Síntese e avaliação biológica de uma coleção de amidas / Síntese e avaliação biológica de uma coleção de amidas

AUTOR(ES)
DATA DE PUBLICAÇÃO

2006

RESUMO

The present study describes the preparation of amides containing the methylenedioxyphenyl group and also their activity against the leaf-cutting ant, Atta sexdens rubropilosa, its symbiotic fungus Leucoagaricus gongylophorus and the fall armyworm, Spodoptera frugiperda, larvae. From the bioassays it was observed that N-piperidine-3-(3,4- methylenedioxyphenyl)-2-(E)-propenamide (65) was the most promising as insecticide agent among the compounds studied against S. frugiperda with an LD50=1.07 g/mg larvae. Amide 65 and N,N-diethyl-3-(3,4- methylenedioxyphenyl)-2-(E)-propenamide (66) were the most active against the symbiotic fungus; and N-pirrolidine-3-(3,4-methylenedioxyphenyl)-2-(E)- propenamide (67) and N-benzyl-3-(3,4-methylenedioxyphenyl)-2-(E)- propenamide (72) against the leaf-cutting ant. Additional studies were necessary to establish the structure activity relationship for piperamides. Thus, Combinatorial Chemistry technologies were employed and a solution-phase synthesis of indexed collection of amides was carried out, identified by Gas Chromatography coupled with Mass Spectroscopy (GC/MS), and screened against S. frugiperda. From this library, the most active compound identified was 1-[4- (trifluoromethoxy)benzoyl]piperidine, A8B1, which was then individually synthesized and evaluated. It has shown a LD50 = 8,15 g/mg larvae, thus less active than amide 65 against S. frugiperda.

ASSUNTO(S)

quimica piperamidas química combinatória spodoptera frugiperda síntese orgânica

ACESSO AO ARTIGO

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