{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,9]],"date-time":"2026-07-09T14:17:33Z","timestamp":1783606653858,"version":"3.55.0"},"reference-count":29,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2021,5,14]],"date-time":"2021-05-14T00:00:00Z","timestamp":1620950400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Key R&amp;D Program of China","award":["2017YFD0200903"],"award-info":[{"award-number":["2017YFD0200903"]}]},{"DOI":"10.13039\/501100004001","name":"Science and Technology Foundation of Guizhou Province","doi-asserted-by":"publisher","award":["ZK[2021]137"],"award-info":[{"award-number":["ZK[2021]137"]}],"id":[{"id":"10.13039\/501100004001","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Kaili University Doctoral Program","award":["BS201811"],"award-info":[{"award-number":["BS201811"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of novel thiochromanone derivatives containing a sulfonyl hydrazone moiety were designed and synthesized. Their structures were determined by 1H-NMR, 13C-NMR, and HRMS. Bioassay results showed that most of the target compounds revealed moderate to good antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri. Compound 4i had the best inhibitory activity against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri, with the EC50 values of 8.67, 12.65, and 10.62 \u03bcg\/mL, which were superior to those of Bismerthiazol and Thiodiazole-copper. Meanwhile, bioassay results showed that all of the target compounds proved to have lower antifungal activities against Sclerotinia sclerotiorum, Fusarium oxysporum, Gibberella zeae, Rhizoctonia solani, Verticillium dahlia, and Botrytis cinerea than those of Carbendazim.<\/jats:p>","DOI":"10.3390\/molecules26102925","type":"journal-article","created":{"date-parts":[[2021,5,14]],"date-time":"2021-05-14T10:54:22Z","timestamp":1620989662000},"page":"2925","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation"],"prefix":"10.3390","volume":"26","author":[{"given":"Lu","family":"Yu","sequence":"first","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jiyan","family":"Chi","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lingling","family":"Xiao","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jie","family":"Li","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhangfei","family":"Tang","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuming","family":"Tan","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7276-6337","authenticated-orcid":false,"given":"Pei","family":"Li","sequence":"additional","affiliation":[{"name":"School of Liquor and Food Engineering, Guizhou University, Guiyang 550025, China"},{"name":"Qiandongnan Engineering and Technology Research Center for Comprehensive Utilization of National Medicine, Kaili University, Kaili 556011, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,5,14]]},"reference":[{"key":"ref_1","first-page":"1479","article-title":"An overview of fungal and bacterial biopesticides to control plant pathogens\/diseases","volume":"8","author":"Bhattacharjee","year":"2014","journal-title":"Afr. J. Microbiol. Res."},{"key":"ref_2","first-page":"71","article-title":"Agronanotechnology for plant fungal disease management: A review","volume":"3","author":"Patel","year":"2014","journal-title":"Int. J. Curr. Microbiol. App. Sci."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"465","DOI":"10.1039\/np9860300465","article-title":"Chromanols, chromanones, and chromones","volume":"3","author":"Saengchantara","year":"1986","journal-title":"Nat. Prod. Rep."},{"key":"ref_4","first-page":"622","article-title":"Synthesis and antifungal activity of 3-substituted-benzylidene-6,7-methylenedioxy-4-chromanone","volume":"15","author":"Wang","year":"2013","journal-title":"Chin. J. Pest. Sci."},{"key":"ref_5","first-page":"481","article-title":"Recent advances in the research of chromone and thiochromone derivatives as antifungal agents","volume":"36","author":"Yu","year":"2011","journal-title":"Chin. J. Antibiot."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1549","DOI":"10.1080\/00397911.2011.647222","article-title":"Convenient one-pot synthesis of chromone derivatives and their antifungal and antibacterial evaluation","volume":"43","author":"Mugisha","year":"2013","journal-title":"Synth. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2508","DOI":"10.1021\/acs.jnatprod.0c00587","article-title":"Synthesis and antifungal activity of chromones and benzoxepines from the leaves of Ptaeroxylon Obliq","volume":"83","author":"Malefo","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"347","DOI":"10.1016\/j.bioorg.2018.11.054","article-title":"The synthesis and anticancer activities of chiral epoxy-substituted chromone analogs","volume":"84","author":"Jo","year":"2019","journal-title":"Bioorg. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"126945","DOI":"10.1016\/j.bmcl.2019.126945","article-title":"Design, synthesis and anti-TMV activities of novel chromone derivatives containing dithioacetal moiety","volume":"30","author":"Li","year":"2020","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"575","DOI":"10.1016\/j.apsb.2012.10.005","article-title":"Synthesis and antiviral activities of a novel class of thioflavone and flavonoid analogues","volume":"2","author":"Zhang","year":"2012","journal-title":"Acta Pharm. Sin. B"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"2417","DOI":"10.1002\/jhet.2838","article-title":"Synthesis, antimicrobial activity and molecular docking study of thiazole derivatives","volume":"54","author":"Farghaly","year":"2017","journal-title":"J. Heterocycl. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"3808","DOI":"10.1016\/j.bmc.2016.06.025","article-title":"An expeditious four-component domino protocol for the synthesis of novel thiazolo[3,2-a]thiochromeno[4,3-d]pyrimidine derivatives as antibacterial and antibiofilm agents","volume":"24","author":"Suresh","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1037","DOI":"10.6023\/cjoc201808016","article-title":"Design, synthesis, and antifungal activity of novel thiochromanone derivatives containing 1,3,4-oxadiazole skeleton","volume":"39","author":"Sun","year":"2019","journal-title":"Chin. J. Org. Chem."},{"key":"ref_14","first-page":"1518","article-title":"Synthesis, antifungal activity and molecular docking of (E)-3-(((1,3,4-thiadiazol-2-yl)amino)methylene)-thiochroman-4-ones","volume":"53","author":"Li","year":"2018","journal-title":"Acta Pharm. Sin."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2455","DOI":"10.1007\/s11696-017-0239-z","article-title":"Design, synthesis and antifungal activity of novel selenochroman-4-one derivatives","volume":"71","author":"Xu","year":"2017","journal-title":"Chem. Pap."},{"key":"ref_16","unstructured":"Ichiro, N., Mitsuru, S., Masashi, S., and Kazuyoshi, K. (1994). Preparation of 4-(6-Thiochromancarbonyl) Pyrazole Derivatives as Herbicides. (WO 9401431), PCT Int. Appl."},{"key":"ref_17","unstructured":"Szucs, S.S. (2001). Thiono-thiochroman and -dihydrobenzothiophene Compounds as Herbicidal Agents. (WO 2001029033), PCT International Application."},{"key":"ref_18","unstructured":"Steiner, G., Schmidt, T., Kordes, M., Von Deyn, W., Hofmann, M., Baumann, E., Puhl, M., Heffernan, G., Culbertson, D.L., and Treacy, M.F. (2004). Amino-Substituted Benzo(hetero)cyclic Derivatives, particularly 1-alkyl-4-benzo(hetero)Cyclicsubstituted Piperazines, Useful as Insecticides, Acaricides, and Nematocides, and their Preparation, Uses, and Compositions. (WO 2004080170), PCT International Application."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"813","DOI":"10.1016\/j.bmc.2013.12.010","article-title":"Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones","volume":"22","author":"Neumann","year":"2014","journal-title":"Bioorg. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1067","DOI":"10.1016\/j.ejmech.2004.07.005","article-title":"Synthesis and antifungal activity of cholesterol-hydrazone derivatives","volume":"39","author":"Loncle","year":"2004","journal-title":"Eur. J. Med. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2128","DOI":"10.1002\/jhet.3932","article-title":"Discovery of a new fungicide by screening triazole sulfonylhydrazone derivatives and its downy mildew inhibition in cucumber","volume":"57","author":"Li","year":"2020","journal-title":"J. Heterocycl. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1016\/j.jphotobiol.2013.12.002","article-title":"Screening of novel chemical compounds as possible inhibitors of carbonic anhydrase and photosynthetic activity of photosystem II","volume":"137","author":"Karacan","year":"2014","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"3255","DOI":"10.1007\/s00044-013-0907-7","article-title":"Synthesis, characterization, electrochemical behavior, and antimicrobial activities of aromatic\/heteroaromatic sulfonylhydrazone derivatives","volume":"23","author":"Gunduzalp","year":"2014","journal-title":"Med. Chem. Res."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1021\/jm00180a010","article-title":"Synthesis and antineoplastic activity of phenyl-substituted benzenesulfonylhydrazones of 2-pyridinecarboxaldehyde 1-oxide","volume":"23","author":"Loh","year":"1980","journal-title":"J. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2513","DOI":"10.1021\/jm502018y","article-title":"Design and optimization of a series of 1-sulfonylpyrazolo[4,3-b]pyridines as selective c-met inhibitors","volume":"58","author":"Ma","year":"2015","journal-title":"J. Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"7677","DOI":"10.1016\/j.bmc.2007.08.062","article-title":"Synthesis, biological evaluation and molecular modeling of sulfonohydrazides as selective PI3K p110a inhibitors","volume":"15","author":"Kendall","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2621","DOI":"10.1016\/j.bmcl.2014.04.074","article-title":"Synthesis and insecticidal activity of novel hydrazone compounds derived from a naturally occurring lignan podophyllotoxin against Mythimna separata (Walker)","volume":"24","author":"Wang","year":"2014","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_28","first-page":"449","article-title":"An improved infiltration technique to test the pathogenicity of Xanthomonas oryzae pv. oryzae in rice seedlings","volume":"24","author":"Schaad","year":"1996","journal-title":"Seed Sci. Technol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2129","DOI":"10.1021\/jf052792s","article-title":"Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones","volume":"54","author":"Tarun","year":"2006","journal-title":"J. Agric. Food Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/10\/2925\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T06:00:53Z","timestamp":1760162453000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/10\/2925"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,5,14]]},"references-count":29,"journal-issue":{"issue":"10","published-online":{"date-parts":[[2021,5]]}},"alternative-id":["molecules26102925"],"URL":"https:\/\/doi.org\/10.3390\/molecules26102925","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,5,14]]}}}