{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T09:18:11Z","timestamp":1788254291086,"version":"build-2803163510"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"33","license":[{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T00:00:00Z","timestamp":1786665600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["32402427"],"award-info":[{"award-number":["32402427"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100015401","name":"Key Research and Development Projects of Shaanxi Province","doi-asserted-by":"publisher","award":["2024SF2-GJHX-60"],"award-info":[{"award-number":["2024SF2-GJHX-60"]}],"id":[{"id":"10.13039\/501100015401","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>A series of 30 novel \u03b1-methylene-\u03b3-butyrolactone (MBL) derivatives were designed and synthesized. Bioassays revealed that several compounds exhibited potent fungicidal activities against Valsa mali, Rhizoctonia solani, and Phytophthora capsici. A25 showed the highest activity against V. mali (EC50 = 0.70 mg\/L). Against R. solani, A5 (EC50 = 0.94 mg\/L) and A21 (EC50 = 0.69 mg\/L) were highly active. Against P. capsici, A14 (EC50 = 0.69 mg\/L), A21 (EC50 = 0.59 mg\/L), and A24 (EC50 = 0.71 mg\/L) displayed potent antioomycete activity. At 200 mg\/L, A21 provided protective (88.9%) and curative (67.0%) effects in potted rice against R. solani as well as protective (91.0%) and curative (85.4%) effects on pepper plants against P. capsici. Mechanistic studies indicated that A21 blocks ATP synthesis and impairs energy metabolism. Toxicity assessment showed that A21 was nontoxic to earthworms and silkworms at the tested concentrations. This work provides insights for developing MBL derivatives as potential fungicides.<\/jats:p>","DOI":"10.1021\/acs.jafc.6c06097","type":"journal-article","created":{"date-parts":[[2026,8,14]],"date-time":"2026-08-14T17:02:56Z","timestamp":1786726976000},"page":"26017-26030","source":"Crossref","is-referenced-by-count":0,"title":["Design, Synthesis,\nand Fungicidal Activity of Novel\n\u03b1-Methylene-\u03b3-Butyrolactone Derivatives Bearing\nBenzofuran-2-yl Moiety"],"prefix":"10.1021","volume":"74","author":[{"given":"Deyou","family":"Yang","sequence":"first","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Heng","family":"Li","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiaying","family":"Xu","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luwei","family":"Li","sequence":"additional","affiliation":[{"name":"Yangling Agriculture Technology Industry Group Co., Ltd , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4358-8740","authenticated-orcid":true,"given":"He","family":"Yan","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1685-9517","authenticated-orcid":true,"given":"Peng","family":"Lei","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8052-4258","authenticated-orcid":true,"given":"Yong","family":"Wang","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiqing","family":"Ma","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4217-5549","authenticated-orcid":true,"given":"Xingyu","family":"Ren","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5320-1178","authenticated-orcid":true,"given":"Juntao","family":"Feng","sequence":"additional","affiliation":[{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]},{"name":"Northwest A&F University , , , ,","place":["Yangling, Shaanxi, China, 712100"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,14]]},"reference":[{"issue":"6390","key":"2026090104465955100_cit1","doi-asserted-by":"publisher","first-page":"739","DOI":"10.1126\/science.aap7999","article-title":"Worldwide emergence\nof resistance to antifungal drugs challenges human health and food\nsecurity","volume":"360","author":"Fisher","year":"2018","journal-title":"Science."},{"issue":"6","key":"2026090104465955100_cit2","doi-asserted-by":"publisher","first-page":"332","DOI":"10.1038\/s43016-020-0075-0","article-title":"Threats to global food security from\nemerging fungal and oomycete\ncrop pathogens","volume":"1","author":"Fones","year":"2020","journal-title":"Nat. Food."},{"issue":"6","key":"2026090104465955100_cit3","doi-asserted-by":"publisher","first-page":"1353","DOI":"10.1111\/mpp.12619","article-title":"The feruloyl\nesterase genes are required for full pathogenicity of the apple tree\ncanker pathogen Valsa mali","volume":"19","author":"Xu","year":"2018","journal-title":"Mol. Plant Pathol."},{"key":"2026090104465955100_cit4","doi-asserted-by":"publisher","first-page":"59","DOI":"10.1016\/j.pestbp.2019.05.014","article-title":"Antifungal activity\nof zedoary turmeric oil against Phytophthora capsici through damaging cell membrane","volume":"159","author":"Wang","year":"2019","journal-title":"Pestic. Biochem. Physiol."},{"key":"2026090104465955100_cit5","doi-asserted-by":"publisher","first-page":"128","DOI":"10.1016\/j.plaphy.2021.05.045","article-title":"Role of silicon in elevating\nresistance against sheath\nblight and blast diseases in rice (Oryza sativa L.)","volume":"166","author":"Sathe","year":"2021","journal-title":"Plant Physiol. Biochem."},{"issue":"5","key":"2026090104465955100_cit6","doi-asserted-by":"publisher","first-page":"1387","DOI":"10.1007\/s00425-019-03246-8","article-title":"Sheath blight of rice:\na review and identification of priorities for future research","volume":"250","author":"Singh","year":"2019","journal-title":"Planta."},{"issue":"12","key":"2026090104465955100_cit7","doi-asserted-by":"publisher","first-page":"5407","DOI":"10.1002\/ps.6580","article-title":"Discovery of zeylenone from Uvaria grandiflora as\na potential botanical fungicide","volume":"77","author":"He","year":"2021","journal-title":"Pest Manag.\nSci."},{"key":"2026090104465955100_cit8","doi-asserted-by":"publisher","first-page":"941527","DOI":"10.3389\/fnut.2022.941527","article-title":"Insight into\nthe incredible effects of microwave heating: Driving changes in the\nstructure, properties and functions of macromolecular nutrients in\nnovel food","volume":"9","author":"Deng","year":"2022","journal-title":"Front. Nutr."},{"issue":"6","key":"2026090104465955100_cit9","doi-asserted-by":"publisher","first-page":"1495","DOI":"10.1111\/ppa.14126","article-title":"Epigenetic\nRegulation of Fungicide Resistance in Plant-Pathogenic Fungi","volume":"74","author":"Kumar","year":"2025","journal-title":"Plant Pathol."},{"issue":"2","key":"2026090104465955100_cit10","doi-asserted-by":"publisher","first-page":"399","DOI":"10.1002\/ps.6653","article-title":"Impact of natural products\non discovery of, and innovation\nin, crop protection compounds","volume":"78","author":"Sparks","year":"2022","journal-title":"Pest Manag. Sci."},{"issue":"2","key":"2026090104465955100_cit11","doi-asserted-by":"publisher","first-page":"111","DOI":"10.1038\/nrd4510","article-title":"The re-emergence of natural products\nfor drug discovery in the genomics era","volume":"14","author":"Harvey","year":"2015","journal-title":"Nat.\nRev. Drug Discovery"},{"issue":"9","key":"2026090104465955100_cit12","doi-asserted-by":"publisher","first-page":"2325","DOI":"10.1002\/ps.5433","article-title":"Pesticidal\nnatural products - status and future potential","volume":"75","author":"Marrone","year":"2019","journal-title":"Pest Manag. Sci."},{"key":"2026090104465955100_cit13","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1016\/j.cbpa.2018.12.007","article-title":"Natural product derived\nprivileged scaffolds in drug\ndiscovery","volume":"52","author":"Davison","year":"2019","journal-title":"Curr. Opin. Chem. Biol."},{"issue":"1","key":"2026090104465955100_cit14","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1021\/acs.jafc.7b03913","article-title":"Mitochondrial Signs\nand Subcellular Imaging Provide Insight into\nthe Antifungal Mechanism of Carabrone against Gaeumannomyces graminis var. tritici","volume":"66","author":"Wang","year":"2018","journal-title":"J. Agric. Food. Chem."},{"issue":"9","key":"2026090104465955100_cit15","doi-asserted-by":"publisher","first-page":"6485","DOI":"10.3390\/molecules15096485","article-title":"Synthesis\nand Antifungal Activity of Carabrone Derivatives","volume":"15","author":"Feng","year":"2010","journal-title":"Molecules."},{"issue":"3","key":"2026090104465955100_cit16","doi-asserted-by":"publisher","first-page":"4257","DOI":"10.3390\/ijms15034257","article-title":"Synthesis, Antifungal Activities\nand Qualitative Structure Activity\nRelationship of Carabrone Hydrazone Derivatives as Potential Antifungal\nAgents","volume":"15","author":"Wang","year":"2014","journal-title":"Int. J. Mol. Sci."},{"issue":"1","key":"2026090104465955100_cit17","doi-asserted-by":"publisher","first-page":"147","DOI":"10.3987\/COM-11-12349","article-title":"Lignan derivatives\nfrom the leaves of Nicotiana tabacum and their biological\nactivities","volume":"85","author":"Gao","year":"2012","journal-title":"Heterocycles."},{"issue":"33","key":"2026090104465955100_cit18","doi-asserted-by":"publisher","first-page":"10316","DOI":"10.1021\/acs.jafc.2c03632","article-title":"Discovery of Novel \u03b1-Methylene-\u03b3-Butyrolactone\nDerivatives Containing Vanillin Moieties as Antiviral and Antifungal\nAgents","volume":"70","author":"He","year":"2022","journal-title":"J. Agric. Food. Chem."},{"issue":"12","key":"2026090104465955100_cit19","doi-asserted-by":"publisher","first-page":"5015","DOI":"10.1002\/ps.7703","article-title":"Discovery\nof novel salicylaldehyde derivatives incorporating an \u03b1-methylene-\u03b3-butyrolactone moiety as fungicidal\nagents","volume":"79","author":"He","year":"2023","journal-title":"Pest Manag. Sci."},{"issue":"16","key":"2026090104465955100_cit20","doi-asserted-by":"publisher","first-page":"9521","DOI":"10.1021\/acs.jafc.4c11005","article-title":"Discovery of \u03b1-Methylene-\u03b3-Butyrolactone\nDerivatives with Hydrazide Moieties as Novel Fungicidal\nAgents","volume":"73","author":"Wang","year":"2025","journal-title":"J. Agric. Food. Chem."},{"issue":"8","key":"2026090104465955100_cit21","doi-asserted-by":"publisher","first-page":"3776","DOI":"10.1002\/ps.8080","article-title":"Design, synthesis and antifungal\nactivity of novel \u03b1-methylene-\u03b3-butyrolactone derivatives containing benzothiophene moiety","volume":"80","author":"Li","year":"2024","journal-title":"Pest Manag. Sci."},{"issue":"1","key":"2026090104465955100_cit22","doi-asserted-by":"publisher","first-page":"147","DOI":"10.1021\/acs.jafc.4c07402","article-title":"Design, Synthesis,\nand Fungicidal Activity of \u03b1-Methylene-\u03b3-Butyrolactone\nDerivatives Bearing a Diphenyl Ether Moiety","volume":"73","author":"Chen","year":"2025","journal-title":"J. Agric. Food. Chem."},{"issue":"29","key":"2026090104465955100_cit23","doi-asserted-by":"publisher","first-page":"11008","DOI":"10.1021\/acs.jafc.3c02117","article-title":"Heterocycle-Substituted \u03b1-Methylene-\u03b3-Butyrolactone\nDerivatives Synthesis, Antifungal\nActivity, and 3D-QSAR","volume":"71","author":"Li","year":"2023","journal-title":"J. Agric. Food. Chem."},{"issue":"12","key":"2026090104465955100_cit24","doi-asserted-by":"publisher","first-page":"e202401955","DOI":"10.1002\/cbdv.202401955","article-title":"Natural \u03b1-Methylene-\u03b3-Butyrolactone\nAnalogues: Synthesis and Evaluation\nof Isoaurone Derivatives as Antifungal Agents","volume":"21","author":"Li","year":"2024","journal-title":"Chem. Biodivers."},{"issue":"47","key":"2026090104465955100_cit25","doi-asserted-by":"publisher","first-page":"18087","DOI":"10.1021\/acs.jafc.3c00765","article-title":"Applications\nof Bioisosteres in the Design of Biologically Active Compounds","volume":"71","author":"Meanwell","year":"2023","journal-title":"J. Agric. Food. Chem."},{"issue":"36","key":"2026090104465955100_cit26","doi-asserted-by":"publisher","first-page":"11075","DOI":"10.1021\/acs.jafc.1c07910","article-title":"A Competitive\nEdge: Competitor Inspired Scaffold Hopping in Herbicide Lead Optimization","volume":"70","author":"Barber","year":"2022","journal-title":"J. Agric. Food. Chem."},{"key":"2026090104465955100_cit27","doi-asserted-by":"publisher","first-page":"104183","DOI":"10.1016\/j.bioorg.2020.104183","article-title":"\u03b2,\u03b3-Diaryl \u03b1-methylene-\u03b3-butyrolactones\nas potent antibacterials against methicillin-resistant Staphylococcus aureus","volume":"104","author":"Hamann","year":"2020","journal-title":"Bioorg. Chem."},{"issue":"9","key":"2026090104465955100_cit28","doi-asserted-by":"publisher","first-page":"1539","DOI":"10.1002\/adsc.201000122","article-title":"A General\nApproach to the Synthesis of (\u03b22-Amino Acid Derivatives via Highly Efficient Catalytic Asymmetric Hydrogenation\nof \u03b1-Aminomethylacrylates","volume":"352","author":"Guo","year":"2010","journal-title":"Adv. Synth. Catal."},{"issue":"15","key":"2026090104465955100_cit29","doi-asserted-by":"publisher","first-page":"4393","DOI":"10.1016\/j.bmcl.2013.05.073","article-title":"New antifungal\nscaffold derived from a natural pharmacophore: Synthesis of \u03b1-methylene-\u03b3-butyrolactone\nderivatives and their antifungal activity against Colletotrichum lagenarium","volume":"23","author":"Jun-Tao","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"issue":"1","key":"2026090104465955100_cit30","doi-asserted-by":"publisher","first-page":"491","DOI":"10.1021\/acs.jafc.0c06700","article-title":"Bioactivity-Guided Synthesis Accelerates the Discovery of 3-(Iso)quinolinyl-4-chromenones\nas Potent Fungicide Candidates","volume":"69","author":"Wang","year":"2021","journal-title":"J. Agric. Food.\nChem."},{"issue":"2","key":"2026090104465955100_cit31","doi-asserted-by":"publisher","first-page":"1693","DOI":"10.1002\/ps.70315","article-title":"Design, synthesis,\nand antifungal activity of novel pogostone-based derivatives containing\namide active moieties","volume":"82","author":"Dong","year":"2026","journal-title":"Pest Manag. Sci."},{"issue":"46","key":"2026090104465955100_cit32","doi-asserted-by":"publisher","first-page":"17700","DOI":"10.1021\/acs.jafc.3c04869","article-title":"Discovery of Novel\nPyrazol-5-yl-benzamide Derivatives\nContaining a Thiocyanato Group as Broad-Spectrum Fungicidal Candidates","volume":"71","author":"Li","year":"2023","journal-title":"J. Agric. Food. Chem."},{"issue":"15","key":"2026090104465955100_cit33","doi-asserted-by":"publisher","first-page":"4582","DOI":"10.1021\/acs.jafc.1c07879","article-title":"Indole\/Tetrahydroquinoline\nas Renewable Natural ResourceInspired Scaffolds in the Devising and\nPreparation of Potential Fungicide Candidates","volume":"70","author":"Wang","year":"2022","journal-title":"J. Agric. Food. Chem."},{"issue":"37","key":"2026090104465955100_cit34","doi-asserted-by":"publisher","first-page":"10448","DOI":"10.1021\/acs.jafc.9b02951","article-title":"Oxidative\nStress and Apoptosis of Gaeumannomyces graminis (Get) Induced by Carabrone","volume":"67","author":"Wang","year":"2019","journal-title":"J. Agric.\nFood. Chem."},{"issue":"16","key":"2026090104465955100_cit35","doi-asserted-by":"publisher","first-page":"6249","DOI":"10.1021\/acs.jafc.2c09144","article-title":"Design, Synthesis,\nand Antifungal\/Antioomycete Activity of Thiohydantoin Analogues Containing\nSpirocyclic Butenolide","volume":"71","author":"Li","year":"2023","journal-title":"J. Agric. Food. Chem."},{"issue":"11","key":"2026090104465955100_cit36","doi-asserted-by":"publisher","first-page":"1542","DOI":"10.1002\/cbic.201200295","article-title":"Rieske Iron-Sulfur\nProtein of the Cytochrome bc1 Complex:\nA Potential Target for Fungicide Discovery","volume":"13","author":"Yang","year":"2012","journal-title":"Chembiochem."},{"issue":"10","key":"2026090104465955100_cit37","doi-asserted-by":"publisher","first-page":"2774","DOI":"10.1021\/acs.jafc.8b06195","article-title":"Natural Product Neopeltolide as a\nCytochrome bc1 Complex Inhibitor: Mechanism\nof Action and Structural Modification","volume":"67","author":"Zhu","year":"2019","journal-title":"J. Agric.\nFood. Chem."},{"key":"2026090104465955100_cit38","doi-asserted-by":"publisher","first-page":"110461","DOI":"10.1016\/j.ijfoodmicro.2023.110461","article-title":"Natural terpene-based\nderivatives to control postharvest\nsclerotinia rot and the involved potential mechanism","volume":"409","author":"Ye","year":"2024","journal-title":"Int. J. Food Microbiol."},{"key":"2026090104465955100_cit39","doi-asserted-by":"publisher","first-page":"114310","DOI":"10.1016\/j.indcrop.2021.114310","article-title":"Inhibition efficacy of Tetradium glabrifolium fruit essential oil against Phytophthora capsici and potential mechanism","volume":"176","author":"Wang","year":"2022","journal-title":"Ind.\nCrop. Prod."},{"issue":"5","key":"2026090104465955100_cit40","doi-asserted-by":"publisher","first-page":"704","DOI":"10.2174\/138161282005140214163327","article-title":"Structural\nBasis of Resistance to Anti-Cytochrome bc1 Complex Inhibitors: Implication for Drug\nImprovement","volume":"20","author":"Esser","year":"2014","journal-title":"Curr. Pharm. Design."}],"container-title":["Journal of Agricultural\nand Food Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.jafc.6c06097","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/33\/26017\/66554923\/acs.jafc.6c06097.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/jafcau\/article-pdf\/74\/33\/26017\/66554923\/acs.jafc.6c06097.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,1]],"date-time":"2026-09-01T08:47:24Z","timestamp":1788252444000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/jafcau\/article\/74\/33\/26017\/5256019\/Design-Synthesis-and-Fungicidal-Activity-of-Novel"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,14]]},"references-count":40,"journal-issue":{"issue":"33","published-online":{"date-parts":[[2026,8,14]]},"published-print":{"date-parts":[[2026,8,26]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.jafc.6c06097","relation":{},"ISSN":["0021-8561","1520-5118"],"issn-type":[{"value":"0021-8561","type":"print"},{"value":"1520-5118","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,14]]}}}