Toxic Phosphorus Esters

Preface1. Introduction Plan of this Book History Nomenclature of Esterases and Organophosphates Structure of Cholinesterase Biological Significance of Cholinesterase References2. Nonenzymic Reactions Hydrolysis Effect of Substituents Site of Cleavage Secondary Hydrolysis Catalysis Isomerization Thiono-Thiolo Isomerization Cis-Trans Isomerism Methodology Transalkylation Oxidation Dehydrohalogenation Effects of Light References3. The Reaction with Cholinesterase in Vitro Phosphorylation of the Enzyme Kinetics Site The Relationship between Structure and Anticholinesterase Activity Protection from Inhibition Reversal of Inhibition (Reactivation) Spontaneous Induced "Aging" Selectivity for Different Cholinesterases Conclusion References4. Enzymic Degradation and Activation in Vitro Degradation Phosphatase Action Esterase and Amidase Action Insect Hydrolases Oxidative Degradation Activation Phosphoramidate Oxidation by Mammalian Tissues Phosphoramidate Oxidation by Insect Tissues Phosphorothionate Oxidation by Mammalian Tissues Phosphorothionate Oxidation by Insect Tissues Thioether Oxidation Triphenyl Phosphate Activation by Liver References5. Effects on Isolated Whole Tissues Ion Permeability Muscle Contraction Nerve Transmission Animals Other than Insects Insects References6. Effects in Mammals Results of Poisoning Symptoms Cause of Death Cholinesterase after Poisoning Acetylcholine after Poisoning Demyelination Mode of Administration Degrading Enzymes Protection and Therapy Antagonism to Acetylcholine Reversal of Inhibited Cholinesterase Raising of Esterase Levels Blockade of Cholinesterase Antagonism of Activating Enzymes Synergism ("Potentiation") Metabolism and Residues in Intact Animals Co-ral Diazinon Delnav Dimethoate Dipterex Malathion Parathion Phosdrin Ronnel (Viozene, Trolene, Dow ET14, Dow ET57) Systox Influence of Rumen Microorganisms References7. Effects in Insects Results of Poisoning Symptoms Inhibition of Cholinesterase Accumulation of Acetylcholine Other Effects; the Cause of Death Ovicidal Action Differential Toxicity Distribution Metabolism Hydrolysis Oxidation Dehydrochlorination Resistance Occurrence Cross Resistance Mechanisms of Resistance Antagonism and Synergism Antagonism Synergism References8. Effects in Plants Systemic Activity Metabolism Schradan Thioethers Sulfinylphenates Dimethoate Phosdrin Residues Phytotoxicity Dimefox Guthion Malathion Parathion Schradan TEPP References9. Selective Toxicity Absorption Excretion and Storage Metabolism Carboxyesters Other Selective Organophosphates Penetration to the Target Nature of the Target Design of New Selective Compounds References10. Techniques Radio Tracer Synthesis Exchange Preparation of the Intermediate Coupling Purification Product Analysis Extraction of Metabolites from Homogenates Separation and Identification of Solvent-Extractable Metabolites Separation of Solvent-Unextractable Metabolites Spectroscopy Ultraviolet Spectroscopy Infrared Spectroscopy Nuclear Magnetic Resonance Refractive Index Esterase Determinations Manometric Techniques Potentiometric Methods Spectrophotometric Methods ReferencesAppendix 1. Electronic Interpretations The Underlying Concepts The Inductive Effect Polarity Acidity and Basicity Reaction Rates The Field Effect The Mesomeric EffectAppendix 2. Structure of OrganophosphatesAuthor IndexSubject Index