Synthesis and Nematicidal Activities of 1,2,3-Benzotriazin-4-one Derivatives against Meloidogyne incognita

J Agric Food Chem. 2015 Aug 12;63(31):6883-9. doi: 10.1021/acs.jafc.5b01762. Epub 2015 Aug 4.

Abstract

A series of novel 1,2,3-benzotriazin-4-one derivatives were synthesized by the reaction of 3-bromoalkyl-1,2,3-benzotriazin-4-ones with potassium salt of 2-cyanoimino-4-oxothiazolidine in the presence of potassium iodide. Nematicidal assays in vivo showed that some of them exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita, up to 100% at the concentration of 10.0 mg L(-1), which indicated that 1,2,3-benzotriazin-4-one derivatives might be potential for novel promising nematicides. The nematicidal activity was influenced by the combination of substituent type, substituted position, and linker length in the molecule. The inhibition rate data at the concentrations of 5.0 and 1.0 mg L(-1) for the compounds with high inhibitory activities were also provided. When tested in vitro, none of them showed direct inhibition against M. incognita. The investigation of a significant difference between in vivo and in vitro data is in progress.

Keywords: 1,2,3-benzotriazin-4-one; 2-cyanoiminothiazolidin-4-one; Meloidogyne incognita; in vivo; nematicide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antinematodal Agents / chemical synthesis
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / toxicity*
  • Cucumis sativus / parasitology
  • Molecular Structure
  • Plant Diseases / parasitology
  • Triazines / chemical synthesis
  • Triazines / chemistry
  • Triazines / toxicity*
  • Tylenchoidea / drug effects*
  • Tylenchoidea / physiology

Substances

  • Antinematodal Agents
  • Triazines
  • 1,2,3-benzotriazin-4-one