In Vitro conjugation of chloroacetanilide herbicides and atrazine with thiols and contribution of nonenzymatic conjugation to their glutathione-mediated metabolism in corn

I. Jablonkai, Kriton K. Hatzios

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Abstract

The contribution of nonenzymatic conjugation of acetochlor, alachlor, metolachlor, pretilachlor, and atrazine with glutathione (GSH) in the metabolism of these herbicides by roots and shoots of the Cargill 7567 and Northrup-King 9283 hybrids of corn (Zea mays L.) was investigated. Treatment with 50 μM of each herbicide revealed the following order of chloroacetanilide phytotoxicity: acetochlor > alachlor > metolachlor > pretilachlor. Atrazine did not injure any of the corn hybrids. Cargill 7567 was more tolerant than Northrup-King 9283 to metolachlor and pretilachlor, but the two corn lines did not differ in their response to acetochlor and alachlor. Total nonprotein thiol, GSH, and cysteine contents were similar in the two corn hybrids. Glutathione S-transferase (GST) activities were comparable in the two corn hybrids. Chloroacetanilide-specific GST activities were 2-4-fold greater in roots than in shoots of either hybrid, and enzymatic conjugation with GSH was more efficient with acetochlor and alachlor than with metolachlor and pretilachlor as substrates. Assays on the in vitro chemical reactivities of acetochlor, alachlor, metolachlor, pretilachlor, and atrazine with GSH and cysteine revealed that the higher the ratio of thiol to herbicidal substrate concentrations, the higher the amount of conjugate formed. Nonenzymatic conjugation with GSH may contribute significantly to the overall glutathionemediated metabolism of chloroacetanilide herbicides and atrazine in corn and seems to be dependent on the concentration and molecular structure of the herbicidal substrate as well as on the GSH content of plant tissues (root vs shoot).

Original languageEnglish
Pages (from-to)1736-1742
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume41
Issue number10
Publication statusPublished - 1993

Fingerprint

chloroacetanilide herbicides
Atrazine
pretilachlor
acetochlor
alachlor
atrazine
metolachlor
thiols
Sulfhydryl Compounds
Metabolism
Zea mays
Glutathione
glutathione
metabolism
corn
Herbicides
Glutathione Transferase
Cysteine
glutathione transferase
Substrates

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

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title = "In Vitro conjugation of chloroacetanilide herbicides and atrazine with thiols and contribution of nonenzymatic conjugation to their glutathione-mediated metabolism in corn",
abstract = "The contribution of nonenzymatic conjugation of acetochlor, alachlor, metolachlor, pretilachlor, and atrazine with glutathione (GSH) in the metabolism of these herbicides by roots and shoots of the Cargill 7567 and Northrup-King 9283 hybrids of corn (Zea mays L.) was investigated. Treatment with 50 μM of each herbicide revealed the following order of chloroacetanilide phytotoxicity: acetochlor > alachlor > metolachlor > pretilachlor. Atrazine did not injure any of the corn hybrids. Cargill 7567 was more tolerant than Northrup-King 9283 to metolachlor and pretilachlor, but the two corn lines did not differ in their response to acetochlor and alachlor. Total nonprotein thiol, GSH, and cysteine contents were similar in the two corn hybrids. Glutathione S-transferase (GST) activities were comparable in the two corn hybrids. Chloroacetanilide-specific GST activities were 2-4-fold greater in roots than in shoots of either hybrid, and enzymatic conjugation with GSH was more efficient with acetochlor and alachlor than with metolachlor and pretilachlor as substrates. Assays on the in vitro chemical reactivities of acetochlor, alachlor, metolachlor, pretilachlor, and atrazine with GSH and cysteine revealed that the higher the ratio of thiol to herbicidal substrate concentrations, the higher the amount of conjugate formed. Nonenzymatic conjugation with GSH may contribute significantly to the overall glutathionemediated metabolism of chloroacetanilide herbicides and atrazine in corn and seems to be dependent on the concentration and molecular structure of the herbicidal substrate as well as on the GSH content of plant tissues (root vs shoot).",
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AU - Hatzios, Kriton K.

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