Hennessy, D. J., Fratantoni, J., Hartigan, J., Moorefield, H. H., and Weiden, M. H. J., Toxicity of 2-(2-halogen-
4-chlorophenyl)-2-(4-chlorophenyl)-l,l,l-trichloroethanes to normal and to DDT-resistant houseflies, N atu re
(L o n d ), 190, 341, 1961.
616. Kimura, T., Duffy, J. R., and Brown, A. W. A., Dehydrochlorination and DDT-resistance in Culex mosquitos, Bull.
W.H.O., 32,557, 1965.
617. Pillai, M. K. K., Hennessy, D. J., and Brown, A. W. A., Deuterated analogues as remedial insecticides against
DDT-resistant A edes aegypti, M o sq u ito N ew s, 23, 118, 1963.
618. Pillai, M. K. K. and Brown, A. W. A., Physiological and genetical studies on resistance to DDT substitutes in A e d e s
aegypti, J. Econ. E n to m o l, 58, 255, 1965.
619. Busvine, J. R. and Townsend, M. G., The significance o f BHC degradation in resistant houseflies, B u ll E n tom ol.
R e s , 53,763, 1963.
620. Decker, G. C. and Bruce, W. N., Housefly resistance to chemicals, A m J. Trop. Med. H yg., 1, 395, 1952.
621. Bridges, R. G. and Cox, J. T., Resistance of houseflies to 7 -benzene hexachloride and dieldrin, N a tu re (L on d.), 184,
1740, 1959.
622. Balabaskeran, S. and Smith, J. N., The inhibition of l,l,l-trichloro-2,2-bis(p-chlorophenyl)ethane(DDT)dehydro-
chlorinase and glutathione S-aryltransferase in grass-grub and housefly preparations, B ioch em . J., 117, 989, 1970.
623. Brooks, G. T. and Harrison, A., The oxidative metabolism of aldrin and dihydroaldrin by houseflies, housefly
microsomes and pig liver microsomes and the effect of inhibitors, Biochem . Pharm acol., 18, 557, 1969.
624. Gillette, J. R., Conney, A. H., Cosmides, G. J., Estabrook, R. W., Fouts, J., and Mannering, G. J., Eds., M icrosom es
and D rug O xidations, Academic Press, New York, London, 1969.
625. Gillett, J. W. and Chan, T. M., Cyclodiene insecticides as inducers, substrates and inhibitors of microsomal
epoxidation, J. Agrie. F o o d Chenu, 16, 590, 1968.
626. Kinoshita, F. K., Frawley, J. P., and DuBois, K. P., Quantitative measurement of induction of hepatic microsomal
enzymes by various dietary levels o f DDT and toxaphene in rats, T o x ic o l A p p i Pharm acol., 9, 505, 1966.
627. Poland, A., Smith, D., Kuntzman, R., Jacobson, M., and Conney, A. H., Effect of intensive occupational exposure
to DDT on phenylbutazone and cortisol metabolism in human subjects, Clin. P harm acol Ther., 1 1, 724, 1970.
628. Cram, R. L. and Fouts, J. R., The influence of DDT and 7 -chlordane on the metabolism of hexobarbital and
zoxazolamine in two mouse strains, B iochem . P h arm acol, 16, 1001, 1967.
629. Stephen, B. J., Gerlich, J. D., and Guthrie, F. E., Effect of DDT on induction of microsomal enzymes and
deposition of calcium in the domestic hen, s,Bull Environ. Contam. Toxicol, 5, 5 6 9 , 1971.
630. deposition of calcium in the domestic hen, B u ll E n viro n Contam . T o x ic o l, 5, 569, 1971.
630. Alary, J. G. and Brodeur, J., Studies on the mechanism o f phenobarbital-induced protection against parathion in
adult female rats, J. Pharmacol. Exp. Ther., 169, 159, 1969.
631. Triolo, A. J., Mata, E., and Coon, J. M., Effects of organochlorine insecticides on the toxicity and in v itro plasma
detoxication o f paraoxon, T oxicol. A p p i P h arm acol, 17, 174, 1970.
632. Chapman, S. K. and Leibman, K. G, The effect o f chlordane, DDT and 3-methylcholanthrene upon the metabolism
and toxicity of diethyl-4-nitrophenyl phosphorothionate [parathion], Toxicol. A p p i P h arm acol, 18, 977, 1971.
633. Wright, A. S., Potter, D., Wooder, M. F., Donninger, G, and Greenland, R. D., The effects of dieldrin on the
subcellular structure and function of mammalian liver cells, F o o d C osm et. T oxicol., 10, 311, 1972.
634. Gillett, J. W., Chan, T. M., and Terriere, L. G , Interactions between DDT analogues and microsomal epoxidase
systems, J. Agrie. F o o d Chem ., 14, 540, 1966.
635. Street, J. G, Modification of animal responses to toxicants, in E n zym a tic O x id a tio n s o f T oxicants, Hodgson, E.,
Ed., North Carolina State University, 1968, 197.
636. Street, J. G , Urry, F. M., Wagstaff, D. J., and Blau, S. E., Induction by different inducers: structure-activity
relationships among DDT analogues, in Proc. 2 n d Int. IU PA C Congress o f P esticide C hem istry, Tahori, A. S., Ed.,
Gordon Breach, London, 1972.
637. Abernathy, C. O., Hodgson, E., and Guthrie, F. E., Structure-activity relations on the induction of hepatic
microsomal enzymes in the mouse by l,l,l-trichloro-2,2-bis(p-chlorophenyl)ethane(DDT) analogues, B iochem .
Pharm acol., 20, 2385, 1971.
638. Chadwick, R. W., Cranmer, M. F., and Peoples, A. J., Comparative stimulation of 7 -HCH metabolism by
pretreatment of rats with 7 -HCH, DDT, and DDT plus 7-HCH, Toxicol. A p p i Pharm acol., 18, 685, 1971.

229
639. Mayer, F. L., Jr., Street, J. C., and Neuhold, J. M., Organochlorine insecticide interactions affecting residue storage
in rainbow trout, B u ll E n v iro n C ontam . T oxicol., 5, 300, 1970.
640. Kuntzman, R., Drugs and enzyme induction, A n n . R ev. Pharm acol., 9, 21,1969.
641. Welch, R. M., Levin, W., and Conney, A. H., Insecticide inhibition and stimulation of steroid hydroxylases in rat
liver,/. Pharm acol. Exp. Ther., 155,167, 1967.
642. Bitman, J., Cecil, H. C., Harris, S. J., and Fries, G. F., Estrogenic activity of o,p'-DDT in the mammalian uterus and
avian oviduct, Science, 162, 371,1968.
643. Bitman, J. and Cecil, H. C., Estrogenic activity of DDT analogs and polychlorinated biphenyls, /. Agrie. F o o d
Chem ., 18,1108,1970.
644. Bitman, J., Cecil, H. C., Harris, S. J., and Fries, E. F., DDT induces a decrease in eggshell calcium, N atu re (L on d.),
224,44,1969.
645. Heath, R. G., Spann, J. W., and Kreitzer, J. F., Marked DDE impairment of Mallard reproduction in controlled
studies, N ature (L o n d.), 224 ,4 7 ,1 9 6 9 .
646. Porter, R. D. and Wiemeyer, S. N., Dieldrin and DDT: effects on Sparrow Hawk eggshells and reproduction, Science,
165, 199,1969.
647. Robinson, J., Birds and pest control chemicals, B ird S tu d y, 17, 195, 1970.
648. Sun, Y. P., Correlation between laboratory and field data on testing insecticides,/. Econ. E n tom oL , 59, 1131, 1966.
649. Sternburg, J. and Kearns, C. W., Metabolic fate of DDT when applied to certain naturally tolerant insects, /. Econ.
E n to m o l., 45, 497, 1952.
650. Brooks, G. T., Harrison, A., and Power, S. V., in Pest Infestation Research 1964, Annual Report of the Pest
Infestation Laboratory, Agricultural Research Council, HMSO London, 1965, 58.
651. Holán, G., Rational design of degradable insecticides, N ature (L on d.), 232, 644,1971.
652. Holán, G., Rational design of insecticides, Bull. W.H.O., 44, 355, 1971.
652a. Hirwe, A. S., Metcalf, R. L., and Kapoor, I. P., a-Trichloromethylbenzylanilines and a-trichloromethylbenzyl phenyl
ethers with DDT-like insecticidal action,/. Agrie. F o o d Chem ., 20, 818, 1972.
653. Metcalf, R. L. and Georghiou, G. P., Cross tolerances of dieldrin-resistant flies and mosquitos to various cyclodiene
insecticides, Bull. W.H.O., 27, 251, 1962.
654. Brooks, G. T., Harrison, A., and Cox, J. T., Significance of the epoxidation of the isomeric insecticides aldrin and
isodrin by the adult housefly in vivo, N ature (L on d.), 197, 311,1963.
655. Brooks, G. T., The design of insecticidal chlorohydrocarbon derivatives, in D rug Design, Vol. IV, Ariens, E. J., Ed.,
Academic Press, New York, 1973, 379.
656. Wang, C. M., Narahashi, T., and Yamada, M., The neurotoxic action of dieldrin and its derivatives in the cockroach,
Pestic. B ioch em . P h y sio l, 1 ,8 4 ,1 9 7 1 .
657. Kurihara, N., personal communication, 1973.
658. Spector, W. S., Ed., H an dbook o f T oxicology, Voi. 1, NAS-NRS Wright Air Development Center Tech. Rep. 55-16,
1955,408.
659. Rogers, A. J., Eagles, affluence and pesticides, M o sq u ito N ew s, 32, 151, 1972.
660. Robinson, J., Organochlorine insecticides and bird populations in Britain, in Chem ical F allout, Miller, M. W., and
Berg, G. C., Eds., Charles C Thomas, Springfield, Illinois, 1969, 113.
661. Gaines, T. B., Acute toxicity of pesticides, Toxicol. A ppi. Pharm acol., 14, 515, 1969.
662. Su m m ary o f T oxicology o f A ldrin an d D ieldrin, Shell International Chemical Company, Toxicology Division, 1971.
663. Deichmann, W. B., MacDonald, W. E., Blum, E., Bevilacqua, M., Radomski, J., Keplinger, M., and Balkus, M.,
Tumorigenicity of aldrin, dieldrin and endrin in the albino rat, Ind. M ed., 39, 37, 1970.
664. Alabaster, J. S., Evaluating Risks of Pesticides to Fish, Proc. 5th Br. Insectic. Fungic. Conf. Voi. 2, 1969, 370.
665. Hercules Incorporated, (Agricultural Chemicals Department), H ercules T oxaphene, S u m m ary o f T oxicological
In vestigations, Bulletin T-105, 1962.
666. Winteringham, F. P. W. and Barnes, J. M., Comparative response of insects and mammals to certain halogenated
hydrocarbons used as insecticides, Physiol. R ev., 35, 701, 1955.
667. Dale,'W. E., Gaines, T. B., Hayes, W. J., Jr., and Pearce, G. W., Poisoning by DDT: relation between clinical signs
and concentration in rat brain, Science, 142, 1474, 1963.
668. Yeager, J. F. and Munson, S. C., Site of actioriof DDT in Periplaneta, Science, 102, 305, 1945.
669. Hoffman, R. A. and Lindquist, A. W., Temperature coefficients for chlorinated hydrocarbons, /. Econ. E n tom ol.,
42, 891, 1949.
670. Guthrie, F. E., Holding temperature and insecticidal mortality; Blattella, /. Econ. E n to m o l, 43, 559, 1950.
671. Holán, G., New halocyclopropane insecticides and the mode of action of DDT, N ature (L on d.), 221, 1025, 1969.
672. Eaton, J. L. and Sternburg, J. G., Temperature effects on nerve activity in DDT-treated American cockroaches,/.
Econ. E n to m o l., 60, 1358, 1967.
673. Eaton, J. L. and Sternburg, J. G., Uptake of DDT by the American cockroach central nervous system, /. Econ.
E n to m o l., 60, 1699, 1967.
674. Stemburg, J. and Kearns, C. W., The presence of toxins other than DDT in the blood of DDT-poisoned roaches,
Science, 116,144,1952.
675. Casida, J. E. and Maddrell, S. H. P., Diuretic hormone release on poisoning Rhodnius with insecticide chemicals,
Pestic. B ioch em . P h y sio l, 1, 71, 1971.

230 Chlorinated Insecticides

676. Stemburg, J* G. and Hewitt, P., In vivo protection of cholinesterase against inhibition by TEPP and its methyl
homologue by prior treatment with DDT, /. In sect P h ysio l. , 8 , 643,1962.
677. Winteringham, F. P. W., Heilyer, G. C., and McKay, M. A., Effects of the insecticides DDT and dieldrin on
phosphorus metabolism of the adult housefly M usca do m estica L ., B ioch em . /., 76, 543, 1960.
678. Matsumuia, F. and O’Brien, R. D., Interactions of DDT with components of American cockroach nerve, J. A grie .
F o o d Chem ., 14, 39,1966.
679. Matsumura, F. and Patii, K. C., Adenosine triphosphatase sensitive to DDT in synapses of rat brain, Science, 166,
121,1969.
680. Koch, R. B., Cutkomp, L. K., and Do, F. M., Chlorinated hydrocarbon insecticide inhibition of cockroach and
honeybee ATPase, L ife S c i (Oxford), 8 , 289, 1969.
681. Weiss, D. E., A molecular mechanism for the permeability changes in nerve during the passage o f an action potential,
A ust. J. B io l S c i, 22, 1355, 1969.
682. Martin, H. and Wain, R. L., Properties versus toxicity o f DDT analogues, N atu re (L on d. ), 154,512, 1944.
683. Riemschneider, R., Chemical structure and activity of DDT analogs, with special consideration of their spatial
structures, in A d va n ces in P est C on trol R esearch, VoL 2, Metcalf, R. L., Ed., Interscience, New York, 1958, 307.
684. Gunther, F. A., Blinn, R. C., Carman, G. E., and Metcalf, R. L., Mechanisms of insecticidal action. The structural
topography theory and DDT-type compounds, Arch. B ioch em . B io p h ys. , 50, 504, 1954.
685. Mullins, L. J., Structure-toxicity in hexachlorocyclohexane isomers, Science, 122, 118, 1955.
685a. Fahmy, M. A. H., Fukuto, T. R., Metcalf, R. L., and Holmstead, R. L., Structure-activity correlations in DDT
analogs, J. Agrie. F o o d Chem ., 21, 585,1973.
686. Wilson, W. E., Fishbein, L., and Clements, S. T., DDT; participation in ultraviolet-detectable, charge-transfer
complexation, Sc/eflce, 171, 180, 1971.
687. O’Brien, R. D. and Matsumura, F., DDT; A new hypothesis of its mode o f action, Science, 146, 657, 1964.
688. Baranyovits, F. L. C., cited in Winteringham, F. P. W. and Barnes, J. M., Comparative response o f insects and
mammals to certain halogenated hydrocarbons used as insecticides, Physiol. R ev., 35, 701, 1955.
689. McNamara, B. P. and Krop, S., Pharmacology of BHC isomers, J. Pharmacol. E xp. Ther., 92, 140, 1948.
690. Naksyima, E., Shindo, H., and Kurihara, N., Whole body autoradiographic studies in the distribution of a-, ß- and
7 -BHC in mice, R a d io iso to p es, 19, 532,1970.
691. Telford, J. N. and Matsumura, F., Electron microscopic and autoradiographic studies on distribution of dieldrin in
the intact nerve tissues of German cockroaches, J. Econ. E ntom oL , 64, 230, 1971.
692. Cherkin, A., Mechanisms of general anaesthesia by non-hydrogen-bonding molecules, Ann. R ev. P h arm acol, 9, 259,
1969.
693. Wang, C. M., Narahashi, T., and Yamada, M., The neurotoxic action of dieldrin and its derivatives in the cockroach,
Pestic. B iochem . P hysiol., 1, 84,1971.
694. Ryan, W. H. and Shankland, D. L., Synergistic action of cyclodiene insecticides with DDT on the membrane of giant
axons of the American cockroach, P eriplaneta americana, L ife S c i (O xford), 10, 193, 1971.
695. Matsumura, F., Studies on the Biochemical Mechanisms of Resistance in the German Cockroach Strains, paper
presented at the 2nd International Congress of Pesticide Chemistry, Tel Aviv, 1971.
696. Narahashi, T., personal communication, 1971.
697. Brooks, G. T. and Harrison, A., The metabolism o f some cyclodiene insecticides in*relation to dieldrin resistance in
the adult housefly, M usca dom estica L .,/. In se c t P h y s io l, 10, 633, 1964.
698. Sellers, L. G. and Guthrie, F. E., Distribution and metabolism of 14 C-dieldrin in the resistant and susceptible
housefly, J. Econ. E n tom ol., 65, 378, 1972.
699. Colhoun, E. H., Approaches to mechanisms of insecticidal action,/. Agrie. F ood Chem., 8 , 252, 1960.
700. Yamasaki, T. and Narahashi, T., Resistance of houseflies to insecticides and the susceptibility of nerve to
insecticides. Studies on the mechanism o f action of insecticides XVII, B otyu -kagaku, 23, 146, 1958.
701. Sun, Yun-Pei, Schaefer, G H., and Johnson, E. R., Effects o f application methods on the toxicity and distribution
of dieldrin in houseflies, J. E c o n E n to m o l ., 60, 1033, 1967.
702. Ray, J. W., Insecticide absorbed by the central nervous system o f susceptible and resistant cockroaches exposed to
dieldrin, N a tu re (L o n d. ), 197, 1226, 1963.
703. Matsumura, F. and Hayashi, M., Dieldrin resistance; biochemical mechanisms in the German cockroach, / Agrie.
F o o d Chem ., 17,231, 1969.
704. Hayashi, M. and Matsumura, F., Insecticide mode of action: effect of dieldrin on ion movement in the nervous
system of Periplaneta am ericana and B la tt ella germ anica cockroaches,/. Agrie. F o o d Chem ., 16, 622,1967.
705. Welsh, J. H. and Gordon, H. T., The mode of action of certain insecticides on the arthropod nerve axon, /. Cell.
C om p. P h y sio l, 30,147,1947.
706. Hodge, H. C., Boyce, A. M., Deichmann, W. B., and Kraybill, H. F., Toxicology and no-effect levels of aldrin and
dieldrin, T oxicol. A p p i Pharm acol ., 10, 613,1967.
707. Hathway, D. E. and Mallinson, A., Effect of Telodrin on the liberation and utilisation of ammonia in rat brain,
B ioch em . J., 9 0 ,51, 1964.
708. Hathway, D. E., Mallinson, A., and Akintonwa, D. A. A., Effects of dieldrin, picrotoxin and Telodrin on the
metabolism of ammonia in brain, B iochem . J., 94, 676, 1965.
709. Hathway, D. E., The biochemistry of Telodrin and dieldrin, A rch. Environ. H ealth, 11, 380, 1965.

231
710. Pocker, Y., Beug, W. M., and Ainardi, V. R., Carbonic anhydrase interaction with DDT, DDE and Dieldrin, Scien ce ,
174,1336,1971.
711. Gair, R., Agricultural Development and Advisory Service, Cambridge, U.K., cited in Hessayon, D. G., Tennant
Memorial Lecture - H o m o Sapiens, the species the conservationist forgot, Chem. Ind. (L on d.), 407, 1972.
712. Sherma, J. and Zweig, G., Paper C h rom atograph y : Paper C hrom atography a n d E lectroph oresis, Voi. 2, Zweig, G.
and Whitaker, J. R., Eds., Academic Press, New York, 1971.
713. DeLacy, T. P. and Kennard, C. H. L., Crystal structure of l,l-bis(p-chlorophenyl)-2,2-dichloropropane and 1,1-
bis(p-ethoxyphenyl)-2,2-dimethylpropane,/. Chem. Soc. (L o n d .), Perkin II, 2141, 1972.
713a. DeLacy, T. P. and Kennard, C. H. L., Crystal structures of l,l-bis(p-chlorophenyl-2 ,2 ,2 -trichloroethane (p,p'-DDT)
and l-(o-chlorophenyl)-l-(p-chlorophenyl)-2,2,2-trichloroethane (o,p'-DDT), J. Chem. Soc. (L o n d .), Perkin II,
2148, 1972.
714. Hoskins, W. M. and Gordon, H. T., Arthropod resistance to chemicals, A nn . Rev. E n to m o l., 1, 89,1956.
715. Hill, R. L. and Teipel, J. W., Fumarase and Crotonase, in The E n zym es, 3rd ed., Boyer, P. D., Ed., Academic Press,
New York, London, 1971, 539.
716. Moriarty, F., The sublethal effects of synthetic insecticides on insects, Biol. R ev., 44, 321, 1969.
717. Kagan, Yu. S., Fudel-Ossipova, S. L, Khaikina, B. J., Kuzminskaya, U. A., and Kouton, S. D., On the problem of the
harmful effect of DDT and its mechanism of action, R esidu e R ev., 2 7,43, 1969.
718. Davies, J. E., Edmundson, W. F., Eds., Community Studies on Pesticides, Dade County, Florida: E p id em io lo g y o f
D D T , Futura Publishing, Mount Kisco, New York, 1972, Chap. 10, 11, 13.
719. Lykken, L., Relation of U.S. Food Production to Pesticides, paper presented at the Symposium on Nutrition and
Public Policy in the U.S., 163rd American Chemical Society National Meeting, Boston, April 1972.
720. Van Tiel, N., Pesticides in environment and food, in E n viron m en tal Q u ality an d S a fety, Vol. I, Coulston, F. and
Korte, F., Eds., Georg Thieme, Stuttgart, Academic Press, New York, 1972, 180.
721. Hurtig, H., A commentary on pesticides and perspective, Chem . Ind. (L on d.), 8 8 8 , 1969.
722. Polen, P. B., Fate of insecticidal chlorinated hydrocarbons in storage and processing of foods, in P esticid e Term inal
R esidues, Invited papers from the IUPAC International Symposium on Terminal Residues, Tel Aviv, 1971, Tahori,
A. S., Ed., Butterworth’s London, 1971, 137.
723. Kenaga, E. E., Factors related to the bioconcentration of pesticides, in E n viron m en tal T o x ico lo g y o f P esticides,
Matsumura, F., Boush, G. M., and Misato, T., Eds., Academic Press, New York and London, 1972, 193.
724. Robinson, J., Richardson, A., Crabtree, A. N., Coulson, J. C., and Potts, G. R., Organo chlorine residues in marine
organisms, N atu re (L on d.), 214,1307, 1967.
725. Hurtig, H., Significance of conversion products and metabolites of pesticides in the environment, in E n viron m en tal
Q u ality a n d S a fety, Vol. I, Coulston, F. and Korte, F., Eds., Georg Thieme, Stuttgart, Academic Press, New York,
1972,58.
726. Walker, C. H E n viron m en tal P ollu tion b y Chem icals, Hutchinson Educational, London, 1971, Chap. V.
727. Robinson, J., Residues of organochlorine insecticides in dead birds in the United Kingdom, Chem. Ind. (L on d.),
1974, 1967.
728. Rudd, R. L. and Herman, S. G., Ecosystemic transferal of pesticides residues in an aquatic environment,yin
E n viron m en tal T o x ico lo g y o f P esticides, Matsumura, F., Boush, G. M., and Misato, T., Eds., Academic Press, New
York and London, 1972, 471.
729. Rudd, R. L., P esticid es a n d th e L iving Landscape, Faber and Faber, London, 1965, 41.

232 Chlorinated Insecticides