{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T02:05:04Z","timestamp":1790820304939,"version":"4.1.0"},"reference-count":61,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,10]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Fungal and oomycete phytopathogens account for 10%\u201320% of annual global crop losses, and the escalating resistance to synthetic fungicides has intensified demand for plant\u2010derived alternatives. The essential oil (EO) of\n                    <jats:italic>Clinopodium nepeta<\/jats:italic>\n                    (L.) Kuntze, obtained by hydrodistillation from aerial parts harvested in northeastern Morocco, was profiled by gas chromatography\u2013mass spectrometry (GC\u2013MS) and evaluated for antifungal and anti\u2010oomycete activity against\n                    <jats:italic>Verticillium dahliae<\/jats:italic>\n                    ,\n                    <jats:italic>Phytophthora infestans<\/jats:italic>\n                    , and\n                    <jats:italic>Macrophomina phaseolina<\/jats:italic>\n                    using broth microdilution minimum inhibitory concentration (MIC) assays. The EO was dominated by two oxygenated monoterpene ketones, pulegone (42.16%) and menthone (41.43%), which were additionally evaluated as isolated compounds. The whole EO yielded MIC values of 31.25\u00a0\u00b5g\/mL (\n                    <jats:italic>P. infestans<\/jats:italic>\n                    ), 62.5\u00a0\u00b5g\/mL (\n                    <jats:italic>V. dahliae<\/jats:italic>\n                    ), and 125\u00a0\u00b5g\/mL (\n                    <jats:italic>M. phaseolina<\/jats:italic>\n                    ). Both isolated constituents outperformed the native matrix by 2\u2010 to 16\u2010fold, revealing antagonistic interactions within the complex EO. Pulegone showed superior activity against\n                    <jats:italic>V. dahliae<\/jats:italic>\n                    and\n                    <jats:italic>P. infestans<\/jats:italic>\n                    , while menthone was more potent against\n                    <jats:italic>M. phaseolina<\/jats:italic>\n                    , a selectivity pattern consistent with the greater electrophilic reactivity of pulegone's \u03b1,\u03b2\u2010unsaturated ketone (Michael acceptor) moiety. These findings identify pulegone and menthone as priority biopesticide candidates, pending formulation optimization, in planta validation, and toxicological assessment of pulegone under field\u2010exposure conditions. Because the GC\u2013MS analysis was performed on an achiral stationary phase, the enantiomeric composition of the oil was not determined; its constituents are therefore reported without stereodescriptors, and the compounds assayed as isolated agents were the commercial reference standards (R)\u2010(+)\u2010pulegone and (2S,5R)\u2010(\u2212)\u2010menthone. The structure\u2013activity relationship described here is consequently constitutional rather than configurational.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71781","type":"journal-article","created":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T01:37:20Z","timestamp":1790818640000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["<i>Clinopodium nepeta<\/i>\n                    Essential Oil and Its Major Constituents Pulegone and Menthone: Composition and Activity Against\n                    <i>Verticillium dahliae<\/i>\n                    ,\n                    <i>Phytophthora infestans<\/i>\n                    , and\n                    <i>Macrophomina phaseolina<\/i>"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5682-3538","authenticated-orcid":false,"given":"Mohamed","family":"Taibi","sequence":"first","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0314-8484","authenticated-orcid":false,"given":"Amine","family":"Elbouzidi","sequence":"additional","affiliation":[{"name":"Laboratoire d'Am\u00e9lioration des Productions Agricoles, Biotechnologie et Ecophysiologie (LAPABE), Facult\u00e9 des Sciences Universit\u00e9 Mohammed Premier  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-4366-843X","authenticated-orcid":false,"given":"Mounir","family":"Haddou","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-5814-9929","authenticated-orcid":false,"given":"Abdessamad","family":"Beraich","sequence":"additional","affiliation":[{"name":"Physical Chemistry of Natural Resources and Process Team, Laboratory of Applied Chemistry and Environment (LCAE) Faculty of Sciences, Mohammed First University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7483-6738","authenticated-orcid":false,"given":"Abdellah","family":"Baraich","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Reda","family":"Bellaouchi","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3973-6694","authenticated-orcid":false,"given":"Mohamed","family":"Addi","sequence":"additional","affiliation":[{"name":"Laboratoire d'Am\u00e9lioration des Productions Agricoles, Biotechnologie et Ecophysiologie (LAPABE), Facult\u00e9 des Sciences Universit\u00e9 Mohammed Premier  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Khalid","family":"Chaabane","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5182-7353","authenticated-orcid":false,"given":"Bassem","family":"Jaouadi","sequence":"additional","affiliation":[{"name":"Laboratoire des Biotechnologies Microbiennes et Enzymatiques et Biomol\u00e9cules (LBMEB) Centre de Biotechnologie de Sfax (CBS), Universit\u00e9 de Sfax (USF)  Sfax Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nadia","family":"Zarai","sequence":"additional","affiliation":[{"name":"Laboratoire des Biotechnologies Microbiennes et Enzymatiques et Biomol\u00e9cules (LBMEB) Centre de Biotechnologie de Sfax (CBS), Universit\u00e9 de Sfax (USF)  Sfax Tunisia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bouchra El","family":"Guerrouj","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5195-8217","authenticated-orcid":false,"given":"Abdeslam","family":"Asehraou","sequence":"additional","affiliation":[{"name":"Laboratory of Bioresources, Biotechnology, and Sustainable Development (L2BD), Faculty of Sciences Mohammed Premier University  Oujda Morocco"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1017\/S0021859605005708"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1111\/srt.70191"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.3390\/pathogens11020273"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants15020239"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1093\/jxb\/eraa444"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cropro.2019.01.012"},{"key":"e_1_2_10_8_1","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1007\/s12571-021-01141-3","article-title":"Pathogens Which Threaten Food Security: Phytophthora infestans, the Potato Late Blight Pathogen","volume":"13","author":"Yuen J.","year":"2021","journal-title":"Food Security"},{"key":"e_1_2_10_9_1","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1038\/s41579-025-01248-w","article-title":"Oomycete Plant Pathogens: Biology, Pathogenesis and Emerging Control Strategies","volume":"24","author":"Wang Y.","year":"2026","journal-title":"Nature Reviews Microbiology"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.1007\/s10570\u2010020\u201003362\u20109"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1111\/avj.70054"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.3390\/jof10030171"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1094\/PDIS\u201012\u201023\u20102798\u2010PDN"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2021.634397"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/bs.aambs.2014.09.001"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1094\/PHYTO\u201010\u201022\u20100370\u2010KD"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1094\/PHYTO\u201005\u201015\u20100129\u2010R"},{"key":"e_1_2_10_18_1","unstructured":"J. C.Williams \u201cNew EU Pesticide Legislation\u2010the View of a Manufacturer \u201dinProceedings of the Crop Protection in Northern Britain 2012 (The Dundee Conference) 28\u201329 February 2012 (2012) 7\u201314."},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1093\/erae\/jbab016"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.3389\/fsufs.2025.1504001"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants12040706"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2025.1588462"},{"key":"e_1_2_10_23_1","doi-asserted-by":"crossref","first-page":"1144","DOI":"10.3390\/biom13071144","article-title":"Essential Oils: Chemistry and Pharmacological Activities","volume":"13","author":"De Sousa D. P.","year":"2023","journal-title":"Biomolecules"},{"key":"e_1_2_10_24_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules25030678"},{"key":"e_1_2_10_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/ffj.3165"},{"key":"e_1_2_10_26_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules22010070"},{"key":"e_1_2_10_27_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11356\u2010017\u20101008\u20109"},{"key":"e_1_2_10_28_1","doi-asserted-by":"publisher","DOI":"10.3390\/medicines3040025"},{"key":"e_1_2_10_29_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants12244098"},{"key":"e_1_2_10_30_1","doi-asserted-by":"publisher","DOI":"10.7275\/jmap.2034"},{"key":"e_1_2_10_31_1","doi-asserted-by":"crossref","first-page":"2137","DOI":"10.3390\/molecules25092137","article-title":"Chemical Composition, Antifungal and Insecticidal Activities of the Essential Oils From Tunisian Clinopodium nepeta Subsp. Nepeta and Clinopodium nepeta Subsp. Glandulosum","volume":"25","author":"Debbabi H.","year":"2020","journal-title":"Molecules"},{"key":"e_1_2_10_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202403372"},{"key":"e_1_2_10_33_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0003\u20109861(03)00390\u20104"},{"key":"e_1_2_10_34_1","doi-asserted-by":"publisher","DOI":"10.7717\/peerj.14914"},{"key":"e_1_2_10_35_1","doi-asserted-by":"crossref","first-page":"105","DOI":"10.1186\/s13568-025-01911-8","article-title":"Expediting Multiple Biological Properties of Main Bioactive Compounds of Mentha pulegium L","volume":"15","author":"El Omari N.","year":"2025","journal-title":"AMB Express"},{"key":"e_1_2_10_36_1","doi-asserted-by":"crossref","first-page":"290","DOI":"10.3390\/molecules22020290","article-title":"Savi and Its Main Essential Oil Constituent Pulegone: Biological Activities and Chemistry","volume":"22","author":"Bo\u017eovi\u0107 M.","year":"2017","journal-title":"Molecules"},{"key":"e_1_2_10_37_1","first-page":"16","article-title":"Pulegone: An Emerging Oxygenated Cyclic Monoterpene Ketone Scaffold Delineating Synthesis, Chemical Reactivity, and Biological Potential","volume":"18","author":"Dhingra A. K.","year":"2023","journal-title":"Recent Advances in Anti\u2010Infective Drug Discovery Formerly Recent Patents on Anti\u2010Infective Drug Discovery"},{"key":"e_1_2_10_38_1","doi-asserted-by":"publisher","DOI":"10.3389\/fphar.2022.1033003"},{"key":"e_1_2_10_39_1","doi-asserted-by":"publisher","DOI":"10.3390\/ijms21051558"},{"key":"e_1_2_10_40_1","doi-asserted-by":"publisher","DOI":"10.5650\/jos.ess23031"},{"key":"e_1_2_10_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pestbp.2019.05.008"},{"key":"e_1_2_10_42_1","doi-asserted-by":"publisher","DOI":"10.2174\/1871530323666230914103731"},{"key":"e_1_2_10_43_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbdv.202502486"},{"key":"e_1_2_10_44_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11356\u2010017\u20109991\u20104"},{"key":"e_1_2_10_45_1","doi-asserted-by":"publisher","DOI":"10.1007\/s11356\u2010023\u201029270\u20106"},{"key":"e_1_2_10_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/fsn3.71671"},{"key":"e_1_2_10_47_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1472\u2010765X.2008.02407.x"},{"key":"e_1_2_10_48_1","doi-asserted-by":"publisher","DOI":"10.1590\/0037\u20108682\u20100190\u20102016"},{"key":"e_1_2_10_49_1","doi-asserted-by":"publisher","DOI":"10.1111\/jam.14740"},{"key":"e_1_2_10_50_1","doi-asserted-by":"publisher","DOI":"10.1128\/mBio.01755\u201018"},{"key":"e_1_2_10_51_1","doi-asserted-by":"publisher","DOI":"10.3109\/00498259209051869"},{"key":"e_1_2_10_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx00011a013"},{"key":"e_1_2_10_53_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chemphyslip.2016.05.002"},{"key":"e_1_2_10_54_1","doi-asserted-by":"publisher","DOI":"10.1128\/MMBR.00010\u201015"},{"key":"e_1_2_10_55_1","doi-asserted-by":"publisher","DOI":"10.3390\/jof9121162"},{"key":"e_1_2_10_56_1","doi-asserted-by":"publisher","DOI":"10.1111\/mmi.13262"},{"key":"e_1_2_10_57_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201909803"},{"key":"e_1_2_10_58_1","first-page":"e02084","article-title":"Superoxide Initiates the Hyphal Differentiation to Microsclerotia Formation of Macrophomina phaseolina","volume":"10","author":"Liu H.\u2010H.","year":"2022","journal-title":"Microbiology Spectrum"},{"key":"e_1_2_10_59_1","doi-asserted-by":"crossref","first-page":"571","DOI":"10.1016\/S1572-5995(00)80014-9","article-title":"Biological Activity of Essential Oils and Their Constituents","volume":"21","author":"Nakatsu T.","year":"2000","journal-title":"Studies in Natural Products Chemistry"},{"key":"e_1_2_10_60_1","doi-asserted-by":"publisher","DOI":"10.3390\/foods11030464"},{"key":"e_1_2_10_61_1","first-page":"298","article-title":"Pulegone and Menthofuran in Flavourings\u2010Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact With Food (AFC)","volume":"6","author":"(EFSA), E.F.S.A","year":"2008","journal-title":"EFSA Journal"},{"key":"e_1_2_10_62_1","doi-asserted-by":"publisher","DOI":"10.3390\/foods13182906"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71781","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.71781","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71781","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T01:37:24Z","timestamp":1790818644000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.71781"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,30]]},"references-count":61,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2026,10]]}},"alternative-id":["10.1002\/cbdv.71781"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.71781","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,30]]},"assertion":[{"value":"2026-06-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-21","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71781"}}