Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole against Meloidogyne incognita

Bioorg Med Chem Lett. 2020 Sep 1;30(17):127369. doi: 10.1016/j.bmcl.2020.127369. Epub 2020 Jun 30.

Abstract

Based on the characteristic of benzo[d][1,2,3]thiadiazole to induce the systemic acquired resistance and improve the immunity of plants, benzo[d][1,2,3]thiadiazole was introduced into 1,2,3-benzotriazin-4-one, thirty-one novel 1,2,3-benzotriazin-4-one derivatives containing benzo[d][1,2,3]thiadiazole were designed and synthesized. Nematicidal activity showed that most of the synthesized compounds exhibited great inhibitory activity in vivo against Meloidogyne incognita at 20 mg/L. Among 31 tested compounds, A2 and A3 showed an excellent nematicidal activity with the inhibition rate of 50.4% and 53.1% at the concentration of 1.0 mg/L, respectively. The influence of substituent type and position was investigated. The relationship between structure and activity was also preliminary analyzed.

Keywords: 1,2,3-benzotriazin-4-one; Benzo[d][1,2,3]thiadiazole; Meloidogyne incognita; Nematicidal activity; Plant activator.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antinematodal Agents / chemical synthesis*
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / pharmacology
  • Drug Design
  • Plant Roots / parasitology
  • Plants / parasitology
  • Structure-Activity Relationship
  • Thiadiazoles / chemistry*
  • Triazines / chemical synthesis
  • Triazines / chemistry*
  • Triazines / pharmacology
  • Tylenchoidea / drug effects

Substances

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