Synthesis and efficacy of herbicidal ionic liquids with chlorsulfuron as the anion

Abstract

In the framework of this research, four new herbicidal ionic liquids (HILs) comprising chlorsulfuron as the anion were synthesized and characterized. The new salts with chlorsulfuron contained the following cations: tetramethylammonium, didecyldimethylammonium, benzyltrimethylammonium and cholinium. All products were obtained with high yields exceeding 90% via acid-base reaction or ion exchange reaction, by the use of environment-friendly solvents. The structures of all synthesized HILs were confirmed by FT-IR, 1H NMR and 13C NMR analyses. Their efficacy against weeds has been studied under field conditions in fiber flax. All HILs showed herbicidal activity but efficiency was highly dependent on the type of cation and weed species. There were no statistically significant differences in the effectiveness of HILs toward common lambsquarters compared to the reference herbicide, except for salt with cholinium cation that showed significantly lower efficiency. As regards barnyard grass control, all HILs exhibited significantly lower efficacy than that of the reference herbicide, except for didecyldimethylammonium salt that showed similar activity. The synthesized products did not cause damage to flax plants. The obtained results confirmed that the herbicidal effectiveness of the active ingredient (chlorsulfuron) in the form of an ionic liquid can be adjusted by the selection of an appropriate cation in the synthesis.