{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T15:56:09Z","timestamp":1791302169831,"version":"4.1.0"},"reference-count":47,"publisher":"American Chemical Society (ACS)","issue":"39","license":[{"start":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T00:00:00Z","timestamp":1790035200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006087","name":"Direcci?n General de Asuntos del Personal Acad?mico, Universidad Nacional Aut?noma de M?xico","doi-asserted-by":"publisher","award":["PAPIIT UNAM IN228226"],"award-info":[{"award-number":["PAPIIT UNAM IN228226"]}],"id":[{"id":"10.13039\/501100006087","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100013395","name":"Sistema Nacional de Investigadores","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100013395","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,10,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The development of potent synthetic antifungal agents for plants is an ongoing challenge of modern chemistry that impacts biological, medicinal and environmental sciences. Herein, a concise Structure\u2013Activity Relationship (SAR) model involving seven synthetic azidopyrazoles toward three pathogens of agricultural products and ornamental plants: Fusarium oxysporum, Rhizoctonia sp., and Alternaria alternata is described. The set of azidopyrazoles 1\u20137 includes a central fragment of 3-azido-1H-pyrazole substitutes in different positions of the ring (5-substituted, R = H, 1; R = \u2212CH3, 2; R = \u2013Ph, 3; R = \u2013PhOCH3, 5; 4-substituted, R = \u2013Ph, 4; R = \u2013(4-Cl-Ph), 6) and 3-substituted 5-azido-1H-pyrazole (R = thiophene, 7) which are prepared via a high-yielding (&amp;gt;85%), one-step synthesis from commercial cheap aminopyrazoles. Compounds 3 and 7 showed the greatest inhibition with IC50 values of 26.52 \u00b1 1.14 and 26.75 \u00b1 1.36 \u03bcg\/mL for F. oxysporum; 18.63 \u00b1 1.08 and 14.39 \u00b1 1.09 \u03bcg\/mL for Rhizoctonia sp.; and 15.53 \u00b1 1.14 and 21.02 \u00b1 1.37 \u03bcg\/mL for A. alternata. SAR analysis revealed that aryl substitution at C5 increased markedly the antifungal potency. In contrast, unsubstituted and alkyl-substituted pyrazoles (1, 2) had low activity. Combining 3 with Ag-nanoparticles (NPs) doubled its efficacy only against Rhizoctonia sp. (AgNPs, 10 nm, 100 ng\/mL). From IC50 = 18.63 \u00b1 1.08 to 9.65 \u00b1 1.38 \u03bcg\/mL). Molecular docking with MEP36 supported these results: compound 3 had the highest binding affinity (\u22126.8 kcal\/mol) due to \u03c0\u2013alkyl interaction with Val274 residue. Furthermore, root mean square deviation analyses confirmed the tight binding mode.<\/jats:p>","DOI":"10.1021\/acsomega.6c07653","type":"journal-article","created":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T22:01:50Z","timestamp":1790114510000},"page":"60170-60183","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis, SAR\nAnalysis, and Antifungal Potency against\nPlant Pathogenic Fungi of New Azidopyrazoles"],"prefix":"10.1021","volume":"11","author":[{"given":"Daniel","family":"Canseco-Gonza\u0301lez","sequence":"first","affiliation":[{"name":"Universidad Auto\u0301noma Chapingo , , , ,","place":["Texcoco de Mora, Me\u0301xico, CP 56230"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rosa E.","family":"Sa\u0301nchez-Ferna\u0301ndez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma Chapingo , , , ,","place":["Texcoco de Mora, Me\u0301xico, CP 56230"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elizabeth","family":"Navarro-Cero\u0301n","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma Chapingo , , , ,","place":["Texcoco de Mora, Me\u0301xico, CP 56230"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephania","family":"Olivares-Sa\u0301nchez","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma Chapingo , , , ,","place":["Texcoco de Mora, Me\u0301xico, CP 56230"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alejandro O.","family":"Viviano-Posadas","sequence":"additional","affiliation":[{"name":"Universidad Nacional Auto\u0301noma de Me\u0301xico , , Circuito Exterior, Ciudad Universitaria , CDMX ,","place":["Me\u0301xico, Me\u0301xico, CP 04510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7056-4237","authenticated-orcid":true,"given":"Alejandro","family":"Dorazco-Gonza\u0301lez","sequence":"additional","affiliation":[{"name":"Universidad Nacional Auto\u0301noma de Me\u0301xico , , Circuito Exterior, Ciudad Universitaria , CDMX ,","place":["Me\u0301xico, Me\u0301xico, CP 04510"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ricardo","family":"Parra-Unda","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de Sinaloa , , , ,","place":["Culiaca\u0301n, Sinaloa, Me\u0301xico, CP 80013"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gilmar","family":"Lo\u0301pez-Armenta","sequence":"additional","affiliation":[{"name":"Universidad Auto\u0301noma de Sinaloa , , , ,","place":["Culiaca\u0301n, Sinaloa, Me\u0301xico, CP 80013"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Adria\u0301n L.","family":"Orjuela","sequence":"additional","affiliation":[{"name":"Instituto de Investigaciones Cienti\u0301ficas y Servicios de Alta Tecnologi\u0301a (INDICASAT AIP) ,","place":["Panama\u0301 City, Panama\u0301, 0801"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1354-8713","authenticated-orcid":true,"given":"Jorge","family":"Ali\u0301-Torres","sequence":"additional","affiliation":[{"name":"Universidad Nacional de Colombia - Sede Bogota\u0301 , , ,","place":["Bogota, Colombia, 111321"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,22]]},"reference":[{"issue":"2","key":"2026100610480210900_cit1","doi-asserted-by":"publisher","first-page":"297","DOI":"10.1021\/cr00084a001","article-title":"Azides: their preparation and synthetic uses","volume":"88","author":"Scriven","year":"1988","journal-title":"Chem. 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In  Theoretical sudy of\nthe Aza-Wittig reaction, Me3P = NR (R = methyl or phenyl) with aldehyde\nusing the DFT and DFT-D methods; The 24th International Electronic\nConference on Synthetic Organic Chemistry MDPI, 2021; p 4710.3390\/ecsoc-24-08349."},{"key":"2026100610480210900_cit5","doi-asserted-by":"publisher","DOI":"10.1016\/j.cej.2023.141689","article-title":"Azido azole-1,3,4-triazine\nfused energetic materials: A bioinspired strategy for tuning thermal\nstability and sensitivity of metal-free primary explosives via hierarchical\nhydrogen-bond self-assembly","volume":"459","author":"Yang","year":"2023","journal-title":"Chem. Eng. J."},{"issue":"33","key":"2026100610480210900_cit6","doi-asserted-by":"publisher","first-page":"5188","DOI":"10.1002\/anie.200400657","article-title":"Organic azides: an exploding diversity\nof a unique class of compounds","volume":"44","author":"Bra\u0308se","year":"2005","journal-title":"Angew. Chem.\nInt. 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