New allyldithiocarbimate salts: Synthesis, structure and antifungal activity

Autor(es):Mostrar menos -

Albuini-Oliveira, Nathalia M. ^[1] ; Rubinger, Mayura M. M. ^[1] ; Guilardi, Silvana ^[2] ; Souza, Rafael A. C. ^[2] ; Ellena, Javier ^[3] ; Alvarez, Natalia ^[4] ; Tavares, Eder C. ^[5] ; Zacchi, Carlos H. C. ^[6] ; Vidigal, Antonio E. C. ^[1] ; Lima, Marcelo S. ^[1] ; Zambolim, Laercio ^[7]

Afiliação do(s) autor(es)

^[1] Univ Fed Vicosa, Dept Quim, BR-36570900 Vicosa, MG - Brazil

^[2] Univ Fed Uberlandia, Inst Quim, BR-39400902 Uberlandia, MG - Brazil

^[3] Univ Sao Paulo, Inst Fis Sao Carlos, BR-13566590 Sao Carlos, SP - Brazil

^[4] Univ Republica, Fac Quim, Montevideo 2124 - Uruguay

^[5] Univ Fed Itajuba, Inst Fis & Quim, BR-37500903 Itajuba, MG - Brazil

^[6] Ctr Fed Educ Tecnol Minas Gerais, Dept Quim, BR-30421169 Belo Horizonte, MG - Brazil

^[7] Univ Fed Vicosa, Dept Fitopatol, BR-36570900 Vicosa, MG - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Molecular Structure; v. 1214, AUG 15 2020.
• Citações Web of Science: 0

Resumo

Fifteen new allyldithiocarbimates were prepared from different allylic bromides and various potassium dithiocarbimates, yielding (Z)-2-(methoxycarbonyl)-3-(X-nitrophenyl)allyl-(N-R-sulfonyl)dithiocarbi mates (where X = 2, 3 and 4; R = phenyl, 4-fluorophenyl, 4-chlorophenyl, 4-bromophenyl and 4iodophenyl). These anions were isolated as tetraphenylphosphonium salts and characterized by HRMS, infrared, H-1 and C-13 NMR spectroscopies. Molecular electrostatic potentials were used to evaluate intermolecular interactions present in the new substances and to explain variations observed on their melting points. Single crystal X-ray diffraction experiments confirmed the Z stereochemistry of the allyldithiocarbimate anions. C-H center dot center dot center dot O, C-H center dot center dot center dot N, C-H center dot center dot center dot S and C-H center dot center dot center dot p intermolecular interactions in the solid state were studied by X-ray diffraction and Hirshfeld surface analyses. The new compounds inhibited the mycelial growth of various fungi species responsible for severe plant diseases. The allylithiocarbimates were especially active against Botrytis cinerea, with IC50 values as low as 20 mu M, being more effective than the active principals of the commercial fungicides Ziram and Mancozeb. (C) 2020 Elsevier B.V. All rights reserved. (AU)

• Processo FAPESP: 16/08823-4 - Estudos de Densidade Eletrônica de Fármacos Antirretrovirais como uma ferramenta para o Desenho de Novas Fases Sólidas.
• Beneficiário: Juan Carlos Tenorio Clavijo
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado