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Based on the various activities of tryptanthrin, a series of tryptanthrin analogues bearing F and piperazine moieties were designed, synthesized, and evaluated for their biological activities against three plant bacteria and tobacco mosaic virus (TMV).<\/jats:p><\/jats:sec><jats:sec><jats:title>RESULTS<\/jats:title><jats:p>Bioassay results indicated that compounds <jats:bold>6a<\/jats:bold>\u2013<jats:bold>6l<\/jats:bold> displayed excellent antibacterial activities <jats:italic>in vitro<\/jats:italic> and <jats:bold>6a<\/jats:bold>\u2013<jats:bold>6c and 6g<\/jats:bold> exhibited better antiviral activities against TMV than commercial ribavirin. In particular, <jats:bold>6b<\/jats:bold> showed the most effect on <jats:italic>Xanthomonas oryzae<\/jats:italic> pv. <jats:italic>oryzae<\/jats:italic> (<jats:italic>Xoo<\/jats:italic>) with a half\u2010maximal effective concentration (EC<jats:sub>50<\/jats:sub>) of 1.26\u2009\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>, compared with the commercial pesticide bismerthiazol (BT; EC<jats:sub>50<\/jats:sub>\u2009=\u200934.3\u2009\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>) and thiodiazole copper (TC; EC<jats:sub>50<\/jats:sub>\u2009=\u200973.3\u2009\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup>). Meanwhile, <jats:bold>6a<\/jats:bold> also had the best antiviral activity at 500\u2009\u03bcg\u2009mL<jats:sup>\u22121<\/jats:sup> for curative, protection, and inactivation purposes, compared with ribavirin <jats:italic>in vivo<\/jats:italic>.<\/jats:p><\/jats:sec><jats:sec><jats:title>CONCLUSION<\/jats:title><jats:p>Compound <jats:bold>6b<\/jats:bold> could cause changes in bacterial morphology, induce the accumulation of reactive oxygen species, promote apoptosis of bacterial cells, inhibit the formation of biofilm, and block the growth of <jats:italic>Xoo<\/jats:italic> cells. Proteomic analysis revealed major differences in the bacterial secretory system pathways T2SS and T6SS, which inhibited membrane transport. Molecular docking revealed that <jats:bold>6a<\/jats:bold> and <jats:bold>6g<\/jats:bold> could interact with TMV coat protein preventing virus assembly. These results suggest that tryptanthrin analogues bearing F and piperazine moieties could be promising candidate agents for antibacterial and antiviral use in agricultural production. \u00a9 2023 Society of Chemical Industry.<\/jats:p><\/jats:sec>","DOI":"10.1002\/ps.7834","type":"journal-article","created":{"date-parts":[[2023,10,16]],"date-time":"2023-10-16T06:55:26Z","timestamp":1697439326000},"page":"1026-1038","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Discovery of tryptanthrin analogues bearing F and piperazine moieties as novel phytopathogenic antibacterial and antiviral agents"],"prefix":"10.1002","volume":"80","author":[{"ORCID":"https:\/\/orcid.org\/0009-0009-3653-8762","authenticated-orcid":false,"given":"Guang\u2010Long","family":"Zhang","sequence":"first","affiliation":[{"name":"National Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry 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