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PPO herbicides, because of their low dosage, rapid action on weeds, slow accumulation in the environment and low toxicity to mammals, have become an important field of research in the development of new herbicides. This study presents a novel molecular scaffold with remarkably potent herbicidal activity.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>\n                      A series of novel oxime ether derivatives containing 1,5\u2010dimethyl\u20106\u2010thioxo\u20101,3,5\u2010triazinane\u20102,4\u2010dione\n                      <jats:bold>6a\u20136z<\/jats:bold>\n                      were designed and synthesized based on bioisosterism and substructure splicing, and characterized by\n                      <jats:sup>1<\/jats:sup>\n                      H and\n                      <jats:sup>13<\/jats:sup>\n                      C nuclear magnetic resonance spectroscopies, and high\u2010resolution mass spectrometry. The configuration of compound\n                      <jats:bold>6u<\/jats:bold>\n                      was confirmed by single\u2010crystal X\u2010ray diffraction. Compound\n                      <jats:bold>6r<\/jats:bold>\n                      displayed excellent herbicidal activity of &gt;95% against\n                      <jats:italic>Echinochloa\u2009crus\u2010galli<\/jats:italic>\n                      ,\n                      <jats:italic>Digitaria sanguinalis<\/jats:italic>\n                      ,\n                      <jats:italic>Medicago sativa<\/jats:italic>\n                      and\n                      <jats:italic>Conyza canadensis<\/jats:italic>\n                      at a dosage of 37.5\u2009g\u2009hm\u20132 in the glasshouse. At a dosage of 75\u2009g\u2009hm\u20132,\n                      <jats:bold>6r<\/jats:bold>\n                      was safe for application on rice and showed low toxicity (&gt;200\u2009\u03bcg\u2009g\u20131) towards\n                      <jats:italic>Apis mellifera<\/jats:italic>\n                      . Transcriptomics analysis of\n                      <jats:italic>E.\u2009crus\u2010galli<\/jats:italic>\n                      treated by compound\n                      <jats:bold>6r<\/jats:bold>\n                      , using oxadiazon as a positive control, revealed the compound's mode\u2010of\u2010action. There were eight metabolic and biosynthetic pathways of DEGs containing \u2018photosynthesis\u2019, \u2018porphyrin metabolism\u2019, \u2018carotenoid biosynthesis\u2019 and so on between\n                      <jats:bold>6r<\/jats:bold>\n                      and oxadiazon as same. Scaffold94.443 (coproporphyrinogen\u2010III oxidase) as upstream protoporphyrinogen IX changes were downregulated with quantitative reverse transcription PCR combined analysis treated\n                      <jats:bold>6r<\/jats:bold>\n                      and oxadiazon in chlorophyll biosynthesis. Compound\n                      <jats:bold>6r<\/jats:bold>\n                      target may be PPO and the\n                      <jats:italic>Nt<\/jats:italic>\n                      PPO inhibitory effects, as represented by\n                      <jats:italic>K<\/jats:italic>\n                      i, was 30.34\u2009n\n                      <jats:sc>m<\/jats:sc>\n                      <jats:italic>in vitro<\/jats:italic>\n                      . Molecular docking showed that\n                      <jats:bold>6r<\/jats:bold>\n                      could form two hydrogen bonds with Arg98.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSION<\/jats:title>\n                    <jats:p>\n                      Through bioisosterism and substructure splicing, we successfully developed compound\n                      <jats:bold>6r<\/jats:bold>\n                      as lead compound exhibiting herbicidal activity, with no harm to rice and honeybees. Further development of herbicides based on this scaffold is warranted. \u00a9 2025 Society of Chemical Industry.\n                    <\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/ps.8703","type":"journal-article","created":{"date-parts":[[2025,2,14]],"date-time":"2025-02-14T02:30:33Z","timestamp":1739500233000},"page":"3302-3311","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Design, synthesis, and biological evaluation of oxime ether derivatives containing 1,5\u2010dimethyl\u20106\u2010thioxo\u20101,3,5\u2010triazinane\u20102,4\u2010dione as protoporphyrinogen\n                    <scp>IX<\/scp>\n                    oxidase inhibitors"],"prefix":"10.1002","volume":"81","author":[{"given":"Dingfeng","family":"Luo","sequence":"first","affiliation":[{"name":"Hunan Provincial Key Laboratory for Biology and Control of Weeds Hunan Academy of Agricultural Sciences  Changsha China"},{"name":"Yuelushan 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