Propachlor metabolism in soybean plants, excised soybean tissues, and soil

Lamoureux, Gerald L.; Rusness, Donald G.

doi:10.1016/0048-3575(89)90158-2

Cited by 47 publications

(39 citation statements)

References 15 publications

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“…Metazachlor [N-(2,6-dimethoxyphenyl)-N-(pyrazol-1-ylmethyl)chloroacetanilide; BAS 479 H; R-CH 2 -Cl] is the parent compound from which the ethanesulfonate metabolite R-CH 2 -SO 3 -is derived. R-CH 2 -SO 3…”

Section: Methodsmentioning

confidence: 99%

“…The glutathione conjugate is then subject to further biotransformation, which leads to the formation of, for example, the "ethanesulfonate" metabolite (2-4), whose formation from alachlor (4), propachlor (2), acetochlor (3), and metazachlor (5) (Figure 1) has been detected. The ethanesulfonate metabolite seems to be stable in the soils studied (6).…”

Section: Introductionmentioning

confidence: 99%

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Bacterial Desulfonation of the Ethanesulfonate Metabolite of the Chloroacetanilide Herbicide Metazachlor

Laue

Field

Cook

1996

Environ. Sci. Technol.

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Metazachlor (R-CH 2 -Cl), a chloroacetanilide herbicide, is converted in soil to products including the ethanesulfonate metabolite (R-CH 2 -SO 3 -; BH 479-8). Nothing is known about the degradation of the ethanesulfonates of this class of herbicides. We used inocula derived from five sources for enrichment cultures to utilize R-CH 2 -SO 3 -as a sole sulfur source for the growth of microorganisms. Each culture yielded bacteria that caused the disappearance of R-CH 2 -SO 3 -and the formation of a product identified as the glycolate metabolite (R-CH 2 -OH; BH 479-1) by mass spectrometry. A pure culture, strain HL1, was isolated, and this bacterium quantitatively desulfonated R-CH 2 -SO 3 -, the sulfur being recovered in cell protein. Recovery of the organic moiety was usually about 80%. A second ethanesulfonate (R′-CH 2 -SO 3 -) and two alkylsulfonates, but not taurine, were utilized by strain HL1 as sulfur sources.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Bacterial Desulfonation of the Ethanesulfonate Metabolite of the Chloroacetanilide Herbicide Metazachlor

Laue

Field

Cook

1996

Environ. Sci. Technol.

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“…Ammeline and 2-hydroxy-4-amino-6-isopropylamino-.striazine were also observed in atrazine metabolism in sorghum, a species in which hydrolytic dehalogenation was not thought to occur at a significant rate (2,5). In sorghum, it is not clear whether the 2-hydroxy-5-triazines are formed by hydrolytic dehalogenation or by metabolism of GSH conjugates as is thought to occur during propachlor metabolism in corn (27). Ammelide and cyanuric acid were reported as minor residues in several plant species following extended exposure to 2-chloro-,s-triazine herbicides or their hydroxylated metabolites (1,28), but they were not reported as metabolites in a 28-day metabolism study of simazine in corn (2) or a 30-day metabolism study of atrazine in sorghum (3).…”

Section: Hydrolytic Dehalogenationmentioning

confidence: 90%

The Metabolism of Atrazine and Related 2-Chloro-4,6-bis(alkylamino)-s-triazines in Plants

Lamoureux¹,

Simoneaux²,

Larson³

1998

ACS Symposium Series

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The metabolism of atrazine and related 2-chloro-4,6-bis(alkylamino)-s -triazine herbicides in plants is reviewed and the structures of 13 metabolites recently identified from mature plants grown in the field are reported. The 2-chloro-4,6-bis(alkylamino)-s-triazines are initially metabolized in plants by three competing reactions: hydrolytic dehalogenation, N-dealkylation, and glutathione (GSH) conjugation. Metabolites produced by N-dealkylation can be further metabolized by hydrolytic dehalogenation or GSH conjugation, those produced by hydrolytic dehalogenation can be further metabolized by N-dealkylation and it is proposed that those from the GSH conjugation pathway may slowly become hydroxylated at the 2-position of the triazine ring. Ten metabolites of atrazine have been identified from the N-dealkylation and hydroxylation pathways and 14 have been identified from the GSH conjugation pathway. Three additional metabolites that have an amino function on the 2-position of the triazine ring have been identified, but their route of formation is uncertain.2-Chloro-4,6-bis(alkylamino)-i-triazine (2-chloro-.s-triazine) metabolism in plants has been extensively studied and comprehensive reviews have been written on the chemical and physical properties, metabolism and mode of action of these compounds (7) and on their metabolism and selectivity in plants (2). Based upon numerous studies conducted since the first patent was filed for these herbicides in 1954, the 2-chloro-5"-triazines such as atrazine (2-chloro-4-ethylamino-6-isopropylamino-5-triazine), simazine (2-chloro-4,6-bis[ethylamino]-s-triazine), and propazine (2-chloro-4,6-bis[isopropylamino]-^-triazine) have been shown to be metabolized in plants by three competing initial reactions: N-dealkylation of the side-4 Current Address: ABC Laboratori es Cal i forni a, Madera, CA 93638 60

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“…Formation of homoglutathione conjugates is characteristic mainly of soybean plant. Thus, the herbicide propachlor in soybean seedlings forms a conjugate with homoglutathione (Lamoureux and Rusness, 1989). Homoglutathionic conjugate, as the main product of chlorimuron-ethyl transformation, is formed in soybean plants (Brown and Neighborns 1987;Brown et al, 1990).…”

Section: Conjugation Of Xenobiotics With Peptidesmentioning

confidence: 98%