{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,22]],"date-time":"2026-09-22T19:36:01Z","timestamp":1790105761867,"version":"4.0.1"},"reference-count":31,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2024,1,5]],"date-time":"2024-01-05T00:00:00Z","timestamp":1704412800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["32302417"],"award-info":[{"award-number":["32302417"]}]},{"name":"National Natural Science Foundation of China","award":["KF202310"],"award-info":[{"award-number":["KF202310"]}]},{"name":"National Natural Science Foundation of China","award":["2023AFB287"],"award-info":[{"award-number":["2023AFB287"]}]},{"name":"National Natural Science Foundation of China","award":["2022M710917"],"award-info":[{"award-number":["2022M710917"]}]},{"name":"Open Fund of Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education","award":["32302417"],"award-info":[{"award-number":["32302417"]}]},{"name":"Open Fund of Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education","award":["KF202310"],"award-info":[{"award-number":["KF202310"]}]},{"name":"Open Fund of Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education","award":["2023AFB287"],"award-info":[{"award-number":["2023AFB287"]}]},{"name":"Open Fund of Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education","award":["2022M710917"],"award-info":[{"award-number":["2022M710917"]}]},{"name":"Nature Science Foundation of Hubei Province","award":["32302417"],"award-info":[{"award-number":["32302417"]}]},{"name":"Nature Science Foundation of Hubei Province","award":["KF202310"],"award-info":[{"award-number":["KF202310"]}]},{"name":"Nature Science Foundation of Hubei Province","award":["2023AFB287"],"award-info":[{"award-number":["2023AFB287"]}]},{"name":"Nature Science Foundation of Hubei Province","award":["2022M710917"],"award-info":[{"award-number":["2022M710917"]}]},{"name":"China Postdoctoral Science Foundation","award":["32302417"],"award-info":[{"award-number":["32302417"]}]},{"name":"China Postdoctoral Science Foundation","award":["KF202310"],"award-info":[{"award-number":["KF202310"]}]},{"name":"China Postdoctoral Science Foundation","award":["2023AFB287"],"award-info":[{"award-number":["2023AFB287"]}]},{"name":"China Postdoctoral Science Foundation","award":["2022M710917"],"award-info":[{"award-number":["2022M710917"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>To effectively control the infection of plant pathogens, we designed and synthesized a series of phenylthiazole derivatives containing a 1,3,4-thiadiazole thione moiety and screened for their antibacterial potencies against Ralstonia solanacearum, Xanthomonas oryzae pv. oryzae, as well as their antifungal potencies against Sclerotinia sclerotiorum, Rhizoctonia solani, Magnaporthe oryzae and Colletotrichum gloeosporioides. The chemical structures of the target compounds were characterized by 1H NMR, 13C NMR and HRMS. The bioassay results revealed that all the tested compounds exhibited moderate-to-excellent antibacterial and antifungal activities against six plant pathogens. Especially, compound 5k possessed the most remarkable antibacterial activity against R. solanacearum (EC50 = 2.23 \u03bcg\/mL), which was significantly superior to that of compound E1 (EC50 = 69.87 \u03bcg\/mL) and the commercial agent Thiodiazole copper (EC50 = 52.01 \u03bcg\/mL). Meanwhile, compound 5b displayed the most excellent antifungal activity against S. sclerotiorum (EC50 = 0.51 \u03bcg\/mL), which was equivalent to that of the commercial fungicide Carbendazim (EC50 = 0.57 \u03bcg\/mL). The preliminary structure-activity relationship (SAR) results suggested that introducing an electron-withdrawing group at the meta-position and ortho-position of the benzene ring could endow the final structure with remarkable antibacterial and antifungal activity, respectively. The current results indicated that these compounds were capable of serving as promising lead compounds.<\/jats:p>","DOI":"10.3390\/molecules29020285","type":"journal-article","created":{"date-parts":[[2024,1,5]],"date-time":"2024-01-05T03:43:00Z","timestamp":1704426180000},"page":"285","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":22,"title":["Design, Synthesis, Antibacterial, and Antifungal Evaluation of Phenylthiazole Derivatives Containing a 1,3,4-Thiadiazole Thione Moiety"],"prefix":"10.3390","volume":"29","author":[{"given":"Guoqing","family":"Mao","sequence":"first","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yao","family":"Tian","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jinchao","family":"Shi","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Changzhou","family":"Liao","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiwei","family":"Huang","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yiran","family":"Wu","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhou","family":"Wen","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Linhua","family":"Yu","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiang","family":"Zhu","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"},{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junkai","family":"Li","sequence":"additional","affiliation":[{"name":"Engineering Research Center of Ecology and Agricultural Use of Wetland, Ministry of Education, Hubei Key Laboratory of Waterlogging Disaster and Agricultural Use of Wetland, College of Agriculture, Yangtze University, Jingzhou 434025, China"},{"name":"Institute of Pesticides, Yangtze University, Jingmi Road 88, Jingzhou 434025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,5]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Yu, L., Chi, J., Xiao, L., Li, J., Tang, Z., Tan, S., and Li, P. (2021). Novel thiochromanone derivatives containing a sulfonyl hydrazone moiety: Design, synthesis, and bioactivity evaluation. Molecules, 26.","DOI":"10.3390\/molecules26102925"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6125","DOI":"10.1021\/acs.jafc.9b00606","article-title":"Antifungal activity of griseofulvin derivatives against phytopathogenic fungi in vitro and in vivo and three-dimensional quantitative structure-activity relationship analysis","volume":"67","author":"Bai","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1036","DOI":"10.1021\/jf203772d","article-title":"Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety","volume":"60","author":"Xu","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"e449","DOI":"10.1002\/fes3.449","article-title":"Fluorinated or brominated meta-diamides as the new scaffolds for the treatment of rice bacterial leaf blight","volume":"12","author":"Guo","year":"2023","journal-title":"Food Energy Secur."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4294","DOI":"10.1016\/j.bmcl.2017.08.040","article-title":"Synthesis and biological evaluation of pyridinium-functionalized carbazole derivatives as promising antibacterial agents","volume":"27","author":"Wang","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Snigdha, M., and Prasath, D. (2021). Transcriptomic analysis to reveal the differentially expressed miRNA targets and their miRNAs in response to Ralstonia solanacearum in ginger species. BMC Plant Biol., 21.","DOI":"10.1186\/s12870-021-03108-0"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1221","DOI":"10.1094\/PDIS-10-13-1072-RE","article-title":"Dimethachlon resistance in Sclerotinia sclerotiorum in China","volume":"98","author":"Zhou","year":"2014","journal-title":"Plant Dis."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"114827","DOI":"10.1016\/j.envpol.2020.114827","article-title":"Enhancement and improvement of selenium in soil to the resistance of rape stem against Sclerotinia sclerotiorum and the inhibition of dissolved organic matter derived from rape straw on mycelium","volume":"265","author":"Cheng","year":"2020","journal-title":"Environ. Pollut."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"6803","DOI":"10.1021\/acs.jafc.2c08027","article-title":"Synthesis, structure\u2013activity relationship, and mechanism of a series of diarylhydrazide compounds as potential antifungal agents","volume":"71","author":"Liu","year":"2023","journal-title":"J. Agric. Food Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5529","DOI":"10.1002\/ps.6593","article-title":"Synthesis and fungicidal activity of novel benzimidazole derivatives bearing pyrimidine-thioether moiety against Botrytis cinerea","volume":"77","author":"Sun","year":"2021","journal-title":"Pest Manag. Sci."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"11804","DOI":"10.1021\/acs.jafc.1c03087","article-title":"Novel cinnamic acid derivatives containing the 1,3,4-oxadiazole moiety: Design, synthesis, antibacterial activities, and mechanisms","volume":"69","author":"Wang","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"508","DOI":"10.1016\/j.indcrop.2019.05.055","article-title":"Insecticidal and antifungal activities of Rheum palmatum L. anthraquinones and structurally related compounds","volume":"137","author":"Shang","year":"2019","journal-title":"Ind. Crops Prod."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"11340","DOI":"10.1021\/acs.jafc.9b04224","article-title":"Design, synthesis and antifungal evaluation of novel quinoline derivatives inspired from natural quinine alkaloids","volume":"67","author":"Yang","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Wang, S., Gan, X., Wang, Y., Li, S., Yi, C., Chen, J., He, F., Yang, Y., Hu, D., and Song, B. (2019). Novel 1,3,4-oxadiazole derivatives containing a cinnamic acid moiety as potential bactericide for rice bacterial diseases. Int. J. Mol. Sci., 20.","DOI":"10.3390\/ijms20051020"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"548","DOI":"10.1021\/np500929z","article-title":"Thiasporines A-C, thiazine and thiazole derivatives from a marine-derived Actinomycetospora chlora","volume":"78","author":"Fu","year":"2015","journal-title":"J. Nat. Prod."},{"key":"ref_16","doi-asserted-by":"crossref","unstructured":"Tian, Y., Shi, J., Deng, X., Yu, T., Hu, Y., Hu, R., Lei, Y., Yu, L., Zhu, X., and Li, J. (2023). Design, synthesis, and antifungal activity of some novel phenylthiazole derivatives containing an acylhydrazone moiet. Molecules, 28.","DOI":"10.3390\/molecules28207084"},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"3439","DOI":"10.1002\/ps.7481","article-title":"Design, synthesis and antifungal evaluation of phenylthiazole-1,3,4-oxadiazole thione (ketone) derivatives inspired by natural thiasporine A","volume":"79","author":"Shi","year":"2023","journal-title":"Pest Manag. Sci."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1021\/cr010123h","article-title":"Solid phase heterocyclic chemistry","volume":"102","author":"Krchnak","year":"2002","journal-title":"Chem. Rev."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4029","DOI":"10.1007\/s11164-021-04510-x","article-title":"W.; Lin, G.; Chen, M.; Lei, F. Synthesis, antifungal activity and 3D-QSAR study of novel nopol-based 1,3,4-thiadiazole\u2013thioether compounds","volume":"47","author":"Wang","year":"2021","journal-title":"Res. Chem. Intermed."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1203","DOI":"10.1016\/j.bmcl.2019.03.017","article-title":"Novel amide derivatives containing 1,3,4-thiadiazole moiety: Design, synthesis, nematocidal and antibacterial activities","volume":"29","author":"Chen","year":"2019","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3818","DOI":"10.1016\/j.bmcl.2016.04.094","article-title":"Synthesis and biological activities of novel 1,3,4-thiadiazole-containing pyrazole oxime derivatives","volume":"26","author":"Dai","year":"2016","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2644","DOI":"10.1080\/00397911.2021.1945106","article-title":"Design, synthesis and insecticidal activity of new 1,3,4-thiadiazole and 1,3,4-thiadiazolo[3,2-a] pyrimidine derivatives under solvent-free conditions","volume":"51","author":"Ismail","year":"2021","journal-title":"Synth. Commun."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4227","DOI":"10.5012\/bkcs.2011.32.12.4227","article-title":"Antimicrobial activity of newly synthesized 2,5-disubstituted 1,3,4-thiadiaozle derivatives","volume":"32","author":"Ramiz","year":"2011","journal-title":"Bull. Korean Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"844","DOI":"10.1002\/ps.4762","article-title":"Novel bisthioether derivatives containing a 1,3,4-oxadiazole moiety: Design, synthesis, antibacterial and nematocidal activities","volume":"74","author":"Li","year":"2018","journal-title":"Pest Manag. Sci."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"997","DOI":"10.1002\/ps.4080","article-title":"Photochemical degradation of bismerthiazol: Structural characterisation of the photoproducts and their inhibitory activities against Xanthomonas oryzae pv. oryzae","volume":"72","author":"Liang","year":"2016","journal-title":"Pest Manag. Sci."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"10018","DOI":"10.1021\/acs.jafc.9b04093","article-title":"Optimization, structure-activity relationship, and mode of action of nortopsentin analogues containing thiazole and oxazole moieties","volume":"67","author":"Guo","year":"2019","journal-title":"J. Agric. Food Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"352","DOI":"10.1016\/j.ejmech.2018.12.069","article-title":"Discovery of first-in-class thiazole-based dual FFA1\/PPAR\u03b4 agonists as potential anti-diabetic agents","volume":"164","author":"Li","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"2145","DOI":"10.1080\/14786419.2018.1489389","article-title":"Synthesis and fungicidal activity of 1,3,4-oxadiazol-2-yl thioether derivatives containing a phenazine-1-carboxylic acid scaffold","volume":"33","author":"Lu","year":"2019","journal-title":"Nat. Prod. Res."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"3981","DOI":"10.1016\/j.bmc.2007.04.014","article-title":"Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives","volume":"15","author":"Chen","year":"2007","journal-title":"Bioorg. Med. Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"15084","DOI":"10.1021\/acs.jafc.1c02144","article-title":"Synthesis, structural characterization, and antibacterial and antifungal activities of novel 1,2,4-triazole thioether and thiazolo[3,2-b]-1,2,4-triazole derivatives bearing the 6-fluoroquinazolinyl moiety","volume":"69","author":"Ding","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"11096","DOI":"10.1021\/acs.jafc.0c01322","article-title":"Design, synthesis, and antifungal evaluation of 8-hydroxyquinoline metal complexes against phytopathogenic fungi","volume":"68","author":"Yin","year":"2020","journal-title":"J. Agric. Food Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/2\/285\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:40:24Z","timestamp":1760103624000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/2\/285"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,5]]},"references-count":31,"journal-issue":{"issue":"2","published-online":{"date-parts":[[2024,1]]}},"alternative-id":["molecules29020285"],"URL":"https:\/\/doi.org\/10.3390\/molecules29020285","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,5]]}}}