Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives
In this study, a series of meta‐diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the tit...
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| Veröffentlicht in: | Chemistry & biodiversity 2023-04, Vol.20 (4), p.e202300060-n/a |
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| creator | Wang, Jiaxuan Xiang, Juncheng Wu, Minghui Long, Huanyuan Wu, Daoxin Liu, Jiyong |
| description | In this study, a series of meta‐diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. Especially compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(4‐cyanobenzoyl)glycinate and ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC50 against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta‐diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides. |
| doi_str_mv | 10.1002/cbdv.202300060 |
| format | Article |
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Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. Especially compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(4‐cyanobenzoyl)glycinate and ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC50 against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta‐diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.202300060</identifier><identifier>PMID: 36908182</identifier><language>eng</language><publisher>Switzerland: Wiley Subscription Services, Inc</publisher><subject>Acetic acid ; Alfalfa ; Animals ; Bioassays ; broflanilide ; Diamide - analogs & derivatives ; Diamide - pharmacology ; Ethyl acetate ; ethyl acetate group ; insecticidal activity ; Insecticides ; Insecticides - chemistry ; Insecticides - pharmacology ; meta-diamide compounds ; Molecular Structure ; Moths ; Perfluoro compounds ; Plutella xylostella ; Spodoptera ; Spodoptera frugiperda ; Structure-Activity Relationship</subject><ispartof>Chemistry & biodiversity, 2023-04, Vol.20 (4), p.e202300060-n/a</ispartof><rights>2023 Wiley‐VHCA AG, Zurich, Switzerland</rights><rights>2023 Wiley-VHCA AG, Zurich, Switzerland.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3730-76411cf77c5cb449e9879f0d82a1570990057ace8446f8964b3dd0c97d3211063</citedby><cites>FETCH-LOGICAL-c3730-76411cf77c5cb449e9879f0d82a1570990057ace8446f8964b3dd0c97d3211063</cites><orcidid>0000-0002-5832-998X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.202300060$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.202300060$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36908182$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Jiaxuan</creatorcontrib><creatorcontrib>Xiang, Juncheng</creatorcontrib><creatorcontrib>Wu, Minghui</creatorcontrib><creatorcontrib>Long, Huanyuan</creatorcontrib><creatorcontrib>Wu, Daoxin</creatorcontrib><creatorcontrib>Liu, Jiyong</creatorcontrib><title>Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives</title><title>Chemistry & biodiversity</title><addtitle>Chem Biodivers</addtitle><description>In this study, a series of meta‐diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. Especially compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(4‐cyanobenzoyl)glycinate and ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC50 against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta‐diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides.</description><subject>Acetic acid</subject><subject>Alfalfa</subject><subject>Animals</subject><subject>Bioassays</subject><subject>broflanilide</subject><subject>Diamide - analogs & derivatives</subject><subject>Diamide - pharmacology</subject><subject>Ethyl acetate</subject><subject>ethyl acetate group</subject><subject>insecticidal activity</subject><subject>Insecticides</subject><subject>Insecticides - chemistry</subject><subject>Insecticides - pharmacology</subject><subject>meta-diamide compounds</subject><subject>Molecular Structure</subject><subject>Moths</subject><subject>Perfluoro compounds</subject><subject>Plutella xylostella</subject><subject>Spodoptera</subject><subject>Spodoptera frugiperda</subject><subject>Structure-Activity Relationship</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1uEzEURi1ERUthyxJZYsOiCdeeGf8s26TQShUsKGwtx77TuJrxhPFMUFb0EfqMPAlO0waJDSt_ss49urofIW8YTBkA_-AWfj3lwAsAEPCMHDHB-IQpBc_3WfJD8jKl28znf_WCHBZCg2KKH5Ffc0zhJp7Qr5s4LHNOJ9RGTy9jQjcEF7xt6GlO6zAETLSr6edujQ1tcbC_7-7nwbbBI5117aobo085xcGGGOINPR-Wm-10Rgd80F4vMfR0jn1Y2-zE9Ioc1LZJ-PrxPSbfPp5fzy4mV18-Xc5OryaukAVMpCgZc7WUrnKLstSoldQ1eMUtqyRoDVBJ61CVpaiVFuWi8B6clr7gjIEojsn7nXfVdz9GTINpQ3LYNDZiNybDpRIVYwWvMvruH_S2G_uYtzNcgchEvnWmpjvK9V1KPdZm1YfW9hvDwGyrMdtqzL6aPPD2UTsuWvR7_KmLDOgd8DM0uPmPzszO5t__yv8A2v2aqg</recordid><startdate>202304</startdate><enddate>202304</enddate><creator>Wang, Jiaxuan</creator><creator>Xiang, Juncheng</creator><creator>Wu, Minghui</creator><creator>Long, Huanyuan</creator><creator>Wu, Daoxin</creator><creator>Liu, Jiyong</creator><general>Wiley Subscription Services, Inc</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7TM</scope><scope>8FD</scope><scope>FR3</scope><scope>K9.</scope><scope>M7N</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-5832-998X</orcidid></search><sort><creationdate>202304</creationdate><title>Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives</title><author>Wang, Jiaxuan ; Xiang, Juncheng ; Wu, Minghui ; Long, Huanyuan ; Wu, Daoxin ; Liu, Jiyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3730-76411cf77c5cb449e9879f0d82a1570990057ace8446f8964b3dd0c97d3211063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetic acid</topic><topic>Alfalfa</topic><topic>Animals</topic><topic>Bioassays</topic><topic>broflanilide</topic><topic>Diamide - analogs & derivatives</topic><topic>Diamide - pharmacology</topic><topic>Ethyl acetate</topic><topic>ethyl acetate group</topic><topic>insecticidal activity</topic><topic>Insecticides</topic><topic>Insecticides - chemistry</topic><topic>Insecticides - pharmacology</topic><topic>meta-diamide compounds</topic><topic>Molecular Structure</topic><topic>Moths</topic><topic>Perfluoro compounds</topic><topic>Plutella xylostella</topic><topic>Spodoptera</topic><topic>Spodoptera frugiperda</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Jiaxuan</creatorcontrib><creatorcontrib>Xiang, Juncheng</creatorcontrib><creatorcontrib>Wu, Minghui</creatorcontrib><creatorcontrib>Long, Huanyuan</creatorcontrib><creatorcontrib>Wu, Daoxin</creatorcontrib><creatorcontrib>Liu, Jiyong</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Algology Mycology and Protozoology Abstracts (Microbiology C)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Jiaxuan</au><au>Xiang, Juncheng</au><au>Wu, Minghui</au><au>Long, Huanyuan</au><au>Wu, Daoxin</au><au>Liu, Jiyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chem Biodivers</addtitle><date>2023-04</date><risdate>2023</risdate><volume>20</volume><issue>4</issue><spage>e202300060</spage><epage>n/a</epage><pages>e202300060-n/a</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>In this study, a series of meta‐diamide compounds containing ethyl acetate group and their derivatives were designed and synthesized. Their insecticidal activities against Plutella xylostella, Spodoptera frugiperda and Alfalfa sprouts were evaluated. Preliminary bioassays showed that some of the title compounds exhibited excellent insecticidal activities. Especially compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(4‐cyanobenzoyl)glycinate and ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate showed 100 % mortality at 0.1 mg/L against Plutella xylostella and Spodoptera frugiperda, same to broflanilide. Their LC50 against Plutella xylostella is 0.286 mg/L and 0.0218 mg/L, respectively. Moreover, compound ethyl N‐(3‐((2‐bromo‐4‐(perfluoropropan‐2‐yl)‐6‐(trifluoromethyl)phenyl)carbamoyl)‐2‐fluorophenyl)‐N‐(6‐fluoronicotinoyl)glycinate displayed faster control efficacy than broflanilide at 0.1 mg/L. The results indicated that meta‐diamide compounds containing ethyl acetate group could be developed as novel and promising insecticides.</abstract><cop>Switzerland</cop><pub>Wiley Subscription Services, Inc</pub><pmid>36908182</pmid><doi>10.1002/cbdv.202300060</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-5832-998X</orcidid></addata></record> |
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| subjects | Acetic acid Alfalfa Animals Bioassays broflanilide Diamide - analogs & derivatives Diamide - pharmacology Ethyl acetate ethyl acetate group insecticidal activity Insecticides Insecticides - chemistry Insecticides - pharmacology meta-diamide compounds Molecular Structure Moths Perfluoro compounds Plutella xylostella Spodoptera Spodoptera frugiperda Structure-Activity Relationship |
| title | Design, Synthesis, and Insecticidal Activities of Novel meta‐Diamide Compounds Containing Ethyl Acetate and Their Derivatives |
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