Synthesis and bioassay evaluation of 1-(4-substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl)ureas

Bioorg Med Chem. 2007 Jun 1;15(11):3678-83. doi: 10.1016/j.bmc.2007.03.049. Epub 2007 Mar 18.

Abstract

A variety of novel 1-(4-substitutedideneaminooxymethyl)-phenyl-3-(2,6-difluorobenzoyl)ureas were designed and synthesized by the reaction of 4-substitutedideneaminooxymethyl aniline with 2,6-difluorobenzoyl isocyanates in good yields. The title compounds were soluble in most organic solvents, which should make them easier to use. The preliminary bioassay showed that some of the title compounds show excellent insecticidal activity against Mythimna separata at the dosage of 25 mg kg(-1) and moderate insecticidal activity against Nephotettix cincticeps at the dosage of 500 mg kg(-1). Toxicity assays indicated that these title compounds cause in M. separata and N. cincticeps such symptoms of toxicity as discolouration, and weight loss, and cessation of feeding and lethal. One title compound exhibited acaricidal activity against Tetranychus urticae.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry
  • Animals
  • Biological Assay
  • Hemiptera / drug effects
  • Insecticides / chemistry*
  • Insecticides / pharmacology*
  • Isocyanates / chemistry
  • Lepidoptera / drug effects
  • Solvents / chemistry
  • Tetranychidae / drug effects
  • Urea / chemistry*

Substances

  • Aniline Compounds
  • Insecticides
  • Isocyanates
  • Solvents
  • Urea