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Toxicities of 4,5-Dihydroisoxazoles Against Root-Knot Nematodes and in Silico Studies of Their Modes of Action.
- Source :
-
Journal of agricultural and food chemistry [J Agric Food Chem] 2020 Jan 15; Vol. 68 (2), pp. 523-529. Date of Electronic Publication: 2020 Jan 07. - Publication Year :
- 2020
-
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 <superscript>-1</superscript> , respectively, to kill 50% of M. incognita J2 (LC <subscript>50</subscript> values), while the value for carbofuran (positive control) was 168 μg mL <superscript>-1</superscript> . 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.
- Subjects :
- Animals
Antinematodal Agents chemistry
Computer Simulation
Helminth Proteins chemistry
Helminth Proteins metabolism
Isoxazoles chemistry
Solanum lycopersicum parasitology
Plant Roots parasitology
Receptors, Nicotinic chemistry
Receptors, Nicotinic metabolism
Tylenchoidea growth & development
Tylenchoidea metabolism
Antinematodal Agents toxicity
Isoxazoles toxicity
Plant Diseases parasitology
Tylenchoidea drug effects
Subjects
Details
- Language :
- English
- ISSN :
- 1520-5118
- Volume :
- 68
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Journal of agricultural and food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31908169
- Full Text :
- https://doi.org/10.1021/acs.jafc.9b07839