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Article

Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas

by
Witold Stachowiak
,
Radosław Szumski
,
Jan Homa
,
Marta Woźniak-Karczewska
,
Anna Parus
,
Beata Strzemiecka
,
Łukasz Chrzanowski
* and
Michał Niemczak
Department of Chemical Technology, Poznan University of Technology, 60-965 Poznan, Poland
*
Author to whom correspondence should be addressed.
Molecules 2021, 26(15), 4396; https://doi.org/10.3390/molecules26154396
Submission received: 23 June 2021 / Revised: 17 July 2021 / Accepted: 19 July 2021 / Published: 21 July 2021
(This article belongs to the Special Issue New Frontiers Regarding Surfactants and Biosurfactants: Production, Characterization and Application)
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Abstract

Efficient use of herbicides for plant protection requires the application of auxiliary substances such as surfactants, stabilizers, wetting or anti-foaming agents, and absorption enhancers, which can be more problematic for environment than the herbicides themselves. We hypothesized that the combination of sulfonylurea (iodosulfuron-methyl) anion with inexpensive, commercially available quaternary tetraalkylammonium cations could lead to biologically active ionic liquids (ILs) that could become a convenient and environment-friendly alternative to adjuvants. A simple one-step synthesis allowed for synthesizing iodosulfuron-methyl based ILs with high yields ranging from 88 to 96% as confirmed by UV, FTIR, and NMR. The obtained ILs were found to possess several favorable properties compared to the currently used sodium salt iodosulfuron-methyl, such as adjustable hydrophobicity (octanol-water partition coefficient) and enhanced stability in aqueous solutions, which was supported by molecular calculations showing cation–anion interaction energies. In addition, soil mobility and volatility of ILs were more beneficial compared to the parental herbicide. Herbicidal activity tests toward oil-seed rape and cornflower revealed that ILs comprising at least one alkyl chain in the decyl to octadecyl range had similar or better efficacy compared to the commercial preparation without addition of any adjuvant. Furthermore, results of antimicrobial activity indicated that they were practically harmless or slightly toxic toward model soil microorganisms such as Pseudomonas putida and Bacillus cereus.
Keywords: HILs; weed killer; plant protection; sulfonylurea herbicide; ALS inhibitors; volatility; soil mobility; stability HILs; weed killer; plant protection; sulfonylurea herbicide; ALS inhibitors; volatility; soil mobility; stability

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MDPI and ACS Style

Stachowiak, W.; Szumski, R.; Homa, J.; Woźniak-Karczewska, M.; Parus, A.; Strzemiecka, B.; Chrzanowski, Ł.; Niemczak, M. Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas. Molecules 2021, 26, 4396. https://doi.org/10.3390/molecules26154396

AMA Style

Stachowiak W, Szumski R, Homa J, Woźniak-Karczewska M, Parus A, Strzemiecka B, Chrzanowski Ł, Niemczak M. Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas. Molecules. 2021; 26(15):4396. https://doi.org/10.3390/molecules26154396

Chicago/Turabian Style

Stachowiak, Witold, Radosław Szumski, Jan Homa, Marta Woźniak-Karczewska, Anna Parus, Beata Strzemiecka, Łukasz Chrzanowski, and Michał Niemczak. 2021. "Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas" Molecules 26, no. 15: 4396. https://doi.org/10.3390/molecules26154396

APA Style

Stachowiak, W., Szumski, R., Homa, J., Woźniak-Karczewska, M., Parus, A., Strzemiecka, B., Chrzanowski, Ł., & Niemczak, M. (2021). Transformation of Iodosulfuron-Methyl into Ionic Liquids Enables Elimination of Additional Surfactants in Commercial Formulations of Sulfonylureas. Molecules, 26(15), 4396. https://doi.org/10.3390/molecules26154396

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