Degradation of imazosulfuron in soil

Pest Manag Sci. 2001 Apr;57(4):360-5. doi: 10.1002/ps.294.

Abstract

Imazosulfuron, 1-(2-chloroimidazo[1,2-alpha]pyridin-3-ylsulfonyl)-3- (4,6-dimethoxypyrimidin-2-yl)urea, is a new post-emergence sulfonylurea herbicide applied once per growing season, highly active at low application levels, used to control most annual and perennial broad-leaf weeds and sedges in paddy rice (75-95 g AI ha-1) and turf (500-1000 g AI ha-1), and characterised by low mammalian toxicity. The degradation of imazosulfuron in a sandy loam soil (10-15 cm depth) has been investigated under aerobic and anaerobic laboratory conditions to evaluate its likely environmental fate. Test soils were treated with imazosulfuron in acetonitrile to give a final concentration of 0.2 mg kg-1 (100 g ha-1). The treated soils were extracted with methylene chloride + acetonitrile + 1 M ammonium hydroxide (4 + 15 + 1 by volume) and analysed by HPLC. Recoveries from spiked soils ranged from 80% to 95% (RSD 0.5-2.5%; n = 3) for imazosulfuron and its metabolites 2-chloroimidazo[1,2-alpha]pyridin-3-sulfonamide (IPSN), 1-(2-chloroimidazo[1,2-alpha]pyridin-3-ylsulfonyl)-3-(4-hydroxy-6- methoxypyrimidin-2-yl)urea (HMS) and 2-amino-4,6-dimethoxypyrimidine (ADPM). The limits of quantitation ranged from 0.001 mg kg-1 to 0.005 mg kg-1. Chemical cleavage of the sulfonylurea bond to give ADPM and IPSN was the main degradation pathway in aerobic conditions, whereas a remarkable production of HMS under anaerobic conditions suggested that degradation was due to micro-organisms which had the ability to demethylate imazosulfuron. In aerobic and anaerobic conditions, imazosulfuron disappeared from the soil with a half-life of approximately 70 (90% CL 62-75; r2 = 0.98) and 4 (90% CL 3.2-4.2; r2 = 0.97) days, respectively.

MeSH terms

  • Aerobiosis
  • Anaerobiosis
  • Biodegradation, Environmental
  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Environmental Monitoring / methods
  • Half-Life
  • Herbicides / chemistry
  • Herbicides / metabolism*
  • Molecular Structure
  • Pyridines / chemistry
  • Pyridines / metabolism*
  • Pyrimidines / chemistry
  • Pyrimidines / metabolism*
  • Soil / analysis*
  • Soil Microbiology
  • Soil Pollutants / analysis
  • Soil Pollutants / metabolism*
  • Sulfonylurea Compounds*

Substances

  • Herbicides
  • Pyridines
  • Pyrimidines
  • Soil
  • Soil Pollutants
  • Sulfonylurea Compounds
  • 1-(2-chloroimidazo(1,2-a)pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea