{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T06:26:16Z","timestamp":1788330376967,"version":"build-2803163510"},"reference-count":73,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2019,3,5]],"date-time":"2019-03-05T00:00:00Z","timestamp":1551744000000},"content-version":"vor","delay-in-days":4,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemPlusChem"],"published-print":{"date-parts":[[2019,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>This study presents a new group of herbicidal ionic liquids (HILs) based on a cation occurs commonly in nature\u2212acetylcholine. The HILs were obtained with a high yield through ion exchange between acetylcholine chloride and potassium or sodium salts of selected acids with herbicidal activity. The results of the herbicidal activity measurement against common oilseed rape (<jats:italic>Brassica napus L<\/jats:italic>.) exceeded those of the commercial products. Spray solutions of the synthesized HILs revealed high surface activity and wetting properties which further manifested as higher herbicidal activity. The reduction of surface tension and low contact angles together with the specific action of acetylcholine allowed for better penetration of synthesized HILs into plant tissues. In addition, OECD 301F tests confirmed high mineralization of the HILs. The simple transformation of commercial herbicides into acetylcholine HILs proved to be a very effective method of increasing their activity, and constitutes an interesting solution to the problem of weed infestation with the use of a substance commonly found in nature.<\/jats:p>","DOI":"10.1002\/cplu.201800651","type":"journal-article","created":{"date-parts":[[2019,2,7]],"date-time":"2019-02-07T11:18:01Z","timestamp":1549538281000},"page":"268-276","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":18,"title":["Herbicidal Ionic Liquids Containing the Acetylcholine Cation"],"prefix":"10.1002","volume":"84","author":[{"given":"Daria","family":"Czuryszkiewicz","sequence":"first","affiliation":[{"name":"Department of Chemical Technology Poznan University of Technology  Berdychowo 4 Poznan 60-965 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adam","family":"Ma\u0107kowiak","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology Poznan University of Technology  Berdychowo 4 Poznan 60-965 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katarzyna","family":"Marcinkowska","sequence":"additional","affiliation":[{"name":"Institute of Plant Protection National Research Institute  W\u0119gorka 20 Poznan 60-318 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrzej","family":"Borkowski","sequence":"additional","affiliation":[{"name":"Faculty of Geology University of Warsaw  \u017bwirki i Wigury 93 Warsaw 02-089 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2171-4913","authenticated-orcid":false,"given":"\u0141ukasz","family":"Chrzanowski","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology Poznan University of Technology  Berdychowo 4 Poznan 60-965 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juliusz","family":"Pernak","sequence":"additional","affiliation":[{"name":"Department of Chemical Technology Poznan University of Technology  Berdychowo 4 Poznan 60-965 Poland"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2019,3,5]]},"reference":[{"key":"e_1_2_7_1_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1752-4571.2010.00140.x"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.indcrop.2017.06.002"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/hdy.2012.104"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2014.05.041"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1614\/WS-D-11-00171.1"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/elsc.200620165"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.05.016"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1093\/jxb\/erw199"},{"key":"e_1_2_7_9_1","first-page":"544","volume":"31","author":"Ozdemir S.","year":"2012","journal-title":"Environ. Prot. Eng."},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.14199\/ppp-2014-001"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NJ01186D"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcatb.2004.02.007"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3gc37143c"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1039\/b706677p"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527621194"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12551-018-0419-2"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2016.11.123"},{"key":"e_1_2_7_18_1","volume-title":"The Pesticide Manual, A World Compendium, 15th","author":"Tomlin C. D. S.","year":"2009"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2015.05.025"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pestbp.2017.05.006"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature04451"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010518)40:10<1808::AID-ANIE1808>3.0.CO;2-1"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2015.00222"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10532-015-9737-2"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.6b00553"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700285"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA06703D"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5NJ00609K"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC01424H"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.rvsc.2017.04.019"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0167861"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00396-015-3648-y"},{"key":"e_1_2_7_33_1","first-page":"7267","volume":"594","author":"Wilson C.","year":"2016","journal-title":"J. Phys. Chem."},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1007\/BF02858764"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.8b02584"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cropro.2017.03.011"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2017.11.032"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8NJ03435D"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b04382"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf505782p"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA16151C"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1002\/cplu.201800251"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ01474K"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200700965"},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA12152G"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/aic.12786"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/B513231B"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jct.2009.01.012"},{"key":"e_1_2_7_49_1","doi-asserted-by":"crossref","unstructured":"S. Handy (ed.) Progress and Developments in Ionic Liquids IntechOpen 2017.","DOI":"10.5772\/62621"},{"key":"e_1_2_7_50_1","doi-asserted-by":"publisher","DOI":"10.1021\/je201289w"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jct.2012.09.004"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp804319a"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b04528"},{"key":"e_1_2_7_54_1","volume-title":"Octanol-Water Partition Coefficients: Fundamentals and Physical Chemistry","author":"Sangter J.","year":"1997"},{"key":"e_1_2_7_55_1","doi-asserted-by":"publisher","DOI":"10.1021\/es00136a007"},{"key":"e_1_2_7_56_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CP06611E"},{"key":"e_1_2_7_57_1","first-page":"4489","volume":"33","author":"Sablji\u0107 A.","year":"1996","journal-title":"Chemosphere"},{"key":"e_1_2_7_58_1","doi-asserted-by":"publisher","DOI":"10.1002\/etc.3212"},{"key":"e_1_2_7_59_1","volume-title":"Critical Revision and Development Perspectives of Herbicide Residues Analysis in Agro Ecosystems, Herbicides and ENVIRONMENT","author":"Cesio V.","year":"2011"},{"key":"e_1_2_7_60_1","doi-asserted-by":"crossref","first-page":"174","DOI":"10.3998\/ark.5550190.0010.a17","volume":"2009","author":"Spafiu F.","year":"2009","journal-title":"Arkivoc"},{"key":"e_1_2_7_61_1","doi-asserted-by":"publisher","DOI":"10.1039\/B410891D"},{"key":"e_1_2_7_62_1","doi-asserted-by":"crossref","unstructured":"W.\u2005R. Carlile Pesticide Selectivity Health and the Environment first ed. Cambridge University Press 2006.","DOI":"10.1017\/CBO9780511617874"},{"key":"e_1_2_7_63_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7NJ01694H"},{"key":"e_1_2_7_64_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2016.01.058"},{"key":"e_1_2_7_65_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201601952"},{"key":"e_1_2_7_66_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2017.08.026"},{"key":"e_1_2_7_67_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NJ00463A"},{"key":"e_1_2_7_68_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2016.04.109"},{"key":"e_1_2_7_69_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8NJ01239C"},{"key":"e_1_2_7_70_1","volume-title":"Vogel's Textbook of Practical Organic Chemistry, 5th","author":"Furniss B. S.","year":"1989"},{"key":"e_1_2_7_71_1","unstructured":"OECD Product Properties Test Guidelines OPPTS 830.7550 Partition Coefficient (n-Octanol\/Water) Shake Flask Method."},{"key":"e_1_2_7_72_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2016.04.004"},{"key":"e_1_2_7_73_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b01224"}],"container-title":["ChemPlusChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcplu.201800651","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.201800651","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cplu.201800651","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cplu.201800651","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T16:43:52Z","timestamp":1760373832000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cplu.201800651"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3]]},"references-count":73,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2019,3]]}},"alternative-id":["10.1002\/cplu.201800651"],"URL":"https:\/\/doi.org\/10.1002\/cplu.201800651","archive":["Portico"],"relation":{},"ISSN":["2192-6506","2192-6506"],"issn-type":[{"value":"2192-6506","type":"print"},{"value":"2192-6506","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3]]},"assertion":[{"value":"2018-12-14","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-03-05","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}