Pesticide Synthesis Through Rational Approaches, Copyright, ACS

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Pesticide Synthesis Through Rational Approaches

Magee et al.; Pesticide Synthesis Through Rational Approaches ACS Symposium Series; American Chemical Society: Washington, DC, 1984.



ACS

SYMPOSIUM

SERIES

255


Pesticide Synthesis Through Rational Approaches Philip S. Magee, EDITOR BIOSAR Research Project

Gustave Κ. Kohn, EDITOR Zoecon Corporation

Julius J. Menn, EDITOR Zoecon Corporation

Based on a symposium sponsored by the Division of Pesticide Chemistry at the 186th Meeting of the American Chemical Society, Washington, D.C., August 28-September 2, 1983

American Chemical Society, Washington, D.C. 1984



Library of Congress Cataloging in Publication Data Pesticide synthesis through rational approaches. (ACS symposium series, ISSN 0097-6156; 255) "Based on a symposium sponsored by the Division of Pesticide Chemistry at the 186th Meeting of the American Chemical Society, Washington, D.C., August-September, 1983." Includes bibliographies and indexes. 1. Pesticides—Synthesis—Congresses. 2. Pesticides— Structure-activity relationships—Congresses. I. Magee, Philip, 1926. II. Kohn, Gustave Κ., 1910. III. Menn, Julius J. IV. American Chemical Society. Division of Pesticide Chemistry. V. American Chemical Society. Meeting (186th: 1983: Washington, D.C.) VI. Series. TP248.P47P49 1984 ISBN 0-8412-0852-2

668'.65

84-11062

Copyright © 1984 American Chemical Society All Rights Reserved. The appearance of the code at the bottom of the first page of each chapter in this volume indicates the copyright owner's consent that reprographic copies of the chapter may be made for personal or internal use or for the personal or internal use of specific clients. This consent is given on the condition, however, that the copier pay the stated per copy fee through the Copyright Clearance Center, Inc., 21 Congress Street, Salem, M A 01970, for copying beyond that permitted by Sections 107 or 108 of the U . S . Copyright Law. This consent does not extend to copying or transmission by any means—graphic or electronic—for any other purpose, such as for general distribution, for advertising or promotional purposes, for creating a new collective work, for resale, or for information storage and retrieval systems. The copying fee for each chapter is indicated in the code at the bottom of the first page of the chapter. The citation of trade names and/or names of manufacturers in this publication is not to be construed as an endorsement or as approval by A C S of the commercial products or services referenced herein; nor should the mere reference herein to any drawing, specification, chemical process, or other data be regarded as a license or as a conveyance of any right or permission, to the holder, reader, or any other person or corporation, to manufacture, reproduce, use, or sell any patented invention or copyrighted work that may in any way be related thereto. Registered names, trademarks, etc., used in this publication, even without specific indication thereof, are not to be considered unprotected by law. P R I N T E D IN THE U N I T E D S T A T E S

OF

AMERICA



ACS Symposium Series M . Joan Comstock, Series Editor Advisory Board Robert Baker

Geoffrey D. Parfitt

U.S. Geological Survey

Carnegie-Mellon University

Martin L. Gorbaty

Theodore Provder

Exxon Research and Engineering Co.

Glidden Coatings and Resins

Herbert D. Kaesz

James C. Randall

University of California—Los Angeles

Phillips Petroleum Company

Rudolph J. Marcus

Charles N. Satterfield

Office of Naval Research

Massachusetts Institute of Technology

Marvin Margoshes

Dennis Schuetzle

Technicon Instruments Corporation

Ford Motor Company Research Laboratory

Donald E. Moreland USDA, Agricultural Research Service

Davis L. Temple, Jr. Mead Johnson

W. H. Norton J. T. Baker Chemical Company

Charles S. Tuesday General Motors Research Laboratory

Robert Ory USDA, Southern Regional Research Center

C. Grant Willson IBM Research Department



FOREWORD The ACS SYMPOSIUM SERIES was founded in 1974 to provide

a medium for publishing symposia quickly in book form. The format of the Series parallels that of the continuing ADVANCES IN CHEMISTRY SERIES except that in order to save time the papers are not typeset but are reproduced as they are submitted by the authors in camera-ready form. Papers are reviewed under the supervision of the Editors with the assistance of the Series Advisory Board and are selected to maintain the integrity of the symposia; however, verbatim reproductions of previously published papers are not accepted. Both reviews and reports of research are acceptable since symposia may embrace both types of presentation.



This book is dedicated to the memory of John Brian Siddall 1939-1981




IN MEMORIAM


JOHN

B R I A N S I D D A L L , a brilliant young scientist and

member of

the

Executive Committee of the American Chemical Society's Division of Pesticide Chemistry, died from a sudden attack of acute leukemia on April 26, 1981, at the age of 41, during the course of organizing the symposium on which this book is based. This book and that symposium are dedicated to his memory. John Siddall was born in Chesterfield, England, in 1939, and obtained his Ph.D. degree at Manchester University under Arthur Birch in 1963. In the same year, he began work in pharmaceutical chemistry, in Mexico, for the Syntex Company, becoming senior chemist in 1964 and group leader in 1967 at the new research facilities of Syntex in Palo Alto. While at Syntex, he headed a group working on the chemistry of insect molting hormones (the ecdysones) and insect juvenile hormones, work that led to the establishment of Zoecon Corporation. John served as the first director of research at Zoecon, then as vice president of research, and later as its first senior scientist. The work on juvenile hormones was a prelude to the discovery of the first commercially produced and registered insect growth regulator, Methoprene, as well as to other useful homologs. John Siddall was a prolific scientist who published a large number of articles and patents. He always maintained a complementary interest in insect physiology, as well as in chemical synthesis, particularly of chiral compounds. In fact, just before he entered the hospital, he and Steven Fung completed a total synthesis of the plant growth regulator Brassinolide, a complex steroid with many asymmetric centers. In addition to being a member of the American Chemical Society and an officer of its Division of Pesticide Chemistry, John was also a member of the Chemical Society of London, the American Association for the Advancement of Science, and the Federation of American Scientists, and was on the editorial staff of the Journal of Chemical Ecology. He was a gentleman in manner and in action. He had a keen analytical mind and an excellent sense of humor. He enjoyed outdoor sports, particularly sailing and skiing, at which he excelled, and he maintained a long and active interest in the Boy Scouts. John was also a loving husband and father. John Siddall had intense scientific interest in two areas covered in this book. The chemical structures of the new bioactive substances discussed in the first section reveal configurations in which biological activity and specificity are highly dependent on isomeric differentiation, an area of synthesis that he understood and avidly pursued. He also advocated more extensive use of ix


approaches to quantitative structure-activity relationships such as those discussed in the first and third sections of the book. It is entirely fitting that we dedicate this book on the discovery of new pesticides to the memory of this brilliant young scientist: a fine gentleman, a man of sterling qualities, an inspiring colleague, and a friend to many of us. GUSTAVE Κ. K O H N

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February 8, 1984

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Pesticide Synthesis Through Rational Approaches, Copyright, ACS

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