{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,12]],"date-time":"2026-09-12T02:41:21Z","timestamp":1789180881951,"version":"build-2803163510"},"reference-count":53,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2023,3,8]],"date-time":"2023-03-08T00:00:00Z","timestamp":1678233600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Pest Management Science"],"published-print":{"date-parts":[[2023,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:sec>\n                    <jats:title>BACKGROUND<\/jats:title>\n                    <jats:p>Whilst there are several methods to control weeds, which continuously plague farmers around the globe, the application of small molecular compounds is still the most effective technology to date. Plants can evolve to become resistant to PPO\u2010inhibitors, a class of herbicides in commercial use since the 1960s. It is therefore essential to continuously develop new herbicides based on this mode\u2010of\u2010action with enhanced intrinsic activity, an improved resistance profile and favourable physicochemical properties. Based on an Amaranthus PPO crystal structure and subsequent modelling studies, halogen\u2010substituted pyrazoles have been investigated as isosteres of uracil\u2010based PPO\u2010inhibitors.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>\n                      By combining structural features from the commercial PPO\u2010inhibitors tiafenacil and pyraflufen\u2010ethyl and by investigating receptor\u2010binding properties, we identified new promising pyrazole\u2010based lead structures showing strong activity\n                      <jats:italic>in vitro<\/jats:italic>\n                      and\n                      <jats:italic>in vivo<\/jats:italic>\n                      against economically important weeds of the\n                      <jats:italic>Amaranthus<\/jats:italic>\n                      genus:\n                      <jats:italic>A.\u00a0retroflexus<\/jats:italic>\n                      , and resistant\n                      <jats:italic>A.\u00a0palmeri<\/jats:italic>\n                      and\n                      <jats:italic>A.\u00a0tuberculatus.<\/jats:italic>\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSION<\/jats:title>\n                    <jats:p>The present work covers a series of novel PPO\u2010inhibiting compounds that contain a pyrazole ring and a substituted thioacetic acid sidechain attached to the core phenyl group. These compounds show good receptor fit in line with excellent herbicidal activity against weeds that plague corn and rice crops with low application rates. This, in combination with promising selectivity in corn, have the potential to mitigate and affect weeds that have become resistant to some of the current market standards. Remarkably, some of the novel PPO\u2010inhibitors outlined herein show efficacies against economically important weeds that were superior to recently commercialized and structurally related tiafenacil. \u00a9 2023 Society of Chemical Industry.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/ps.7425","type":"journal-article","created":{"date-parts":[[2023,2,23]],"date-time":"2023-02-23T06:54:34Z","timestamp":1677135274000},"page":"2264-2280","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":42,"title":["Design, synthesis and screening of herbicidal activity for new phenyl pyrazole\u2010based protoporphyrinogen oxidase\u2010inhibitors (\n                    <scp>PPO<\/scp>\n                    ) overcoming resistance issues"],"prefix":"10.1002","volume":"79","author":[{"given":"Rebecca L.","family":"Mattison","sequence":"first","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3109-388X","authenticated-orcid":false,"given":"Roland","family":"Beffa","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Guido","family":"Bojack","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Birgit","family":"Bollenbach\u2010Wahl","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Christine","family":"D\u00f6rnbrack","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nicole","family":"Dorn","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"J\u00f6rg","family":"Freigang","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elmar","family":"Gatzweiler","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rahel","family":"Getachew","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia","family":"Hartfiel","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ines","family":"Heinemann","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hendrik","family":"Helmke","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sabine","family":"Hohmann","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Harald","family":"Jakobi","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Gudrun","family":"Lange","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"L\u00fcmmen","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lothar","family":"Willms","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3457-0290","authenticated-orcid":false,"given":"Jens","family":"Frackenpohl","sequence":"additional","affiliation":[{"name":"Research &amp; Development, Weed Control, Division Crop Science Bayer AG, Industriepark H\u00f6chst  Frankfurt am Main Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,3,8]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1614\/WS-D-12-00032.1"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c05955"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1080\/09670874.2013.821212"},{"key":"e_1_2_7_5_1","unstructured":"Heap I.The International survey of herbicide resistant weeds database. Available from:http:\/\/www.weedscience.org\/."},{"key":"e_1_2_7_6_1","first-page":"27","volume-title":"Modern Crop Protection Compounds","author":"Thompson ME","year":"2007"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.3987\/REV-07-613"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.1000956107"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/sj.emboj.7600189"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619580.ch3"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.3390\/plants8090341"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.3728"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4744"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4241"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1017\/wet.2020.74"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.3390\/genes13061044"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbapap.2010.04.004"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4821"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2020.614618"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.5445"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0215431"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.3390\/agriculture11080760"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.3389\/fpls.2019.00568"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.6111"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.6111"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2020.115959"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.1c05210"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.0c00947"},{"key":"e_1_2_7_29_1","unstructured":"Goddard S. JHerbicidal 2\u2010substituted aryl\u20104 5 6 7\u2010tetrahydro\u20102H\u2010isoindole\u20101 3\u2010diones. United States Patent US4032326A(1977)."},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.9b04844"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pestbp.2018.08.010"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1584\/jpestics.27.39"},{"key":"e_1_2_7_33_1","unstructured":"Frackenpohl J Heinemann I Willms L Beffa R Dietrich H Gatzweiler E Machettira A. B Rosinger C. H Luemmen P.Preparation of substituted thiophenyluracils and salts thereof and the use thereof as herbicidal agents. Germany Patent WO2019121547(2019)."},{"key":"e_1_2_7_34_1","unstructured":"Frackenpohl J Heinemann I Willms L Beffa R Dietrich H Gatzweiler E Machettira A. B Rosinger C. H Luemmen P.Preparation of substituted thiophenyluracils and salts thereof and the use thereof as herbicidal agents. Germany Patent WO2019121544(2019)."},{"key":"e_1_2_7_35_1","unstructured":"Petkova D. S Witschel M Seiser T Newton T. W Souillart L.Herbicidal uracilpyridines. Germany Patent WO2021018664(2021)."},{"key":"e_1_2_7_36_1","unstructured":"Young K. K Chung K. H Ryu J. W Woo J. C Koo D. W Kim D. W Kim T. J Choi I. Y Kim Y. K Oh T. H Choi J. H Seok M. Y Kim K. S Chung B. J.Preparation of uracil\u2010based compounds as herbicides. South Korea Patent WO2010038953(2010)."},{"key":"e_1_2_7_37_1","doi-asserted-by":"crossref","DOI":"10.1021\/acs.jafc.3c01420","article-title":"Designing new protoporphyrinogen oxidase\u2010inhibitors carrying potential side chain isosteres to enhance crop safety and spectrum of activity","volume":"71","author":"Alnafta N","year":"2023","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_38_1","unstructured":"Ko Y. G Ryu J. U Ku D. W Kim T. J Choi I. Y Kim Y. G Choi J. H Kim G. S Jung B J.Herbicidal Uracil compounds. South Korea Patent KR20111110420(2011)."},{"key":"e_1_2_7_39_1","unstructured":"Lee W. H Kwon Y. B Lee K. H Kim J. H Kim J.Preparation of uracil\u2010based compounds and herbicidal compositions comprising them. South Korea Patent WO2020013500(2020)."},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.1c00796"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2021.116165"},{"key":"e_1_2_7_42_1","unstructured":"Seiser T Johnnes M Witschel M Parra Rapado L Aponte R MietznerT Massa D Seitz T Dombo P Landes A Tresch S Newton T.Phenyltriazolinones as herbicides and their preparation. Germany Patent WO2018108695(2018)."},{"key":"e_1_2_7_43_1","unstructured":"Kawahara F.Herbicide composition comprising a pyrazolyl\u2010pyrazole derivative and other active agent. Japan Patent JP2018016573(2018)."},{"key":"e_1_2_7_44_1","unstructured":"Shigefuji T.Herbicide composition containing a pyrazolyl pyrazole derivative. Japan Patent WO2016121900(2016)."},{"key":"e_1_2_7_45_1","unstructured":"Nebel K Brunner H Schurter R.Preparation of pyridylpyrazoles as herbicides. Switzerland Patent WO9821199(1998)."},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1002\/cmdc.200700319"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444909042589"},{"key":"e_1_2_7_48_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444904019158"},{"key":"e_1_2_7_49_1","doi-asserted-by":"publisher","DOI":"10.1107\/S0907444911001314"},{"key":"e_1_2_7_50_1","unstructured":"Freigang J Koch M Breithaupt C Kiefersauer R Messerschmidt A Huber R Crystal structure of a plant mitochondrial protoporphyrinogen IX oxidase and its use in drug design. Germany Patent EP1584676(2005)."},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1042\/BJ20061321"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201701687"},{"key":"e_1_2_7_53_1","unstructured":"Frackenpohl J Heinemann I Willms L Beffa R Dietrich H Gatzweiler E Machettira A. B Rosinger C. H Luemmen P.Preparation of substituted thiophenyluracils and salts thereof and the use thereof as herbicidal agents. Germany Patent WO2019121543(2019)."},{"key":"e_1_2_7_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.1c07910"}],"container-title":["Pest Management Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ps.7425","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ps.7425","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ps.7425","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T14:36:47Z","timestamp":1761057407000},"score":1,"resource":{"primary":{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/10.1002\/ps.7425"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3,8]]},"references-count":53,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2023,6]]}},"alternative-id":["10.1002\/ps.7425"],"URL":"https:\/\/doi.org\/10.1002\/ps.7425","archive":["Portico"],"relation":{},"ISSN":["1526-498X","1526-4998"],"issn-type":[{"value":"1526-498X","type":"print"},{"value":"1526-4998","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3,8]]},"assertion":[{"value":"2022-11-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-23","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-03-08","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}