Glyphosate-Based Herbicidal Ionic Liquids with Increased Efficacy
Eight new glyphosate-based herbicidal ionic liquids (HILs), containing both mono- and dianions of glyphosate (benzalkonium glyphosate, bis(2-hydroxyethyl)cocomethylammonium glyphosate, oleylmethylbis(2-hydroxyethyl)ammonium glyphosate, didecyldimethylammonium glyphosate, di(hydrogenated tallow)...
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Published in | ACS sustainable chemistry & engineering Vol. 2; no. 12; pp. 2845 - 2851 |
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Main Authors | , , , , , , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
01.12.2014
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Subjects | |
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Abstract | Eight new glyphosate-based herbicidal ionic liquids (HILs), containing both mono- and dianions of glyphosate (benzalkonium glyphosate, bis(2-hydroxyethyl)cocomethylammonium glyphosate, oleylmethylbis(2-hydroxyethyl)ammonium glyphosate, didecyldimethylammonium glyphosate, di(hydrogenated tallow)dimethylammonium glyphosate, 4-decyl-4-ethylmorpholinium glyphosate, di(benzalkonium) glyphosate, and di(bis(2-hydroxyethyl)cocomethylammonium) glyphosate) were prepared via acid–base reaction between the corresponding ammonium hydroxides (some premade) and glyphosate free acid. The transformation of glyphosate free acid into ionic liquids led to an elimination of melting points in all but one compound and significant change in solubilities. All HILs exhibited higher thermal stability than glyphosate free acid. Greenhouse testing indicated that while at a higher application rate of 360 g/ha the efficacy of all the HILs was comparable to the commercial herbicide control, at a lower application rate of 180 g/ha, the efficacy of all HILs was as much as two and a half to three times higher when compared to the commercial formulation, and the dianionic glyphosates were the most effective. In field trials, all but one of the tested HILs demonstrated excellent efficacy. Laboratory regrowth tests established that the ionic liquids of glyphosate are efficiently translocated to rhizomes preventing the regrowth of plants. |
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AbstractList | Eight new glyphosate-based herbicidal ionic liquids (HILs), containing both mono- and dianions of glyphosate (benzalkonium glyphosate, bis(2-hydroxyethyl)cocomethylammonium glyphosate, oleylmethylbis(2-hydroxyethyl)ammonium glyphosate, didecyldimethylammonium glyphosate, di(hydrogenated tallow)dimethylammonium glyphosate, 4-decyl-4-ethylmorpholinium glyphosate, di(benzalkonium) glyphosate, and di(bis(2-hydroxyethyl)cocomethylammonium) glyphosate) were prepared via acid–base reaction between the corresponding ammonium hydroxides (some premade) and glyphosate free acid. The transformation of glyphosate free acid into ionic liquids led to an elimination of melting points in all but one compound and significant change in solubilities. All HILs exhibited higher thermal stability than glyphosate free acid. Greenhouse testing indicated that while at a higher application rate of 360 g/ha the efficacy of all the HILs was comparable to the commercial herbicide control, at a lower application rate of 180 g/ha, the efficacy of all HILs was as much as two and a half to three times higher when compared to the commercial formulation, and the dianionic glyphosates were the most effective. In field trials, all but one of the tested HILs demonstrated excellent efficacy. Laboratory regrowth tests established that the ionic liquids of glyphosate are efficiently translocated to rhizomes preventing the regrowth of plants. |
Author | Gurau, Gabriela Rogers, Robin D Niemczak, Michał Giszter, Rafał Shamshina, Julia L Pernak, Juliusz Cojocaru, O. Andreea Praczyk, Tadeusz Marcinkowska, Katarzyna |
AuthorAffiliation | Institute of Plant ProtectionNational Research Institute 525 Solutions, Inc Poznan University of Technology Center for Green Manufacturing and Department of Chemistry The University of Alabama Department of Chemical Technology |
AuthorAffiliation_xml | – name: Department of Chemical Technology – name: 525 Solutions, Inc – name: Poznan University of Technology – name: The University of Alabama – name: Institute of Plant ProtectionNational Research Institute – name: Center for Green Manufacturing and Department of Chemistry |
Author_xml | – sequence: 1 givenname: Juliusz surname: Pernak fullname: Pernak, Juliusz email: juliusz.pernak@put.poznan.pl organization: Poznan University of Technology – sequence: 2 givenname: Michał surname: Niemczak fullname: Niemczak, Michał organization: Poznan University of Technology – sequence: 3 givenname: Rafał surname: Giszter fullname: Giszter, Rafał organization: Poznan University of Technology – sequence: 4 givenname: Julia L surname: Shamshina fullname: Shamshina, Julia L organization: 525 Solutions, Inc – sequence: 5 givenname: Gabriela surname: Gurau fullname: Gurau, Gabriela organization: 525 Solutions, Inc – sequence: 6 givenname: O. Andreea surname: Cojocaru fullname: Cojocaru, O. Andreea organization: The University of Alabama – sequence: 7 givenname: Tadeusz surname: Praczyk fullname: Praczyk, Tadeusz organization: Institute of Plant ProtectionNational Research Institute – sequence: 8 givenname: Katarzyna surname: Marcinkowska fullname: Marcinkowska, Katarzyna organization: Institute of Plant ProtectionNational Research Institute – sequence: 9 givenname: Robin D surname: Rogers fullname: Rogers, Robin D email: RDRogers@ua.edu organization: The University of Alabama |
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