Synthetic Pyrethroid Insecticides: Structures and Properties

ISBN-13: 9783642748516 / Angielski / Miękka / 2014 / 244 str.

Klaus Naumann

Opis

The idea of Volums 4 and 5 of this series is a combination of a very condensed but broad review, handbook and textbook on most of the theoretical and practical aspects of pyrethroids of interest to chemists, biologists, pharmacologists, toxicologists and other people involved in insecticidal research, development, ecotoxicolo- gy, application, patenting and commercialization of pyrethroids, as seen from a point of view of an industrial chemist once actively in volved in pyrethroid research. In order to provide a mode1 data base for testing quantitative structure activity relationships, the unique wealth of the numerous and diverse biological data dispersed in the literature is listed in about 110 tables, put in relation to each other and other standard compounds, together with many structural formulas of the com- pounds involved. A number of data are published for the first time. Some of the more important reeent QSAR-studies are briefly acknowledged. Conformational aspects of bioactive pyrethroids are discussed (from synthesis, QSAR, X-ray); some of the X-ray derived conformations are published for the first time. The molecular basis of pyrethroid biological action is taken into consideration as intensively as possible. Stereochemical aspects are considered wherever they are involved in synthesis, biological activity, mode of action, metabolism (Vol. 4), and particularly in the complex problems in the production and relation of iso- merically enriched trade products (Vol. 5). Since pyrethroid research is now, in manyaspeets, a finished chapter of applied research, a historieal treatment of the course of inventions is given (inventions, patent priorities).

Spis treści

A. Biologically Active Pyrethroids.- 1 Naturally Occuring Pyrethrins.- 2 Synthetic Pyrethroids.- 2.1 General Structure and Activity Remarks on the Synthetic Pyrethroids.- 2.2 Collection of Structure-Activity Data.- 2.2.1 Structure-Activity-Data of Ester-Pyrethroids.- 2.2.1.1 Variation of the Acid Moiety.- 2.2.1.2 Variation of Alcohol Components.- 2.2.1.2.1 Structurally Flexible Alcohols.- 2.2.1.2.2 Structurally Rigidized Alcohols.- 2.2.2 Non-ester Pyrethroids.- 2.2.3 Structure and Speed of Action.- 2.3 Structure-Activity-Analysis.- 2.3.1 Stereochemical Considerations.- 2.3.2 Conformational Analysis of Pyrethroids.- 2.3.3 Influence of Substituents.- B. Biological Action of Pyrethroids Against Living Organisms.- 3 Action of Pyrethroids Against Arthropod Pests.- 3.1 Action of Pyrethroids on Living Insects.- 3.2 Effect of Pyrethroids on Acarina Pests.- 3.3 Factors Lowering Efficacy of Pyrethroids Against Insects; Resistance.- 3.4 Factors Enhancing the Action of Pyrethroids Against Insects.- 3.4.1 Metabolism Inhibitors as Synergists.- 3.4.1.1 Esterase Inhibitors.- 3.4.1.2 Oxidase Inhibitors.- 3.4.2 Other Synergistic Mixtures.- 3.4.3 Metabolic Activation.- 3.4.4 Improvement of Performance of Pyrethroids by Physical Means.- 4 Action of Pyrethroids Against Non-Target Organisms.- 4.1 Ecotoxicology.- 4.1.1 Effects on Beneficial Arthropods.- 4.1.2 Action of Pyrethroid on Aquatic Organisms.- 4.1.3 Effects of Pyrethroids on Plants and Microorganisms.- 4.2 Toxicology in Warmblooded Animals.- 4.2.1 Effects of Pyrethroids on Rats, Mice, Birds.- 4.2.2 Metabolism in Warmblooded Animals.- 4.2.3 Effects of Pyrethroids on Humans.- 4.2.4 Interaction of Pyrethroids within Vertebrates with Other Drugs.- 4.2.5 Antidots Against Pyrethroid Action.- C. Mode of Biological Action of Pyrethroids.- 5 Poisoning Events of Pyrethroids in Insects.- 6 In-vitro Neurotoxicology/Electrophysiology.- 7 Molecular Neurotoxicology.- 7.1 Pyrethroids as Ion Channel Effectors.- 7.1.1 The Effect of Pyrethroids on Sodium Mediated Nerve Conduction.- 7.1.2 Action of Pyrethroids on the Presynaptic Sodium Channels.- 7.1.3 Neurophysiological Alterations in Pyrethroid Resistant Insects.- 7.2 Specific Action of Pyrethroids on Other Important Target Sites in the Nervous System.- 7.2.1 Effects of Pyrethroids on Calcium and Oligophosphate Turnover in Nerve Cells.- 7.3 Involvement of Pyrethroids in Oxidative Processes.- 7.4 Effects of Pyrethroids on Postsynaptic Cholinergic Sodium Channels.- 7.5 The Effect of Pyrethroids on Gabaergic Chloride Channels.- 7.6 The Effect of Pyrethroids on the Release of Transmitters and Hormons.- 7.7 Various Effects of Pyrethroids on Other Nerve Membrane Targets.- D. Pyrethroids as Commercial Insecticides.- 8 Pyrethroids as Commercial Insecticides.- 8.1 Compilation and Characterization of Developmental and Commercial Pyrethroids.- Abbreviations.- Literature.