Synthesis of a series of monosaccharide-fipronil conjugates and their phloem mobility

J Agric Food Chem. 2013 May 8;61(18):4236-41. doi: 10.1021/jf400888c. Epub 2013 Apr 24.

Abstract

To test the effect of adding different monosaccharide groups to a non-phloem-mobile insecticide on the phloem mobility of the insecticide, a series of conjugates of different monosaccharides and fipronil were synthesized using the trichloroacetimidate method. Phloem mobility tests in castor bean ( Ricinus communis L.) seedlings indicated that the phloem mobility of these conjugates varied markedly. L-Rhamnose-fipronil and D-fucose-fipronil displayed the highest phloem mobility among all of the tested conjugates. Conjugating hexose, pentose, or deoxysugar to fipronil through an O-glycosidic linkage can confer phloem mobility to fipronil in R. communis L. effectively, while the -OH orientation of the monosaccharide substantially affected the phloem mobility of the conjugates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Insecticides / chemical synthesis*
  • Insecticides / pharmacology
  • Larva
  • Lethal Dose 50
  • Monosaccharides / chemical synthesis*
  • Monosaccharides / pharmacology
  • Phloem / chemistry*
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / pharmacology
  • Ricinus communis
  • Seedlings
  • Spodoptera

Substances

  • Insecticides
  • Monosaccharides
  • Pyrazoles
  • fipronil