Loading…
Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide
An aqueous photolysis study was conducted with radiolabeled thiamethoxam, 4H-1,3,5-oxadiazin-2-imine, 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro, to establish the relevance of aqueous photolysis as a transformation process for 14 C-[thiazolyl]-thiamethoxam. 14 C-[thiazolyl]-thiameth...
Saved in:
| Published in: | Journal of agricultural and food chemistry 2000-10, Vol.48 (10), p.4671-4675 |
|---|---|
| Main Authors: | , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-a375t-61818f3851dd6a8d5841b8e5db6f9f0e9de5a3c7f85cce2dad4702a37358c50c3 |
|---|---|
| cites | |
| container_end_page | 4675 |
| container_issue | 10 |
| container_start_page | 4671 |
| container_title | Journal of agricultural and food chemistry |
| container_volume | 48 |
| creator | Schwartz, Barb J Sparrow, F. Kay Heard, Nina E Thede, Bruce M |
| description | An aqueous photolysis study was conducted with radiolabeled thiamethoxam, 4H-1,3,5-oxadiazin-2-imine, 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro, to establish the relevance of aqueous photolysis as a transformation process for 14 C-[thiazolyl]-thiamethoxam. 14 C-[thiazolyl]-thiamethoxam was applied to sterile sodium acetate pH 5 buffer solution at a dose rate of approximately 10 ppm. The resulting samples were incubated for up to 30 days at 25 °C under irradiated and nonirradiated conditions. The irradiated samples were exposed to a 12-hour-on and 12-hour-off light cycle. Volatile fractions accounted for up to an average of 56.76% of the total dose for the irradiated incubations and |
| doi_str_mv | 10.1021/jf990966y |
| format | article |
| fullrecord | <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_jf990966y</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>g4810206</sourcerecordid><originalsourceid>FETCH-LOGICAL-a375t-61818f3851dd6a8d5841b8e5db6f9f0e9de5a3c7f85cce2dad4702a37358c50c3</originalsourceid><addsrcrecordid>eNpt0MtO4zAUBmALDYJyWfACyNJoFiwCdoITZ4k63ASCihYWbKxTX6hLErd2gihPj6FV2bCwvPi_Y_n8CB1QckxJSk-mpixJmeeLDdSjLCUJo5T_QT0Sw4SznG6jnRCmhBDOCrKFtiklLC1o0UPzoa27qoVGuy7g_9rbN2jtRzyuwdAoPPIwm9nmBTuDn1wVg0rjgXeqk23Axrsan8277-nBxLWuWgQbvvBoYqHW7cS9Q42vm6Bla6VVeg9tGqiC3l_du-jx4nzUv0pu7y-v-2e3CWQFa5OccspNxhlVKgeuGD-lY66ZGuemNESXSjPIZGE4k1KnCtRpQdI4mzEuGZHZLjpaviu9C8FrI2be1uAXghLxVZtY1xbt4dLOunGt1Y9c9RTB3xWAIKEyHhppw9rxjKcpjypZKhta_b5Owb-KvIhbidFgKO6G6c3V882D6Ef_b-lBBjF1nW9iIb987xP07ZLR</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)</source><creator>Schwartz, Barb J ; Sparrow, F. Kay ; Heard, Nina E ; Thede, Bruce M</creator><creatorcontrib>Schwartz, Barb J ; Sparrow, F. Kay ; Heard, Nina E ; Thede, Bruce M</creatorcontrib><description>An aqueous photolysis study was conducted with radiolabeled thiamethoxam, 4H-1,3,5-oxadiazin-2-imine, 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro, to establish the relevance of aqueous photolysis as a transformation process for 14 C-[thiazolyl]-thiamethoxam. 14 C-[thiazolyl]-thiamethoxam was applied to sterile sodium acetate pH 5 buffer solution at a dose rate of approximately 10 ppm. The resulting samples were incubated for up to 30 days at 25 °C under irradiated and nonirradiated conditions. The irradiated samples were exposed to a 12-hour-on and 12-hour-off light cycle. Volatile fractions accounted for up to an average of 56.76% of the total dose for the irradiated incubations and <0.08% for the nonirradiated incubations. These fractions were proposed to be a mixture of carbonyl sulfide (COS) and isocyanic acid (CONH). Verification of these components was accomplished by trapping with cyclohexylamine and formation of the thiocarbamate and the isocyanic acid derivatives. A similar method of trapping thiocarbamate metabolites was reported (Chen and Casida, 1978) where filter paper saturated with isobutylamine in methanol was arranged to trap 14COS and 14CO2 under a positive flow of O2 at 25 °C. Mass spectroscopy of the derivatized components confirmed the presence of carbonyl sulfide as the cyclohexylamine thiocarbamate and of isocyanic acid as its cyclohexylamine derivative. Evidence from this study indicates that thiamethoxam degrades significantly under photolytic conditions. Keywords: Pesticides, photolysis; volatiles; derivatization</description><identifier>ISSN: 0021-8561</identifier><identifier>EISSN: 1520-5118</identifier><identifier>DOI: 10.1021/jf990966y</identifier><identifier>PMID: 11052717</identifier><identifier>CODEN: JAFCAU</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Biological and medical sciences ; Chemical control ; Chemistry ; Control ; Exact sciences and technology ; Fundamental and applied biological sciences. Psychology ; General and physical chemistry ; Insecticides - chemistry ; Insecticides - radiation effects ; Light ; Mass Spectrometry ; Neonicotinoids ; Nitro Compounds - chemistry ; Nitro Compounds - radiation effects ; Oxazines - chemistry ; Oxazines - radiation effects ; Photochemistry ; Photolysis ; Physical chemistry of induced reactions (with radiations, particles and ultrasonics) ; Phytopathology. Animal pests. Plant and forest protection ; Protozoa. Invertebrates ; Spectrophotometry, Ultraviolet ; Thiamethoxam ; Thiazoles</subject><ispartof>Journal of agricultural and food chemistry, 2000-10, Vol.48 (10), p.4671-4675</ispartof><rights>Copyright © 2000 American Chemical Society</rights><rights>2001 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a375t-61818f3851dd6a8d5841b8e5db6f9f0e9de5a3c7f85cce2dad4702a37358c50c3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=838228$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11052717$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Schwartz, Barb J</creatorcontrib><creatorcontrib>Sparrow, F. Kay</creatorcontrib><creatorcontrib>Heard, Nina E</creatorcontrib><creatorcontrib>Thede, Bruce M</creatorcontrib><title>Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide</title><title>Journal of agricultural and food chemistry</title><addtitle>J. Agric. Food Chem</addtitle><description>An aqueous photolysis study was conducted with radiolabeled thiamethoxam, 4H-1,3,5-oxadiazin-2-imine, 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro, to establish the relevance of aqueous photolysis as a transformation process for 14 C-[thiazolyl]-thiamethoxam. 14 C-[thiazolyl]-thiamethoxam was applied to sterile sodium acetate pH 5 buffer solution at a dose rate of approximately 10 ppm. The resulting samples were incubated for up to 30 days at 25 °C under irradiated and nonirradiated conditions. The irradiated samples were exposed to a 12-hour-on and 12-hour-off light cycle. Volatile fractions accounted for up to an average of 56.76% of the total dose for the irradiated incubations and <0.08% for the nonirradiated incubations. These fractions were proposed to be a mixture of carbonyl sulfide (COS) and isocyanic acid (CONH). Verification of these components was accomplished by trapping with cyclohexylamine and formation of the thiocarbamate and the isocyanic acid derivatives. A similar method of trapping thiocarbamate metabolites was reported (Chen and Casida, 1978) where filter paper saturated with isobutylamine in methanol was arranged to trap 14COS and 14CO2 under a positive flow of O2 at 25 °C. Mass spectroscopy of the derivatized components confirmed the presence of carbonyl sulfide as the cyclohexylamine thiocarbamate and of isocyanic acid as its cyclohexylamine derivative. Evidence from this study indicates that thiamethoxam degrades significantly under photolytic conditions. Keywords: Pesticides, photolysis; volatiles; derivatization</description><subject>Biological and medical sciences</subject><subject>Chemical control</subject><subject>Chemistry</subject><subject>Control</subject><subject>Exact sciences and technology</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>General and physical chemistry</subject><subject>Insecticides - chemistry</subject><subject>Insecticides - radiation effects</subject><subject>Light</subject><subject>Mass Spectrometry</subject><subject>Neonicotinoids</subject><subject>Nitro Compounds - chemistry</subject><subject>Nitro Compounds - radiation effects</subject><subject>Oxazines - chemistry</subject><subject>Oxazines - radiation effects</subject><subject>Photochemistry</subject><subject>Photolysis</subject><subject>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Protozoa. Invertebrates</subject><subject>Spectrophotometry, Ultraviolet</subject><subject>Thiamethoxam</subject><subject>Thiazoles</subject><issn>0021-8561</issn><issn>1520-5118</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><recordid>eNpt0MtO4zAUBmALDYJyWfACyNJoFiwCdoITZ4k63ASCihYWbKxTX6hLErd2gihPj6FV2bCwvPi_Y_n8CB1QckxJSk-mpixJmeeLDdSjLCUJo5T_QT0Sw4SznG6jnRCmhBDOCrKFtiklLC1o0UPzoa27qoVGuy7g_9rbN2jtRzyuwdAoPPIwm9nmBTuDn1wVg0rjgXeqk23Axrsan8277-nBxLWuWgQbvvBoYqHW7cS9Q42vm6Bla6VVeg9tGqiC3l_du-jx4nzUv0pu7y-v-2e3CWQFa5OccspNxhlVKgeuGD-lY66ZGuemNESXSjPIZGE4k1KnCtRpQdI4mzEuGZHZLjpaviu9C8FrI2be1uAXghLxVZtY1xbt4dLOunGt1Y9c9RTB3xWAIKEyHhppw9rxjKcpjypZKhta_b5Owb-KvIhbidFgKO6G6c3V882D6Ef_b-lBBjF1nW9iIb987xP07ZLR</recordid><startdate>20001001</startdate><enddate>20001001</enddate><creator>Schwartz, Barb J</creator><creator>Sparrow, F. Kay</creator><creator>Heard, Nina E</creator><creator>Thede, Bruce M</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20001001</creationdate><title>Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide</title><author>Schwartz, Barb J ; Sparrow, F. Kay ; Heard, Nina E ; Thede, Bruce M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a375t-61818f3851dd6a8d5841b8e5db6f9f0e9de5a3c7f85cce2dad4702a37358c50c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>Biological and medical sciences</topic><topic>Chemical control</topic><topic>Chemistry</topic><topic>Control</topic><topic>Exact sciences and technology</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>General and physical chemistry</topic><topic>Insecticides - chemistry</topic><topic>Insecticides - radiation effects</topic><topic>Light</topic><topic>Mass Spectrometry</topic><topic>Neonicotinoids</topic><topic>Nitro Compounds - chemistry</topic><topic>Nitro Compounds - radiation effects</topic><topic>Oxazines - chemistry</topic><topic>Oxazines - radiation effects</topic><topic>Photochemistry</topic><topic>Photolysis</topic><topic>Physical chemistry of induced reactions (with radiations, particles and ultrasonics)</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Protozoa. Invertebrates</topic><topic>Spectrophotometry, Ultraviolet</topic><topic>Thiamethoxam</topic><topic>Thiazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Schwartz, Barb J</creatorcontrib><creatorcontrib>Sparrow, F. Kay</creatorcontrib><creatorcontrib>Heard, Nina E</creatorcontrib><creatorcontrib>Thede, Bruce M</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Journal of agricultural and food chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Schwartz, Barb J</au><au>Sparrow, F. Kay</au><au>Heard, Nina E</au><au>Thede, Bruce M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide</atitle><jtitle>Journal of agricultural and food chemistry</jtitle><addtitle>J. Agric. Food Chem</addtitle><date>2000-10-01</date><risdate>2000</risdate><volume>48</volume><issue>10</issue><spage>4671</spage><epage>4675</epage><pages>4671-4675</pages><issn>0021-8561</issn><eissn>1520-5118</eissn><coden>JAFCAU</coden><abstract>An aqueous photolysis study was conducted with radiolabeled thiamethoxam, 4H-1,3,5-oxadiazin-2-imine, 3-[(2-chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro, to establish the relevance of aqueous photolysis as a transformation process for 14 C-[thiazolyl]-thiamethoxam. 14 C-[thiazolyl]-thiamethoxam was applied to sterile sodium acetate pH 5 buffer solution at a dose rate of approximately 10 ppm. The resulting samples were incubated for up to 30 days at 25 °C under irradiated and nonirradiated conditions. The irradiated samples were exposed to a 12-hour-on and 12-hour-off light cycle. Volatile fractions accounted for up to an average of 56.76% of the total dose for the irradiated incubations and <0.08% for the nonirradiated incubations. These fractions were proposed to be a mixture of carbonyl sulfide (COS) and isocyanic acid (CONH). Verification of these components was accomplished by trapping with cyclohexylamine and formation of the thiocarbamate and the isocyanic acid derivatives. A similar method of trapping thiocarbamate metabolites was reported (Chen and Casida, 1978) where filter paper saturated with isobutylamine in methanol was arranged to trap 14COS and 14CO2 under a positive flow of O2 at 25 °C. Mass spectroscopy of the derivatized components confirmed the presence of carbonyl sulfide as the cyclohexylamine thiocarbamate and of isocyanic acid as its cyclohexylamine derivative. Evidence from this study indicates that thiamethoxam degrades significantly under photolytic conditions. Keywords: Pesticides, photolysis; volatiles; derivatization</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>11052717</pmid><doi>10.1021/jf990966y</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0021-8561 |
| ispartof | Journal of agricultural and food chemistry, 2000-10, Vol.48 (10), p.4671-4675 |
| issn | 0021-8561 1520-5118 |
| language | eng |
| recordid | cdi_crossref_primary_10_1021_jf990966y |
| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| subjects | Biological and medical sciences Chemical control Chemistry Control Exact sciences and technology Fundamental and applied biological sciences. Psychology General and physical chemistry Insecticides - chemistry Insecticides - radiation effects Light Mass Spectrometry Neonicotinoids Nitro Compounds - chemistry Nitro Compounds - radiation effects Oxazines - chemistry Oxazines - radiation effects Photochemistry Photolysis Physical chemistry of induced reactions (with radiations, particles and ultrasonics) Phytopathology. Animal pests. Plant and forest protection Protozoa. Invertebrates Spectrophotometry, Ultraviolet Thiamethoxam Thiazoles |
| title | Simultaneous Derivatization and Trapping of Volatile Products from Aqueous Photolysis of Thiamethoxam Insecticide |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-21T10%3A02%3A13IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Simultaneous%20Derivatization%20and%20Trapping%20of%20Volatile%20Products%20from%20Aqueous%20Photolysis%20of%20Thiamethoxam%20Insecticide&rft.jtitle=Journal%20of%20agricultural%20and%20food%20chemistry&rft.au=Schwartz,%20Barb%20J&rft.date=2000-10-01&rft.volume=48&rft.issue=10&rft.spage=4671&rft.epage=4675&rft.pages=4671-4675&rft.issn=0021-8561&rft.eissn=1520-5118&rft.coden=JAFCAU&rft_id=info:doi/10.1021/jf990966y&rft_dat=%3Cacs_cross%3Eg4810206%3C/acs_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a375t-61818f3851dd6a8d5841b8e5db6f9f0e9de5a3c7f85cce2dad4702a37358c50c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/11052717&rfr_iscdi=true |