A new
family of bio-based herbicidal ionic liquids (HILs) has been
synthesized starting from the renewable resource glycine betaine (a
derivative of natural amino acids). After esterification, the obtained
alkyl betainate bromides containing straight alkyl chains varying
from ethyl to octadecyl were combined with a herbicidal anion from
the sulfonylurea group (iodosulfuron-methyl). The melting points of
the iodosulfuron-methyl-based salts were in a range from 51 to 99
°C, which allows their classification as ionic liquids (ILs).
In addition, the new HILs exhibited good affinity for polar and semipolar
organic solvents, such as DMSO, methanol, acetonitrile, acetone, and
chloroform, while the presence of bulky organic cations reduced their
solubility in water. The synthesized products turned out to be stable
during storage at 25 °C for over 6 months; however, at 75 °C
they underwent fast, progressive degradation and released volatile
byproducts. The values of the logarithm of the octanol–water
partition coefficient of ILs with alkyls longer than hexyl occurred
in the “safe zone” (between 0 and 3); hence, the risk
of their migration into groundwater after application or the possibility
of their bioaccumulation in the environment is lower in comparison
with the currently available commercial form (iodosulfuron-methyl
sodium salt). Greenhouse studies confirmed a very high herbicidal
efficacy for the obtained salts toward tested plants of oilseed rape,
indicating that they may become an attractive replacement for the
currently available sulfonylurea-based formulations.