RESUMEN
In this review, the synthesis of 33 agrochemicals that received an international standardization organization (ISO) name between January 2015 and December 2018 is described. The aim is to showcase the broad range and scope of reactions, reagents and intermediates used to discover and produce the latest active ingredients addressing the crop protection industry's needs.
Asunto(s)
Agroquímicos/síntesis química , Agroquímicos/farmacología , Agroquímicos/normas , Animales , Productos Agrícolas , Fungicidas Industriales/síntesis química , Fungicidas Industriales/normas , Herbicidas/síntesis química , Herbicidas/normas , Insecticidas/síntesis química , Insecticidas/normas , Internacionalidad , Nematodos/efectos de los fármacosRESUMEN
Novel imidazole-based ketene dithioacetals show impressive in planta activity against the economically important plant pathogens Alternaria solani, Botryotinia fuckeliana, Erysiphe necator and Zymoseptoria tritici. Especially derivatives of the topical antifungal lanoconazole, which bear an alkynyloxy or a heteroaryl group in the para-position of the phenyl ring, exhibit excellent control of the mentioned phytopathogens. These compounds inhibit 14α -demethylase in the sterol biosynthesis pathway of the fungi. Synthesis routes starting from either benzaldehydes or acetophenones as well as structure-activity relationships are discussed in detail.
Asunto(s)
Acetales/química , Antifúngicos/síntesis química , Ascomicetos/efectos de los fármacos , Etilenos/química , Imidazoles/química , Cetonas/química , Inhibidores de 14 alfa Desmetilasa/química , Inhibidores de 14 alfa Desmetilasa/metabolismo , Inhibidores de 14 alfa Desmetilasa/farmacología , Acetales/metabolismo , Acetales/farmacología , Alternaria/efectos de los fármacos , Antifúngicos/metabolismo , Antifúngicos/farmacología , Ascomicetos/metabolismo , Sitios de Unión , Familia 51 del Citocromo P450/química , Familia 51 del Citocromo P450/metabolismo , Proteínas Fúngicas/química , Proteínas Fúngicas/metabolismo , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Estructura Terciaria de Proteína , Esterol 14-Desmetilasa/química , Esterol 14-Desmetilasa/metabolismo , Relación Estructura-ActividadRESUMEN
In this review, the synthesis of 30 agrochemicals that received an international standardization organization (ISO) name during the last five years (January 2010 to December 2014) is described. The aim is to showcase the range and scope of chemistries used to discover or produce the latest active ingredients addressing the crop protection industry's needs.
Asunto(s)
Agroquímicos/síntesis química , Antinematodos/síntesis química , Fungicidas Industriales/síntesis química , Herbicidas/síntesis química , Insecticidas/síntesis química , Agroquímicos/historia , Agroquímicos/normas , Antinematodos/historia , Antinematodos/normas , Fungicidas Industriales/historia , Fungicidas Industriales/normas , Herbicidas/historia , Herbicidas/normas , Historia del Siglo XXI , Humanos , Insecticidas/historia , Insecticidas/normasRESUMEN
Every week, articles disclosing new antifungal leads reported as promising starting points for optimization projects are published. In many cases, the mechanism that accounts for their antifungal activity has not been fully elucidated. More significantly, the detrimental impact that could result from certain embedded chemical features has been underestimated or even overlooked. In the course of our research in the agrochemical area, we have concluded that in many cases such leads are actually nonoptimizable because they either contain what are now recognized as pan assay interference compounds (PAINS) or other promiscuous groups. This article is aimed at highlighting the pitfalls we have encountered and hopefully to steer other research groups away from them.
Asunto(s)
Antifúngicos/síntesis química , Fungicidas Industriales/síntesis química , Fungicidas Industriales/farmacología , Animales , Antifúngicos/farmacología , Hongos/efectos de los fármacos , Ensayos Analíticos de Alto Rendimiento , Humanos , Relación Estructura-ActividadRESUMEN
Crop protection chemistry has come a long way from its "alchemic" beginnings in the late 19th century to a high-tech science that supports the sustainable production of food, feed, and fiber for a rapidly growing population. Cutting-edge developments in the design and synthesis of agrochemicals help to tackle today's challenges of weed and pest resistance, higher regulatory safety margins, and higher cost of goods with the invention of selective, environmentally benign, low use rate, and cost-effective active ingredients.
Asunto(s)
Agroquímicos , Química Agrícola , Productos Agrícolas , Plaguicidas , Agroquímicos/síntesis química , Agroquímicos/química , Agroquímicos/farmacología , Técnicas de Química Sintética , Química Agrícola/métodos , Química Agrícola/tendencias , Plaguicidas/síntesis química , Plaguicidas/química , Plaguicidas/farmacología , EstereoisomerismoRESUMEN
This review reports different syntheses of deltamethrinic acid, especially those originating from our laboratory. Deltamethrinic acid is a synthetic compound whose structure is inspired from those present in the flower head of the plant Chrysanthemum cinerariifolium. Its ester 'deltamethrin' exhibits an extremely high insecticidal activity (DDTx35.000) and an extremely low toxicity to mammals.
RESUMEN
This review reports different syntheses of deltamethrinic acid, especially those originating from our laboratory. Deltamethrinic acid is a synthetic compound whose structure is inspired from those present in the flower head of the plant Chrysanthemum cinerariifolium. Its ester 'deltamethrin' exhibits an extremely high insecticidal activity (DDTx35.000) and an extremely low toxicity to mammals.
Asunto(s)
Chrysanthemum cinerariifolium/química , Flores , Piretrinas/síntesis química , Insecticidas , Estructura Molecular , Piretrinas/químicaRESUMEN
(1R)-cis-chrysanthemic acid has been prepared in a few steps with complete control of the relative and absolute stereochemistry. Some mechanistic aspect of the addition of bromine to the C,C double bond of 2,2,5,5-tetramethylcyclohex-3-enol is disclosed.