{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,29]],"date-time":"2025-10-29T06:24:40Z","timestamp":1761719080600,"version":"build-2065373602"},"reference-count":53,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2021,9,30]],"date-time":"2021-09-30T00:00:00Z","timestamp":1632960000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001870","name":"Fundacja na rzecz Nauki Polskiej","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001870","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008530","name":"European Regional Development Fund","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100008530","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100000780","name":"European Commission","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100000780","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001870","name":"Fundacja na rzecz Nauki Polskiej","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001870","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004281","name":"Narodowe Centrum Nauki","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100004281","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Pest Management Science"],"published-print":{"date-parts":[[2022,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:title>BACKGROUND<\/jats:title><jats:p>Development of new plant protection strategies has become an urgent matter in modern agriculture, in view of the evidently proved negative effect of currently used active ingredients of pesticides. In recent years, much effort has been made to eliminate the use of pesticides established to be toxic to pollinators.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>In this study, we present a group of new bifunctional ionic liquids based on dodine (<jats:italic>N<\/jats:italic>\u2010dodecylguanidine) cation whose physical and biological properties have been modified relative to those of the commercially available <jats:italic>N<\/jats:italic>\u2010dodecylguanidine acetate. The decreased level of residue of active substances in plant tissues reduces their availability to pollinators, which increases the safety of their use. Moreover, lower environmental impact in combination with high antifungal activity and an additional biological function, that is the systemic acquired resistance induction, are in line with the goals of sustainable agriculture.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>The presented approach shows the possibility of derivatization of commonly used fungicide into the form of bifunctional salts whose physical and biological properties can be easily modified. The paper reports successful design and synthesis of new sustainable and green chemicals for the modern agriculture, being less toxic to the environment and human health but still effective against pathogens. \u00a9 2021 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.6639","type":"journal-article","created":{"date-parts":[[2021,9,10]],"date-time":"2021-09-10T00:12:03Z","timestamp":1631232723000},"page":"446-455","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Synthesis, characterization and biological activity of bifunctional ionic liquids based on dodine ion"],"prefix":"10.1002","volume":"78","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1073-496X","authenticated-orcid":false,"given":"Rafal","family":"Kukawka","sequence":"first","affiliation":[{"name":"Innosil Sp. z o.o  Rubiez 46 Poznan 61\u2010612 Poland"},{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0681-5433","authenticated-orcid":false,"given":"Maciej","family":"Spychalski","sequence":"additional","affiliation":[{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1369-8164","authenticated-orcid":false,"given":"Ewa","family":"Str\u00f3\u017cyk","sequence":"additional","affiliation":[{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5912-6391","authenticated-orcid":false,"given":"Ewa","family":"Byzia","sequence":"additional","affiliation":[{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5861-0037","authenticated-orcid":false,"given":"Adrian","family":"Zajac","sequence":"additional","affiliation":[{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3511-752X","authenticated-orcid":false,"given":"Piotr","family":"Kaczy\u0144ski","sequence":"additional","affiliation":[{"name":"Plant Protection Institute \u2013 National Research Institute, Laboratory of Pesticide Residues  Che\u0142mo\u0144skiego 22 Bialystok 15\u2010195 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2760-3333","authenticated-orcid":false,"given":"Bo\u017cena","family":"\u0141ozowicka","sequence":"additional","affiliation":[{"name":"Plant Protection Institute \u2013 National Research Institute, Laboratory of Pesticide Residues  Che\u0142mo\u0144skiego 22 Bialystok 15\u2010195 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6769-8931","authenticated-orcid":false,"given":"Henryk","family":"Pospieszny","sequence":"additional","affiliation":[{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"},{"name":"Plant Protection Institute \u2013 National Research Institute, Department of Virology and Bacteriology  W\u0119gorka 20 Poznan 60\u2010318 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4444-5354","authenticated-orcid":false,"given":"Marcin","family":"Smiglak","sequence":"additional","affiliation":[{"name":"Innosil Sp. z o.o  Rubiez 46 Poznan 61\u2010612 Poland"},{"name":"Poznan Science and Technology Park, Adam Mickiewicz University Foundation  Rubiez 46 Poznan 61\u2010612 Poland"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2021,9,30]]},"reference":[{"key":"e_1_2_10_2_1","unstructured":"World apple output declines grape production flat USDA reports. Available:https:\/\/fruitgrowersnews.com\/news\/world-apple-output-declines-grape-production-flat-usda-reports\/[12 April 2021]"},{"key":"e_1_2_10_3_1","first-page":"1","article-title":"Critical review on apple scab (Venturia inaequalis) biology, epidemiology, economic importance, management and defense mechanisms to the causal agent","volume":"5","author":"Belete T","year":"2017","journal-title":"J Plant Physiol Pathol"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.17660\/ActaHortic.2007.737.14"},{"key":"e_1_2_10_5_1","first-page":"283","article-title":"An overview of apple scab, its cause and management strategies","volume":"4","author":"Shafi SM","year":"2019","journal-title":"EC Microbiol"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy10040581"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.14199\/ppp-2016-009"},{"key":"e_1_2_10_8_1","first-page":"886","article-title":"Tolerance of the apple scab fungus to benzimidazole fungicides","volume":"58","author":"Wicks T","year":"1974","journal-title":"Plant Dis Rep"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13592-016-0429-7"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0094482"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0009754"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(10)60274-7"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0155411"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1603\/0022-0493-99.2.253"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1051\/apido\/2010014"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2018.09.102"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1051\/apido\/2010018"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1080\/00218839.2017.1304878"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.31421\/IJHS\/5\/1-2\/33"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2019.01.016"},{"key":"e_1_2_10_21_1","doi-asserted-by":"crossref","unstructured":"KumarG SinghSandNagarajaiahRPK Detailed review on Pesticidal toxicity to honey bees and its Management in Modern Beekeeping in ed. byRanzRER.IntechOpen (2020).https:\/\/doi.org\/10.5772\/intechopen.91196.","DOI":"10.5772\/intechopen.91196"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1111\/1365-2435.13119"},{"key":"e_1_2_10_23_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1022575315413"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.2903\/j.efsa.2010.1631"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1039\/b706677p"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.langmuir.9b00759"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molliq.2019.03.061"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA02475A"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)02070-X"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c02894"},{"key":"e_1_2_10_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c00632"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8NJ00778K"},{"key":"e_1_2_10_33_1","doi-asserted-by":"crossref","unstructured":"Feder\u2010kubisJ CzerwoniecP LewandowskiP PospiesznyHandSmiglakM Ionic liquids with natural origin component: a path to new plant protection products.8:842\u2013852(2020).https:\/\/doi.org\/10.1021\/acssuschemeng.9b04859.","DOI":"10.1021\/acssuschemeng.9b04859"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0RA09136G"},{"key":"e_1_2_10_35_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b00161"},{"key":"e_1_2_10_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.6b00398"},{"key":"e_1_2_10_37_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8GC01424H"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev.phyto.42.040803.140421"},{"key":"e_1_2_10_39_1","doi-asserted-by":"publisher","DOI":"10.1039\/c3nj01613g"},{"key":"e_1_2_10_40_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-9063(199708)50:4<275::AID-PS593>3.0.CO;2-7"},{"key":"e_1_2_10_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/0045-6535(95)00103-F"},{"key":"e_1_2_10_42_1","doi-asserted-by":"publisher","DOI":"10.1038\/447917a"},{"volume-title":"Fungicides, Multisite Inhibitors\u2014Broad Spectrum Surface Protectants Encyclopedia of Agrochemical","year":"2003","author":"Uesugi Y","key":"e_1_2_10_43_1"},{"key":"e_1_2_10_44_1","unstructured":"Label of plant protection product Syllit_65_WP from the website of the Polish Ministry of Agriculture and Rural Development. Available:https:\/\/www.google.com\/url?sa=t&rct=j&q=&esrc=s&source=web&cd=&ved=2ahUKEwiksNuD5LLwAhVBl4sKHdk9C_QQFjAAegQIBhAD&url=https%3A%2F%2Fwww.gov.pl%2Fdocuments%2F912055%2F913531%2FSyllit_65_WP_zast.prof.pdf%2F1c2c211f\u2010611b\u2010f654\u2010ac6a\u2010bc9822d6951e%3Fversion%3D1.0&usg=AOvVaw2sGakpNnPyni2v2ZODxiXV[5 September 2021]"},{"key":"e_1_2_10_45_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.04.108"},{"key":"e_1_2_10_46_1","doi-asserted-by":"publisher","DOI":"10.2903\/j.efsa.2013.3077"},{"key":"e_1_2_10_47_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pestbp.2013.10.003"},{"key":"e_1_2_10_48_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2018.11.470"},{"key":"e_1_2_10_49_1","doi-asserted-by":"publisher","DOI":"10.21005\/asp.2019.18.3.03"},{"key":"e_1_2_10_50_1","doi-asserted-by":"publisher","DOI":"10.1051\/apido:2005043"},{"key":"e_1_2_10_51_1","doi-asserted-by":"publisher","DOI":"10.1080\/17429140903291012"},{"key":"e_1_2_10_52_1","doi-asserted-by":"publisher","DOI":"10.1105\/tpc.12.11.2175"},{"key":"e_1_2_10_53_1","doi-asserted-by":"publisher","DOI":"10.12691\/ajmr-4-5-5"},{"key":"e_1_2_10_54_1","first-page":"322","article-title":"Effect of salicylic acid and salinity in rosemary (Rosmarinus officinalis L.): investigation on changes in gas exchange, water relations, and membrane stabilization","volume":"3","author":"Najafian S","year":"2009","journal-title":"Adv Environ"}],"container-title":["Pest Management Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ps.6639","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ps.6639","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ps.6639","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T14:46:26Z","timestamp":1761057986000},"score":1,"resource":{"primary":{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/10.1002\/ps.6639"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,9,30]]},"references-count":53,"journal-issue":{"issue":"2","published-print":{"date-parts":[[2022,2]]}},"alternative-id":["10.1002\/ps.6639"],"URL":"https:\/\/doi.org\/10.1002\/ps.6639","archive":["Portico"],"relation":{},"ISSN":["1526-498X","1526-4998"],"issn-type":[{"type":"print","value":"1526-498X"},{"type":"electronic","value":"1526-4998"}],"subject":[],"published":{"date-parts":[[2021,9,30]]},"assertion":[{"value":"2021-06-10","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-09-09","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2021-09-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}