{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,18]],"date-time":"2026-08-18T04:48:17Z","timestamp":1787028497226,"version":"build-2736575974"},"reference-count":39,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T00:00:00Z","timestamp":1675036800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Nature Science Foundation of China","doi-asserted-by":"publisher","award":["32072446"],"award-info":[{"award-number":["32072446"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Nature Science Foundation of China","doi-asserted-by":"publisher","award":["20192452"],"award-info":[{"award-number":["20192452"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Nature Science Foundation of China","doi-asserted-by":"publisher","award":["HZSKFKT202208"],"award-info":[{"award-number":["HZSKFKT202208"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Science Foundation of Guizhou Province","award":["32072446"],"award-info":[{"award-number":["32072446"]}]},{"name":"Science Foundation of Guizhou Province","award":["20192452"],"award-info":[{"award-number":["20192452"]}]},{"name":"Science Foundation of Guizhou Province","award":["HZSKFKT202208"],"award-info":[{"award-number":["HZSKFKT202208"]}]},{"name":"Key Laboratory of Institute of Environment and Plant Protection","award":["32072446"],"award-info":[{"award-number":["32072446"]}]},{"name":"Key Laboratory of Institute of Environment and Plant Protection","award":["20192452"],"award-info":[{"award-number":["20192452"]}]},{"name":"Key Laboratory of Institute of Environment and Plant Protection","award":["HZSKFKT202208"],"award-info":[{"award-number":["HZSKFKT202208"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Twenty 1,4-pentadiene-3-one derivatives containing quinazolinone (W1\u2013W20) were designed and synthesized. The bioactivity test results showed that some compounds had antifungal activities in vitro. W12 showed excellent bioactivity against Sclerotinia sclerotiorum (S. sclerotiorum) and Phomopsis sp., with EC50 values of 0.70 and 3.84 \u03bcg\/mL, which are higher than those of the control drug azoxystrobin at 8.15 and 17.25 \u03bcg\/mL. In vivo activity tests were carried out on oilseed rape and kiwifruit. The protective effect of W12 on oilseed rape infected with S. sclerotiorum (91.7 and 87.3%) was better than that of azoxystrobin (90.2 and 79.8%) at 100 and 50 \u03bcg\/mL, respectively, and the protective effect on kiwifruit infected with Phomopsis sp. (96.2%) was better than that of azoxystrobin (94.6%) at 200 \u03bcg\/mL. Scanning electron microscopy results showed the hyphae of S. sclerotiorum treated with compound W12 abnormally collapsed and shriveled, inhibiting the growth of mycelium and, thus, laying the inhibiting effect on S. sclerotiorum. The results of the mechanism research showed that the action of W12 changed the mycelial morphology of S. sclerotiorum, affected the permeability of cells, increased the leakage of cytoplasm and allowed the cell membrane to break down. This study shows that 1,4-pentadiene-3-one derivatives containing quinazolinone have good effects on plant fungi and the potential for becoming new fungicides.<\/jats:p>","DOI":"10.3390\/ijms24032599","type":"journal-article","created":{"date-parts":[[2023,1,30]],"date-time":"2023-01-30T04:58:25Z","timestamp":1675054705000},"page":"2599","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":26,"title":["Design, Synthesis and Antifungal Activity of Novel 1,4-Pentadiene-3-one Containing Quinazolinone"],"prefix":"10.3390","volume":"24","author":[{"given":"Ran","family":"Zhou","sequence":"first","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenliang","family":"Zhan","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chunmei","family":"Yuan","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tao","family":"Zhang","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Piao","family":"Mao","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhiling","family":"Sun","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yousan","family":"An","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4471-5414","authenticated-orcid":false,"given":"Wei","family":"Xue","sequence":"additional","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Center for R&D of Fine Chemicals of Guizhou University, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,1,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"89","DOI":"10.1146\/annurev.phyto.44.070505.143342","article-title":"Quantification and modeling of crop losses: A review of purposes","volume":"44","author":"Savary","year":"2006","journal-title":"Annu. Rev. Phytopathol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1021\/pr200873p","article-title":"Contribution of proteomics to the study of plant pathogenic fungi","volume":"11","year":"2012","journal-title":"J. Proteome Res."},{"key":"ref_3","first-page":"84","article-title":"Research Progress on Resistance Mechanism of Brassica napus to Sclerotinia sclerotiorum","volume":"29","author":"Li","year":"2015","journal-title":"Crop Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"819","DOI":"10.1094\/PHYTO-09-20-0421-R","article-title":"A Method for the Examination of SDHI Fungicide Resistance Mechanisms in Phytopathogenic Fungi Using a Heterologous Expression System in Sclerotinia sclerotiorum","volume":"111","author":"Peng","year":"2021","journal-title":"Phytopathology"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"661","DOI":"10.1016\/j.cj.2021.08.007","article-title":"Host-induced gene silencing of multiple pathogenic factors of Sclerotinia sclerotiorum confers resistance to Sclerotinia rot in Brassica napus","volume":"10","author":"Wu","year":"2022","journal-title":"Crop J."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1111\/ppa.13640","article-title":"Photoinactivation of Colletotrichum truncatum, Corynespora cassiicola, Sclerotinia sclerotiorum and Rhizoctonia solani in soybean seeds by cationic porphyrins","volume":"72","author":"Saulle","year":"2022","journal-title":"Plant. Pathol."},{"key":"ref_7","first-page":"1563","article-title":"Inhibitory effect of low molecular weight chitosan on kiwifruit gray mold caused by Botrytis cinerea","volume":"42","author":"Wang","year":"2019","journal-title":"J. Hefei Univ. Tech."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"7139","DOI":"10.1007\/s00253-022-12196-3","article-title":"Flavonoids from Sedum aizoon L. inhibit Botrytis cinerea by negatively affecting cell membrane lipid metabolism","volume":"106","author":"Wang","year":"2022","journal-title":"Appl. Microbiol. Biot."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"181","DOI":"10.1007\/s10658-011-9919-7","article-title":"Biological control of postharvest diseases of fruit","volume":"133","author":"Nunes","year":"2011","journal-title":"Eur. J. Plant Pathol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"793","DOI":"10.1016\/j.bjm.2016.06.006","article-title":"Is the emergence of fungal resistance to medical triazoles related to their use in the agroecosystems? A mini review","volume":"47","author":"Ribas","year":"2016","journal-title":"Braz. J. Microbiol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"662","DOI":"10.1016\/j.ejmech.2013.02.035","article-title":"Synthesis and antiviral bioactivity of novel (1E,4E)-1-aryl-5-(2-(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3- one derivatives","volume":"63","author":"Luo","year":"2013","journal-title":"Eur. J. Med. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1007\/s11696-018-0422-x","article-title":"Synthesis, antibacterial, and antiviral activities of novel penta-1,4-dien-3-one derivatives containing a benzotriazin-4(3H)-one moiety","volume":"72","author":"Zhang","year":"2018","journal-title":"Chem. Pap."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Yang, X.J., Miao, F., Yao, Y., Cao, F.J., Yang, R., Ma, Y.N., Qin, B.F., and Zhou, L. (2012). In vitro antifungal activity of sanguinarine and chelerythrine derivatives against phytopathogenic fungi. Molecules, 17.","DOI":"10.3390\/molecules171113026"},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"3840","DOI":"10.1016\/j.bmcl.2015.07.068","article-title":"Antiviral activity and interaction mechanisms study of novel glucopyranoside derivatives","volume":"25","author":"Chen","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"242","DOI":"10.1584\/jpestics.D19-041","article-title":"Synthesis and bioactivity evaluation of penta-1,4-diene-3-one oxime ether derivatives","volume":"44","author":"Tang","year":"2019","journal-title":"J. Pestic. Sci."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"765","DOI":"10.1016\/j.jscs.2020.08.005","article-title":"Synthesis and biological evaluation of 1,4-pentadien-3-one derivatives containing 1,2,4-triazole","volume":"24","author":"Chen","year":"2020","journal-title":"J. Saudi Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"732","DOI":"10.1016\/j.ejmech.2015.01.017","article-title":"Design, synthesis, and antiviral activity of novel rutin derivatives containing 1,4-pentadien-3-one moiety","volume":"92","author":"Han","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"16096","DOI":"10.1021\/acs.jafc.2c05731","article-title":"Design, Synthesis, and Biological Evaluation of Novel 1,4-Pentadien-3-one Derivatives Containing a Sulfonamide Moiety","volume":"70","author":"Zhou","year":"2022","journal-title":"J. Agric. Food Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"4604","DOI":"10.1021\/acs.jafc.0c05475","article-title":"Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides","volume":"69","author":"Peng","year":"2021","journal-title":"J. Agric. Food Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"203","DOI":"10.1007\/s00044-018-2276-8","article-title":"Design, synthesis, antiproliferative and antibacterial evaluation of quinazolinone derivatives","volume":"28","author":"Wang","year":"2018","journal-title":"Med. Chem. Res."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1223","DOI":"10.1002\/jhet.3158","article-title":"Synthesis of New Benzoxazinone, Quinazolinone, and Pyrazoloquinazolinone Derivatives and Evaluation of Their Cytotoxic Activity Against Human Breast Cancer Cells","volume":"55","author":"Ali","year":"2018","journal-title":"J. Heterocycl. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"9575","DOI":"10.1021\/jf403193q","article-title":"Synthesis and bioactivity evaluation of novel arylimines containing a 3-aminoethyl-2-[(p- trifluoromethoxy)anilino]-4(3H)-quinazolinone moiety","volume":"61","author":"Wang","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"30826","DOI":"10.1021\/acsomega.1c05256","article-title":"Design, Synthesis, Antibacterial Activity, Antiviral Activity, and Mechanism of Myricetin Derivatives Containing a Quinazolinone Moiety","volume":"6","author":"Liu","year":"2021","journal-title":"ACS Omega"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"El-Sayed, A.A., Ismail, M.F., Amr, A.E.E., and Naglah, A.M. (2019). Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one (thione) Derivatives with DFT Study. Molecules, 24.","DOI":"10.3390\/molecules24203787"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"743","DOI":"10.1002\/jhet.3099","article-title":"Synthesis and Antibacterial Activity of 2-substitued-(3-pyridyl)-quinazolinone Derivatives","volume":"55","author":"Zhang","year":"2018","journal-title":"J. Heterocycl. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"8764","DOI":"10.1021\/acs.jafc.0c04278","article-title":"Luotonin A and Its Derivatives as Novel Antiviral and Antiphytopathogenic Fungus Agents","volume":"68","author":"Hao","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"8928","DOI":"10.1021\/jf502162y","article-title":"Synthesis and antiviral bioactivity of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-qu inazolinon derivatives","volume":"62","author":"Ma","year":"2014","journal-title":"J. Agric. Food Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"104019","DOI":"10.1016\/j.arabjc.2022.104019","article-title":"Design, synthesis, biological activity evaluation and mechanism of action of myricetin derivatives containing thioether quinazolinone","volume":"15","author":"Liu","year":"2022","journal-title":"Arab. J. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"8632","DOI":"10.1021\/jf402388x","article-title":"Synthesis and biological evaluation of benzofuroxan derivatives as fungicides against phytopathogenic fungi","volume":"61","author":"Wang","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1016\/j.indcrop.2015.04.065","article-title":"Anti-phytopathogenic activity of Syzygium cumini essential oil, hydrocarbon fractions and its novel constituents","volume":"74","author":"Saroj","year":"2015","journal-title":"Ind. Crop Prod."},{"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."},{"key":"ref_32","doi-asserted-by":"crossref","unstructured":"Liu, D., Luo, L., Wang, Z.X., Ma, X.Y., and Gan, X.H. (2022). Design, Synthesis and Antifungal\/Nematicidal Activity of Novel 1,2,4-Oxadiazole Derivatives Containing Amide Fragments. Int. J. Mol. Sci., 23.","DOI":"10.3390\/ijms23031596"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"699","DOI":"10.1094\/PDIS-07-14-0727-RE","article-title":"Identification of Botryosphaeriaceae Species Causing Kiwifruit Rot in Sichuan Province, China","volume":"99","author":"Zhou","year":"2015","journal-title":"Plant Dis."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"9598","DOI":"10.1021\/acs.jafc.8b02124","article-title":"Discovery of beta-Carboline Oxadiazole Derivatives as Fungicidal Agents against Rice Sheath Blight","volume":"66","author":"Zhang","year":"2018","journal-title":"J. Agric. Food Chem."},{"key":"ref_35","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. Crop. Prod."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"129218","DOI":"10.1016\/j.foodchem.2021.129218","article-title":"Antibacterial mechanisms of Aronia melanocarpa (Michx.), Chaenomeles superba Lindl. And Cornus mas L. leaf extracts","volume":"350","author":"Nowak","year":"2021","journal-title":"Food Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1016\/j.postharvbio.2019.01.005","article-title":"Efficacy of rapamycin in modulating autophagic activity of Botrytis cinerea for controlling gray mold","volume":"150","author":"Ma","year":"2019","journal-title":"Postharvest Biol. Technol."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"6040","DOI":"10.1021\/acs.jafc.9b06860","article-title":"Safflower (Carthamus tinctorius) Biochemical Properties, Yield, and Oil Content Affected by 24-Epibrassinosteroid and Genotype under Drought Stress","volume":"68","author":"Zafari","year":"2020","journal-title":"J. Agric. Food Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"100091","DOI":"10.1016\/j.chphi.2022.100091","article-title":"Structural benchmarking, density functional theory simulation, Spectrosco pic investigation and molecular docking of N-(1H-pyrrol-2-yl)methylene)-4-methylaniline as castration-resistant prostate cancer chemotherapeutic agent","volume":"5","author":"Asogwa","year":"2022","journal-title":"Chem. Phys. 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