Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate
The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C−N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate...
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| Veröffentlicht in: | Biomacromolecules 2007-02, Vol.8 (2), p.439-447 |
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| container_title | Biomacromolecules |
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| creator | Bogdanova, Aneta Piunova, Victoria Berger, Daniel Fedorov, Andrei V Neckers, Douglas C |
| description | The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C−N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to that of the parent compound. Only the acrylated glyphosate derivatives undergo photopolymerization. The resulting photopolymer of acrylated glyphosate retains the biological activity. The methacrylated glyphosates are unreactive. Differential reactivity is explained by the different conformational preferences of the functionalized glyphosates. The experimental findings are supported by the results of density functional theory geometry optimizations. |
| doi_str_mv | 10.1021/bm060477o |
| format | Article |
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The experimental findings are supported by the results of density functional theory geometry optimizations.</description><identifier>ISSN: 1525-7797</identifier><identifier>EISSN: 1526-4602</identifier><identifier>DOI: 10.1021/bm060477o</identifier><identifier>PMID: 17291067</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acrylates - chemistry ; Applied sciences ; Exact sciences and technology ; Glycine - analogs & derivatives ; Glycine - chemical synthesis ; Glyphosate ; Herbicides - chemical synthesis ; Methacrylates - chemistry ; Organic polymers ; Photochemistry ; Physicochemistry of polymers ; Polymers - chemical synthesis ; Polymers with particular properties ; Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><ispartof>Biomacromolecules, 2007-02, Vol.8 (2), p.439-447</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a343t-74eb50a100acd9f100d9d69b5a01700b7826d6fd564c87fcfb7848cbe8ab5ca93</citedby><cites>FETCH-LOGICAL-a343t-74eb50a100acd9f100d9d69b5a01700b7826d6fd564c87fcfb7848cbe8ab5ca93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/bm060477o$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/bm060477o$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18690497$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17291067$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Bogdanova, Aneta</creatorcontrib><creatorcontrib>Piunova, Victoria</creatorcontrib><creatorcontrib>Berger, Daniel</creatorcontrib><creatorcontrib>Fedorov, Andrei V</creatorcontrib><creatorcontrib>Neckers, Douglas C</creatorcontrib><title>Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate</title><title>Biomacromolecules</title><addtitle>Biomacromolecules</addtitle><description>The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C−N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to that of the parent compound. Only the acrylated glyphosate derivatives undergo photopolymerization. The resulting photopolymer of acrylated glyphosate retains the biological activity. The methacrylated glyphosates are unreactive. Differential reactivity is explained by the different conformational preferences of the functionalized glyphosates. The experimental findings are supported by the results of density functional theory geometry optimizations.</description><subject>Acrylates - chemistry</subject><subject>Applied sciences</subject><subject>Exact sciences and technology</subject><subject>Glycine - analogs & derivatives</subject><subject>Glycine - chemical synthesis</subject><subject>Glyphosate</subject><subject>Herbicides - chemical synthesis</subject><subject>Methacrylates - chemistry</subject><subject>Organic polymers</subject><subject>Photochemistry</subject><subject>Physicochemistry of polymers</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><issn>1525-7797</issn><issn>1526-4602</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0LFOwzAQBmALgWgpDLwAysLAEDgnjh2PpUBBqgQImCPbsamrJK7itFJ4elxaUQamO50-3el-hM4xXGNI8I2sgQJhzB2gIc4SGhMKyeFPn8WMcTZAJ94vAICnJDtGA8wSjoGyIXp965turr31kWjK6Na6yn1aJaporDq7tl0fORO9zF3nlq7qa93aLyErHd2Fbi0C0X4jplW_nDsvOn2KjoyovD7b1RH6eLh_nzzGs-fp02Q8i0VK0i5mRMsMBAYQquQm1JKXlMtMAGYAkuUJLakpM0pUzowyYUJyJXUuZKYET0foartXtc77Vpti2dpatH2BodjEUvzGEuzF1i5XstblXu5yCOByB4QPz5tWNMr6vcspB8L_OKF8sXCrtgkv_nPwG-ild64</recordid><startdate>20070201</startdate><enddate>20070201</enddate><creator>Bogdanova, Aneta</creator><creator>Piunova, Victoria</creator><creator>Berger, Daniel</creator><creator>Fedorov, Andrei V</creator><creator>Neckers, Douglas C</creator><general>American Chemical Society</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></search><sort><creationdate>20070201</creationdate><title>Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate</title><author>Bogdanova, Aneta ; Piunova, Victoria ; Berger, Daniel ; Fedorov, Andrei V ; Neckers, Douglas C</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-74eb50a100acd9f100d9d69b5a01700b7826d6fd564c87fcfb7848cbe8ab5ca93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Acrylates - chemistry</topic><topic>Applied sciences</topic><topic>Exact sciences and technology</topic><topic>Glycine - analogs & derivatives</topic><topic>Glycine - chemical synthesis</topic><topic>Glyphosate</topic><topic>Herbicides - chemical synthesis</topic><topic>Methacrylates - chemistry</topic><topic>Organic polymers</topic><topic>Photochemistry</topic><topic>Physicochemistry of polymers</topic><topic>Polymers - chemical synthesis</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bogdanova, Aneta</creatorcontrib><creatorcontrib>Piunova, Victoria</creatorcontrib><creatorcontrib>Berger, Daniel</creatorcontrib><creatorcontrib>Fedorov, Andrei V</creatorcontrib><creatorcontrib>Neckers, Douglas C</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><jtitle>Biomacromolecules</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bogdanova, Aneta</au><au>Piunova, Victoria</au><au>Berger, Daniel</au><au>Fedorov, Andrei V</au><au>Neckers, Douglas C</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate</atitle><jtitle>Biomacromolecules</jtitle><addtitle>Biomacromolecules</addtitle><date>2007-02-01</date><risdate>2007</risdate><volume>8</volume><issue>2</issue><spage>439</spage><epage>447</epage><pages>439-447</pages><issn>1525-7797</issn><eissn>1526-4602</eissn><abstract>The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C−N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to that of the parent compound. Only the acrylated glyphosate derivatives undergo photopolymerization. The resulting photopolymer of acrylated glyphosate retains the biological activity. The methacrylated glyphosates are unreactive. Differential reactivity is explained by the different conformational preferences of the functionalized glyphosates. The experimental findings are supported by the results of density functional theory geometry optimizations.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17291067</pmid><doi>10.1021/bm060477o</doi><tpages>9</tpages></addata></record> |
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| ispartof | Biomacromolecules, 2007-02, Vol.8 (2), p.439-447 |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Acrylates - chemistry Applied sciences Exact sciences and technology Glycine - analogs & derivatives Glycine - chemical synthesis Glyphosate Herbicides - chemical synthesis Methacrylates - chemistry Organic polymers Photochemistry Physicochemistry of polymers Polymers - chemical synthesis Polymers with particular properties Preparation, kinetics, thermodynamics, mechanism and catalysts |
| title | Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate |
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