RESUMO
The element sulfur has an outstanding role in the crop protection chemistry because it is used in its elemental form as a multisite fungicide, but is also part of agrochemicals in the form of aromatic or aliphatic sulfur-containing rings or sulfur-based functional groups. This review gives an exhaustive overview over the latter category. Several fundamental agrochemical compound classes are named after a sulfur-based functionality, such as the dithiocarbamate fungicides and sulfonylurea herbicides. Altogether, 16 different sulfur-based functional groups are presented with their typical synthesis approaches and most important representatives in crop protection. © 2023 Society of Chemical Industry.
Assuntos
Fungicidas Industriais , Herbicidas , Agroquímicos/química , Fungicidas Industriais/química , Herbicidas/química , Proteção de Cultivos , EnxofreRESUMO
The diamide insecticides act on the ryanodine receptor (RyR). The synthesis of various bicyclic anthranilic derivatives is reported. Their activity against the insect ryanodine receptor (RyR) and their insecticidal activity in the greenhouse is presented, as well as structure activity relationship considerations.
Assuntos
Diamida/farmacologia , Inseticidas/química , Inseticidas/farmacologia , Canal de Liberação de Cálcio do Receptor de Rianodina/metabolismo , Spodoptera/efeitos dos fármacos , ortoaminobenzoatos/farmacologia , Animais , Afídeos , Diamida/síntese química , Diamida/química , Relação Dose-Resposta a Droga , Inseticidas/síntese química , Estrutura Molecular , Spodoptera/metabolismo , Relação Estrutura-Atividade , ortoaminobenzoatos/síntese química , ortoaminobenzoatos/químicaRESUMO
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.
Assuntos
Amidas/química , Amidas/farmacologia , Inseticidas/química , Inseticidas/farmacologia , Animais , Cálcio/metabolismo , Insetos/efeitos dos fármacos , Canal de Liberação de Cálcio do Receptor de Rianodina/metabolismo , Relação Estrutura-AtividadeRESUMO
Novel insecticidal anthranilamides with elaborated sulfur-containing groups are described. The synthesis of compounds with functional groups such as sulfoximines and scarcely reported groups such as sulfonimidoyl hydrazides and hydroxylamides, their in vitro and in vivo biological activity as well as their physical properties are reported.
Assuntos
Diamida/química , Iminas/química , Inseticidas/química , Enxofre/química , Animais , Cristalografia por Raios X , Diamida/síntese química , Diamida/farmacologia , Hemípteros/efeitos dos fármacos , Hemípteros/metabolismo , Iminas/síntese química , Iminas/farmacologia , Inseticidas/síntese química , Conformação Molecular , Canal de Liberação de Cálcio do Receptor de Rianodina/química , Canal de Liberação de Cálcio do Receptor de Rianodina/metabolismo , Spodoptera/efeitos dos fármacos , Spodoptera/metabolismoRESUMO
Isocyanide-based multicomponent reactions of the Ugi- and Passerini-type have been valuable tools for the rapid exploration of the novel fungicidal compound classes of phenylglycinamides and mandelamides. Mandipropamid (6), which was discovered during this derivatisation, displays excellent activity against the economically important phytopathogens Phytophthora infestans (potato and tomato late blight) and Plasmopara viticola (grape downy mildew).
Assuntos
Amidas/síntese química , Amidas/farmacologia , Benzamidinas/síntese química , Benzamidinas/farmacologia , Ácidos Carboxílicos/síntese química , Ácidos Carboxílicos/farmacologia , Fungicidas Industriais/síntese química , Fungicidas Industriais/farmacologia , Amidas/química , Benzamidinas/química , Ácidos Carboxílicos/química , Fungicidas Industriais/química , Estrutura Molecular , Phytophthora/efeitos dos fármacos , Estereoisomerismo , Relação Estrutura-Atividade , Valina/químicaRESUMO
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.