Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

J Agric Food Chem. 2016 Jun 22;64(24):4876-81. doi: 10.1021/acs.jafc.6b02250. Epub 2016 Jun 9.

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.

Keywords: V-ATPase; metabolomics; nematicide; oxidative stress; redox-active metals.

MeSH terms

  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / pharmacology*
  • Maleimides / chemistry
  • Maleimides / pharmacology*
  • Structure-Activity Relationship
  • Tylenchoidea / drug effects*
  • Tylenchoidea / genetics
  • Tylenchoidea / growth & development
  • Tylenchoidea / metabolism

Substances

  • Antinematodal Agents
  • Maleimides
  • maleimide