RESUMO
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.
Assuntos
Agroquímicos/síntese química , Agroquímicos/farmacologia , Agroquímicos/normas , Animais , Produtos Agrícolas , Fungicidas Industriais/síntese química , Fungicidas Industriais/normas , Herbicidas/síntese química , Herbicidas/normas , Inseticidas/síntese química , Inseticidas/normas , Internacionalidade , Nematoides/efeitos dos fármacosRESUMO
Databases of small, potentially bioactive molecules are ubiquitous across the industry and academia. Designed such that each unique compound should appear only once, the multiplicity of ways in which many compounds can be represented means that these databases require methods for standardizing the representation of chemistry. This is commonly achieved through the use of "Chemistry Business Rules", sets of predefined rules that describe the "house style" of the database in question. At Syngenta, the historical approach to the design of chemistry business rules has been to focus on consistency of representation, with chemical relevance given secondary consideration. In this work, we overturn that convention. Through the use of quantum chemistry calculations, we define a set of chemistry business rules for tautomer standardization that reproduces gas-phase energetic preferences. We go on to show that, compared to our historic approach, this method yields tautomers that are in better agreement with those observed experimentally in condensed phases and that are better suited for use in predictive models.
Assuntos
Isomerismo , Bases de Dados Factuais , Padrões de ReferênciaRESUMO
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.
Assuntos
Agroquímicos/síntese química , Antinematódeos/síntese química , Fungicidas Industriais/síntese química , Herbicidas/síntese química , Inseticidas/síntese química , Agroquímicos/história , Agroquímicos/normas , Antinematódeos/história , Antinematódeos/normas , Fungicidas Industriais/história , Fungicidas Industriais/normas , Herbicidas/história , Herbicidas/normas , História do Século XXI , Humanos , Inseticidas/história , Inseticidas/normasRESUMO
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.
Assuntos
Antifúngicos/síntese química , Fungicidas Industriais/síntese química , Fungicidas Industriais/farmacologia , Animais , Antifúngicos/farmacologia , Fungos/efeitos dos fármacos , Ensaios de Triagem em Larga Escala , Humanos , Relação Estrutura-AtividadeRESUMO
Oxidation of various cyclic and acyclic ketones under mild conditions with chlorocatecholborane, a bulky pyridine base, and TEMPO to the corresponding α-aminoxylated products in good to excellent yields (52-99%) is described. For enones as substrates, products of a ß-chloro-α-aminoxylation are obtained (70-89%).
Assuntos
Boro/química , Catecóis/química , Óxidos N-Cíclicos/química , Cetonas/química , Oxirredução , EstereoisomerismoRESUMO
[reaction: see text] The first synthesis of (-)-panacene has been accomplished in concise, highly stereoselective fashion from commercially available 2-methoxy-6-methylbenzoic acid (15 steps, 8.3% overall yield). The synthesis unambiguously establishes the correct relative and absolute configuration of panacene, and demonstrates the serviceability of Pd(II)-mediated tandem intramolecular alkoxycarbonylation-lactonization for the expedient assembly of its tricyclic core, and the dual role of asymmetric alkynylation as an initial source of chirality and as a powerful tool for manipulating diastereoselectivity.