{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T07:57:04Z","timestamp":1791100624244,"version":"4.1.0"},"reference-count":22,"publisher":"Wiley","issue":"8","license":[{"start":{"date-parts":[[2009,5,5]],"date-time":"2009-05-05T00:00:00Z","timestamp":1241481600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"crossref"}]},{"DOI":"10.13039\/501100004901","name":"Funda\u00e7\u00e3o de Amparo \u00e0 Pesquisa do Estado de Minas Gerais","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100004901","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Pest Management Science"],"published-print":{"date-parts":[[2009,8]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    <jats:bold>BACKGROUND:<\/jats:bold>\n                    Pyrethroids are among the most potent pesticides known, with great potential for structural variation with retention or enhancement of potency. The simple methyl ester is easier to prepare (at least one step shorter) than the more complex pyrethroids modified on the alcohol moiety. The objective was to synthesise methyl esters of pyrethroid acids containing an aromatic ring on the acid moiety and evaluate their biological activity against\n                    <jats:italic>Ascia monuste orseis<\/jats:italic>\n                    Latr.,\n                    <jats:italic>Tuta absoluta<\/jats:italic>\n                    Meyrick,\n                    <jats:italic>Periplaneta americana<\/jats:italic>\n                    (L.),\n                    <jats:italic>Musca domestica<\/jats:italic>\n                    L. and\n                    <jats:italic>Sitophilus zeamais<\/jats:italic>\n                    (Motsch.).\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>RESULTS:<\/jats:bold>\n                    The synthetic sequence required seven steps: protection of the hydroxyl groups of\n                    <jats:sc>D<\/jats:sc>\n                    \u2010mannitol, diol oxidative cleavage with sodium metaperiodate, alkene formation by Wittig reaction with methoxycarbonylmethylidene(triphenyl)phosphorane, cyclopropanation, acetal hydrolysis with perchloric acid and oxidative cleavage with sodium metaperiodate gave methyl (1\n                    <jats:italic>S<\/jats:italic>\n                    , 3\n                    <jats:italic>S<\/jats:italic>\n                    )\u20103\u2010formyl\u20102,2\u2010dimethylcyclopropane\u20101\u2010carboxylate. The final step comprised reaction of the aldehyde with five different aromatic phosphorus ylides to give the pyrethroids.\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:bold>CONCLUSION:<\/jats:bold>\n                    An efficient and versatile synthesis of ten new pyrethroid methyl esters has been accomplished from the readily available\n                    <jats:sc>D<\/jats:sc>\n                    \u2010mannitol in seven steps. All compounds showed insecticidal activity, and methyl (1\n                    <jats:italic>S<\/jats:italic>\n                    , 3\n                    <jats:italic>S<\/jats:italic>\n                    )\u20103\u2010[(\n                    <jats:italic>Z<\/jats:italic>\n                    )\u20102\u2010(4\u2010chlorophenyl)vinyl]\u20102,2\u2010dimethylcyclopropane\u20101\u2010carboxylate was the most active, killing 90% of\n                    <jats:italic>A. monuste orseis<\/jats:italic>\n                    and 100% of\n                    <jats:italic>T. absoluta<\/jats:italic>\n                    and\n                    <jats:italic>P. americana<\/jats:italic>\n                    . Copyright \u00a9 2009 Society of Chemical Industry\n                  <\/jats:p>","DOI":"10.1002\/ps.1771","type":"journal-article","created":{"date-parts":[[2009,5,5]],"date-time":"2009-05-05T07:13:09Z","timestamp":1241507589000},"page":"900-905","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":39,"title":["Synthesis and insecticidal activity of new pyrethroids"],"prefix":"10.1002","volume":"65","author":[{"given":"Flaviano O","family":"Silv\u00e9rio","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elson S","family":"de Alvarenga","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shaiene C","family":"Moreno","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcelo C","family":"Pican\u00e7o","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,5,5]]},"reference":[{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1039\/cs9780700473"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1289\/ehp.7254"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf60180a005"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.pharmthera.2005.10.003"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.taap.2003.12.013"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0300-483X(01)00569-8"},{"key":"e_1_2_6_8_2","first-page":"89","article-title":"Structure\u2013activity relationship of pyrethroids against different geographical strains of larvae of malaria vector, Anopheles stephensi, and role of mixed function oxidase in resistance phenomenon","volume":"42","author":"Vatandoost H","year":"2004","journal-title":"Acta Med Iranica"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/jf00056a060"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00012a048"},{"key":"e_1_2_6_11_2","unstructured":"BrownDG Cyanovinyl pyrethroids and pesticidal use thereof. US Patent 4423062 (1983)."},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1603\/0013-8746(2005)098[0726:BALHOA]2.0.CO;2"},{"key":"e_1_2_6_13_2","first-page":"107","article-title":"Biologia da tra\u00e7a\u2010do\u2010tomateiro sob condi\u00e7\u00f5es de laborat\u00f3rio","volume":"23","author":"Haji FNP","year":"1988","journal-title":"Pesquisa Agropecu\u00e1ria Brasileira"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1590\/S1519-566X2005000200027"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1303\/aez.2007.129"},{"key":"e_1_2_6_16_2","first-page":"584","volume-title":"The Housefly, its Natural History, Medical Importance, and Control.","author":"West LS","year":"1951"},{"key":"e_1_2_6_17_2","first-page":"391","volume-title":"Purification of Laboratory Chemicals","author":"Perrin DD","year":"1988"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.4067\/S0717-97072006000300013"},{"key":"e_1_2_6_19_2","first-page":"369","article-title":"A practical synthesis of (S)\u20105\u2010hydroxymethylfuran\u20102(5H)\u2010one from 1,2\u20135,6\u2010di\u2010O\u2010isopropylidene\u2010D\u2010mannose","volume":"137","author":"Mann J","year":"1987","journal-title":"J Chem Res"},{"key":"e_1_2_6_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(88)85340-1"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01918-4"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo962015e"},{"key":"e_1_2_6_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)77659-3"}],"container-title":["Pest Management Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fps.1771","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fps.1771","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ps.1771","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,21]],"date-time":"2025-10-21T11:15:57Z","timestamp":1761045357000},"score":1,"resource":{"primary":{"URL":"https:\/\/scijournals.onlinelibrary.wiley.com\/doi\/10.1002\/ps.1771"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2009,5,5]]},"references-count":22,"journal-issue":{"issue":"8","published-print":{"date-parts":[[2009,8]]}},"alternative-id":["10.1002\/ps.1771"],"URL":"https:\/\/doi.org\/10.1002\/ps.1771","archive":["Portico"],"relation":{},"ISSN":["1526-498X","1526-4998"],"issn-type":[{"value":"1526-498X","type":"print"},{"value":"1526-4998","type":"electronic"}],"subject":[],"published":{"date-parts":[[2009,5,5]]},"assertion":[{"value":"2008-10-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2009-01-27","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2009-05-05","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}