Novel esterquat-based herbicidal ionic liquids incorporating MCPA and MCPP for simultaneous stimulation of maize growth and fighting cornflower

Abstract

Modern agricultural practices are often based on the use of mixtures of specific herbicides to achieve efficient crop protection. The major drawbacks of commercial herbicidal formulations include the necessity to incorporate toxic surfactants and high volatility of active substances. Transformation of herbicides into herbicidal ionic liquids (HILs) seems to be a promising alternative which allows to almost completely reduce volatility due to ionic interactions. In the scope of this research, we transformed (2-methyl-4-chlorophenoxy)acetic acid (MCPA) into a quaternary ester (esterquat) with the use of derivatives of 2-dimethylaminoethanol. The obtained esterquats were later coupled with (±)-2-(4-chloro-2-methylphenoxy)propionic acid (MCPP) in the form of an anion. The combination of MCPA and MCPA is commonly applied in the UK, EU countries and also in the USA to increase the spectrum of targeted weed species. In the framework of this study, novel HILs with an esterquat moiety incorporating a long alkyl chain (C₈, C₉, C₁₀, C₁₁, C₁₂, C₁₄) were prepared and characterized in terms of basic physicochemical properties (solubility and volatility) as well as biodegradability. Their phytotoxicity was assessed towards cornflower (Centaurea cyanus) as a model weed and maize (Zea mays) as a crop plant. The presence of the esterquat cation contributed to satisfactory solubility in water and other low polar solvents, which eliminates the need to add exogenous adjuvants. Further experiments indicated that the tested HILs stimulated the germination stage of maize and maintained high herbicidal activity towards cornflower. No significant differences in terms of properties were observed in case of HILs which included alkyl substituents with an odd number of carbon atoms. Future studies should be focused on structural modifications in order to improve the biodegradability as well as field studies for evaluation of commercial applications.

Keywords: Antimicrobial activity; Biodegradation; Centaurea cyanus; Root and shoot stimulation; Surface activity; Zea mays.