This paper describes the story of the invention of the diamides, a novel chemical class of insecticides. It starts with the pioneering work by Nihon Nohyaku researchers, who developed a herbicide lead with weak insecticidal activity to flubendiamide, a highly potent lepidoptericide. The journey continues with Nissan's isoxazolines and the invention of the anthranilamides by DuPont, culminating in the discovery of the blockbuster chlorantraniliprole and its analogue cyantraniliprole. The next steps are Syngenta's sulfoximines and bicyclic anthranilamides, Ishihara Sangyo Kaisha's cyclopropylamides, Sumitomo's hydrazides, Bayer's pyrazoles and tetrazoles, BASF's sulfoximines and more recent contributions from Chinese agrochemical companies and academic institutions. The diamides affect calcium homeostasis by binding to ryanodine receptors and releasing calcium from the intracellular stores. Investigations at Nihon Nohyaku, DuPont and Bayer on the action of the diamides on ryanodine receptors will be briefly reported.
Approximately 30 % of today's agrochemicals contain at least one sulfur atom. This review article highlights the most important reasons for the fundamental role of sulfur functions in crop protection, such as the occurrence of sulfur in agrochemical pharmacophores, the application of sulfur-containing natural products as lead compounds, the role of sulfur in procidal action, fine-tuning of physico-chemical properties and patent breaking as well as the advantage of sulfur-containing heterocycles compared to their non-sulfur ring isosteres. Case studies from three different mode of action classes give proof, how state-of-the-art organosulfur chemistry enables the synthesis and influences the structure-activity relationships of fungicidally active compounds in the classes of Succinate dehydrogenase inhibitors, tubulin polymerization inhibitors and Cellulose synthase inhibitors.
Novel types of anti-oomycetic compounds have been designed and prepared. The synthetic approach to these mandelamides is outlined. Biological data demonstrate their high efficacy against important plant diseases such as tomato and potato late blight (Phytophthora infestans De Bary) and grape downy mildew (Plasmopara viticola Berliner & de Toni). Structure-activity relationship studies are discussed. The new development product mandipropamid is presented.
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