{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T11:43:22Z","timestamp":1791891802719,"version":"4.3.4"},"reference-count":15,"publisher":"National Academy of Sciences","issue":"23","content-domain":{"domain":["www.pnas.org"],"crossmark-restriction":true},"short-container-title":["Proc. Natl. Acad. Sci. U.S.A."],"published-print":{"date-parts":[[1996,11,12]]},"abstract":"<jats:p>Fipronil is an outstanding new insecticide for crop protection with\n good selectivity between insects and mammals. The insecticidal action\n involves blocking the \u03b3-aminobutyric acid-gated chloride channel with\n much greater sensitivity of this target in insects than in mammals.\n Fipronil contains a trifluoromethylsulfinyl moiety that is unique among\n the agrochemicals and therefore presumably important in its outstanding\n performance. We find that this substituent unexpectedly undergoes a\n novel and facile photoextrusion reaction on plants upon exposure to\n sunlight, yielding the corresponding trifluoromethylpyrazole, i.e., the\n desulfinyl derivative. The persistence of this photoproduct and its\n high neuroactivity, resulting from blocking the \u03b3-aminobutyric\n acid-gated chloride channel, suggest that it may be a significant\n contributor to the effectiveness of fipronil. In addition,\n desulfinylfipronil is not a metabolite in mammals, so the safety\n evaluations must take into account not only the parent compound but\n also this completely new environmental product.<\/jats:p>","DOI":"10.1073\/pnas.93.23.12764","type":"journal-article","created":{"date-parts":[[2002,7,26]],"date-time":"2002-07-26T10:34:16Z","timestamp":1027679656000},"page":"12764-12767","update-policy":"https:\/\/doi.org\/10.1073\/pnas.cm10313","source":"Crossref","is-referenced-by-count":275,"title":["Fipronil insecticide: Novel photochemical desulfinylation with retention\u2009of\u2009neurotoxicity"],"prefix":"10.1073","volume":"93","author":[{"given":"Dominik","family":"Hainzl","sequence":"first","affiliation":[{"name":"Environmental Chemistry and Toxicology Laboratory, Department of\r Environmental Science, Policy, and Management, University of\r California, Berkeley, CA 94720-3112"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"John\u2009E.","family":"Casida","sequence":"additional","affiliation":[{"name":"Environmental Chemistry and Toxicology Laboratory, Department of\r Environmental Science, Policy, and Management, University of\r California, Berkeley, CA 94720-3112"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"341","published-online":{"date-parts":[[1996,11,12]]},"reference":[{"key":"e_1_3_2_1_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.8393587"},{"key":"e_1_3_2_2_2","unstructured":"Perrior T.\u2009R. (1993) Chem. Ind. (London) 883\u2013887."},{"key":"e_1_3_2_3_2","unstructured":"Buntain I.\u2009G. Hatton L.\u2009R. Hawkins D.\u2009W. Pearson C.\u2009J. & Roberts D.\u2009A. (1988) Eur. Patent 0 295 117 A1 40 pp."},{"key":"e_1_3_2_4_2","first-page":"463","volume-title":"The Pesticide Manual","author":"Tomlin C","year":"1994","unstructured":", ed C Tomlin (Crop Protection Publications\/British Crop Protection Council, Farnham, U.K.) The Pesticide Manual, pp. 463 (1994)."},{"key":"e_1_3_2_5_2","first-page":"29","volume":"1","author":"Colliot F","year":"1992","unstructured":"F Colliot, K A Kukorowski, D W Hawkins, D A Roberts Brighton Crop Prot Conf Pests Dis 1, 29\u201334 (1992).","journal-title":"Brighton Crop Prot Conf Pests Dis"},{"key":"e_1_3_2_6_2","first-page":"838","volume":"2","author":"Burris E","year":"1994","unstructured":"E Burris, B R Leonard, S H Martin, C A White, J B Graves, R Shaw, W P Scott Proc Beltwide Cotton Conf 2, 838\u2013844 (1994).","journal-title":"Proc Beltwide Cotton Conf"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1006\/pest.1993.1035"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.90.5.1957"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/0024-3205(95)00006-R"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1995.tb15896.x"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0048-3575(92)90002-H"},{"key":"e_1_3_2_12_2","doi-asserted-by":"crossref","unstructured":"Khait I. L\u00fcdersdorf R. Muszkat K.\u2009A. & Praefcke K. (1981) J. Chem. Soc. Perkin Trans. 2 1417\u20131429.","DOI":"10.1039\/P29810001417"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00122a029"},{"key":"e_1_3_2_14_2","first-page":"873","volume-title":"The Chemistry of Sulfones and Sulfoxides","author":"Still I W J","year":"1988","unstructured":"I W J Still The Chemistry of Sulfones and Sulfoxides, eds S Patai, Z Rappaport, C J M Stirling (Wiley, New York), pp. 873\u2013887 (1988)."},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1038\/238221a0"}],"container-title":["Proceedings of the National Academy of Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pnas.org\/doi\/pdf\/10.1073\/pnas.93.23.12764","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,4,13]],"date-time":"2022-04-13T15:21:27Z","timestamp":1649863287000},"score":1,"resource":{"primary":{"URL":"https:\/\/pnas.org\/doi\/full\/10.1073\/pnas.93.23.12764"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1996,11,12]]},"references-count":15,"journal-issue":{"issue":"23","published-print":{"date-parts":[[1996,11,12]]}},"alternative-id":["10.1073\/pnas.93.23.12764"],"URL":"https:\/\/doi.org\/10.1073\/pnas.93.23.12764","relation":{},"ISSN":["0027-8424","1091-6490"],"issn-type":[{"value":"0027-8424","type":"print"},{"value":"1091-6490","type":"electronic"}],"subject":[],"published":{"date-parts":[[1996,11,12]]},"assertion":[{"value":"1996-08-20","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"1996-11-12","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}