Insect Juvenile Hormones. Chemistry and Action

337 Pages·1972·5.124 MB·English

by  Julius Menn (Eds.)

Insect Juvenile Hormones
Chemistry and Action
EDITED BY
Julius J. Menu
Stauffer Chemical Company
Agricultural Research Center
Mountain View, California
Morton Beroza
Entomology Research Division
Agricultural Research Service
USDA
Beltsville, Maryland
ACADEMIC PRESS New York and London
\
COPYRIGHT © 1972, BY ACADEMIC PRESS, INC.
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PRINTED IN THE UNITED STATES OF AMERICA
CONTRIBUTORS
R. W. Bagley, Chemical Research Department, Hoffmann-La Roche Inc.,
Nutley, New Jersey 07110
/. C. Bauernfeind, Chemical Research Department, Hoffmann-La Roche
Inc., Nutley, New Jersey 07110
M. Beroza, Agricultural Research Service, U. S. Department of Agriculture,
Beltsville, Maryland 20705
D. L. Bull Agricultural Research Service, U. S. Department of Agriculture,
College Station, Texas 77840
H. R. Bullock, Agricultural Research Service, U. S. Department of
Agriculture, Baton Rouge, Louisiana 70803
John E. Casida, Division of Entomology, University of California, Berkeley,
California 94720
W. F. Chamberlain, Agricultural Research Service, U. S. Department of
Agriculture, Kerrville, Texas 78028
Sarjeet S. Gill, Division of Entomology, University of California, Berkeley,
California 94720
Bruce D. Hammock, Division of Entomology, University of California,
Berkeley, California 94720
Joseph ilan, Department of Anatomy and Developmental Biology Center,
Case Western Reserve University, School of Medicine, Cleveland, Ohio
44106
Judith Ilan, Department of Anatomy and Developmental Biology Center,
Case Western Reserve University, School of Medicine, Cleveland, Ohio
44106
M. Jacobson, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
vii
CONTRIBUTORS
Fotis C. Kafatos, The Biological Laboratories, Harvard University,
Cambridge, Massachusetts 02138
Patrick M. McCurry, Jr., Department of Chemistry, Carnegie-Mellon
University, Pittsburgh, Pennsylvania 15213
T. P. McGovern, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
Julius J. Menu, Agricultural Research Center, Stauffer Chemical Company,
Mountain View, California 94040
Andre S. Meyer, Department of Biology, Case Western Reserve University,
Cleveland, Ohio 44106
Ferenc M. Pallos, Western Research Center, Stauffer Chemical Company,
Richmond, California 94804
Narayan G. Patel, Central Research Department, Experimental Station,
Ε. I. duPont de Nemours and Co., Wilmington, Delaware 19898
B. A. Pawson, Hoffman-La Roche Inc., Nutley, New Jersey 07110
R. E. Redfern, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
Lynn M. Riddiford, The Biological Laboratories, Harvard University,
Cambridge, Massachusetts 02138
R. Sarmiento, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
F. Scheidl, Hoffmann-La Roche Inc., Nutley, New Jersey 07110
Howard A. Schneiderman, Center for Pathobiology and Developmental
Biology Laboratory, University of California, Irvine, California 92664
M. Schwarz, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
Michael Slade, * Zoëcon Corporation, Research Laboratories, Palo Alto,
California 94304
P. E. Sonnet, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
*Present Address: 127-20th Ave., San Francisco, California 94121
viii
CONTRIBUTORS
Gerardus Β. Staal, Zoëcon Corporation, Research Laboratories, Palo Alto,
California 94304
Barry M. Trost, Department of Chemistry, University of Wisconsin, Madison,
Wisconsin 53706
F. Vane, Hoffmann-La Roche Inc., Nutley, New Jersey 07110
N. Wakabayashi, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
R. M. Waters, Agricultural Research Service, U. S. Department of
Agriculture, Beltsville, Maryland 20705
Carroll M. Williams, The Biological Laboratories, Harvard University,
Cambridge, Massachusetts 02138
/. E. Wright, Agricultural Research Service, U. S. Department of
Agriculture, College Station, Texas 77840
Izuru Yamamoto, * Division of Entomology, University of California,
Berkeley, California 94720
Charles H. Zibitt, Zoëcon Corporation, Research Laboratories, Palo Alto,
California 94304
•Present Address: Department of Agricultural Chemistry, Tokyo University of
Agriculture, Setagaya, Tokyo, Japan
ix
PREFACE
Although insecticides are invaluable in suppressing damage to our agri­
cultural products and to the health of man and animals, they are not without
side effects on the environment and its biota. Pressure to find alternatives
that do not depend on toxic agents have spurred scientists to delve into the
biological and biochemical transformations within the insect system in search
of an "Achilles heel." The discovery of the juvenile hormone, a vital growth-
regulating chemical in insect metamorphosis, and of chemicals with similar
properties has raised hopes, originally advanced by Professor Carroll Williams
in 1956, that the normal growth patterns of insects could be upset with these
chemicals, thereby preventing their survival. The approach has considerable
appeal because the hormones (and synthetic analogs), while having a powerful
effect on insect development, do not appear to have adverse effects on most
other life forms. The environmental impact of the use of chemicals of this
kind is therefore expected to be negligible.
This book attests to the intense vigor and interdisciplinary activity with
which juvenile hormone chemistry, biochemistry, and biology are currently
being pursued. It brings together in one volume the latest and most complete
survey of knowledge on juvenile hormones and analogs to date. Subject
matter ranges from theoretical discussions contributed by some of our most
distinguished scientists and thinkers to down-to-earth laboratory and field
trials of insect development regulating chemicals found active by empirical
laboratory tests. Its contents will interest chemists, biochemists, biologists,
endocrinologists, entomologists, insect physiologists, and others concerned
with insect development and control.
To speed publication contributors furnished camera copy of their
manuscripts for direct reproduction. This procedure has led to some overlap
in the presentations and some variations in format. The reader may also note
some differences in opinion, apparent contradictions, and inconsistencies in
nomenclature among the presentations, but such discrepancies may be con­
sidered normal at this early stage of knowledge. Indeed, it is hoped that such
divergence will pinpoint problem areas requiring attention in the future.
The book is not meant to be exhaustive, but one that will brief scientists
on current thinking and methodology in the field, as well as provide references
to prior work. Hopefully it will acquaint scientists with studies outside their
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PREFACE
own areas of specialization and catalyze interdisciplinary joint ventures which
are necessary to achieve maximum progress toward the development of safer
means for suppression of undesirable insects.
Julius J. Menn
Morton Beroza
xii
INTRODUCTION
A major objective in recent efforts to improve the quality of our en­
vironment has been the development of means of insect control more selec­
tive in action than the broad-spectrum insecticides, which in some instances
have been implicated in detrimental side effects on nontarget organisms and
on the ecosystem. Among the approaches being explored are biological con­
trol with parasites and predators, microbial and viral insecticides, chemosteri-
lants, resistant varieties of crops and breeds of animals, improved tillage
practices, crop rotation, electromagnetic energy, repellents, attractants, and
antifeedants.
One approach that has captured the imagination of many scientists is
the possibility of controlling insect pests by causing derangement of their
growth processes with their own hormones or related compounds, more
specifically with the juvenile hormones (JH), their analogs (JHA), and other
JH-active chemicals (also referred to as JHA).
At the Symposium on the Chemistry and Action of Insect Juvenile
Hormones, sponsored by the Division of Pesticide Chemistry of the American
Chemical Society at the 162nd National Meeting of the Society in Washington,
D. C, September 12-17, 1971, eminent scientists drawn from a variety of dis­
ciplines and representing universities, government, and industry were invited
to present and discuss their latest findings in the field of JH and JHA chemis­
try and biology. This volume is the outgrowth of their presentations and
deliberations; it summarizes what is known about JH and their analogs, their
chemistry, their biological effects and mode of action, their biochemical fate
in target and nontarget organisms, and their stability. Although divided into
three general areas for convenience—biological, biochemical, and chemical—
the book in its entirety is a multidisciplinary discourse, a foundation upon
which our understanding of the action or inaction of JH and JHA may be
based which hopefully will provide a springboard for future direction and
research.
Insect endocrinology, which includes JH research, has fascinated re­
searchers since the pioneering studies of Sir Vincent Wigglesworth in the
mid-1930's showed that the molting and metamorphosis of Rhodnius pro-
lixus nymphs were regulated by hormones. The possibility that juvenile hor­
mones and synthetic analogs had practical potential in managing insect
xiii
INTRODUCTION
populations was first recognized by Professor Carroll Williams in 1956. Fol­
lowing his discovery that the abdomen of the adult male of Hyalophora
cecropia was a rich source of JH, he proposed JH-active substances as power­
ful "third generation" insect control agents.
In subsequent years, a remarkable proliferation of scientific discoveries
occurred in this field. In 1967, Professor H. Roller and his co-workers at the
University of Wisconsin scored a major breakthrough in their identification
of the major JH in H. cecropia as methyl trans, trans, cw-10,1 l-epoxy-7-
ethyl-3,1 l-dimethyl-2,6-tridecadienoate. This discovery was followed by the
identification of the 7-methyl analog as another natural juvenile hormone.
Many synthetic terpenoid derivatives were synthesized and shown to exert on
insects varying degrees of morphogenetic, gametogenic, and diapause-dis­
rupting activity.
Two events greatly stimulated these synthetic efforts. The first was the
discovery of the extraordinary morphogenetic activity of the "paper factor"
on the linden bug, Pyrrhocoris apterus, by Drs. Karel Slama and Carroll
Williams in 1965, leading to the subsequent identification of this factor as
the methyl ester of todomatuic acid or "juvabione" by Dr. W. S. Bowers and
his co-workers. The second breakthrough occurred when Dr. Bowers found
simple terpene derivatives other than those of farnesol to be highly active
JHA. The significance of the latter discovery was augmented by the fact that
these JHA had activity on a variety of insect species. These discoveries pro­
vided many new leads for synthesis of additional JHA.
The growing interest in recent years in insect juvenile hormones is well
documented by the proliferation of literature on this subject. The number of
papers cited in five reviews appearing between 1968 and 1971 on the subject
of JH and JHA were 52 (1968), 50 (1969), 96 (1970), 134 (1970), and 172
(1971 ). At this rate, publications dealing with JH research could number over
1000 by 1975.
While great strides have been made in elucidating the chemistry and
biological activity of JH and JHA, our understanding of the mode of action
of JH at the subcellular level is still embryonic. The status of our knowledge
in this field and the best current theories on the mode of action are presented
here.
Metabolic studies with JH and JHA, another previously unexplored area
of research, receive detailed treatment in this volume. Knowledge and infor­
mation in this area are vital prerequisites to the launching of extensive de­
velopment programs in which large amounts of JH or JHA are to be released
into the environment. Understanding of the biotransformation steps and
identification of products of JH and JHA metabolism in target and non-
target organisms will help predict the impact and ultimate disposition of
these products in the total environment.
xiv
INTRODUCTION
Finally, pilot field trials with JHA have been promising enough to
consider the practical use of JHA as selective, nonpersistent, and effective
chemical agents for the safe management of at least some insect species that
destroy food and fiber crops or threaten the health and well-being of man
and animals. Prospects for the application of JHA as part of integrated
control programs are also encouraging.
Julius J. Menn
Morton Beroza
XV