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Type: Artigo
Title: Transesterification Reactions With Mg-0/i-2 For The Synthesis Of Sitophilate, (2r*, 3s*) 1-ethylpropyl-2-methyl-3-hydroxypentanoate, An Aggregation Pheromone For Sitophilus Granarius Linnaeus, 1785 (coleoptera: Curculionidae)
Author: Freitas
J. D.; Freitas
A. J. D.; Silva
C. B.; Freitas
J. M. D.; Goulart
H. F.; Sousa
J. S.; Coelho
F. A. S.; Santana
A. E. G.
Abstract: The concern to minimize the environmental impacts caused by the use of pesticides in agriculture has led researchers to develop new pest control methods. Thus, the technology based on the use of pheromones has been noted for being highly specific substances, that is act only on individuals of the same species. In this context, we describe the synthesis of sitophilate, aggregation pheromone of Sitophilus granarius, a important pest of stored cereal grains. The sitophilate was obtained by transesterification of methyl-2-methyl-3-oxopentanoate with 3-pentanol mediated by Mg-0/I-2, with subsequent reduction of the ketone group of 1-ethylpropyl-2-methyl-3-oxopentanoate using NaBH4 in the presence of a Lewis acid (ZnCl2, MgCl2, CaCl2 and MnCl2). The experimental results showed that the MnCl2 is the most effective for the formation of syn diastereoisomers, since these are the compounds that exert biological activity on the insect.
Subject: Synthesis
Sitophilus Granarius
Beta-keto Ester
Editor: Centro Federal Educacao Tecnologia Rio Grande Norte
Rio Grande do Norte
Citation: Holos. Centro Federal Educacao Tecnologia Rio Grande Norte, v. 32, p. 130 - 141, 2016.
Rights: aberto
Identifier DOI: 10.15628/holos.2016.4675
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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