On the Interaction Mechanisms of Atrazine and Hydroxyatrazine with Humic Substances
ABSTRACT Atrazine (6‐chloro‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) is retained against leaching losses in soils principally by sorption to organic matter, but the mechanism of sorption has been a matter of controversy. Conflicting evidence exists for proton transfer, electron transfer, an...
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| Veröffentlicht in: | Journal of environmental quality 2001-03, Vol.30 (2), p.520-525 |
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| creator | Martin‐Neto, Ladislau Traghetta, Dinis Gomes Vaz, Carlos M.P. Crestana, Silvio Sposito, Garrison |
| description | ABSTRACT
Atrazine (6‐chloro‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) is retained against leaching losses in soils principally by sorption to organic matter, but the mechanism of sorption has been a matter of controversy. Conflicting evidence exists for proton transfer, electron transfer, and hydrophobic interactions between atrazine and soil humus, but no data are conclusive. In this paper we add to the database by investigating the role of (i) hydroxyatrazine (6‐hydroxy‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) and (ii) hydrophobicity in the sorption of atrazine by Brazilian soil humic substances. We demonstrate, apparently for the first time, that hydroxyatrazine readily forms electron‐transfer complexes with humic substances. These complexes probably are the cause of the well‐known strong adsorption by humic acids and they may be the undetected cause of apparent electron‐transfer complexes between soil organic matter and atrazine, whose transformation to the hydroxy form is facile. We also present evidence that supports the important contribution of hydrophobic interactions to the pH‐dependent sorption of atrazine by humic substances. |
| doi_str_mv | 10.2134/jeq2001.302520x |
| format | Article |
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Atrazine (6‐chloro‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) is retained against leaching losses in soils principally by sorption to organic matter, but the mechanism of sorption has been a matter of controversy. Conflicting evidence exists for proton transfer, electron transfer, and hydrophobic interactions between atrazine and soil humus, but no data are conclusive. In this paper we add to the database by investigating the role of (i) hydroxyatrazine (6‐hydroxy‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) and (ii) hydrophobicity in the sorption of atrazine by Brazilian soil humic substances. We demonstrate, apparently for the first time, that hydroxyatrazine readily forms electron‐transfer complexes with humic substances. These complexes probably are the cause of the well‐known strong adsorption by humic acids and they may be the undetected cause of apparent electron‐transfer complexes between soil organic matter and atrazine, whose transformation to the hydroxy form is facile. We also present evidence that supports the important contribution of hydrophobic interactions to the pH‐dependent sorption of atrazine by humic substances.</description><identifier>ISSN: 0047-2425</identifier><identifier>EISSN: 1537-2537</identifier><identifier>DOI: 10.2134/jeq2001.302520x</identifier><identifier>PMID: 11285913</identifier><identifier>CODEN: JEVQAA</identifier><language>eng</language><publisher>Madison: American Society of Agronomy, Crop Science Society of America, Soil Science Society</publisher><subject>Adsorption ; Agronomy. Soil science and plant productions ; Applied sciences ; Atrazine - analogs & derivatives ; Atrazine - chemistry ; Biological and medical sciences ; Biological and physicochemical properties of pollutants. Interaction in the soil ; Earth sciences ; Earth, ocean, space ; Electrons ; Engineering and environment geology. Geothermics ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; Herbicides - chemistry ; Humic Substances - chemistry ; Hydrogen-Ion Concentration ; Pollution ; Pollution, environment geology ; Soil and sediments pollution ; Soil and water pollution ; Soil Pollutants - analysis ; Soil science</subject><ispartof>Journal of environmental quality, 2001-03, Vol.30 (2), p.520-525</ispartof><rights>Published in J. Environ. Qual.30:520–525.</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c441X-d80515e95bc4b5e07454dc479e2b9261750daaa29b2580d7c31e6a52c76ae8df3</citedby><cites>FETCH-LOGICAL-c441X-d80515e95bc4b5e07454dc479e2b9261750daaa29b2580d7c31e6a52c76ae8df3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.2134%2Fjeq2001.302520x$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.2134%2Fjeq2001.302520x$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1025177$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11285913$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Martin‐Neto, Ladislau</creatorcontrib><creatorcontrib>Traghetta, Dinis Gomes</creatorcontrib><creatorcontrib>Vaz, Carlos M.P.</creatorcontrib><creatorcontrib>Crestana, Silvio</creatorcontrib><creatorcontrib>Sposito, Garrison</creatorcontrib><title>On the Interaction Mechanisms of Atrazine and Hydroxyatrazine with Humic Substances</title><title>Journal of environmental quality</title><addtitle>J Environ Qual</addtitle><description>ABSTRACT
Atrazine (6‐chloro‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) is retained against leaching losses in soils principally by sorption to organic matter, but the mechanism of sorption has been a matter of controversy. Conflicting evidence exists for proton transfer, electron transfer, and hydrophobic interactions between atrazine and soil humus, but no data are conclusive. In this paper we add to the database by investigating the role of (i) hydroxyatrazine (6‐hydroxy‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) and (ii) hydrophobicity in the sorption of atrazine by Brazilian soil humic substances. We demonstrate, apparently for the first time, that hydroxyatrazine readily forms electron‐transfer complexes with humic substances. These complexes probably are the cause of the well‐known strong adsorption by humic acids and they may be the undetected cause of apparent electron‐transfer complexes between soil organic matter and atrazine, whose transformation to the hydroxy form is facile. We also present evidence that supports the important contribution of hydrophobic interactions to the pH‐dependent sorption of atrazine by humic substances.</description><subject>Adsorption</subject><subject>Agronomy. Soil science and plant productions</subject><subject>Applied sciences</subject><subject>Atrazine - analogs & derivatives</subject><subject>Atrazine - chemistry</subject><subject>Biological and medical sciences</subject><subject>Biological and physicochemical properties of pollutants. Interaction in the soil</subject><subject>Earth sciences</subject><subject>Earth, ocean, space</subject><subject>Electrons</subject><subject>Engineering and environment geology. Geothermics</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Herbicides - chemistry</subject><subject>Humic Substances - chemistry</subject><subject>Hydrogen-Ion Concentration</subject><subject>Pollution</subject><subject>Pollution, environment geology</subject><subject>Soil and sediments pollution</subject><subject>Soil and water pollution</subject><subject>Soil Pollutants - analysis</subject><subject>Soil science</subject><issn>0047-2425</issn><issn>1537-2537</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2001</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkM9LwzAUx4Mobk7P3iQH8VaXpEnTnkTGdIoyRAVvJU1fWUZ_zKRlzr_eSCt685CXx5fP-z7eF6FTSi4ZDfl0De-MEHoZEiYY-dhDYypCGTBf9tGYEO57zsQIHTm39iAjMjpEI0pZLBIajtHzssbtCvBd3YJVujVNjR9Br1RtXOVwU-Dr1qpPUwNWdY4Xu9w2Hzv1o21Nu8KLrjIaP3eZa1WtwR2jg0KVDk6Gf4Jeb-Yvs0XwsLy9m10_BJpz-hbkMRFUQCIyzTMBRHLBc81lAixLWESlILlSiiUZEzHJpQ4pREowLSMFcV6EE3TR-25s896Ba9PKOA1lqWpoOpdSLmQsk8iD0x7UtnHOQpFurKmU3aWUpN85pkOO6ZCjnzgbrLusgvyXH4LzwPkAKKdVWVh_uXF_fJmgUnrsqse2poTdf2vT-_kT-35e66W38AuPn434</recordid><startdate>200103</startdate><enddate>200103</enddate><creator>Martin‐Neto, Ladislau</creator><creator>Traghetta, Dinis Gomes</creator><creator>Vaz, Carlos M.P.</creator><creator>Crestana, Silvio</creator><creator>Sposito, Garrison</creator><general>American Society of Agronomy, Crop Science Society of America, Soil Science Society</general><general>Crop Science Society of America</general><general>American Society of Agronomy</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7ST</scope><scope>C1K</scope><scope>SOI</scope></search><sort><creationdate>200103</creationdate><title>On the Interaction Mechanisms of Atrazine and Hydroxyatrazine with Humic Substances</title><author>Martin‐Neto, Ladislau ; Traghetta, Dinis Gomes ; Vaz, Carlos M.P. ; Crestana, Silvio ; Sposito, Garrison</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c441X-d80515e95bc4b5e07454dc479e2b9261750daaa29b2580d7c31e6a52c76ae8df3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2001</creationdate><topic>Adsorption</topic><topic>Agronomy. Soil science and plant productions</topic><topic>Applied sciences</topic><topic>Atrazine - analogs & derivatives</topic><topic>Atrazine - chemistry</topic><topic>Biological and medical sciences</topic><topic>Biological and physicochemical properties of pollutants. Interaction in the soil</topic><topic>Earth sciences</topic><topic>Earth, ocean, space</topic><topic>Electrons</topic><topic>Engineering and environment geology. Geothermics</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Herbicides - chemistry</topic><topic>Humic Substances - chemistry</topic><topic>Hydrogen-Ion Concentration</topic><topic>Pollution</topic><topic>Pollution, environment geology</topic><topic>Soil and sediments pollution</topic><topic>Soil and water pollution</topic><topic>Soil Pollutants - analysis</topic><topic>Soil science</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Martin‐Neto, Ladislau</creatorcontrib><creatorcontrib>Traghetta, Dinis Gomes</creatorcontrib><creatorcontrib>Vaz, Carlos M.P.</creatorcontrib><creatorcontrib>Crestana, Silvio</creatorcontrib><creatorcontrib>Sposito, Garrison</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Environment Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><jtitle>Journal of environmental quality</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Martin‐Neto, Ladislau</au><au>Traghetta, Dinis Gomes</au><au>Vaz, Carlos M.P.</au><au>Crestana, Silvio</au><au>Sposito, Garrison</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>On the Interaction Mechanisms of Atrazine and Hydroxyatrazine with Humic Substances</atitle><jtitle>Journal of environmental quality</jtitle><addtitle>J Environ Qual</addtitle><date>2001-03</date><risdate>2001</risdate><volume>30</volume><issue>2</issue><spage>520</spage><epage>525</epage><pages>520-525</pages><issn>0047-2425</issn><eissn>1537-2537</eissn><coden>JEVQAA</coden><abstract>ABSTRACT
Atrazine (6‐chloro‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) is retained against leaching losses in soils principally by sorption to organic matter, but the mechanism of sorption has been a matter of controversy. Conflicting evidence exists for proton transfer, electron transfer, and hydrophobic interactions between atrazine and soil humus, but no data are conclusive. In this paper we add to the database by investigating the role of (i) hydroxyatrazine (6‐hydroxy‐N2‐ethyl‐N4‐isopropyl‐1,3,5‐triazine‐2,4‐diamine) and (ii) hydrophobicity in the sorption of atrazine by Brazilian soil humic substances. We demonstrate, apparently for the first time, that hydroxyatrazine readily forms electron‐transfer complexes with humic substances. These complexes probably are the cause of the well‐known strong adsorption by humic acids and they may be the undetected cause of apparent electron‐transfer complexes between soil organic matter and atrazine, whose transformation to the hydroxy form is facile. We also present evidence that supports the important contribution of hydrophobic interactions to the pH‐dependent sorption of atrazine by humic substances.</abstract><cop>Madison</cop><pub>American Society of Agronomy, Crop Science Society of America, Soil Science Society</pub><pmid>11285913</pmid><doi>10.2134/jeq2001.302520x</doi><tpages>6</tpages></addata></record> |
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| ispartof | Journal of environmental quality, 2001-03, Vol.30 (2), p.520-525 |
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| subjects | Adsorption Agronomy. Soil science and plant productions Applied sciences Atrazine - analogs & derivatives Atrazine - chemistry Biological and medical sciences Biological and physicochemical properties of pollutants. Interaction in the soil Earth sciences Earth, ocean, space Electrons Engineering and environment geology. Geothermics Exact sciences and technology Fundamental and applied biological sciences. Psychology Herbicides - chemistry Humic Substances - chemistry Hydrogen-Ion Concentration Pollution Pollution, environment geology Soil and sediments pollution Soil and water pollution Soil Pollutants - analysis Soil science |
| title | On the Interaction Mechanisms of Atrazine and Hydroxyatrazine with Humic Substances |
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