{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,14]],"date-time":"2026-03-14T19:35:54Z","timestamp":1773516954743,"version":"3.50.1"},"reference-count":58,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2023,3,17]],"date-time":"2023-03-17T00:00:00Z","timestamp":1679011200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Pest Management Science"],"published-print":{"date-parts":[[2023,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:sec><jats:title>BACKGROUND<\/jats:title><jats:p><jats:italic>Potato virus Y<\/jats:italic> (PVY) was first discovered by Smith in 1931 and is currently ranked as the fifth most significant plant virus. It can cause severe damage to plants from the family <jats:italic>Solanaceae<\/jats:italic>, which results in billions of dollars of economic loss worldwide every year. To discover new antiviral drugs, a class of multifunctional urazole derivatives bearing a stereogenic C\uf8ffN axis were synthesized with excellent optical purities for antiviral evaluations against PVY.<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>The absolute configurations of the axially chiral compounds exhibited obvious distinctions in antiviral bioactivities, with several of these enantio\u2010enriched axially chiral molecules showing excellent anti\u2010PVY activities. In particular, compound (<jats:italic>R<\/jats:italic>)\u2010<jats:bold>9f<\/jats:bold> exhibited remarkable curative activities against PVY with a 50% maximal effective concentration (EC<jats:sub>50<\/jats:sub>) of 224.9\u00a0\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>, which was better than that of ningnanmycin (NNM), which had an EC<jats:sub>50<\/jats:sub> of 234.0\u00a0\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>. And the EC<jats:sub>50<\/jats:sub> value of the protective activities of compound (<jats:italic>R<\/jats:italic>)\u2010<jats:bold>9f<\/jats:bold>\u00a0was 462.2\u00a0\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>, which was comparable to that of NNM (442.0\u00a0\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>). The mechanisms of two enantiomer of the axially chiral compounds <jats:bold>9f<\/jats:bold>\u00a0were studied by both molecule docking and defensive enzyme activity tests.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>Mechanistic studies demonstrated that the axially chiral configurations of the compounds played significant roles in the molecule PVY\u2010CP (PVY Coat Protein) interactions and could enhance the activities of the defense enzymes. The (S)\u20109f showed only one carbon\u2013hydrogen bond and one \u03c0\u2013cation interaction between the chiral molecule and the PVY\u2010CP amino acid sites. In contrast, the (R)\u2010enantiomer of 9f exhibited three hydrogen bonding interactions between the carbonyl groups and the PVY\u2010CP active sites of ARG157 and GLN158. The current study provides significant information on the roles that axial chiralities play in plant protection against viruses, which will facilitate the development of novel green pesticides bearing axial chiralities with excellent optical purities. \u00a9 2023 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.7428","type":"journal-article","created":{"date-parts":[[2023,3,3]],"date-time":"2023-03-03T01:44:20Z","timestamp":1677807860000},"page":"2527-2538","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Development of axially chiral urazole scaffolds for antiplant virus applications against <i>potato virus Y<\/i>"],"prefix":"10.1002","volume":"79","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-4687-9586","authenticated-orcid":false,"given":"Jiamiao","family":"Jin","sequence":"first","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and 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