{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,22]],"date-time":"2026-07-22T01:03:36Z","timestamp":1784682216266,"version":"3.55.0"},"reference-count":38,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T00:00:00Z","timestamp":1768003200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T00:00:00Z","timestamp":1768003200000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"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":[[2026,4]]},"abstract":"Abstract<\/jats:title>\n \n BACKGROUND<\/jats:title>\n \n The resistant rice stem borer (\n Chilo suppressalis<\/jats:italic>\n ) poses a serious threat to rice yield and food security. For two decades, fipronil was a key insecticide for its control, but its use has been restricted owing to the toxicity of its degradation products to aquatic life and bees. To develop superior alternatives, we structurally modified fipronil\u20105\u2010amino through acylation, benzylation and carbamation, and evaluated the insecticidal activity of the resulting derivatives against resistant\n C<\/jats:italic>\n .\n suppressalis,<\/jats:italic>\n as well as their toxicity to zebrafish and honeybees.\n <\/jats:p>\n <\/jats:sec>\n \n RESULTS<\/jats:title>\n \n Twenty\u2010seven fipronil derivatives were synthesized via acylation, benzylation and carbamate conjugation strategies. Benzylation and carbamate conjugation significantly improved insecticidal activity: benzylated derivatives\n 2d<\/jats:bold>\n ,\n 2h<\/jats:bold>\n and\n 2p<\/jats:bold>\n [median lethal concentration (LC\n 50<\/jats:sub>\n )\u2009=\u20091.43\u20131.71\u2009\u03bcg\u2009mL\n \u22121<\/jats:sup>\n ] and carbamate conjugates\n 4b<\/jats:bold>\n ,\n 4c<\/jats:bold>\n and\n 4g<\/jats:bold>\n (LC\u2085\u2080\u2009\u2264\u20092.00\u2009\u03bcg\u2009mL\n \u22121<\/jats:sup>\n ) showed 3\u2010 to 6\u2010fold greater potency than fipronil (LC\n 50<\/jats:sub>\n \u2009=\u20097.90\u2009\u03bcg\u2009mL\n \u22121<\/jats:sup>\n ). Structure\u2013activity relationship analysis revealed that electron\u2010withdrawing groups (e.g. \u2013CN, \u2013NO\u2082) on benzyl rings, especially at the\n para<\/jats:italic>\n \u2010position, and heterocyclic substitutions (e.g. pyridine) enhanced activity. Optimal clog\n P<\/jats:italic>\n values (5, 6) correlated with peak efficacy. Importantly, these active derivatives exhibited markedly reduced toxicity than fipronil to zebrafish (\n Danio rerio<\/jats:italic>\n ) and bee, indicating improved biosafety.\n <\/jats:p>\n <\/jats:sec>\n \n CONCLUSION<\/jats:title>\n \n Targeted structural modifications at fipronil's 5\u2010amino position\u2014particularly benzylation with electron\u2010withdrawing substituents and carbamate conjugation\u2014yielded derivatives with superior insecticidal activity against resistant\n C.\u2009suppressalis<\/jats:italic>\n and lower aquatic toxicity and honeybee toxicity. This strategy demonstrates the potential of rational molecular design in overcoming pesticide resistance while enhancing environmental safety, offering a promising pathway for developing next\u2010generation, sustainable insecticides. \u00a9 2026 Society of Chemical Industry.\n <\/jats:p>\n <\/jats:sec>","DOI":"10.1002\/ps.70512","type":"journal-article","created":{"date-parts":[[2026,1,10]],"date-time":"2026-01-10T08:39:26Z","timestamp":1768034366000},"page":"3842-3852","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Structural modification of fipronil\u20105\u2010amino and insecticidal activity evaluation of its derivatives against resistant\n \n Chilo suppressalis<\/i>\n <\/scp>"],"prefix":"10.1002","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0009-0006-6864-2685","authenticated-orcid":false,"given":"Zhiping","family":"Liu","sequence":"first","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yinze","family":"Liang","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Junyan","family":"Li","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Weiguo","family":"Li","sequence":"additional","affiliation":[{"name":"Guangxi Tianyuan Biochemical Co. Ltd. Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7366-5239","authenticated-orcid":false,"given":"Yanmin","family":"Huang","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Taichen","family":"Yang","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Qiang","family":"Hu","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1308-6726","authenticated-orcid":false,"given":"Jianguo","family":"Cui","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Natural Polymer Chemistry and Physics Nanning Normal University Nanning China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,1,10]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cropro.2010.06.023"},{"key":"e_1_2_7_3_1","first-page":"1207","article-title":"The occurrence characteristics of rice diseases and insect pests and the integration of green, Chinese journal of biological control","volume":"40","author":"Zhuo F","year":"2024","journal-title":"Chin J Biol Control"},{"key":"e_1_2_7_4_1","first-page":"61","article-title":"Analysis of the occurrence, damage, and control status of rice diseases, insect pests, and weeds in the three 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