Síntese e avaliação da atividade inseticida de N-alquil e N-aril amidas

• Ano de defesa: 2011
• Autor(a) principal: Pereira, Elba Nathalia Corrêa
• Orientador(a): Alvarenga, Elson Santiago de
• Banca de defesa: Maltha, Célia Regina álvares , Demuner, Antônio Jacinto , Fátima, ângelo de
• Tipo de documento: Dissertação
• Tipo de acesso: Acesso aberto
• Idioma: por
• Instituição de defesa: Universidade Federal de Viçosa
• Programa de Pós-Graduação: Mestrado em Agroquímica
• Departamento: Agroquímica analítica; Agroquímica inorgânica e Físico-química; Agroquímica orgânica
• País: BR
• Palavras-chave em Português: Inseticida; Amidas Análogas; Piperina; N-alquil; N-aril
• Palavras-chave em Inglês: Insecticide; Analogous amides; Piperine; N-alkyl; N-aryl
• Área do conhecimento CNPq: CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA::QUIMICA ORGANICA
• Link de acesso: http://locus.ufv.br/handle/123456789/2160

Piperine is an amide found in fruits of Piper species presenting insecticide activity. The synthesis of unsaturated amides is described in this work from potassium sorbate as it has the conjugated double bonds as in piperine. Saturated amides were prepared from hexanoic anhydride and the insecticidal activity was compared with the unsaturated amides. A total of 21 compounds were prepared, where 4 of them are novel. The amides were purified and characterized by infrared spectroscopy and nuclear magnetic resonance, elemental analysis and mass spectrometry. The amides prepared were: (2E,4E)-N-cyclohexylhexa-2,4-dienamide [22], (2E,4E)-N-benzylhexa- 2,4-dienamide [23], (2E,4E)-N-(2-phenylethyl)hexa-2,4-dienamide [24], (2E,4E)-N-pentylhexa-2,4-dienamide [25], (2E,4E)-N-phenylhexa-2,4- dienamide [26], (2E,4E)-N,N-diphenylhexa-2,4-dienamide [27], (2E,4E)-N,Ndi( propan-2-yl)hexa-2,4-dienamide [28], (2E,4E)-N,N-diethylhexa-2,4- dienamide [29], (2E,4E)-1-(pyrrolidin-1-yl)hexa-2,4-dien-1-one [30], (2E,4E)-Nhexylhexa- 2,4-dienamide [31], (2E,4E)-1-(piperidin-1-yl)hexa-2,4-dien-1-one [32], N-phenylhexanamide [33], N-benzylhexanamide [34], Ncyclohexylhexanamide [35], 1-(pyrrolidin-1-yl)hexan-1-one [36], Npentylhexanamide [37], N-(2-phenylethyl)hexanamide [38], N-(3- nitrophenyl)hexanamide [39], N-(4-chlorophenyl)hexanamide [40], N-(3- chlorophenyl)hexanamide [41]. The insecticidal activity of the amides was evaluated against Diaphania hyalinata and Solenopsis saevíssima. The amides which presented the highest mortality rates against Diaphania hyalinata were [38], [32], and [22], showing rates of 85.00%, 96.5% and 100.0% respectively. The mortality rates presented by these amides were higher than piperine s, which was of 88.3%. Piperine has not presented activity against Solenopsis saevíssima, however compounds [28], [29], [30], [31], [32], [36], and [37] presented mortality rate of 100%. The novel amides [24], [25], [31], and [41] presented mortality rates of 51.67%, 53.33%, 78.33%, and 40.00% against Diaphania hyalinata respectively. Therefore from the novel amides only [31] presented high activity and the others presented only moderate activity against Diaphania hyalinata. The novel compounds [25], [31], and [41] presented high toxicity against Solenopsis saevíssima with mortality rates of 85.00%, 100.00%, and 96.67% respectively. While amide [24] presented a moderate activity of 53.33%. Comparing the amides with conjugated double bonds with the amides that don't have these unsaturations, it was observed that as for the Diaphania hyalinata insect species, as for the Solenopsis saevíssima, these structural differences has not affected the compounds toxicity.