The Neonicotinoid Insecticides

Abstract

5.3.1. Introduction 53 5.3.2. Neonicotinoid History 54 5.3.3. Chemical Structure of Neonicotinoids 56 5.3.3.1. Ring Systems Containing Commercial Neonicotinoids 57 5.3.3.2. Neonicotinoids Having Noncyclic Structures 62 5.3.3.3. Bioisosteric Segments of Neonicotinoids 64 5.3.3.4. Physicochemistry of Neonicotinoids 67 5.3.3.5. Proneonicotinoids 70 5.3.4. Biological Activity and Agricultural Uses 72 5.3.4.1. Efficacy on Target Pests 72 5.3.4.2. Agricultural Uses 73 5.3.4.3. Foliar Application 75 5.3.4.4. Soil Application and Seed Treatment 75 5.3.5. Mode of Action 75 5.3.6. Interactions of Neonicotinoids with the Nicotinic Acetylcholine Receptor 76 5.3.6.1. Selectivity for Insect over Vertebrate nAChRs 76 5.3.6.2. Whole Cell Voltage Clamp of Native Neuron Preparations 76 5.3.6.3. Correlation between Electrophysiology and Radioligand Binding Studies 78 5.3.7. Pharmacokinetics and Metabolism 79 5.3.7.1. Metabolic Pathways of Commercial Neonicotinoids 79 5.3.8. Pharmacology and Toxicology 82 5.3.8.1. Safety Profile 83 5.3.9. Resistance 87 5.3.9.1. Activity on Resistant Insect Species 87 5.3.9.2. Mechanisms of Resistance 89 5.3.9.3. Resistance Management 91 5.3.10. Applications in Nonagricultural Fields 91 5.3.10.