The nematicidal activity of selected aromatic aldehydes was tested against the root knot nematode Meloidogyne incognita. The most active aldehyde was phthalaldehyde (1) with an EC(50) value of 11 ± 6 mg/L followed by salicylaldehyde (2) and cinnamic aldehyde (3) with EC(50) values of 11 ± 1 and 12 ± 5 mg/L, respectively. On the other hand, structurally related aldehydes such as 2-methoxybenzaldehyde (21), 3,4-dimethoxybenzaldehyde, and vanillin (23) were not active at the concentration of 1000 mg/L. By liquid chromatography-mass spectrometry the reactivity of tested aldehydes against a synthetic peptide resembling the nematode cuticle was characterized. At the test concentration of 1 mM, the main adduct formation was observed for 3,4-dihydroxybenzaldehyde (22), 2-methoxybenzaldehyde (21), and 3,4-dimethoxybenzaldehyde. Considering that 2-methoxybenzaldehyde (21) and 3,4-dimethoxybenzaldehyde were not active against M. incognita in in vitro experiments led us to hypothesize a different mechanism of action rather than an effect on the external cuticle modification of nematodes. When the toxicity of the V-ATPase inhibitor pyocyanin (10) was tested against M. incognita J2 nematodes, an EC(50) at 24 h of 72 ± 25 mg/L was found. The redox-active compounds such as phthalaldehyde (1) and salicylaldehyde (2) may share a common mode of action inhibiting nematode V-ATPase enzyme. The results of this investigation reveal that aromatic redox-active aldehydes can be considered as potent nematicides, and further investigation is needed to completely clarify their mode of action.
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http://dx.doi.org/10.1021/jf305164m | DOI Listing |
J Econ Entomol
February 2024
Department of Ecology and Evolution, University of Lausanne, Lausanne, Switzerland.
Ants can particularly make for harmful pests, infesting human homes and reducing crop yields. The damage caused by ants and the efforts to mitigate the damage are hugely costly. Broad-spectrum insecticides are used most commonly; however, due to their negative side effects, there is increasing interest in nontoxic alternatives.
View Article and Find Full Text PDFJ Fluoresc
November 2023
Department of Chemistry, Bacha Khan University, Charsadda, Pakistan.
Phenanthrene fluorescence quenching in anionic micellar system of sodium dodecyl sulphate (SDS) was explored for the development of a sensitive and selective method for a group of selected aldehydes (2,6-dichlorobenzaldehyde, 4-(dimethylamino)benzaldehyde, 4-aminobenzaldehyde, 4-nitrobenzaldehyde, 2-chlorobenzaldehyde, benzaldehyde and 2-methoxybenzaldehyde). Experiments were performed in 0.02 mol L SDS.
View Article and Find Full Text PDFPest Manag Sci
August 2023
Nematology Unit, Gilat Research Center, Agricultural Research Organization, Mobile Post Negev 8528000, Israel.
Background: Several benzenoid aromatic compounds were found to attract second-stage juveniles (J2) of Meloidogyne species in previous studies. Here, the attraction of Meloidogyne J2 to the nematicides fluopyram and fluensulfone, with and without aromatic attractants, was evaluated on agar plates and in sand.
Results: Fluensulfone mixed with 2-methoxybenzaldehyde, carvacrol, trans-cinnamic acid, and 2-methoxycinnamaldehyde, attracted Meloidogyne javanica J2 on an agar plate, whereas fluensulfone alone did not.
Sci Rep
February 2023
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, University of Nigeria, Nsukka, 410001, Enugu State, Nigeria.
Corrosion inhibition performance of two synthesized Schiff base ligands; (E)-2-((2-methoxybenzylidene)amino)phenol L1 and (E)-2-((4-methoxybenzylidene)amino)phenol L2 were carried out by weight loss measurement in 0.1 M hydrochloric acid (HCl) solution. Density Functional Theory (DFT) and Molecular dynamics (MD) simulation were applied to theoretically explain the inhibitors' intrinsic properties and adsorption mechanism in the corrosion study.
View Article and Find Full Text PDFMaterials (Basel)
August 2021
Química-Física Molecular, Departamento de Química, Universidade de Coimbra, 3004-535 Coimbra, Portugal.
The dynamics of 2-methoxybenzaldehyde, 4-methoxybenzaldehyde, and 4-ethoxybenzaldehyde in the solid state are assessed through INS spectroscopy combined with periodic DFT calculations. In the absence of experimental data for 4-ethoxybenzaldehyde, a tentative crystal structure, based on its similarity with 4-methoxybenzaldehyde, is considered and evaluated. The excellent agreement between calculated and experimental spectra allows a confident assignment of the vibrational modes.
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