Conjugation of 2-chloro-4,6-bis(alkylamino)-s-triazines in higher plants

Lamoureux, Gerald L.; Stafford, Lester E.; Shimabukuro, Richard H.

doi:10.1021/jf60183a042

Cited by 46 publications

(30 citation statements)

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“…According to Ashton et al 68 (1981) three metabolic pathways for the inactivation of atrazine in maize have been identified, namely: (i) hydroxylation of C-2 of the triazine ring -the chlorine substitute is replaced by an OH (Castelfranco, Foy & Deutsch, 1961); (ii) n-dealkylation of alkylamino groups at positions 4 and 6 (Mueller & Payot, 1965); and (iii) conjugation with the tripeptide glutathione (gammaglutamyl-cysteinyl-glycine) at position 2 of the triazine ring while splitting of the triazine ring may also occur (Frear & Swanson, 1970;Lamoureaux, Stafford & Shimabukuro, 1972;Ashton et al, 1981).…”

Section: Plant Factorsmentioning

confidence: 99%

Factors affecting the activity of atrazine in plants and soil

Nel

Reinhardt

1984

South African Journal of Plant and Soil

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Available research findings concerning the activity of atrazine in the plant and soil are presented in a brief review. The role of the environment is emphasized. This review is supplemented by recent research results of the University of Pretoria concerning evaluation of soil characteristics as a norm for the prediction of atrazine activity in turf soils, the comparison of a few maize hybrids with respect to their resistance towards atrazine and the influence of moisture and temperature on atrazine activity in light· textured soils. Guidelines for future research and for the use of atrazine are given. S. Afr. J. Plant Saif 1984, 1: 67 -72 'n Beknopte oorsig oor beskikbare navorsingsbevindinge betref· fende die aktiwiteit van atrasien in plante en in die grond word aangebied. Klem word gell3 op die rol van omgewingsfaktore. Hierdie oorsig word aangevul deur onlangse navorsingsresultate van die Universiteit van Pretoria, wat handel oor evaluasie van grondeienskappe as norm vir voorspelling van atrasien·aktiwiteit in turfgronde, vergelyking van enkele mieliebasters ten opsigte van verdraagsaamheid teenoor atrasien en die invloed van vog en temperatuur op atrasien·aktiwiteit in ligter gronde. Riglyne vir toekomstige navorsing en die gebruik van atrasien word verskaf. S.·Afr. Tydskr. Plant Grand 1984, 1: 67 -72 IntroductionDespite continuous research on factors affecting the activity of the triazines, conducted over almost a decade in South Africa and two decades in some overseas countries, knowledge of this subject remains insufficient. Unexpected cases of damage to crops or poor weed control still occur and confusion exists among scientists as to the exact cause of such occurrences.Atrazine is the most important herbicide in the summergrain producing regions of South Africa. A better understanding of the effect of the environment on the activity of this herbicide and related herbicides would be of immense value for agriculture in South Africa and the rest of the world.The purpose of this article is to give a concise review of research results concerning the use of atrazine. Emphasis is placed on the role of environmental conditions. An attempt is made to classify published data, while hitherto unpublished results of recent research at the University of Pretoria are briefly presented.

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Section: Plant Factorsmentioning

confidence: 99%

Factors affecting the activity of atrazine in plants and soil

Nel

Reinhardt

1984

South African Journal of Plant and Soil

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“…Metabolism by the GSH pathway and a possible amination pathway is summarized in Figure 17. Except for the N-proline conjugate which was produced from simazine metabolism in citrus and apple, all metabolites described in Figure 17 were produced from atrazine metabolism in sorghum, sugarcane, and com (3,25,33).…”

Section: Discussionmentioning

confidence: 99%

“…Atrazine can enter the GSH pathway directly or after it has been metabolized to desethylatrazine. The GSH conjugates of both atrazine and desethylatrazine appear to be metabolized by parallel pathways to the last products derived from the ^-cysteine and N-cysteine conjugates (3,33,25) (Figure 17). It has also been proposed that GSH conjugates may undergo Af-dealkylation after GSH conjugation (14).…”

Section: Discussionmentioning

confidence: 99%

“…It has also been proposed that GSH conjugates may undergo Af-dealkylation after GSH conjugation (14). The rate of GSH conjugation varies significantly depending upon the 2-chloro-i-triazine (26,33). Therefore, the relative importance of GSH conjugation, hydroxylation, N-dealkylation and/or amination may depend upon both the s-triazine and the plant.…”

Section: Discussionmentioning

confidence: 99%

“…Downloaded by UNIV MASSACHUSETTS AMHERST on October 1, 2012 | http://pubs.acs.org Publication Date: May 14, 1998 | doi: 10.1021/bk-1998-0683.ch006conjugation with GSH in certain j-triazine tolerant plants(32,33) and in a potato cell suspension culture (34) (Figure 5). The reaction is catalyzed by glutathione SAtrazine GSH Conj.…”

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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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