Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Abstract

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

Potent nematicidal activity of phenolic derivatives on Meloidogyne incognita

“…Treatment of helminths with aryl hydrazones and maleimide derivatives altered their metabolic profile by changing fatty acids and rates of ammonia elimination (Eloh et al, 2015, 2016) giving insight into the mode of action of phenolic derivatives.…”

Essential Metal-Based Nanoparticles (Copper/Iron NPs) as Potent Nematicidal Agents against Meloidogyne spp.

“…Considering that the nematicidal activity of copper sulfate has been determined at EC 50/24h = 32.9 μg/mL, the potent activity of CuFe NPs could partially be attributed to copper ions released 24 hours after dispersion of CuFe NPs in water. On the contrary iron has not significant antimicrobial properties [43], while the nematicidal activity of iron sulfate against M. incognita has been reported at 126 ± 48 μg/mL [39], much higher than the concentration of free iron (0.5 μg/mL) released after 24 h of dispersion and therefore the effect of copper/iron based while the bimetallic CuFe NPs resulted in significant increase of fresh shoot and root weight in the three higher doses, indicate an additional beneficial role (Figure 5) (Table 5) and should be considered together with the efficacy parameters in case it would be addressed as a pest management tool.…”

“…The nematicidal activity of the NPs was determined in the descending order of CuFe (Cu 0 ) > Cu (Cu 0 ) = CuFeO 2 (Cu 1+ ), with the last two compositions revealing similar efficacy. Copper salts have already been reported of nematicidal activity when used in combination with maleimide derivatives [39], while metal complexes have been found effective both against the root-knot nematodes and the soil born fungi Fusarium oxysporum [40]. In specific copper sulphate, principally used as a fungicide but also for treating copper-deficient soils, has been reported to exhibit an EC 50 value of 280 μg/mL against M. javanica [41] while Eloh et al [39] reported an EC 50 value of 48.6 μg/mL against M. incognita.…”

“…Copper salts have already been reported of nematicidal activity when used in combination with maleimide derivatives [39], while metal complexes have been found effective both against the root-knot nematodes and the soil born fungi Fusarium oxysporum [40]. In specific copper sulphate, principally used as a fungicide but also for treating copper-deficient soils, has been reported to exhibit an EC 50 value of 280 μg/mL against M. javanica [41] while Eloh et al [39] reported an EC 50 value of 48.6 μg/mL against M. incognita. Also, application of a mixture of maleic acid and copper sulfate reduced RKN disease on tomato by 51.72% in a pot experiment, suppressed gall formation on melon and decreased nematode population density in the soil [42].…”

Pathogenicity and Metabolites of Endoparasitic Nematophagous Fungus Drechmeria coniospora YMF1.01759 against Nematodes

“…The annual economic losses owing to nematode infection of crop production are estimated at $173 billion [ 1 ]. These are parasitic to a variety of crops such as cucumber, melon, pepper, tomato and fruit, and infect the entire plant including the roots, stems, leaves, flowers, fruit and seeds [ 2 , 3 ]. This scenario demands further research to identify effective albeit environment-friendly alternatives to replace legislatively withdrawn highly toxic nematicides [ 4 , 5 , 6 ].…”