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Although organotin compounds were effective antifoulants since the 1960s, they were banned in 2008 due to their toxicity to marine life. Although tin\u2010free alternatives have been developed, they also raise environmental concerns. This underscores the need for effective, nontoxic antifouling agents. We previously synthesized <jats:italic>N<\/jats:italic>\u2010(4\u2010aminobutyl)propylamine (xylemin) and its structural analogs. In this study, we assayed the antifouling activity and toxicity of xylemin, its structural analogs, and related polyamines toward cypris larvae of the barnacle <jats:italic>Amphibalanus amphitrite<\/jats:italic>. Xylemin and its Boc\u2010protected analog exhibited antifouling activities with 50% effective concentrations (EC<jats:sub>50<\/jats:sub>) of 4.25 and 6.11\u00a0\u00b5g\/mL, respectively. Four xylemin analogs did not show a settlement\u2010inhibitory effect at a concentration of 50\u00a0\u00b5g\/mL. Putrescine, spermidine, spermine, and thermospermine, which are xylemin\u2010related polyamines, did not display antifoulant effects (EC<jats:sub>50<\/jats:sub>\u00a0&gt;\u00a050\u00a0\u00b5g\/mL). All evaluated compounds were nontoxic at a concentration of 50\u00a0\u00b5g\/mL. These findings indicate that the size and structure of the <jats:italic>N<\/jats:italic>\u2010alkyl group are essential for the antifouling activity of xylemin. Therefore, xylemin and its analogs hold promise as nontoxic, eco\u2010friendly antifouling agents, offering a sustainable solution to biofouling in marine environments.<\/jats:p>","DOI":"10.1002\/cbdv.202403213","type":"journal-article","created":{"date-parts":[[2025,2,11]],"date-time":"2025-02-11T05:23:50Z","timestamp":1739251430000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":3,"title":["Antifouling Activity of Xylemin, Its Structural Analogs, and Related Polyamines"],"prefix":"10.1002","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8330-969X","authenticated-orcid":false,"given":"Hiroyoshi","family":"Takamura","sequence":"first","affiliation":[{"name":"Department of Chemistry, Graduate School of Natural Science and Technology Okayama University  Okayama Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0320-0350","authenticated-orcid":false,"given":"Takefumi","family":"Yorisue","sequence":"additional","affiliation":[{"name":"Institute of Natural and Environmental Sciences University of Hyogo  Sanda Japan"},{"name":"Division of Nature and Environmental Management Museum of Nature and Human Activities  Sanda Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8253-3561","authenticated-orcid":false,"given":"Kenta","family":"Tanaka","sequence":"additional","affiliation":[{"name":"Research Institute for Interdisciplinary Science Okayama University  Okayama Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Isao","family":"Kadota","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Graduate School of Natural Science and Technology Okayama University  Okayama Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2025,2,18]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.porgcoat.2003.06.001"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr200350v"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2024.153638"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2020.144469"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.1080\/08927014.2012.700478"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8SM01853G"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.1080\/08927010903016543"},{"key":"e_1_2_9_9_1","doi-asserted-by":"publisher","DOI":"10.3390\/md18070371"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.marpolbul.2011.01.012"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.21022"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.5194\/os-14-661-2018"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jclepro.2019.118724"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.apcatb.2017.07.074"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1111\/lam.13032"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.oceaneng.2015.04.070"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/aoc.396"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jenvman.2008.08.017"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.marchem.2019.04.001"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11270-019-4361-0"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.marpolbul.2016.11.047"},{"key":"e_1_2_9_22_1","first-page":"1210","article-title":"Marine Natural Products as Antifouling Molecules \u2013 a Mini\u2010Review (2014\u20132020)","volume":"36","author":"Liu L.\u2010L.","year":"2020","journal-title":"Biofouling"},{"key":"e_1_2_9_23_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00425-008-0772-7"},{"key":"e_1_2_9_24_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.biocel.2009.07.009"},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1093\/aob\/mcp259"},{"key":"e_1_2_9_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202000322"},{"key":"e_1_2_9_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/D2OB02203F"},{"key":"e_1_2_9_28_1","doi-asserted-by":"publisher","DOI":"10.1039\/D4OB00698D"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(96)00025-1"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep21487"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00340-8"}],"container-title":["Chemistry &amp; 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