Metsulfuron-methyl-based herbicidal ionic liquids.
Ten sulfonylurea-based herbicidal ionic liquids (HILs) were prepared by combining the metsulfuron-methyl anion with various cation types including quaternary ammonium ([bis(2-hydroxyethyl)methyloleylammonium](+), [2-hydroxyethyltrimethylammonium](+)), pyridinium ([1-dodecylpyridinium](+)), piperidinium ([1-methyl-1-propylpiperidinium](+)), imidazolium ([1-allyl-3-methylimidazolium](+), [1-butyl-3-methylimidazolium](+)), pyrrolidinium ([1-butyl-1-methylpyrrolidinium](+)), morpholinium ([4-decyl-4-methylmorpholinium](+)), and phosphonium ([trihexyltetradecylphosphonium](+) and [tetrabutylphosphonium](+)). Their herbicidal efficacy was studied in both greenhouse tests and field trials. Preliminary results for the greenhouse tests showed at least twice the activity for all HILs when compared to the activity of commercial Galmet 20 SG, with HILs with phosphonium cations being the most effective. The results of two-year field studies showed significantly less enhancement of activity than observed in the greenhouse; nonetheless, it was found that the herbicidal efficacy was higher than that of the commercial analog, and efficacy varied depending on the plant species.
†Department of Chemical Technology, Poznan University of Technology, Poznan 60-965, Poland.
Juliusz
J
Pernak
†Department of Chemical Technology, Poznan University of Technology, Poznan 60-965, Poland.
Michał
M
Niemczak
‡Center for Green Manufacturing and Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United States.|§525 Solutions, Incorporated, 720 Second Street, Tuscaloosa, Alabama 35401, United States.
Julia L
JL
Shamshina
‡Center for Green Manufacturing and Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United States.|§525 Solutions, Incorporated, 720 Second Street, Tuscaloosa, Alabama 35401, United States.
Gabriela
G
Gurau
∥Institute of Plant Protection, National Research Institute, Poznan 60-318, Poland.
Grzegorz
G
Głowacki
∥Institute of Plant Protection, National Research Institute, Poznan 60-318, Poland.
Tadeusz
T
Praczyk
∥Institute of Plant Protection, National Research Institute, Poznan 60-318, Poland.
Katarzyna
K
Marcinkowska
‡Center for Green Manufacturing and Department of Chemistry, The University of Alabama, Tuscaloosa, Alabama 35487, United States.
Robin D
RD
Rogers
D000838:Anions / Q000737:chemistry; D001190:Arylsulfonates / Q000737:chemistry*; D002152:Calorimetry, Differential Scanning; D002412:Cations / Q000737:chemistry; D004355:Drug Stability; D006540:Herbicides / Q000138:chemical synthesis* / Q000494:pharmacology; D057685:Plant Weeds / Q000187:drug effects; D012995:Solubility; D012996:Solutions; D013816:Thermodynamics
D000838:Anions; D001190:Arylsulfonates; D002412:Cations; D006540:Herbicides; D012996:Solutions; C050296:metsulfuron methyl
Galmet 20 SG; MS-M; efficacy; field test; greenhouse test; herbicidal ionic liquids; metsulfuron-methyl; sulfonylurea