Chlorfenapyr Crystal Polymorphism and Insecticidal Activity

Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffractio...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Crystal growth & design 2024-02, Vol.24 (3), p.1284-1292
Hauptverfasser: Aronin, Reese, Brázda, Petr, Smith, Leilani N., Zhang, Carolyn Jin, Benedict, Jason B., Marr, Zoe Y., Rybtchinski, Boris, Weissman, Haim, Shtukenberg, Alexander G., Kahr, Bart
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1292
container_issue 3
container_start_page 1284
container_title Crystal growth & design
container_volume 24
creator Aronin, Reese
Brázda, Petr
Smith, Leilani N.
Zhang, Carolyn Jin
Benedict, Jason B.
Marr, Zoe Y.
Rybtchinski, Boris
Weissman, Haim
Shtukenberg, Alexander G.
Kahr, Bart
description Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffraction, and electron diffraction. Three of the four structures were considered polytypic. Chlorfenapyr polymorphs show similar lethality against fruit flies (Drosophila melanogaster) and mosquitoes (Anopheles quadrimaculatus) with the least stable polymorph showing slightly higher lethality. Similar activities may be expected to be consistent with structural similarities. Knockdown kinetics, however, depend on an internal metabolic activating step, which further complicates polymorph-dependent bioavailability.
doi_str_mv 10.1021/acs.cgd.3c01257
format Article
fullrecord <record><control><sourceid>proquest_osti_</sourceid><recordid>TN_cdi_osti_scitechconnect_2470159</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2926075522</sourcerecordid><originalsourceid>FETCH-LOGICAL-a355t-d18052de344d31875de82707fbff64c1ec00446e68a926156631f3ecbf24967e3</originalsourceid><addsrcrecordid>eNp1kMtLw0AQhxdRrFbP3iR4EiTtPrK7KZ5K8FEo6EHPy3YfNiXJxt1EyH_vlrTePM3AfPOb4QPgBsEZghjNpQoz9aVnREGEKT8BF4jiPOUU0tNjn-VkAi5D2EEIOSPkHExITrKMcXQBHott5bw1jWwHnxR-CJ2skndXDbXz7bYMdSIbnayaYFRXqlLH6TJ2P2U3XIEzK6tgrg91Cj6fnz6K13T99rIqlutUEkq7VKMcUqxNPKkJyjnVJscccruxlmUKGQVh_MawXC4wQ5QxgiwxamNxtmDckCm4G3Nd6EoRVNkZtVWuaeJLAmccIrqI0P0Itd599yZ0oi6DMlUlG-P6IHDMhpxSjCM6H1HlXQjeWNH6spZ-EAiKvVYRtYqoVRy0xo3bQ3i_qY3-448eI_AwAvvNnet9E4X8G_cLaK-BYg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2926075522</pqid></control><display><type>article</type><title>Chlorfenapyr Crystal Polymorphism and Insecticidal Activity</title><source>ACS Publications</source><creator>Aronin, Reese ; Brázda, Petr ; Smith, Leilani N. ; Zhang, Carolyn Jin ; Benedict, Jason B. ; Marr, Zoe Y. ; Rybtchinski, Boris ; Weissman, Haim ; Shtukenberg, Alexander G. ; Kahr, Bart</creator><creatorcontrib>Aronin, Reese ; Brázda, Petr ; Smith, Leilani N. ; Zhang, Carolyn Jin ; Benedict, Jason B. ; Marr, Zoe Y. ; Rybtchinski, Boris ; Weissman, Haim ; Shtukenberg, Alexander G. ; Kahr, Bart ; Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><description>Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffraction, and electron diffraction. Three of the four structures were considered polytypic. Chlorfenapyr polymorphs show similar lethality against fruit flies (Drosophila melanogaster) and mosquitoes (Anopheles quadrimaculatus) with the least stable polymorph showing slightly higher lethality. Similar activities may be expected to be consistent with structural similarities. Knockdown kinetics, however, depend on an internal metabolic activating step, which further complicates polymorph-dependent bioavailability.</description><identifier>ISSN: 1528-7483</identifier><identifier>EISSN: 1528-7505</identifier><identifier>DOI: 10.1021/acs.cgd.3c01257</identifier><identifier>PMID: 38344671</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Chemistry ; Crystallography ; Materials Science</subject><ispartof>Crystal growth &amp; design, 2024-02, Vol.24 (3), p.1284-1292</ispartof><rights>2024 The Authors. Published by American Chemical Society</rights><rights>2024 The Authors. Published by American Chemical Society.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a355t-d18052de344d31875de82707fbff64c1ec00446e68a926156631f3ecbf24967e3</cites><orcidid>0000-0002-7005-4464 ; 0000-0002-2071-8429 ; 0000-0002-5590-4758 ; 0000000220718429 ; 0000000255904758 ; 0000000270054464</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.cgd.3c01257$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.cgd.3c01257$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>230,314,780,784,885,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38344671$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/2470159$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Aronin, Reese</creatorcontrib><creatorcontrib>Brázda, Petr</creatorcontrib><creatorcontrib>Smith, Leilani N.</creatorcontrib><creatorcontrib>Zhang, Carolyn Jin</creatorcontrib><creatorcontrib>Benedict, Jason B.</creatorcontrib><creatorcontrib>Marr, Zoe Y.</creatorcontrib><creatorcontrib>Rybtchinski, Boris</creatorcontrib><creatorcontrib>Weissman, Haim</creatorcontrib><creatorcontrib>Shtukenberg, Alexander G.</creatorcontrib><creatorcontrib>Kahr, Bart</creatorcontrib><creatorcontrib>Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><title>Chlorfenapyr Crystal Polymorphism and Insecticidal Activity</title><title>Crystal growth &amp; design</title><addtitle>Cryst. Growth Des</addtitle><description>Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffraction, and electron diffraction. Three of the four structures were considered polytypic. Chlorfenapyr polymorphs show similar lethality against fruit flies (Drosophila melanogaster) and mosquitoes (Anopheles quadrimaculatus) with the least stable polymorph showing slightly higher lethality. Similar activities may be expected to be consistent with structural similarities. Knockdown kinetics, however, depend on an internal metabolic activating step, which further complicates polymorph-dependent bioavailability.</description><subject>Chemistry</subject><subject>Crystallography</subject><subject>Materials Science</subject><issn>1528-7483</issn><issn>1528-7505</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kMtLw0AQhxdRrFbP3iR4EiTtPrK7KZ5K8FEo6EHPy3YfNiXJxt1EyH_vlrTePM3AfPOb4QPgBsEZghjNpQoz9aVnREGEKT8BF4jiPOUU0tNjn-VkAi5D2EEIOSPkHExITrKMcXQBHott5bw1jWwHnxR-CJ2skndXDbXz7bYMdSIbnayaYFRXqlLH6TJ2P2U3XIEzK6tgrg91Cj6fnz6K13T99rIqlutUEkq7VKMcUqxNPKkJyjnVJscccruxlmUKGQVh_MawXC4wQ5QxgiwxamNxtmDckCm4G3Nd6EoRVNkZtVWuaeJLAmccIrqI0P0Itd599yZ0oi6DMlUlG-P6IHDMhpxSjCM6H1HlXQjeWNH6spZ-EAiKvVYRtYqoVRy0xo3bQ3i_qY3-448eI_AwAvvNnet9E4X8G_cLaK-BYg</recordid><startdate>20240207</startdate><enddate>20240207</enddate><creator>Aronin, Reese</creator><creator>Brázda, Petr</creator><creator>Smith, Leilani N.</creator><creator>Zhang, Carolyn Jin</creator><creator>Benedict, Jason B.</creator><creator>Marr, Zoe Y.</creator><creator>Rybtchinski, Boris</creator><creator>Weissman, Haim</creator><creator>Shtukenberg, Alexander G.</creator><creator>Kahr, Bart</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>OTOTI</scope><orcidid>https://orcid.org/0000-0002-7005-4464</orcidid><orcidid>https://orcid.org/0000-0002-2071-8429</orcidid><orcidid>https://orcid.org/0000-0002-5590-4758</orcidid><orcidid>https://orcid.org/0000000220718429</orcidid><orcidid>https://orcid.org/0000000255904758</orcidid><orcidid>https://orcid.org/0000000270054464</orcidid></search><sort><creationdate>20240207</creationdate><title>Chlorfenapyr Crystal Polymorphism and Insecticidal Activity</title><author>Aronin, Reese ; Brázda, Petr ; Smith, Leilani N. ; Zhang, Carolyn Jin ; Benedict, Jason B. ; Marr, Zoe Y. ; Rybtchinski, Boris ; Weissman, Haim ; Shtukenberg, Alexander G. ; Kahr, Bart</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a355t-d18052de344d31875de82707fbff64c1ec00446e68a926156631f3ecbf24967e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Chemistry</topic><topic>Crystallography</topic><topic>Materials Science</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Aronin, Reese</creatorcontrib><creatorcontrib>Brázda, Petr</creatorcontrib><creatorcontrib>Smith, Leilani N.</creatorcontrib><creatorcontrib>Zhang, Carolyn Jin</creatorcontrib><creatorcontrib>Benedict, Jason B.</creatorcontrib><creatorcontrib>Marr, Zoe Y.</creatorcontrib><creatorcontrib>Rybtchinski, Boris</creatorcontrib><creatorcontrib>Weissman, Haim</creatorcontrib><creatorcontrib>Shtukenberg, Alexander G.</creatorcontrib><creatorcontrib>Kahr, Bart</creatorcontrib><creatorcontrib>Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>OSTI.GOV</collection><jtitle>Crystal growth &amp; design</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Aronin, Reese</au><au>Brázda, Petr</au><au>Smith, Leilani N.</au><au>Zhang, Carolyn Jin</au><au>Benedict, Jason B.</au><au>Marr, Zoe Y.</au><au>Rybtchinski, Boris</au><au>Weissman, Haim</au><au>Shtukenberg, Alexander G.</au><au>Kahr, Bart</au><aucorp>Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chlorfenapyr Crystal Polymorphism and Insecticidal Activity</atitle><jtitle>Crystal growth &amp; design</jtitle><addtitle>Cryst. Growth Des</addtitle><date>2024-02-07</date><risdate>2024</risdate><volume>24</volume><issue>3</issue><spage>1284</spage><epage>1292</epage><pages>1284-1292</pages><issn>1528-7483</issn><eissn>1528-7505</eissn><abstract>Four crystalline polymorphs of the proinsecticide chlorfenapyr [4-bromo-2-(4-chlorophenyl)-1-ethoxymethyl-5-trifluoromethyl-1H-pyrrole-3-carbonitrile] have been identified and characterized by polarized light optical microscopy, differential scanning calorimetry, Raman spectroscopy, X-ray diffraction, and electron diffraction. Three of the four structures were considered polytypic. Chlorfenapyr polymorphs show similar lethality against fruit flies (Drosophila melanogaster) and mosquitoes (Anopheles quadrimaculatus) with the least stable polymorph showing slightly higher lethality. Similar activities may be expected to be consistent with structural similarities. Knockdown kinetics, however, depend on an internal metabolic activating step, which further complicates polymorph-dependent bioavailability.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>38344671</pmid><doi>10.1021/acs.cgd.3c01257</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-7005-4464</orcidid><orcidid>https://orcid.org/0000-0002-2071-8429</orcidid><orcidid>https://orcid.org/0000-0002-5590-4758</orcidid><orcidid>https://orcid.org/0000000220718429</orcidid><orcidid>https://orcid.org/0000000255904758</orcidid><orcidid>https://orcid.org/0000000270054464</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1528-7483
ispartof Crystal growth & design, 2024-02, Vol.24 (3), p.1284-1292
issn 1528-7483
1528-7505
language eng
recordid cdi_osti_scitechconnect_2470159
source ACS Publications
subjects Chemistry
Crystallography
Materials Science
title Chlorfenapyr Crystal Polymorphism and Insecticidal Activity
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-04T17%3A14%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_osti_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Chlorfenapyr%20Crystal%20Polymorphism%20and%20Insecticidal%20Activity&rft.jtitle=Crystal%20growth%20&%20design&rft.au=Aronin,%20Reese&rft.aucorp=Argonne%20National%20Laboratory%20(ANL),%20Argonne,%20IL%20(United%20States).%20Advanced%20Photon%20Source%20(APS)&rft.date=2024-02-07&rft.volume=24&rft.issue=3&rft.spage=1284&rft.epage=1292&rft.pages=1284-1292&rft.issn=1528-7483&rft.eissn=1528-7505&rft_id=info:doi/10.1021/acs.cgd.3c01257&rft_dat=%3Cproquest_osti_%3E2926075522%3C/proquest_osti_%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2926075522&rft_id=info:pmid/38344671&rfr_iscdi=true