In vitro nematicidal activity of aryl hydrazones and comparative GC-MS metabolomics analysis

J Agric Food Chem. 2015 Nov 18;63(45):9970-6. doi: 10.1021/acs.jafc.5b04815. Epub 2015 Nov 10.

Abstract

A series of aryl hydrazones were synthesized and in vitro assayed for their activity on the root-knot nematode Meloidogyne incognita. The phenylhydrazones of thiophene-2-carboxyaldehyde 5, 3-methyl-2-thiophenecarboxyaldehyde, 6, and salicylaldehyde, 2, were the most potent with EC50/48h values of 16.6 ± 2.2, 23.2 ± 2.7, and 24.3 ± 1.4 mg/L, respectively. A GC-MS metabolomics analysis, after in vitro nematode treatment with hydrazone 6 at 100 mg/L for 12 h, revealed elevated levels of fatty acids such as lauric acid, stearic acid, 2-octenoic acid, and palmitic acid. Whereas control samples showed the highest levels of monoacylglycerols such as monostearin and 2-monostearin, surprisingly, 2 h after treatment with hydrazone 6, nematodes excreted 3 times the levels of ammonia eliminated in the same conditions by controls. Thus, phenylhydrazones may represent a good scaffold in the discovery and synthesis of new nematicidal compounds, and a metabolomics approach may be helpful in understanding their mechanisms of toxicity and mode of action.

Keywords: 2-octenoic acid; M. incognita; ammonia; fatty acid; monoacylglycerols.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / pharmacology*
  • Fatty Acids / chemistry
  • Fatty Acids / metabolism
  • Gas Chromatography-Mass Spectrometry
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Metabolomics
  • Tylenchoidea / chemistry
  • Tylenchoidea / drug effects*
  • Tylenchoidea / metabolism*

Substances

  • Antinematodal Agents
  • Fatty Acids
  • Hydrazones