Two series of allyl sulfonamides, prepared from Morita-Baylis-Hillman adducts and primary aromatic sulfonamides, were fully characterized. The Z configuration for the products derived from 2-[hydroxy(phenyl)methyl]acrylonitrile (1) and E configuration for those derived from methyl 2-[hydroxy(phenyl)methyl]acrylate (2) were confirmed by X-ray diffraction for one compound of each series (1e, 2f). Density functional theory calculations for all allyl sulfonamides agreed with the X-ray crystallographic data. X-ray diffraction studies indicate that these compounds form dimers in their crystal structures. Fingerprint plots show that compound 1e is stabilized by H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N interactions, while the compound 2f has no N⋯H/H⋯N contacts. Hirshfeld surface analyses were performed to gain insight into the behavior of these interactions. Calculated frontier orbitals showed that their highest occupied and lowest unoccupied molecular orbitals are antibonding orbitals. The allyl sulfonamides 1e and 2f are among the most active compounds in each series, inhibiting approximately 60% of the mycelial growth of Botrytis cinerea at 3 mmol L-1.
BACKGROUND The purpose of this work was to investigate the potential use of zinc‐dithiocarbimate salts to control Hemileia vastatrix, the causal agent of the coffee leaf rust disease, and to evaluate their toxicity towards Apis mellifera, one of the most important coffee plant pollinators. RESULTS Zinc‐dithiocarbimate salts were prepared and fully characterized by infrared, proton (1H) and carbon‐13 (13C) nuclear magnetic resonance and elemental analyses of carbon (C), hydrogen (H), nitrogen (N) and zinc (Zn). X‐ray diffraction technique studies confirmed the proposed structures. The salts inhibited the germination of H. vastatrix spores in vitro, with a 50% inhibitory concentration (IC50) from 12 to 18 μmol.L−1 and a 90% inhibitory concentration (IC90) from 23 to 26 μmol.L−1. Zinc‐dithiocarbimate salts with the best in vitro results were selected for in vivo experiments with Coffea arabica var Caturra and with the pollinator A. mellifera. The results were similar to those of Mancozeb, a broad‐spectrum contact fungicide, with a good control of the disease and low toxicity to the honeybee. CONCLUSION The zinc‐dithiocarbimate complex salts have potential to control coffee leaf rust, with low toxicity to the pollinator insect. © 2022 Society of Chemical Industry.
Neste trabalho estão descritas as sínteses e caracterizações de 67 compostos derivados de sulfonamidas, sendo 32 inéditos, com potencial atividade antifúngico para o controle de doenças de plantas. A primeira etapa consistiu na síntese de 55 sais complexos de zinco com diferentes ligantes N-R-sulfonilditiocarbimatos derivados de sulfonamidas. Estes diânions foram isolados na forma de sais de amônio e fosfônio. Os sais foram caracterizados por espectroscopias no infravermelho, de ressonância magnética nuclear de 1 H e 13 C, por análises elementares. Também foram realizados estudos estruturais por difração de raio-X. Estes sais foram submetidos a ensaios biológicos para avaliação de sua atividade inibidora da germinação de Hemileia vastatrix, apresentando uma excelente atividade in vitro. Os mais ativos foram selecionados para testes in vivo e foram capazes de controlar o desenvolvimento da ferrugem do café, sendo um deles mais eficaz que o fungicida mancozeb na dose de 300 µmolL -1 . Estes mesmos sais foram submetidos a testes de inibição de crescimento micelial de fungos dos gêneros Botrytis e Rhizoctonia, in vitro, nas concentrações de 50 e 150 µmolL -1 , onde apresentaram boa atividade. O composto mais ativo foi submetido a testes de toxicidade com abelha (Apis mellifera) e foi verificada baixa toxicidade. A segunda etapa consistiu na síntese de alilsulfonamidas derivadas de adutos de Morita-Baylis-Hillman (MBH). Dois adutos MBH foram sintetizados através do acoplamento de um aldeído e alquenos contendo os grupos retiradores de elétrons CN e CO 2 CH 3 . Os adutos de MBH foram utilizados como intermediários para a obtenção de doze alilsulfonamidas por meio de reações com sulfonamidas primárias. As alilsulfonamidas foram totalmente caracterizadas por métodos espectroscópicos. Estudos por difração de Raios-X confirmaram a estereoquímica E para alilsulfonamidas contendo um grupo éster, e Z quando possuem o grupo ciano. Testes in vitro mostraram que as alilsulfonamidas apresentam uma ação antifúngica moderada, inibindo o crescimento micelial de B. cinerea.Palavras-chave: Alilsulfonamida. Ditiocarbimato de zinco. Fungicida. Hemileia vastatrix. Botrytis cinerea. Rizoctonia solani.
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