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Title: | Toxicities of 4,5-Dihydroisoxazoles Against Root-Knot Nematodes and in Silico Studies of Their Modes of Action |
Keywords: | Meloidogyne spp. Nematicidal Nicotinic acetylcholine receptor Acetylcholine-binding protein Nematoide das galhas Nematicida Receptor nicotínico de acetilcolina Receptores colinérgicos |
Issue Date: | Jan-2020 |
Publisher: | American Chemical Society |
Citation: | FRÁGUAS, R. M. et al. Toxicities of 4,5-Dihydroisoxazoles Against Root-Knot Nematodes and in Silico Studies of Their Modes of Action. Journal of Agricultural and Food Chemistry, Washington, v. 68, n. 2, p. 523-529, 2020. DOI: 10.1021/acs.jafc.9b07839. |
Abstract: | The present work sought to contribute to the development of new nematicides. Benzaldehydes were initially converted to nitrile oxides that underwent 1,3-dipolar cycloaddition reactions with methyl acrylate to generate 4,5-dihydroisoxazoles. In in vitro tests, methyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate (1) and methyl 3-(4-chlorophenyl)-4,5-dihydroisoxazole-5-carboxylate (4) increased the mortality of Meloidogyne exigua and Meloidogyne incognita second-stage juveniles (J2). Compounds 1 and 4 presented necessary concentrations of 398 and 501 μg mL–1, respectively, to kill 50% of M. incognita J2 (LC50 values), while the value for carbofuran (positive control) was 168 μg mL–1. In in vivo tests, compounds 1 and 4 reduced the number of M. incognita galls in tomato roots by 70 and 40%, respectively, and the number of eggs by 89 and 44%. Using an in silico approach, we showed that compounds 1 and 4 were toxic to the nematodes by binding to the allosteric binding sites of the agonist-binding domains of the nematode nicotinic acetylcholine receptors. These results opened up possibilities for further investigations aimed at developing novel commercial nematicides. |
URI: | https://pubs.acs.org/doi/abs/10.1021/acs.jafc.9b07839 http://repositorio.ufla.br/jspui/handle/1/42447 |
Appears in Collections: | DFP - Artigos publicados em periódicos DQI - Artigos publicados em periódicos |
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