Synthesis and Chemistry of Agrochemicals III

471 Pages·1992·32.24 MB·English

by  Don R. Baker

ACS SYMPOSIUM SERIES 504
Synthesis and Chemistry
of Agrochemicals III
1 Don R. Baker, EDITOR
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p://puk-199 Joseph G. Fenyes, EDITOR
2 | htt021/b Buckman Laboratories International, Inc.
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n June 992 | d E. I. du Pont de Nemours and Company
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American Chemical Society, Washington, DC 1992
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
Library of Congress Cataloging-in-Publication Data
Synthesis and chemistry of agrochemicals III / Don. R. Baker, editor,
Joseph G. Fenyes, editor, James J. Steffens, editor.
p. cm—(ACS symposium series, ISSN 0097-6156; 504)
"Developed from symposia sponsored by the Division of
Agrochemicals of the American Chemical Society."
Includes bibliographical references and index.
01 ISBN 0-8412-2473-0
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PRINTED IN THE UNITED STATES OF AMERICA
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
1992 Advisory Board
ACS Symposium Series
M. Joan Comstock, Series Editor
V. Dean Adams Bonnie Lawlor
Tennessee Technological Institute for Scientific Information
University
John L. Massingill
Mark Arnold Dow Chemical Company
University of Iowa
Robert McGorrin
1
0 David Baker Kraft General Foods
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p://k-1 University of California—Berkeley U.S. Department of Agriculture
2 | htt021/b Arindam Bose Vincent Pecoraro
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16, 20oi: 10. Pfizer Central Research University of Michigan
une 2 | d Robert F. Brady, Jr. Marshall Phillips
on J199 Naval Research Laboratory Delmont Laboratories
63.35.42 mber 22, Margaret A. Cavanaugh A. Truman Schwartz
1e National Science Foundation Macalaster College
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Conoco Inc.
Madeleine M. Joullie
University of Pennsylvania Robert A. Weiss
University of Connecticut
Mary A. Kaiser
Ε. I. du Pont de Nemours and Peter Willett
Company University of Sheffield (England)
Gretchen S. Kohl
Dow-Corning Corporation
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
Foreword
THE ACS SYMPOSIUM SERIES was first published in 1974 to
provide a mechanism for publishing symposia quickly in book
form. The purpose of this series is to publish comprehensive
books developed from symposia, which are usually "snapshots
in time" of the current research being done on a topic, plus
1
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bs.acs.or2-0504.f sary tBhaeft otrhee ap saypmerpso bseiu mpu-bblaissehde db oaso kq uisic pkluyt ausn pdoers scibolnet.r act, the
u9 proposed table of contents is reviewed for appropriateness to
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2 | htt021/b papers are excluded at this point, and others are added to
11 round out the scope of the volume. In addition, a draft of each
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9.1pte editors, who check that all necessary revisions have been made.
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wnloaation tions of previously published papers are not accepted.
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Pu M. Joan Comstock

Series Editor
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
Preface
IN A WORLD WITH AN EXPANDING POPULATION of approximately 5.5
billion people, where nearly 1.5 billion are underfed or starving, increased
production of food crops and fiber is of utmost importance. In addition
to natural adversities, such as early frost and drought, crops are also
exposed to attack by a variety of fungal, bacterial, and viral diseases and
to competition for nutrients by numerous types of weeds. Even after har
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bs.ac2-05 be emphasized too strongly.
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une 2 | d current direction of agrochemical research.
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63.mb symposia reviewing the discovery of new agrochemicals. These symposia
9.1pte were organized by the editors of these monographs and were sponsored
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We wish to express our appreciation to all of those who have
participated in our symposia and who have shared the results of their
work with us. Special thanks go to those who have toiled at writing the
chapters that appear in this volume. We hope that our readers will find
the contents to be interesting, useful, and, above all, stimulating.
We also wish to thank our employers, Buckman Laboratories
International, Inc., E. I. du Pont de Nemours and Company, and ICI
xi
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
Americas Inc.; without their generous support, this volume and the previ
ous two volumes could not have been published.
DON R. BAKER
ICI Americas Inc.
Richmond, CA 94804
JOSEPH G. FENYES
Buckman Laboratories International, Inc.
Memphis, TN 38108
JAMES J. STEFFENS
1
0 E. I. du Pont de Nemours and Company
s.org 04.pr0 Stine-Haskell Research Center
bs.ac2-05 Newark, DE 19714
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xii
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
Chapter 1
Progress in a Time of Change
Don R. Baker1, Joseph G. Fenyes2, and James J. Steffens3
1ICI Americas Inc., 1200 South 47th Street, Richmond, CA 94804
2Buckman Laboratories International, Inc., 1256 North McLean Boulevard,
Memphis, TN 38108
3E. I. du Pont de Nemours and Company, Stine-Haskell Research Center,
Newark, DE 19714
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n J99 product safety provide opportunities for new materials which are safer
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A chemist, like a painter or poet, is a maker of concepts. If these concepts are more
permanent than theirs, it is because they are made with ideas. Ideas are the core of
the chemist's creation. No discussion here can be more than a reflection of each
individual undertaking. Moreover, only by studying how the road was traveled in the
past can we gain an understanding of the future. The case histories we present here,
commercially successful or not, provide that insight into that process which lies
behind that creative leap from the old to the new. These considerations have inspired
our previous volumes on this subject (7,2) and our ongoing ACS Agrochemicals
Division Symposium series on which these volumes are based.
0097-6156/92/0504-O001S06.00/0
© 1992 American Chemical Society
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
2 SYNTHESIS AND CHEMISTRY OF AGROCHEMICALS III
We seem to be always in a period of change. However, only with change is
progress possible. Concern for man himself and his fate must be the chief interest
of all technical endeavors. The solutions to these unsolved problems coming from
the creations of our minds must be a blessing to mankind and not a curse. The
memory of the Silent Spring should be a reminder of our responsibility to future
generations.
The Environment for New Agrochemicals
In our lifetime we have seen a tremendous change in how science is perceived in the
community (5). In the middle decades of the twentieth century science was a major
vitality in our society. Scientists ranked high in our community and what they said
was believed. Scientific knowledge expanded at a tremendous rate. The world's
1
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o1 variety of technical issues. Major decisions are often not made according to rational
63.35.42 mber 22, pisr iannc iipnlfeosr,m beudt eblyec vtoargautee. inAtunidti ownit oh rt hpeo lvitaiscta le xepxapnesdiioenn coyf. knTohwel ebdagsies moof sot uorf ssoocciieettyy
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Mankind has always been faced with a changing variety of risks. Science and
technology have contributed toward the reduction of many of the historic major risks.
Modern medicine has minimized many of the old health risks. Life expectancy has
greatly increased to the point that aging processes are now the major cause of death.
Counteracting the effects of aging is the new medical challenge. Modern
transportation has made mankind much more mobile. However, the increase in speed
has generated a variety of new risks. Technology associated with warfare has
brought its own group of risks. Relations between nations are now much more
critical for an increasing variety of reasons. There is an expanding list of economic
and social risks. The steadily increasing population creates another group of risks.
As society becomes more and more complex and interdependent, new risks and
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.
1. BAKER ET AL. Progress in a Time of Change 3
problems are created. The benefits of modern civilization are many, however, this
has created its own challenges for the future. Increasingly, society seems to be
unwilling to accept many of these new risks, however small, even if the benefit is
great. With this seems to come an ever increasing resistance to change.
The media has fostered a disproportionate awareness of risks in those areas
that create headlines. As an example, if an airliner crashes and kills 100 people,
within a few hours most of the world has heard about it. This increased public
awareness has contributed toward making air travel by far the safest form of
transportation in terms of deaths per mile traveled. The death of a single individual
on the highways receives almost no publicity unless the death is unusual for other
reasons. And yet there are over 100 deaths each day on the U. S. highways without
any apparent recognition. Everyone has heard about Chernobyl and the disaster
resulting from that nuclear power plant. However, nuclear power is still the safest
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9.1pte The agrochemical industry responds to these increasing public demands for
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Pu increased costs in the registration and re-registration of products, many organizations

are dropping the registrations on those materials that are less profitable. For farmers
growing so-called minor crops, this usually means that there are fewer and fewer
materials that are available and registered for use on these crops.
In any risk benefit analysis dealing with these major issues of society such as
nuclear power, genetic manipulation, and use of agrochemicals the question becomes
"What is the acceptable risk?" In the light of other risks that everyone faces each
day, the risks inherent with agrochemicals must be evaluated (4-7). As an example,
consider the risk of cancer which is many times greater when eating broiled meat
once a week as compared to eating an apple each week with a certain pesticide
residue. What level of risk is perceived as acceptable?
In Synthesis and Chemistry of Agrochemicals III; Baker, D., et al.;
ACS Symposium Series; American Chemical Society: Washington, DC, 1992.