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Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids.
J Agric Food Chem. 2017 Jan 18; 65(2):260-269.JA

Abstract

In the framework of this study a synthesis methodology and characterization of long alkyl herbicidal ionic liquids (HILs) based on four commonly used herbicides (2,4-D, MCPA, MCPP, and dicamba) are presented. New HILs were obtained with high efficiency (>95%) using an acid-base reaction between herbicidal acids and hexadecyltrimethylammonium, octadecyltrimethylammonium, and behenyltrimethylammonium hydroxides in alcoholic medium. Among all synthesized salts, only three compounds comprising the MCPP anion were liquids at room temperature. Subsequently, the influence of both the alkyl chain length and the anion structure on their physicochemical properties (thermal decomposition profiles, solubility in 10 representative solvents, surface activity, density, viscosity, and refractive index) was determined. All HILs exhibited high thermal stability as well as surface activity; however, their solubility notably depended on both the length of the carbon chain and the structure of the anion. The herbicidal efficacy of the obtained salts was tested in greenhouse and field experiments. Greenhouse testing performed on common lambsquarters (Chenopodium album L.) and flixweed (Descurainia sophia L.) as test plants indicated that HILs were characterized by similar or higher efficacy compared to commercial herbicides. The results of field trials confirmed the high activity of HILs, particularly those containing phenoxyacids as anions (MCPA, 2,4-D, and MCPP).

Authors+Show Affiliations

Department of Chemical Technology, Poznan University of Technology , Poznan 60-965, Poland.Department of Chemical Technology, Poznan University of Technology , Poznan 60-965, Poland.Department of Chemical Technology, Poznan University of Technology , Poznan 60-965, Poland.Department of Chemical Technology, Poznan University of Technology , Poznan 60-965, Poland.ADOB Sp. z o.o. Sp.k. , Poznan 61-070, Poland.Institute of Plant Protection - National Research Institute , Poznan 60-318, Poland.Institute of Plant Protection - National Research Institute , Poznan 60-318, Poland.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

27997185

Citation

Pernak, Juliusz, et al. "Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids." Journal of Agricultural and Food Chemistry, vol. 65, no. 2, 2017, pp. 260-269.
Pernak J, Giszter R, Biedziak A, et al. Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. J Agric Food Chem. 2017;65(2):260-269.
Pernak, J., Giszter, R., Biedziak, A., Niemczak, M., Olszewski, R., Marcinkowska, K., & Praczyk, T. (2017). Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. Journal of Agricultural and Food Chemistry, 65(2), 260-269. https://doi.org/10.1021/acs.jafc.6b04528
Pernak J, et al. Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. J Agric Food Chem. 2017 Jan 18;65(2):260-269. PubMed PMID: 27997185.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Alkyl(C16, C18, C22)trimethylammonium-Based Herbicidal Ionic Liquids. AU - Pernak,Juliusz, AU - Giszter,Rafał, AU - Biedziak,Agnieszka, AU - Niemczak,Michał, AU - Olszewski,Radosław, AU - Marcinkowska,Katarzyna, AU - Praczyk,Tadeusz, Y1 - 2017/01/06/ PY - 2016/12/21/pubmed PY - 2017/5/4/medline PY - 2016/12/21/entrez KW - efficacy KW - growth regulators KW - herbicidal ionic liquids KW - long alkyl KW - phenoxyacids SP - 260 EP - 269 JF - Journal of agricultural and food chemistry JO - J. Agric. Food Chem. VL - 65 IS - 2 N2 - In the framework of this study a synthesis methodology and characterization of long alkyl herbicidal ionic liquids (HILs) based on four commonly used herbicides (2,4-D, MCPA, MCPP, and dicamba) are presented. New HILs were obtained with high efficiency (>95%) using an acid-base reaction between herbicidal acids and hexadecyltrimethylammonium, octadecyltrimethylammonium, and behenyltrimethylammonium hydroxides in alcoholic medium. Among all synthesized salts, only three compounds comprising the MCPP anion were liquids at room temperature. Subsequently, the influence of both the alkyl chain length and the anion structure on their physicochemical properties (thermal decomposition profiles, solubility in 10 representative solvents, surface activity, density, viscosity, and refractive index) was determined. All HILs exhibited high thermal stability as well as surface activity; however, their solubility notably depended on both the length of the carbon chain and the structure of the anion. The herbicidal efficacy of the obtained salts was tested in greenhouse and field experiments. Greenhouse testing performed on common lambsquarters (Chenopodium album L.) and flixweed (Descurainia sophia L.) as test plants indicated that HILs were characterized by similar or higher efficacy compared to commercial herbicides. The results of field trials confirmed the high activity of HILs, particularly those containing phenoxyacids as anions (MCPA, 2,4-D, and MCPP). SN - 1520-5118 UR - https://www.unboundmedicine.com/medline/citation/27997185/Alkyl_C16_C18_C22_trimethylammonium_Based_Herbicidal_Ionic_Liquids_ L2 - https://dx.doi.org/10.1021/acs.jafc.6b04528 DB - PRIME DP - Unbound Medicine ER -