{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T18:58:08Z","timestamp":1790708288439,"version":"4.1.0"},"reference-count":31,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2025,6,19]],"date-time":"2025-06-19T00:00:00Z","timestamp":1750291200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001809","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":[[2025,10]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:title>BACKGROUND<\/jats:title><jats:p>3\u2010(Pyridin\u20102\u2010yl)benzothiazol\u20102\u2010one derivatives are a novel class of protoporphyrinogen oxidase (PPO) inhibitors. Although they demonstrate extraordinary herbicidal activity against broadleaf weeds, their efficacy against grass weeds remains limited. To develop broad\u2010spectrum herbicide candidates, a series of 3\u2010(pyridin\u20102\u2010yl)benzothiazol\u20102\u2010one derivatives bearing acylalanine moiety were designed in this study.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>Using a hybridization\u2010substructure\u2010combination strategy, the active groups of acylalanine fungicides were incorporated into the 3\u2010(pyridin\u20102\u2010yl)benzothiazol\u20102\u2010one scaffold. Starting from benzothiazol\u20102\u2010one, 20 title compounds were synthesized <jats:italic>via<\/jats:italic> aromatic nucleophilic substitution, nitration, reduction, <jats:italic>N<\/jats:italic>\u2010alkylation and acylation successively. The herbicidal activities of these compounds against <jats:italic>Echinochloa crus\u2010galli<\/jats:italic> and <jats:italic>Portulaca oleracea<\/jats:italic> were preliminarily evaluated by Petri dish assays. Additionally, the post\u2010emergence herbicidal activity of the most potent compounds, <jats:bold>I\u201009<\/jats:bold> and <jats:bold>I\u201013<\/jats:bold>, was further assessed against multiple weed species in greenhouse pot experiments. Compound <jats:bold>I\u201009<\/jats:bold> demonstrated 100% post\u2010emergence herbicidal efficacy against broadleaf weeds (<jats:italic>Solanum nigrum; Capsella bursa\u2010pastoris; Descurainia sophia; Veronica polita<\/jats:italic>) at an application rate of 75\u2009g a.i.\/ha. Structure\u2013activity relationship (SAR) analysis revealed that the herbicidal activity was determined by the synergistic effects of substituents on the pyridine ring and side chains attached to the aniline moiety. The 3\u2010fluoro\u20105\u2010trifluoromethyl\u2010pyridine group was identified as the optimal substitution pattern at the 3\u2010position of benzothiazol\u20102\u2010one, and the simultaneous introduction of ethyl acetyl and propionyl groups was found to be essential for maintaining activity.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>A new class of acylalanine\u2010containing 3\u2010(pyridin\u20102\u2010yl)benzothiazol\u20102\u2010one derivatives was discovered as promising candidates for herbicides. We hope these findings will provide valuable information for the development of herbicides. \u00a9 2025 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.70003","type":"journal-article","created":{"date-parts":[[2025,6,20]],"date-time":"2025-06-20T00:24:45Z","timestamp":1750379085000},"page":"6455-6463","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis and herbicidal activities of acylalanine\u2010containing 3\u2010(pyridin\u22122\u2010yl)benzothiazol\u20102\u2010ones"],"prefix":"10.1002","volume":"81","author":[{"ORCID":"https:\/\/orcid.org\/0009-0006-6291-5742","authenticated-orcid":false,"given":"Xiao","family":"Yu","sequence":"first","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mengnan","family":"Ren","sequence":"additional","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yanrong","family":"Li","sequence":"additional","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Juan","family":"He","sequence":"additional","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0202-7966","authenticated-orcid":false,"given":"Shaopeng","family":"Wei","sequence":"additional","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"},{"name":"Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1257-9238","authenticated-orcid":false,"given":"Zhiqin","family":"Ji","sequence":"additional","affiliation":[{"name":"College of Plant Protection, Northwest A&amp;F University  Yangling China"},{"name":"Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education College of Plant Protection, Northwest A&amp;F University  Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,6,19]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1017\/wet.2022.88"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1017\/S0021859605005708"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1186\/s13765-022-00734-6"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2007.09.042"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/etc.5620181007"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pestbp.2025.106312"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.6800"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.RA118.003441"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/minf.201600008"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c07411"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2020.115959"},{"key":"e_1_2_7_13_1","unstructured":"HagaT NaganoE SatoRandMoritaK Benzothiazolones and Their Production and Use(1987)."},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1017\/wsc.2023.15"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf200616y"},{"key":"e_1_2_7_16_1","first-page":"382","article-title":"Target\u2010site mutations conferring herbicide resistance","volume":"8","author":"Murphy BP","year":"2019","journal-title":"Plan Theory"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1584\/jpestics.J16-06"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/bkcs.12205"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4744"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy13061595"},{"key":"e_1_2_7_21_1","unstructured":"HagaT NaganoE SatoRandMoritaK Preparation and testing of 6\u2010fluorobenzothiazol\u20102\u2010ones useful as herbicides. 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