{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T19:17:41Z","timestamp":1788290261968,"version":"build-2803163510"},"reference-count":51,"publisher":"American Chemical Society (ACS)","issue":"47","license":[{"start":{"date-parts":[[2020,11,10]],"date-time":"2020-11-10T00:00:00Z","timestamp":1604966400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_ccby_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","award":["2018\/31\/D\/ST5\/01057"],"award-info":[{"award-number":["2018\/31\/D\/ST5\/01057"]}],"id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2020,11,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>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 \u00b0C, 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 \u00b0C for over 6 months; however, at 75 \u00b0C they underwent fast, progressive degradation and released volatile byproducts. The values of the logarithm of the octanol\u2013water partition coefficient of ILs with alkyls longer than hexyl occurred in the \u201csafe zone\u201d (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.<\/jats:p>","DOI":"10.1021\/acs.jafc.0c05850","type":"journal-article","created":{"date-parts":[[2020,11,10]],"date-time":"2020-11-10T17:06:40Z","timestamp":1605028000000},"page":"13661-13671","source":"Crossref","is-referenced-by-count":31,"title":["Iodosulfuron-Methyl-Based Herbicidal Ionic Liquids\nComprising Alkyl Betainate Cation as Novel Active Ingredients with\nReduced Environmental Impact and Excellent Efficacy"],"prefix":"10.1021","volume":"68","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-4364-8267","authenticated-orcid":true,"given":"Micha\u0142","family":"Niemczak","sequence":"first","affiliation":[{"name":"Poznan University of Technology , , ,","place":["Poznan, Poland, 60-965"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"\u0141ukasz","family":"Sobiech","sequence":"additional","affiliation":[{"name":"Poznan University of Life Sciences , , ,","place":["Poznan, Poland, 60-637"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Monika","family":"Grzanka","sequence":"additional","affiliation":[{"name":"Poznan University of Life Sciences , , ,","place":["Poznan, Poland, 60-637"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2020,11,10]]},"reference":[{"key":"2026090114543725800_cit1","doi-asserted-by":"publisher","first-page":"15","DOI":"10.1515\/jppr-2016-0003","article-title":"Effect of different\ndoses of post-emergence-applied iodosulfuron on weed control and grain\nyield of malt barley (Hordeum distichum L.), under\nMediterranean conditions","volume":"56","author":"Barros","year":"2016","journal-title":"J. Plant Prot. Res."},{"key":"2026090114543725800_cit2","doi-asserted-by":"publisher","first-page":"57","DOI":"10.1016\/j.eja.2011.03.002","article-title":"White mustard (Sinapis alba) resistance to ALS-inhibiting herbicides and\nalternative herbicides for control in Spain","volume":"35","author":"Rosario","year":"2011","journal-title":"Eur. J. Agron."},{"key":"2026090114543725800_cit3","doi-asserted-by":"publisher","first-page":"522","DOI":"10.4236\/fns.2013.45067","article-title":"Herbicide-resistant mutations in acetolactate synthase can reduce\nfeedback inhibition and lead to accumulation of branched-chain amino\nacids","volume":"04","author":"Endo","year":"2013","journal-title":"Food Nutr. Sci."},{"key":"2026090114543725800_cit4","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1186\/s12302-018-0136-2","article-title":"5-Point programme\nfor sustainable plant protection","volume":"30","author":"Frische","year":"2018","journal-title":"Environ. Sci.\nEur."},{"key":"2026090114543725800_cit5","doi-asserted-by":"publisher","first-page":"48","DOI":"10.1002\/fes3.108","article-title":"Pesticides,\nenvironment, and food safety","volume":"6","author":"Carvalho","year":"2017","journal-title":"Food Energy Secur."},{"key":"2026090114543725800_cit6","doi-asserted-by":"publisher","first-page":"812","DOI":"10.1126\/science.1185383","article-title":"Food Security:\nThe challenge of feeding\n9 billion people","volume":"327","author":"Godfray","year":"2010","journal-title":"Science"},{"key":"2026090114543725800_cit7","doi-asserted-by":"publisher","first-page":"103","DOI":"10.5586\/aa.2013.044","article-title":"The effect\nof reduced rates of crop protection agents\nand adjuvants on productivity, weed infestation and health of spring\nbarley (Hordeum sativum L.)","volume":"66","author":"Kwiatkowski","year":"2013","journal-title":"Acta Agrobot."},{"key":"2026090114543725800_cit8","doi-asserted-by":"publisher","first-page":"328","DOI":"10.1016\/j.cropro.2005.06.012","article-title":"Analysis of adjuvants effects and their interactions\nwith variable applications parameters","volume":"26","author":"Kudsk","year":"2007","journal-title":"Crop\nProt."},{"key":"2026090114543725800_cit9","doi-asserted-by":"publisher","first-page":"024","DOI":"10.29328\/journal.hvsr.1001003","article-title":"Mechanism-related\nteratogenic, hormone modulant and other toxicological effects of veterinary\nand agricultural surfactants","volume":"1","author":"Sze\u0301ka\u0301cs","year":"2017","journal-title":"Insights Vet Sci."},{"key":"2026090114543725800_cit10","doi-asserted-by":"publisher","first-page":"137","DOI":"10.1016\/j.fct.2019.03.053","article-title":"Insight\ninto the confusion over surfactant\nco-formulants in glyphosate-based herbicides","volume":"128","author":"Mesnage","year":"2019","journal-title":"Food Chem. Toxicol."},{"key":"2026090114543725800_cit11","doi-asserted-by":"publisher","first-page":"4838","DOI":"10.1016\/j.tet.2011.05.016","article-title":"Ionic liquids\nwith herbicidal anions","volume":"67","author":"Pernak","year":"2011","journal-title":"Tetrahedron"},{"key":"2026090114543725800_cit12","doi-asserted-by":"publisher","first-page":"4764","DOI":"10.1039\/C8GC01424H","article-title":"Ionic liquids as bioactive chemical\ntools for use in\nagriculture and the preservation of agricultural products","volume":"20","author":"Zajac","year":"2018","journal-title":"Green Chem."},{"key":"2026090114543725800_cit13","doi-asserted-by":"publisher","first-page":"8650","DOI":"10.1039\/C7NJ01694H","article-title":"Ionic liquids\nbased on bromoxynil for reducing adverse impacts on the environment\nand human health","volume":"41","author":"Tang","year":"2017","journal-title":"New J. Chem."},{"key":"2026090114543725800_cit14","doi-asserted-by":"publisher","first-page":"5590","DOI":"10.1039\/C4NJ01186D","article-title":"Ionic liquids based on bromoxynil for reducing adverse\nimpacts on the environment and human health","volume":"38","author":"Ding","year":"2014","journal-title":"New J. Chem."},{"key":"2026090114543725800_cit15","doi-asserted-by":"publisher","first-page":"128","DOI":"10.1016\/j.scitotenv.2017.10.288","article-title":"Developing\nionic liquid forms of picloram with reduced negative effects on the\naquatic environment","volume":"616\u2013617","author":"Tang","year":"2018","journal-title":"Sci. Total Environ."},{"key":"2026090114543725800_cit16","doi-asserted-by":"publisher","first-page":"8066","DOI":"10.1039\/C7NJ01474K","article-title":"Biodegradable herbicidal\nionic liquids based on synthetic auxins and analogues of betaine","volume":"41","author":"Niemczak","year":"2017","journal-title":"New J. Chem."},{"key":"2026090114543725800_cit17","doi-asserted-by":"publisher","first-page":"12012","DOI":"10.1002\/chem.201601952","article-title":"Betaine and carnitine\nderivatives as herbicidal ionic liquids","volume":"22","author":"Pernak","year":"2016","journal-title":"Chem.\n- Eur. J."},{"key":"2026090114543725800_cit18","doi-asserted-by":"publisher","first-page":"431","DOI":"10.1016\/j.molliq.2018.12.013","article-title":"Influence of the alkyl chain length\non the physicochemical properties and biological activity in a homologous\nseries of dichlorprop-based herbicidal ionic liquids","volume":"276","author":"Niemczak","year":"2019","journal-title":"J. Mol. Liq."},{"key":"2026090114543725800_cit19","doi-asserted-by":"publisher","first-page":"6048","DOI":"10.1021\/acs.jafc.0c00842","article-title":"Preparation of acifluorfen-based\nionic liquids with fluorescent properties for enhancing biological\nactivities and reducing the risk to the aquatic environment","volume":"68","author":"Tang","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"2026090114543725800_cit20","doi-asserted-by":"publisher","first-page":"16620","DOI":"10.1021\/acssuschemeng.9b03948","article-title":"Ionic liquid\nforms of mesotrione with enhanced stability and reduced leaching risk","volume":"7","author":"Wang","year":"2019","journal-title":"ACS Sustainable Chem. Eng."},{"key":"2026090114543725800_cit21","doi-asserted-by":"publisher","first-page":"52781","DOI":"10.1039\/C6RA06703D","article-title":"Herbicidal\nionic liquids\nderived from renewable sources","volume":"6","author":"Pernak","year":"2016","journal-title":"RSC Adv."},{"key":"2026090114543725800_cit22","doi-asserted-by":"publisher","first-page":"268","DOI":"10.1002\/cplu.201800651","article-title":"Herbicidal ionic liquids containing\nthe acetylcholine cation","volume":"84","author":"Czuryszkiewicz","year":"2019","journal-title":"ChemPlusChem"},{"key":"2026090114543725800_cit23","doi-asserted-by":"publisher","first-page":"207","DOI":"10.1007\/BF02942500","article-title":"Agroindustrial\nuses of glycinebetaine","volume":"6","author":"Ma\u0308kela\u0308","year":"2004","journal-title":"Sugar Tech"},{"key":"2026090114543725800_cit24","doi-asserted-by":"publisher","first-page":"60","DOI":"10.1016\/j.molliq.2015.03.016","article-title":"Ionic liquids derived\nfrom esters of glycine betaine: synthesis and characterization","volume":"207","author":"De Gaetano","year":"2015","journal-title":"J. Mol. Liq."},{"key":"2026090114543725800_cit25","doi-asserted-by":"publisher","first-page":"191","DOI":"10.2903\/j.efsa.2005.191","article-title":"Opinion of the Scientific Panel on Dietetic Products,\nNutrition and\nallergies on a request from the commission related to an application\nconcerning the use of betaine as a novel food in the EU","volume":"3","year":"2005","journal-title":"EFSA J."},{"key":"2026090114543725800_cit26","doi-asserted-by":"publisher","first-page":"90","DOI":"10.1097\/01.GIM.0000117334.84388.F4","article-title":"2nd, Cystathionine\nbeta-synthase deficiency: effects of betaine supplementation after\nmethionine restriction in B6-nonresponsive homocystinuria","volume":"6","author":"Singh","year":"2004","journal-title":"Genet. Med."},{"key":"2026090114543725800_cit27","doi-asserted-by":"publisher","first-page":"9","DOI":"10.1016\/j.scienta.2013.01.003","article-title":"Application\nof sugarbeet pure and\ncrude extracts containing glycine betaine affects root growth, yield,\nand photosynthesis of tomato grown during summer","volume":"152","author":"Kanechi","year":"2013","journal-title":"Sci. Hortic."},{"key":"2026090114543725800_cit28","doi-asserted-by":"publisher","first-page":"15628","DOI":"10.1021\/acssuschemeng.9b03645","article-title":"Toward designing\n\u201csweet\u201d\nionic liquids containing a natural terpene moiety as effective wood\npreservatives","volume":"7","author":"Feder-Kubis","year":"2019","journal-title":"ACS Sustainable Chem. Eng."},{"key":"2026090114543725800_cit29","doi-asserted-by":"publisher","first-page":"32344","DOI":"10.1039\/C7RA03310A","article-title":"Renewable\nsources from plants as\nthe starting material for designing new terpene chiral ionic liquids\nused for the chromatographic separation of acidic enantiomers","volume":"7","author":"Feder-Kubis","year":"2017","journal-title":"RSC Adv."},{"key":"2026090114543725800_cit30","doi-asserted-by":"publisher","first-page":"92707","DOI":"10.1039\/C5RA18462B","article-title":"Modernization\nof surfactant chemistry in the age of gemini and bio-surfactants:\na review","volume":"5","author":"Mondal","year":"2015","journal-title":"RSC Adv."},{"key":"2026090114543725800_cit31","first-page":"1203","volume-title":"Textbook of Practical\nOrganic Chemistry","author":"Vogel","year":"1989","edition":"5"},{"key":"2026090114543725800_cit32","doi-asserted-by":"publisher","first-page":"165","DOI":"10.1016\/j.jcis.2017.09.096","article-title":"Carnitine\nalkyl ester bromides as novel biosourced ionic liquids, cationic hydrotropes\nand surfactants","volume":"511","author":"Ha\u0308ckl","year":"2018","journal-title":"J. Colloid Interface Sci."},{"key":"2026090114543725800_cit33","doi-asserted-by":"publisher","first-page":"1475","DOI":"10.1063\/1.2204959","article-title":"Physical properties\nof ionic liquids: database and evaluation","volume":"35","author":"Zhang","year":"2006","journal-title":"J.\nPhys. Chem. Ref. Data"},{"key":"2026090114543725800_cit34","doi-asserted-by":"publisher","first-page":"6357","DOI":"10.1021\/cr500411q","article-title":"Structure and nanostructure in ionic\nliquids","volume":"115","author":"Hayes","year":"2015","journal-title":"Chem. Rev."},{"key":"2026090114543725800_cit35","doi-asserted-by":"publisher","first-page":"3357","DOI":"10.1021\/jf505782p","article-title":"Metsulfuron-methyl-based\nherbicidal ionic liquids","volume":"63","author":"Pernak","year":"2015","journal-title":"J. Agric. Food Chem."},{"key":"2026090114543725800_cit36","doi-asserted-by":"publisher","first-page":"12301","DOI":"10.1039\/D0CP01214A","article-title":"Tuning the melting point of selected ionic liquids\nthrough adjustment\nof the cation\u2019s dipole moment","volume":"22","author":"Rabideau","year":"2020","journal-title":"Phys.\nChem. Chem. Phys."},{"key":"2026090114543725800_cit37","doi-asserted-by":"publisher","first-page":"2741","DOI":"10.1021\/acssuschemeng.7b04382","article-title":"Bioherbicidal ionic\nliquids","volume":"6","author":"Pernak","year":"2018","journal-title":"ACS Sustainable Chem. Eng."},{"key":"2026090114543725800_cit38","doi-asserted-by":"publisher","first-page":"967","DOI":"10.1515\/zna-2002-1210","article-title":"Infrared\nand NMR Spectra of Arylsulphonamides,\n4-X-C6H4SO2NH2 and i-X, j-YC6H3SO2NH2 (X = H; CH3; C2H5; F; Cl; Br;\nI or NO2 and i-X, j-Y = 2,3-(CH3)2; 2,4-(CH3)2; 2,5- (CH3)2; 2-CH3,\n4-Cl; 2-CH3, 5-Cl; 3-CH3, 4-Cl; 2,4-Cl2 or 3,4-Cl2)","volume":"57","author":"Gowda","year":"2002","journal-title":"Z. Naturforsch., A: Phys. Sci."},{"key":"2026090114543725800_cit39","doi-asserted-by":"publisher","first-page":"7017","DOI":"10.1039\/C9NJ06005G","article-title":"Sweet\u201d\nionic liquids comprising the acesulfame anion \u2013 synthesis,\nphysicochemical properties and antifeedant activity towards stored\nproduct insects","volume":"44","author":"Stachowiak","year":"2020","journal-title":"New J. Chem."},{"key":"2026090114543725800_cit40","doi-asserted-by":"publisher","first-page":"4588","DOI":"10.1021\/acs.jafc.0c00632","article-title":"Dicamba-based herbicides: herbicidal ionic liquids\nversus commercial forms","volume":"68","author":"Pernak","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"2026090114543725800_cit41","doi-asserted-by":"publisher","first-page":"831","DOI":"10.1038\/nature04451","article-title":"The distillation\nand volatility of ionic liquids","volume":"439","author":"Earle","year":"2006","journal-title":"Nature"},{"key":"2026090114543725800_cit42","doi-asserted-by":"publisher","first-page":"10362","DOI":"10.1021\/acs.jafc.8b02584","article-title":"Dicationic ionic liquids\nof herbicide 2,4-dichlorophenoxyacetic acid\nwith reduced negative effects on environment","volume":"66","author":"Niu","year":"2018","journal-title":"J. Agric. Food Chem."},{"key":"2026090114543725800_cit43","doi-asserted-by":"publisher","first-page":"2110","DOI":"10.1039\/c3gc37143c","article-title":"Ionic liquid forms\nof the herbicide\ndicamba with increased efficacy and reduced volatility","volume":"15","author":"Cojocaru","year":"2013","journal-title":"Green Chem."},{"key":"2026090114543725800_cit44","doi-asserted-by":"publisher","first-page":"112077","DOI":"10.1016\/j.molliq.2019.112077","article-title":"Effect\nof large anions in thermal properties and cation-anion interaction\nstrength of dicationic ionic liquids","volume":"298","author":"Vieira","year":"2020","journal-title":"J. Mol.\nLiq."},{"key":"2026090114543725800_cit45","doi-asserted-by":"publisher","first-page":"3412","DOI":"10.1021\/acssuschemeng.9b07598","article-title":"Quantifying the mineralization of 13C-labeled cations\nand anions reveals differences in microbial biodegradation of herbicidal\nionic liquids between water and soil","volume":"8","author":"Wilms","year":"2020","journal-title":"ACS Sustainable\nChem. Eng."},{"key":"2026090114543725800_cit46","doi-asserted-by":"publisher","first-page":"827","DOI":"10.1039\/C8NJ05903A","article-title":"Novel herbicide ionic\nliquids based on nicosulfuron with increased efficacy","volume":"43","author":"Wang","year":"2019","journal-title":"New J. Chem."},{"key":"2026090114543725800_cit47","doi-asserted-by":"publisher","first-page":"444","DOI":"10.1016\/j.jcis.2007.03.044","article-title":"Cationic ester-containing\ngemini surfactants: chemical hydrolysis and biodegradation","volume":"312","author":"Tehrani-Bagha","year":"2007","journal-title":"J. Colloid Interface Sci."},{"key":"2026090114543725800_cit48","doi-asserted-by":"publisher","first-page":"184","DOI":"10.1016\/j.jhazmat.2016.10.048","article-title":"Identification\nof sulfonylurea biodegradation\npathways enabled by a novel nicosulfuron-transforming strain Pseudomonas fluorescens SG-1: Toxicity assessment and effect\nof formulation","volume":"324","author":"Carles","year":"2017","journal-title":"J. Hazard. Mater."},{"key":"2026090114543725800_cit49","doi-asserted-by":"publisher","first-page":"233","DOI":"10.1002\/ps.2780340308","article-title":"Holloway\nP. Surfactant-enhanced foliar\nuptake of some organic compounds: interaction with two model polyoxyethylene\naliphatic alcohols","volume":"34","author":"Stock","year":"1992","journal-title":"Pestic. Sci."},{"key":"2026090114543725800_cit50","first-page":"27","article-title":"Mode of action of herbicides\nand recent trends in development:\nA Reappraisal","volume":"2","author":"Das","year":"2014","journal-title":"Int. Inv. J. Agric. Soil Sci."},{"key":"2026090114543725800_cit51","doi-asserted-by":"publisher","first-page":"206","DOI":"10.1016\/j.envexpbot.2005.12.006","article-title":"Roles of glycine\nbetaine and proline in improving plant\nabiotic stress resistance","volume":"59","author":"Ashraf","year":"2007","journal-title":"Environ. Exp. Bot."}],"container-title":["Journal of Agricultural and Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.0c05850","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/68\/47\/13661\/67500893\/acs.jafc.0c05850.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/68\/47\/13661\/67500893\/acs.jafc.0c05850.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T18:54:42Z","timestamp":1788288882000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/68\/47\/13661\/1516165\/Iodosulfuron-Methyl-Based-Herbicidal-Ionic-Liquids"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,11,10]]},"references-count":51,"journal-issue":{"issue":"47","published-online":{"date-parts":[[2020,11,10]]},"published-print":{"date-parts":[[2020,11,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.0c05850","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,11,10]]}}}