Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of Chloroacetanilide Herbicides

Martha D Morton, F. H. Walters, D. S. Aga, E. M. Thurman, C. K. Larive

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.

Original languageEnglish (US)
Pages (from-to)1240-1243
Number of pages4
JournalJournal of Agricultural and Food Chemistry
Volume45
Issue number4
DOIs
StatePublished - Jan 1 1997

Fingerprint

chloroacetanilide herbicides
Sulfonic Acids
sulfonic acid
Herbicides
Metabolites
nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
metabolites
propachlor
butachlor
acetochlor
Fast Atom Bombardment Mass Spectrometry
alachlor
metolachlor
herbicides
Groundwater
Pesticides
Drinking Water
Glutathione

Keywords

  • Acetochlor
  • Alachlor
  • Chloroacetanilide metabolites
  • Metolachlor
  • Propachlor

ASJC Scopus subject areas

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Cite this

Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of Chloroacetanilide Herbicides. / Morton, Martha D; Walters, F. H.; Aga, D. S.; Thurman, E. M.; Larive, C. K.

In: Journal of Agricultural and Food Chemistry, Vol. 45, No. 4, 01.01.1997, p. 1240-1243.

Research output: Contribution to journalArticle

Morton, Martha D ; Walters, F. H. ; Aga, D. S. ; Thurman, E. M. ; Larive, C. K. / Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of Chloroacetanilide Herbicides. In: Journal of Agricultural and Food Chemistry. 1997 ; Vol. 45, No. 4. pp. 1240-1243.
@article{7ea48cb323364580896a2d49070dedbb,
title = "Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of Chloroacetanilide Herbicides",
abstract = "The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.",
keywords = "Acetochlor, Alachlor, Chloroacetanilide metabolites, Metolachlor, Propachlor",
author = "Morton, {Martha D} and Walters, {F. H.} and Aga, {D. S.} and Thurman, {E. M.} and Larive, {C. K.}",
year = "1997",
month = "1",
day = "1",
doi = "10.1021/jf960453g",
language = "English (US)",
volume = "45",
pages = "1240--1243",
journal = "Journal of Agricultural and Food Chemistry",
issn = "0021-8561",
publisher = "American Chemical Society",
number = "4",

}

TY - JOUR

T1 - Nuclear Magnetic Resonance Identification of New Sulfonic Acid Metabolites of Chloroacetanilide Herbicides

AU - Morton, Martha D

AU - Walters, F. H.

AU - Aga, D. S.

AU - Thurman, E. M.

AU - Larive, C. K.

PY - 1997/1/1

Y1 - 1997/1/1

N2 - The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.

AB - The detection of the sulfonic acid metabolites of the chloroacetanilide herbicides acetochlor, alachlor, butachlor, propachlor, and, more recently, metolachlor in surface and ground water suggests that a common mechanism for dechlorination exists via the glutathione conjugation pathway. The identification of these herbicides and their metabolites is important due to growing public awareness and concern about pesticide levels in drinking water. Although these herbicides are regulated, little is known about the fate of their metabolites in soil. The sulfonic acid metabolites were synthesized by reaction of the parent compounds with an excess of sodium sulfite. Acetochlor, alachlor, butachlor, metolachlor, and propachlor and their sulfonic acid metabolites were studied by nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. This paper provides a direct method for the preparation and characterization of these compounds that will be useful in the analysis and study of chloracetanilide herbicides and their metabolites.

KW - Acetochlor

KW - Alachlor

KW - Chloroacetanilide metabolites

KW - Metolachlor

KW - Propachlor

UR - http://www.scopus.com/inward/record.url?scp=0000488222&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000488222&partnerID=8YFLogxK

U2 - 10.1021/jf960453g

DO - 10.1021/jf960453g

M3 - Article

VL - 45

SP - 1240

EP - 1243

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

SN - 0021-8561

IS - 4

ER -