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Previous issue date: 2016-03-23 / Coordenação de Aperfeiçoamento de Pessoal de Nível Superior / Este trabalho descreve a síntese de 34 organometálicos de estanho(IV) derivados de N- R-sulfonilditiocarbimatos de potássio, com as seguintes fórmulas gerais: (Ph4P)2[Sn(Bu)2(RSO2N=CS2)2], [Ph4P = cátion tetrafenilfosfônio, R = C6H5 (3a), 4- FC6H4 (3b), 4-ClC6H4 (3c), 4-BrC6H4 (3d), 4-IC6H4 (3e), CH3 (3f), C2H5(3g) e C4H9 (3h); [Fe(phen)3][Sn(Bu)2(RSO2N=CS2)2], fenantrolina)ferro(II), R = CH3 (4f), [Fe(phen)3 C2H5 (4g) = cátion e C4H9 tris(1,10- (4h)]; (Ph4P)[Sn(C6H11)3(RSO2N=CS2)], [R = C6H5 (5a), 4-FC6H4 (5b), 4-ClC6H4 (5c), 4- BrC6H4 (5d), 4-IC6H4 (5e), CH3 (5f) e CH2CH3 (5g)]; (A)[Sn(C6H11)3(4- ClC6H5SO2N=CS2)] [A = metiltrifenisfosfônio (5c1), etiltrifenilfosfônio (5c2), butiltrifenilfosfônio (5c3) e tetrabutilamônio (5c4)]; (Ph4P)[Sn(Ph)3(RSO2N=CS2)2][R = C6H5 (6a), 4-FC6H4 (6b), 4-ClC6H4 (6c), 4-BrC6H4 (6d), 4-IC6H4 (6e), CH3 (6f)] e [Fe(phen)3][Sn(Ph)3(RSO2N=CS2)2] [R = C6H5 (7a), 4-FC6H4 (7b), 4-ClC6H4 (7c), 4- BrC6H4 (7d), 4-IC6H4 (7e), CH3 (7f)]. As técnicas utilizadas na caracterização dos compostos incluem: análises elementares de C, H, N, Fe e Sn, espectrometria de massa de alta resolução, espectroscopias vibracional, de ressonância magnética nuclear de 1H, 13 C e 119Sn; e Mössbauer. A atividade antifúngica dos organometálicos de estanho, 3f-h, 4f-h, 5a-g, 5c1-c4 e 7a-e, foi testada in vitro frente às espécies de fungos, Colletotrichum acutatum e Botrytis cinerea, ambas isoladas de frutos doentes de morango. Os resultados foram analisados por regressão não linear, utilizando a concentração versus o percentual de inibição. Todos os compostos avaliados se mostraram ativos, inibindo o crescimento de ambas as espécies de fungo. No teste com B. cinerea, 3g, 3h, 4g, 5a-g foram os que apresentaram os menores valores de IC50 e no teste com C. acutatum, destacaram-se os compostos 3g, 4g, 5b, 5d e 5f.Os complexos 3a-e e 5a-f mostraram-se ativos como aceleradores no processo de vulcanização da borracha nitrílica. Os compostos 3a, 3b, 3c, 3d, 5d e 5e, se destacaram por apresentarem menores valores de t90 que os demais organoestânicos testados e que os aceleradores comerciais TBBS e TMTD. / This work describes the synthesis of 34 tin(IV) organometallic compounds derived from potassium N-R-sulfonyldithiocarbimates, having the following general formula: (Ph4P)2[Sn(Bu)2(RSO2N=CS2)2], [Ph4P = tetraphenylphosphoniumcation, R = C6H5 (3a), 4-FC6H4 (3b), 4-ClC6H4 (3c), 4-BrC6H4 (3d), 4-IC6H4 (3e), CH3 (3f), C2H5 (3g) e C4H9 (3h); [Fe(phen)3][Sn(Bu)2(RSO2N=CS2)2], phenanthroline)iron(II)cation, R = CH3 (4f), [Fe(phen)3 C2H5 (4g) and = tris(1,10- C4H9 (4h)]; (Ph4P)[Sn(C6H11)3(RSO2N=CS2)], [R = C6H5 (5a), 4-FC6H4 (5b), 4-ClC6H4 (5c), 4- BrC6H4 (5d), 4-IC6H4 (5e), CH3 (5f) and CH2CH3 (5g)]; (A)[Sn(C6H11)3(4- ClC6H5SO2N=CS2[A = methyltriphenylphosphonium(5c1), ethyltriphenylphosphonium (5c2), butyltriphenylphosphonium(5c3) and tetrabutylammonium (5c4)], (Ph4P)[Sn(Ph)3(RSO2N=CS2)2], [R = C6H5 (6a), 4-FC6H4 (6b), 4-ClC6H4 (6c), 4- BrC6H4 (6d), 4-IC6H4 (6e), CH3 (6f)] and[Fe(phen)3][Sn(Ph)3(RSO2N=CS2)2] [R = C6H5 (7a), 4-FC6H4 (7b), 4-ClC6H4 (7c), 4-BrC6H4 (7d), 4-IC6H4 (7e), CH3 (7f)]. The techniques used for the characterization of the compounds include: elemental analyzes of C, H, N, Fe and Sn; vibrational, Mössbauer and nuclear magnetic resonance of 1H, 13 C and 119 Sn spectroscopies, and high-resolution mass spectrometry. The antifungal activity of the tin organometallic compounds 3f-h, 4f-h, 5a-e, 5c1-c4 and 7a-e, was studiedin vitro against Colletotrichum acutatum and Botrytis cinerea isolated from strawberry infected fruits. The results were analyzed by nonlinear regression using concentration versus inhibition percentages. All tested compounds are active. Compounds 3g, 3h, 4g, 5a-g presented the lowest IC50 values against B. cinerea, and 3g, 4g, 5b, 5d and 5f were the most active against C. acutatum.The complexes 3a-e and 5a-f were also active as accelerators in the vulcanization of nitrile rubber. Compounds 3a, 3b, 3c, 3d, 5d and 5e presented the lowest values of t90, being faster than the commercial accelerators TBBS and TMTD.
| Identifer | oai:union.ndltd.org:IBICT/oai:localhost:123456789/9628 |
| Date | 23 March 2016 |
| Creators | Bottega, Fernanda Christina |
| Contributors | Oliveira, Marcelo Ribeiro Leite de |
| Publisher | Universidade Federal de Viçosa |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Source | reponame:Repositório Institucional da UFV, instname:Universidade Federal de Viçosa, instacron:UFV |
| Rights | info:eu-repo/semantics/openAccess |
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