Cinnamaldehyde and related phenylpropanoids, natural repellents, and insecticides against Sitophilus zeamais (Motsch.): a chemical structure-bioactivity relationship
- Autores: Yésica P Zaio, Gerardo Gatti, Andrés A Ponce, Natalia A Saavedra Larralde, María J Martinez, Maria P Zunino, Julio A. Zygadlo
- Localización: Journal of the science of food and agriculture, ISSN 0022-5142, Vol. 98, Nº 15, 2018, págs. 5822-5831
- Idioma: inglés
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Resumen
The insecticidal and repellent effects on adult Sitophilus zeamais of 12 cinnamaldehyde-related compounds was evaluated by contact toxicity bioassays and a two-choice olfactometer. To determine non-toxicity in mammals, body weight, serum biochemical profiles, liver weight, physiological parameters, sperm motility, and histopathological data were obtained as complementary information in C57BL/6 mice treated with the best natural compound.; Results: Based on 24 h LC95 and LC50 values, α-methyl-cinnamaldehyde and cinnamaldehyde exhibited better insecticidal action than the other compounds. The best repellent effect was observed with α-bromo-cinnamaldehyde, which even repelled at the lowest concentration studied (0.28 µmol L-1 ). The evaluation of a quantitative structure-activity relationship found a linear relationship between the LC50 values for adult weevil toxicity and dipolo with Q values (giving the difference between orbital electronegativity carbon 1 and orbital electronegativity carbon 3 of the molecule) in cinnamaldehyde-related compounds. The polar surface and Log P descriptors also revealed a linear relationship with the S. zeamais repellent effect for cinnamaldehyde analogues. Cinnamaldehyde did not show toxicity in the parameters evaluated in mice.; Conclusion: From the phenylpropanoid components studied, the natural compound that had the best insecticidal and repellent action against S. zeamais was cinnamaldehyde. It presented no mammalian toxicity. © 2018 Society of Chemical Industry.; © 2018 Society of Chemical Industry.
