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Lactones 46. Synthesis, antifeedant and antibacterial activity of γ ‐lactones with a p ‐methoxyphenyl substituent
Author(s) -
Mazur Marcelina,
Skrobiszewski Andrzej,
Gładkowski Witold,
Podkowik Magdalena,
Bania Jacek,
Nawrot Jan,
Klejdysz Tomasz,
Wawrzeńczyk Czesław
Publication year - 2016
Publication title -
pest management science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.296
H-Index - 125
eISSN - 1526-4998
pISSN - 1526-498X
DOI - 10.1002/ps.4012
Subject(s) - substituent , antibacterial activity , lactone , chemistry , context (archaeology) , biological activity , organic chemistry , toxicology , stereochemistry , biology , bacteria , biochemistry , paleontology , genetics , in vitro
BACKGROUND Lactones are well known for their biological activity. Grosheimin and repin are potent deterrents against storage pests. The unsaturated lactones have exhibited a wide spectrum of antibacterial activity. In our study we focused on the synthesis and evaluation of the biological activity of anisaldehyde derivatives containing lactone function. RESULTS Four new lactones were synthesized in one‐step reductive dehalogenation or dehydrohalogenation reactions. These compounds, together with halolactones synthesized earlier, were tested for their antifeedant activity towards Sitophilus granaries , Trogoderma granarium and Tribolium confusum . The results of the tests showed that the highest activity, comparable with that of azadirachtin, towards all tested pests (total coefficient of deterrence 143.3–183.9) was observed for lactone with a vinyl substituent. The antibacterial activity of these compounds was also evaluated. The most potent lactone was active towards gram‐positive bacteria strains. CONCLUSIONS The results of biological tests showed that halogen atom removal significantly increased the antifeedant properties of γ ‐lactones with a p ‐methoxyphenyl substituent. Unsaturated lactones are most promising in the context of their possible industrial application as crop protection agents. Further structural modifications of lactones with aromatic rings are needed to find important structural factors increasing the antibacterial activity. © 2015 Society of Chemical Industry