Simazine dealkylation in conjunction with citrus roots

Jordan, L. S.; Jolliffe, Virgil A.

doi:10.1002/ps.2780040405

Cited by 1 publication

(4 citation statements)

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“…Ammeline appears to be formed by the slow N-dealkylation of the 2-hydroxy-4-amino-6- alkylamino-5-triazines and perhaps also by the hydroxylation of 2-chloro-4,6-bis-(amino)-s-triazine ( Figure 4). 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).…”

Section: Hydrolytic Dehalogenationmentioning

confidence: 88%

“…Bound residues frequently account for a high percent of the TRR in crops treated with the 2-chloro-5 , -triazine herbicides (7,5). Some bound residues may be formed from the GSH pathway, but the mechanism of this transformation is uncertain (7).…”

Section: Discussionmentioning

confidence: 98%

“…Hydrolytic dehalogenation is observed during 2-chloro-s-triazine metabolism in highly tolerant corn and Coix Lacryma-jobi and in susceptible wheat and rye, but it is unimportant in other plants such as tolerant sorghum and intermediately susceptible oat, barley and soybean (2). Hydrolytic dehalogenation has also been reported in the metabolism of the 2-chloro-i-triazines in wild cane (sorghum bicolor), spruce, potato, yellow poplar (Liriodendron tulipifera L.) and various Setaria and Panicum species (1,2,4,5,12,(17)(18)(19)(20).…”

Section: Hydrolytic Dehalogenationmentioning

confidence: 96%

“…The 2-chloro-5-triazines such as atrazine and simazine are metabolized partially by N-dealkylation in many plants including com, sorghum, cotton, soybean, wheat, sugarcane, pea, citrus, black walnut, yellow poplar, and Canada Thistle (Crisium arvense L.) (1)(2)(3)(4)(5)(6)(7). In pea and sorghum, N-dealkylation of atrazine occurs more readily with the ethyl side-chain than with the isopropyl sidechain and the concentration of desethyl atrazine (I) can be twice the concentration of desisopropyl atrazine (II) or atrazine (2) (Figure 2).…”

Section: Metabolism Of the N-alkyl Side-chainsmentioning

confidence: 99%

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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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Section: Hydrolytic Dehalogenationmentioning

confidence: 88%