Tetraphenylphosphonium allyldithiocarbimates derived from Morita-Baylis-Hillman adducts: Synthesis, characterization, crystal structure and antifungal activity

Tavares, Eder C.; Rubinger, Mayura M. M.; Filho, Eclair V.; Oliveira, Marcelo R. L.; Piló‐Veloso, Dorila; Ellena, Javier; Guilardi, Silvana; Souza, Rafael Aparecido Carvalho; Zambolim, Laércio

doi:10.1016/j.molstruc.2015.10.097

Cited by 6 publications

(5 citation statements)

References 32 publications

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“…The syntheses of compounds 4a – d (Scheme ) were performed by following an adapted procedure from Tavares et al A solution of 1 mmol of acetate 2 in 5 mL of acetone was added dropwise to a stirring solution of the appropriate potassium N -R-sulfonyldithiocarbimate salt (1.2 mmol) in 5 mL of water. The mixture was stirred for 15 min at room temperature, and the reaction was monitored by thin-layer chromatography (TLC).…”

Section: Methodsmentioning

confidence: 99%

“…Recently, Tavares and co-workers have published an efficient and environmentally benign protocol that involves synthesizing a novel class of dithiocarbimate derivatives termed allyldithiocarbimates. However, the aim of the investigation was to study the antifungal potential of the compound, and, to the best of our knowledge, allyldithiocarbimates as a whole have not been employed as vulcanization accelerators.…”

Section: Introductionmentioning

confidence: 99%

“…To our knowledge, the application of dithiocarbimates and derivatives as vulcanization accelerators is rather limited according to the literature, 17−20 which is also true regarding their activity as a potential class of antifungal compounds. 21,22 Recently, Tavares and co-workers 23 have published an efficient and environmentally benign protocol that involves synthesizing a novel class of dithiocarbimate derivatives termed allyldithiocarbimates. However, the aim of the investigation was to study the antifungal potential of the compound, and, to the best of our knowledge, allyldithiocarbimates as a whole have not been employed as vulcanization accelerators.…”

Section: ■ Introductionmentioning

confidence: 99%

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Tetraphenylphosphonium Allyldithiocarbimates: A Novel Safe Amine Class of Morita–Baylis–Hillman-Derived NBR Vulcanization Accelerators

Carvalho,

Venturelli,

Lopes

et al. 2023

ACS Sustainable Chem. Eng.

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Eliminating N-nitrosamines from rubber products, which are introduced by common vulcanization accelerators, is a significant challenge faced by the industry. The class of tetraphenylphosphonium allyldithiocarbimate salts offers a green and operationally simple alternative to traditional accelerators. This study describes the synthesis of four novel compounds and their application as accelerators for nitrile-butadiene rubber (NBR) vulcanization. The compounds were synthesized from easily accessible Morita−Baylis−Hillman acetates and potassium dithiocarbimate salts using acetone:water (1:1, v:v) as the solvent, which produced a precipitate that was washable with water. Compared to vulcanizates with tetramethyl thiuram disulfide (TMTD), those with the allyldithiocarbimate compounds showed longer t 90 times, faster t s1 times, comparable tensile strength, and better tear resistance, indicating that these compounds can be a viable alternative for producing good-quality rubber artifacts.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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Tetraphenylphosphonium Allyldithiocarbimates: A Novel Safe Amine Class of Morita–Baylis–Hillman-Derived NBR Vulcanization Accelerators

Carvalho,

Venturelli,

Lopes

et al. 2023

ACS Sustainable Chem. Eng.

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“…The significance of reactions that proceed through Carbon-Carbon bond forming, which in turn involves the coupling of the α-position of activated alkenes with carbon electrophiles under the influence of a catalyst, cannot be overlooked in atom economy. 1,2 The reaction ends up in the formation of Michael type dimers. There are many other synthetic routes by which effectual and perfect C-C bond emerging reactions take place.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Nisar¹,

Ishfaq

Ali³

et al. 2022

ACSi

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Taking cognizance of the medicinal significance and diverse functions of synthetic Morita-Baylis-Hillman adducts (MBHA), the title ligand was synthesized and purified through column chromatography. Cr+3, Mn+2, Co+3, Ni+2, Cu+2 complexes of the ligand were synthesized under basic conditions, subjected to characterization through spectral analyses and verified with the IR spectrum that was generated computationally by the DFT B3LYP method, with 6-311++ G (d,p) basis set and Hartree Fock (HF) B3LYP method in conjunction with 3-21G(d,p) basis set. Powder XRD helped to testify crystals of the complexes. Moreover, the antibacterial, and antioxidant characteristics of MBHA and its complexes were also established. All of them were found to be active antioxidants. The antibacterial activities, examined against S. aureus, E. coli, B. pumilis and S. typhi have revealed that its Cobalt complex has an excellent potential to act against all of them. Hence, these compounds maybe having potentialities for the discovery of new, cheaper and efficient drugs against various infectious diseases. The study also uncovers the first example of utilization of MBHA towards metal complex formation.

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“…No composto 9e (Tabela 15), C10-O3 é uma ligação dupla formal, a ligação C10-O4 apresenta caráter intermediário, enquanto o comprimento da ligação C11-O4 está na faixa normal para uma ligação simples C-O, conforme observado em compostos relacionados (TAVARES et al, 2016;VIDIGAL et al, 2020) Figura 24 -Superfícies de Hirshfeld mapeadas com índice de forma dos compostos 8f e 9e.…”

Section: Fonte: Próprio Autorunclassified

Utilização de sulfonamidas como blocos de construção de novos agroquímicos protetores para o controle de doenças fúngicas

Rabello¹

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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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Tetraphenylphosphonium allyldithiocarbimates derived from Morita-Baylis-Hillman adducts: Synthesis, characterization, crystal structure and antifungal activity

Cited by 6 publications

References 32 publications

Tetraphenylphosphonium Allyldithiocarbimates: A Novel Safe Amine Class of Morita–Baylis–Hillman-Derived NBR Vulcanization Accelerators

Tetraphenylphosphonium Allyldithiocarbimates: A Novel Safe Amine Class of Morita–Baylis–Hillman-Derived NBR Vulcanization Accelerators

Synthesis, Characterization, Biological Activities and Ab-initio Study of Transition Metal Complexes of [Methyl 2-((4-chlorophenyl)(hydroxy)methyle) Acrylate]

Utilização de sulfonamidas como blocos de construção de novos agroquímicos protetores para o controle de doenças fúngicas

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