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Herbicidal Ionic Liquids with 2,4-D

Published online by Cambridge University Press:  20 January 2017

Tadeusz Praczyk ,
Przemysław Kardasz ,
Ewa Jakubiak ,
Anna Syguda ,
Katarzyna Materna  and
Juliusz Pernak
Tadeusz Praczyk
Affiliation:
Institute of Plant Protection–National Research Institute, Poznan, 60-318, Poland
Przemysław Kardasz
Affiliation:
Institute of Plant Protection–National Research Institute, Poznan, 60-318, Poland
Ewa Jakubiak
Affiliation:
Institute of Plant Protection–National Research Institute, Poznan, 60-318, Poland
Anna Syguda
Affiliation:
Department of Chemical Technology, Poznan University of Technology, pl. M. Sklodowskiej-Curie 5, Poznan, 60-965, Poland
Katarzyna Materna
Affiliation:
Department of Chemical Technology, Poznan University of Technology, pl. M. Sklodowskiej-Curie 5, Poznan, 60-965, Poland
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Abstract

Three herbicidal ionic liquids (HILs)—alkyldi(2-hydroxyethyl)methylammonium (2,4-dichlorophenoxy)acetate, dialkyldimethylammonium (2,4-dichlorophenoxy)acetate, and alkyltrimethylammonium (2,4-dichlorophenoxy)acetate—were synthesized and their activity against broad-leaved weeds was investigated under field conditions. HILs as [cation][2,4-D] used in winter wheat were much more active compared to 2,4-D-dimethylammonium salt and demonstrated efficacy similar to 2,4-D 2-ethylhexyl ester. HILs exhibited desirable surface properties such as low contact angle of droplets and low surface tension. Moreover, the HILs may be safer to operators and neighboring plants due to their nonvolatile nature. HILs at 450 g ha−1 of 2,4-D did not injure wheat.

Keywords

Alkyldi(2-hydroxyethyl)methylammonium (2,4-dichlorophenoxy)acetatedialkyldimethylammonium (2,4-dichlorophenoxy)acetatealkyltrimethylammonium (2,4-dichlorophenoxy)acetate2,4-Dionic liquidsweed controlselectivitywinter wheat
Type
Physiology, Chemistry, and Biochemistry
Information
Weed Science , Volume 60 , Issue 2 , June 2012 , pp. 189 - 192
Copyright
Copyright © Weed Science Society of America 

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References

Literature Cited

Chowdhury, S., Mohan, R. S., and Scott, J. L. 2007. Reactivity of ionic liquids. Tetrahedron. 63:2363–2389.Google Scholar
Heap, I. 2011. International Survey of Herbicide Resistant Weeds. http://www.weedscience.org. Accessed: October 3, 2011.Google Scholar
Hough, W. L. and Rogers, R. D. 2007. Ionic liquids then and now: from solvents to materials to active pharmaceutical ingredients. Bull. Chem. Soc. Jpn. 80:2262–2269.Google Scholar
Hough, W. L., Smiglak, M., Rodriguez, H., Swatloski, R. P., Spear, S. K., Daly, D. T., Pernak, J., Grisel, J. E., Carliss, R. D., Soutullo, D. M., Davis, J. H., and Rogers, R. D. 2007. The third evolution of ionic liquids: active pharmaceutical ingredients. New J. Chem. 31:1429–1436.Google Scholar
Katritzky, A. R., Singh, S., Kirichenko, K., Smiglak, M., Holbrey, J. D., Reichert, W. M., Spear, S. K., and Rogers, R. D. 2006. In search of ionic liquids incorporating azolate anions. Chem. Eur. J. 12:4630–4641.Google Scholar
Li, W., Sun, N., Stroner, B., Jiang, X., Lu, X., and Rogers, R. D. 2011. Rapid dissolution of lignocellulosic biomass in ionic liquids using temperatures above the glass transition of lignin. Green Chem. 13:2038–2047.Google Scholar
Malec, A. D., Figley, T. M., and Turpin, K. L. 2010. The use of dimethylethanolamine based esterquats in liquid agricultural formulations. Pages 63–70 in Proceedings of the 9th International Symposium on Adjuvants for Agrochemicals (Freising-Weihenstephan). Wageningen, The Netherlands International Society for Agrochemical Adjuvants.Google Scholar
Matthews, G. 2006. Spray drift, bystander, resident and worker exposure. Pages 108–132 in Pesticides, Health, Safety and the Environment. Blackwell Publishing.Google Scholar
Mithila, J., Hall, J. C., Johnson, W. G., Kelley, K. B., and Riechers, D. F. 2011. Evolution of resistance to auxin herbicides: historical perspectives, mechanism of resistance, and implications for broadleaf weed management in agronomic crops. Weed Sci. 59:445–457.Google Scholar
Olivier-Bourbigou, H., Magna, L., and Morvan, D. 2010. Ionic liquids and catalysis: recent progress from knowledge to applications. Appl. Catal. A: General. 373:1–56.Google Scholar
Pernak, J., Syguda, A., Janiszewska, D., Materna, K., and Praczyk, T. 2011. Ionic liquids with herbicidal anions. Tetrahedron. 67:4838–4844.Google Scholar
Rogers, R. D. and Seddon, K. R. 2003. Ionic liquids—solvents of the future? Science. 302:792–793.Google Scholar
Stark, A. and Seddon, K. R. 2007. Pages 836–920 in Seidel, A., ed. Kirk-Othmer Encyclopedia of Chemical Technology. Hoboken, NJ J. Wiley.Google Scholar
Steckel, L. E., Main, C. H., and Mueller, T. C. 2010. Glyphosate-resistant horseweed in the United States. Pages 185–193 in Nandula, V. K., ed. Glyphasate Resistance in Crops and Weeds. Hoboken, NJ J. Wiley.Google Scholar
Strachan, S. D., Casini, M. C., Heldreth, K. M., Scocas, J. A., Nissen, S. J., Bukun, B., Lindenmayer, R. B., Shaner, D. L., Westra, P., and Brunk, G. 2010. Vapor movement of synthetic auxin herbicides: aminocyclopyrachlor, aminocyclopyrachlor-methyl ester, dicamba, and aminopyralid. Weed Sci. 58:103–108.Google Scholar
Sun, N., Rodriguez, H., Rahman, M., and Rogers, R. D. 2011. Where are ionic liquid strategies most suited in the pursuit of chemicals and energy from lignocellulosic biomass? Chem. Commun. 47:1405–1421.Google Scholar
Swatloski, R. P., Spear, S. K., Holbrey, J. D., and Rogers, R. D. 2002. Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 124:4974–4975.Google Scholar
Van Rantwijk, F. and Sheldon, R. A. 2007. Biocatalysis in ionic liquids. Chem. Rev. 107:2757–2785.Google Scholar
Wasserscheid, P. and Welton, T. 2008. Ionic Liquids in Synthesis. Weinheim, Germany Wiley-VCH. Pp. 1–6.Google Scholar
Zimdahl, R. L. 1999. Auxin-like herbicides. Pages 324–332 in Fundamentals of Weed Science. San Diego Academic.Google Scholar
Zimmerman, P. W. and Hitchcock, A. E. 1942. Substituted phenoxy and benzoic acid growth substances and the relation of structure to physiological activity. Contrib. Boyce Thompson Inst. 12:321–343.Google Scholar
Zollinger, R. K. and Nalewaja, J. D. 2010. Adjuvants for herbicides. Pages 165–176 in Proceedings of the 9th International Symposium on Adjuvants for Agrochemicals (Freising-Weihenstephan). Wageningen, The Netherlands International Society for Agrochemical Adjuvants.Google Scholar