Comparative metabolism of the pyrethroids bifenthrin and deltamethrin in the bulb mite Rhizoglyphus robini
The fate of {sup 14}C-radiolabeled bifenthrin and deltamethrin was studied in the mite, Rhizoglyphus robini. Administered either by ingestion or by contact, both pyrethroids were efficiently metabolized, but deltamethrin was degraded to a much greater extent. The identified metabolites arise from a...
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| Veröffentlicht in: | Journal of agricultural and food chemistry 1988-09, Vol.36 (5), p.1040-1043 |
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| creator | Ruzo, Luis O Cohen, Ephraim Capua, Shlomo |
| description | The fate of {sup 14}C-radiolabeled bifenthrin and deltamethrin was studied in the mite, Rhizoglyphus robini. Administered either by ingestion or by contact, both pyrethroids were efficiently metabolized, but deltamethrin was degraded to a much greater extent. The identified metabolites arise from a combination of ester cleavage, oxidation, and conjugation reactions. With {sup 14}C-acid- and {sup 14}C-alcohol-labeled bifenthrin, the free metabolites detected were the 4{prime}-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4{prime}-hydroxy derivative from the alcohol moiety, as well as several unidentified metabolites. Using {sup 14}C-alcohol-labeled deltamethrin, 3-phenoxybenzoic acid and its 4{prime}-hydroxylated product and several unknown metabolites were detected. Conjugates comprised the bulk of total pyrethroid metabolites. In addition to ester cleavage products, the 4{prime}-hydroxylated bifenthrin was also identified. For the first time in invertebrates, a conjugated pyrethroid ester was observed. |
| doi_str_mv | 10.1021/jf00083a033 |
| format | Article |
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Administered either by ingestion or by contact, both pyrethroids were efficiently metabolized, but deltamethrin was degraded to a much greater extent. The identified metabolites arise from a combination of ester cleavage, oxidation, and conjugation reactions. With {sup 14}C-acid- and {sup 14}C-alcohol-labeled bifenthrin, the free metabolites detected were the 4{prime}-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4{prime}-hydroxy derivative from the alcohol moiety, as well as several unidentified metabolites. Using {sup 14}C-alcohol-labeled deltamethrin, 3-phenoxybenzoic acid and its 4{prime}-hydroxylated product and several unknown metabolites were detected. Conjugates comprised the bulk of total pyrethroid metabolites. In addition to ester cleavage products, the 4{prime}-hydroxylated bifenthrin was also identified. For the first time in invertebrates, a conjugated pyrethroid ester was observed.</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf00083a033</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>553003 - Agriculture & Food Technology- Pest & Disease Control- (1987-) ; 60 APPLIED LIFE SCIENCES ; ACARIEN NUISIBLE ; ACAROS NOCIVOS ; ANIMALS ; ARACHNIDS ; ARTHROPODS ; Biological and medical sciences ; CARBON 14 COMPOUNDS ; Control ; CONTROL DE PLAGAS ; Fundamental and applied biological sciences. Psychology ; Generalities ; INSECTICIDAS ; INSECTICIDE ; INSECTICIDES ; INVERTEBRATES ; ISOTOPE APPLICATIONS ; LABELLED COMPOUNDS ; LUTTE ANTI-PARASITE ; METABOLISM ; METABOLISME ; METABOLISMO ; METABOLITES ; MITES ; PEST CONTROL ; PEST MITES ; PESTICIDES ; Physical control ; Phytopathology. Animal pests. Plant and forest protection ; PIRETRINAS ; Protozoa. Invertebrates ; PYRETHRINE ; PYRETHRINS ; TRACER TECHNIQUES</subject><ispartof>Journal of agricultural and food chemistry, 1988-09, Vol.36 (5), p.1040-1043</ispartof><rights>1990 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a376t-90cb2006c50bb19d8d0e74a68253405f5c1d8cf71fa41341bb96f3777d499db63</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jf00083a033$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jf00083a033$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2764,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=6873531$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/7059806$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Ruzo, Luis O</creatorcontrib><creatorcontrib>Cohen, Ephraim</creatorcontrib><creatorcontrib>Capua, Shlomo</creatorcontrib><title>Comparative metabolism of the pyrethroids bifenthrin and deltamethrin in the bulb mite Rhizoglyphus robini</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>The fate of {sup 14}C-radiolabeled bifenthrin and deltamethrin was studied in the mite, Rhizoglyphus robini. Administered either by ingestion or by contact, both pyrethroids were efficiently metabolized, but deltamethrin was degraded to a much greater extent. The identified metabolites arise from a combination of ester cleavage, oxidation, and conjugation reactions. With {sup 14}C-acid- and {sup 14}C-alcohol-labeled bifenthrin, the free metabolites detected were the 4{prime}-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4{prime}-hydroxy derivative from the alcohol moiety, as well as several unidentified metabolites. Using {sup 14}C-alcohol-labeled deltamethrin, 3-phenoxybenzoic acid and its 4{prime}-hydroxylated product and several unknown metabolites were detected. Conjugates comprised the bulk of total pyrethroid metabolites. In addition to ester cleavage products, the 4{prime}-hydroxylated bifenthrin was also identified. For the first time in invertebrates, a conjugated pyrethroid ester was observed.</description><subject>553003 - Agriculture & Food Technology- Pest & Disease Control- (1987-)</subject><subject>60 APPLIED LIFE SCIENCES</subject><subject>ACARIEN NUISIBLE</subject><subject>ACAROS NOCIVOS</subject><subject>ANIMALS</subject><subject>ARACHNIDS</subject><subject>ARTHROPODS</subject><subject>Biological and medical sciences</subject><subject>CARBON 14 COMPOUNDS</subject><subject>Control</subject><subject>CONTROL DE PLAGAS</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Generalities</subject><subject>INSECTICIDAS</subject><subject>INSECTICIDE</subject><subject>INSECTICIDES</subject><subject>INVERTEBRATES</subject><subject>ISOTOPE APPLICATIONS</subject><subject>LABELLED COMPOUNDS</subject><subject>LUTTE ANTI-PARASITE</subject><subject>METABOLISM</subject><subject>METABOLISME</subject><subject>METABOLISMO</subject><subject>METABOLITES</subject><subject>MITES</subject><subject>PEST CONTROL</subject><subject>PEST MITES</subject><subject>PESTICIDES</subject><subject>Physical control</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>PIRETRINAS</subject><subject>Protozoa. Invertebrates</subject><subject>PYRETHRINE</subject><subject>PYRETHRINS</subject><subject>TRACER TECHNIQUES</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1988</creationdate><recordtype>article</recordtype><recordid>eNpt0M-L1DAUB_AgCo67nrx5CiJ4kK4vk-ZHj-6grrCyuj_OIUmTbca2KUlGnP3rbaksHoRAyPt-8ng8hF4ROCOwJR_2HgAk1UDpE7QhbAsVI0Q-RRuY40oyTp6jFznvF8YEbNB-F4dJJ13CL4cHV7SJfcgDjh6XzuHpmFzpUgxtxiZ4N86PMGI9trh1fdGDWwvzWbg59AYPoTh83YWHeN8fp-6QcYomjOEUPfO6z-7l3_sE3X3-dLu7qC6vvnzdfbysNBW8VA1YswXgloExpGllC07UmsstozUwzyxppfWCeF0TWhNjGu6pEKKtm6Y1nJ6gN2vfmEtQ2c7j2M7GcXS2KAGskbCg9yuyKeacnFdTCoNOR0VALbtU_-xy1m9XPelsde-THm3Ij1-4FJRRMrNqZSEX9_sx1umn4oIKpm6_3yjOLsT5tx_XSs7-9eq9jkrfp7nl3Y1sCAO6hO_WUNus9vGQxnlp_53uD5DemCM</recordid><startdate>19880901</startdate><enddate>19880901</enddate><creator>Ruzo, Luis O</creator><creator>Cohen, Ephraim</creator><creator>Capua, Shlomo</creator><general>American Chemical Society</general><scope>FBQ</scope><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>OTOTI</scope></search><sort><creationdate>19880901</creationdate><title>Comparative metabolism of the pyrethroids bifenthrin and deltamethrin in the bulb mite Rhizoglyphus robini</title><author>Ruzo, Luis O ; Cohen, Ephraim ; Capua, Shlomo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a376t-90cb2006c50bb19d8d0e74a68253405f5c1d8cf71fa41341bb96f3777d499db63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1988</creationdate><topic>553003 - Agriculture & Food Technology- Pest & Disease Control- (1987-)</topic><topic>60 APPLIED LIFE SCIENCES</topic><topic>ACARIEN NUISIBLE</topic><topic>ACAROS NOCIVOS</topic><topic>ANIMALS</topic><topic>ARACHNIDS</topic><topic>ARTHROPODS</topic><topic>Biological and medical sciences</topic><topic>CARBON 14 COMPOUNDS</topic><topic>Control</topic><topic>CONTROL DE PLAGAS</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Generalities</topic><topic>INSECTICIDAS</topic><topic>INSECTICIDE</topic><topic>INSECTICIDES</topic><topic>INVERTEBRATES</topic><topic>ISOTOPE APPLICATIONS</topic><topic>LABELLED COMPOUNDS</topic><topic>LUTTE ANTI-PARASITE</topic><topic>METABOLISM</topic><topic>METABOLISME</topic><topic>METABOLISMO</topic><topic>METABOLITES</topic><topic>MITES</topic><topic>PEST CONTROL</topic><topic>PEST MITES</topic><topic>PESTICIDES</topic><topic>Physical control</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>PIRETRINAS</topic><topic>Protozoa. Invertebrates</topic><topic>PYRETHRINE</topic><topic>PYRETHRINS</topic><topic>TRACER TECHNIQUES</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ruzo, Luis O</creatorcontrib><creatorcontrib>Cohen, Ephraim</creatorcontrib><creatorcontrib>Capua, Shlomo</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>OSTI.GOV</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ruzo, Luis O</au><au>Cohen, Ephraim</au><au>Capua, Shlomo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Comparative metabolism of the pyrethroids bifenthrin and deltamethrin in the bulb mite Rhizoglyphus robini</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>1988-09-01</date><risdate>1988</risdate><volume>36</volume><issue>5</issue><spage>1040</spage><epage>1043</epage><pages>1040-1043</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>The fate of {sup 14}C-radiolabeled bifenthrin and deltamethrin was studied in the mite, Rhizoglyphus robini. Administered either by ingestion or by contact, both pyrethroids were efficiently metabolized, but deltamethrin was degraded to a much greater extent. The identified metabolites arise from a combination of ester cleavage, oxidation, and conjugation reactions. With {sup 14}C-acid- and {sup 14}C-alcohol-labeled bifenthrin, the free metabolites detected were the 4{prime}-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4{prime}-hydroxy derivative from the alcohol moiety, as well as several unidentified metabolites. Using {sup 14}C-alcohol-labeled deltamethrin, 3-phenoxybenzoic acid and its 4{prime}-hydroxylated product and several unknown metabolites were detected. Conjugates comprised the bulk of total pyrethroid metabolites. In addition to ester cleavage products, the 4{prime}-hydroxylated bifenthrin was also identified. For the first time in invertebrates, a conjugated pyrethroid ester was observed.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><doi>10.1021/jf00083a033</doi><tpages>4</tpages></addata></record> |
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| ispartof | Journal of agricultural and food chemistry, 1988-09, Vol.36 (5), p.1040-1043 |
| issn | 0021-8561 1520-5118 |
| language | eng |
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| source | ACS Publications |
| subjects | 553003 - Agriculture & Food Technology- Pest & Disease Control- (1987-) 60 APPLIED LIFE SCIENCES ACARIEN NUISIBLE ACAROS NOCIVOS ANIMALS ARACHNIDS ARTHROPODS Biological and medical sciences CARBON 14 COMPOUNDS Control CONTROL DE PLAGAS Fundamental and applied biological sciences. Psychology Generalities INSECTICIDAS INSECTICIDE INSECTICIDES INVERTEBRATES ISOTOPE APPLICATIONS LABELLED COMPOUNDS LUTTE ANTI-PARASITE METABOLISM METABOLISME METABOLISMO METABOLITES MITES PEST CONTROL PEST MITES PESTICIDES Physical control Phytopathology. Animal pests. Plant and forest protection PIRETRINAS Protozoa. Invertebrates PYRETHRINE PYRETHRINS TRACER TECHNIQUES |
| title | Comparative metabolism of the pyrethroids bifenthrin and deltamethrin in the bulb mite Rhizoglyphus robini |
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