Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Pro,ress in the Che,mistl'J of Oreanie ,Natural Produets

Founded", LZeehmeister Edited", W Ben, B. GrlselHleh,G. W Kin,

Authors: P. AI"ersheim, J. M. Brand, A. G. Darvill, J. Hliusler, M. McNeil, Be Ohler, H. Poisel, V. Schmidt, R.M. Silverstein, J. Chr. Young

Sprin,er-Verla, Men New Yor. 1979

Dr. W. HERZ, Professor of Chemistry, Department of Chemistry, The Florida State University, Tallahassee, Florida, U. S. A. Prof. Dr. H. GRISEBACH, Biologisches Institut II, Lehrstuhl fiir Biochemie der Pflanzen, Albert-Ludwigs-Universitat, Freiburg i. Br., Federal Republic of Germany G. W. KIRBY, Sc. D., Regius Professor of Chemistry, Chemistry Department, The University, Glasgow, Scotland

With 8 Figures

This work is subject to copyright All rights are reserved, whether the whole or part of the material is concerned, specifically those of translation, reprinting, re-use of illustrations, broadcasting, reproduction by photocopying machine or similar means, and storage in data banks

© 1979 by Springer-Verlag/Wien Softcover reprint of the hardcover 1st edition 1979 Library of Congress Catalog Card Number AC 39-1015

ISSN 0071-7886

ISBN-13: 978-3-7091-8547-6 e-ISBN-13: 978-3-7091-8545-2 DOl: 10.1 007/978-3-7091-8545-2

Contents

List of Contributors . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. IX Insect Pheromones: A Critical Review of Recent Advances in Their Chemistry, Biology, and Application. By J. M. BRAND, J. CHR. YOUNG, and R. M. SILVERSTEIN ... I. Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

2

II. Structure Elucidation ..................................................

A. Isolation ..........................................................

4 4

B. Identification ......................................................

6

III. Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..

15 15 51 52

A. Coleoptera. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. B. Diptera ........................................................... C. Homoptera . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . ..

D. Hymenoptera.. . .. .. .. . .. .. .. .. . ... . .. .. . .. .. .. . . .. . . . .......... ... E. Isoptera . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. F. Lepidoptera........................................................ G. Orthoptera ........................................................

55 65 68 87

IV. Stereo biology ............................................... . . . . . . . . .. A. Geometric Isomers ................................................. B. Enantiomers .. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. C. Chemorecognition ...........