Novas dialquilfosforilidrazonas: síntese, caracterização e avaliação da atividade biológica

Abstract

A series of twelve novel organophosphorus compounds, derived from dialkylphosphorylydrazone ketones were synthesized in three steps of reaction: the first step is the synthesis of various dialkyl phosphonates which are obtained by reaction of phosphorus trichloride (PCl3) with three Mols the corresponding alcohois. In the second step, the reaction of the dialkyl phosphonates with hydrazine in a biphasic system leads to the formation of dialkylphosphorylhydrazines and the last step is the condensation of ketones with different dialkylphosphorylhydrazines. The analysis of NMR spectra of 1H and 31P NMR allowed to show a mixture of two possible diastereoisomers (E / Z) for the compounds derived from non-symmetrical ketones. All compounds were characterized by the 1H NMR, and 13C NMR of the 31P NMR, IR and mass. The effects of dialkylphosphorylydrazones in the germination of lettuce (Lactuca sativa) and on the development of the isolated fungus Rhizoctonia solani were observed and their activities were evaluated on antiprotozoária trypanosomatids. P O RO RO NH P N O RO RO NH N P O RO RO NH N P O RO RO NH N O P RO RO N N H O O R= isopropil (1) R= butil (5) R= isopropil (2) R= butil (6) R= isopropil (3) R= butil (7) R= isopropil (4) R= butil (8) R= isobutil (9) R= butil (10) R= secbutil (11) R= isopentil (12) Figure 1: Organophosphorus hydrazones synthesized.