Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures
BACKGROUND: Pyrazole and hydrazone derivatives possess good insecticidal activities; their substructural units are widely used in pesticide design. In an effort to discover new molecules with good insecticidal activities, a series of pyrazole amide derivatives containing hydrazone substructures were...
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| Veröffentlicht in: | Pest management science 2012-05, Vol.68 (5), p.801-810 |
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| creator | Wu, Jian Song, Bao-An Hu, De-Yu Yue, Min Yang, Song |
| description | BACKGROUND: Pyrazole and hydrazone derivatives possess good insecticidal activities; their substructural units are widely used in pesticide design. In an effort to discover new molecules with good insecticidal activities, a series of pyrazole amide derivatives containing hydrazone substructures were synthesised and bioassayed.
RESULTS: Bioassays demonstrated that some of the title compounds exhibited notable control of Plutella xylostella (Linnaeus), Helicoverpa armigera (Hübner), Culex pipiens pallens, Laphygma exigua (Hübner), Spodoptera litura (Fabricius), Nilaparvata lugens (Stål) and Rhopalosiphum maidis (Fitch) at 5, 10, 0.25, 200, 20, 100 and 500 mg L−1 respectively. Comparative molecular field analysis (CoMFA) based on the bioactivities for P. xylostella was studied; the values of q2 and r2 for the CoMFA model were 0.701 and 0.964 respectively.
CONCLUSION: Some of the title compounds displayed good and broad‐spectrum insecticidal activities against different insect species; the CoMFA model revealed that a bulky and negatively charged group at the 4‐position of benzene could enhance insecticidal activity. These results could provide useful information for the design of novel insecticide containing substructural units of pyrazole amide and hydrazone. Copyright © 2011 Society of Chemical Industry |
| doi_str_mv | 10.1002/ps.2329 |
| format | Article |
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RESULTS: Bioassays demonstrated that some of the title compounds exhibited notable control of Plutella xylostella (Linnaeus), Helicoverpa armigera (Hübner), Culex pipiens pallens, Laphygma exigua (Hübner), Spodoptera litura (Fabricius), Nilaparvata lugens (Stål) and Rhopalosiphum maidis (Fitch) at 5, 10, 0.25, 200, 20, 100 and 500 mg L−1 respectively. Comparative molecular field analysis (CoMFA) based on the bioactivities for P. xylostella was studied; the values of q2 and r2 for the CoMFA model were 0.701 and 0.964 respectively.
CONCLUSION: Some of the title compounds displayed good and broad‐spectrum insecticidal activities against different insect species; the CoMFA model revealed that a bulky and negatively charged group at the 4‐position of benzene could enhance insecticidal activity. These results could provide useful information for the design of novel insecticide containing substructural units of pyrazole amide and hydrazone. Copyright © 2011 Society of Chemical Industry</description><identifier>ISSN: 1526-498X</identifier><identifier>EISSN: 1526-4998</identifier><identifier>DOI: 10.1002/ps.2329</identifier><identifier>PMID: 22190278</identifier><identifier>CODEN: PMSCFC</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>Amides - chemistry ; Amides - pharmacology ; Animals ; Bioassays ; Biological and medical sciences ; Butterflies & moths ; Chemical compounds ; CoMFA ; Control ; Drug Design ; Fundamental and applied biological sciences. Psychology ; hydrazone ; Hydrazones - chemistry ; Hydrazones - pharmacology ; Insecta - drug effects ; insecticidal activity ; Insecticides - chemical synthesis ; Insecticides - chemistry ; Insecticides - pharmacology ; Molecular Structure ; Pest control ; Pesticides ; Phytopathology. Animal pests. Plant and forest protection ; Protozoa. Invertebrates ; pyrazole amide derivatives ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; synthesis</subject><ispartof>Pest management science, 2012-05, Vol.68 (5), p.801-810</ispartof><rights>Copyright © 2011 Society of Chemical Industry</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 Society of Chemical Industry.</rights><rights>Copyright John Wiley and Sons, Limited May 2012</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4779-874ff1fbbffb44b7d0d15ed4fd4d6bbff71490938a53ddbb8852ed90518152e13</citedby><cites>FETCH-LOGICAL-c4779-874ff1fbbffb44b7d0d15ed4fd4d6bbff71490938a53ddbb8852ed90518152e13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fps.2329$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fps.2329$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25727216$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22190278$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wu, Jian</creatorcontrib><creatorcontrib>Song, Bao-An</creatorcontrib><creatorcontrib>Hu, De-Yu</creatorcontrib><creatorcontrib>Yue, Min</creatorcontrib><creatorcontrib>Yang, Song</creatorcontrib><title>Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures</title><title>Pest management science</title><addtitle>Pest. Manag. Sci</addtitle><description>BACKGROUND: Pyrazole and hydrazone derivatives possess good insecticidal activities; their substructural units are widely used in pesticide design. In an effort to discover new molecules with good insecticidal activities, a series of pyrazole amide derivatives containing hydrazone substructures were synthesised and bioassayed.
RESULTS: Bioassays demonstrated that some of the title compounds exhibited notable control of Plutella xylostella (Linnaeus), Helicoverpa armigera (Hübner), Culex pipiens pallens, Laphygma exigua (Hübner), Spodoptera litura (Fabricius), Nilaparvata lugens (Stål) and Rhopalosiphum maidis (Fitch) at 5, 10, 0.25, 200, 20, 100 and 500 mg L−1 respectively. Comparative molecular field analysis (CoMFA) based on the bioactivities for P. xylostella was studied; the values of q2 and r2 for the CoMFA model were 0.701 and 0.964 respectively.
CONCLUSION: Some of the title compounds displayed good and broad‐spectrum insecticidal activities against different insect species; the CoMFA model revealed that a bulky and negatively charged group at the 4‐position of benzene could enhance insecticidal activity. These results could provide useful information for the design of novel insecticide containing substructural units of pyrazole amide and hydrazone. Copyright © 2011 Society of Chemical Industry</description><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Animals</subject><subject>Bioassays</subject><subject>Biological and medical sciences</subject><subject>Butterflies & moths</subject><subject>Chemical compounds</subject><subject>CoMFA</subject><subject>Control</subject><subject>Drug Design</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>hydrazone</subject><subject>Hydrazones - chemistry</subject><subject>Hydrazones - pharmacology</subject><subject>Insecta - drug effects</subject><subject>insecticidal activity</subject><subject>Insecticides - chemical synthesis</subject><subject>Insecticides - chemistry</subject><subject>Insecticides - pharmacology</subject><subject>Molecular Structure</subject><subject>Pest control</subject><subject>Pesticides</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Protozoa. Invertebrates</subject><subject>pyrazole amide derivatives</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>synthesis</subject><issn>1526-498X</issn><issn>1526-4998</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10FFr1TAUB_AiiptT_AYSBNmDdiZp0iSPsqtzbFNBRd9C2iRbZm_a5bTT-ulNudc7EHzKn5wf5ySnKJ4SfEQwpq8HOKIVVfeKfcJpXTKl5P1dlt_3ikcA1xhjpRR9WOxRShSmQu4XYeUgXMZXCOY4XuUMyESLQgTXjqEN1nTI5HQbxuAA9R7F_tZ1aJiT-d13Dpl1sLnQ9nE0IYZ4ia5mu9SiQzA1MKapHafk4HHxwJsO3JPteVB8fff2y_H78vzjyenxm_OyZUKoUgrmPfFN433DWCMstoQ7y7xltl5uBWEKq0oaXlnbNFJy6qzCnMj8XUeqg-Jw03dI_c3kYNTrAK3rOhNdP4FWqqoIrznL8vk_8rqfUsyPWxCvKSHyrl2beoDkvB5SWJs0a4L1sns9gF52n-WzbbupWTu7c3-XncGLLTDQms4nE9sAd44LKiips3u5cT9D5-b_zdOfPm_HlhsdYHS_dtqkH7oWleD624cTfXEh2OpsJTWr_gB2BKqK</recordid><startdate>201205</startdate><enddate>201205</enddate><creator>Wu, Jian</creator><creator>Song, Bao-An</creator><creator>Hu, De-Yu</creator><creator>Yue, Min</creator><creator>Yang, Song</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</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><scope>7QR</scope><scope>7SS</scope><scope>7ST</scope><scope>7T7</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>SOI</scope><scope>7X8</scope></search><sort><creationdate>201205</creationdate><title>Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures</title><author>Wu, Jian ; Song, Bao-An ; Hu, De-Yu ; Yue, Min ; Yang, Song</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4779-874ff1fbbffb44b7d0d15ed4fd4d6bbff71490938a53ddbb8852ed90518152e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Animals</topic><topic>Bioassays</topic><topic>Biological and medical sciences</topic><topic>Butterflies & moths</topic><topic>Chemical compounds</topic><topic>CoMFA</topic><topic>Control</topic><topic>Drug Design</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>hydrazone</topic><topic>Hydrazones - chemistry</topic><topic>Hydrazones - pharmacology</topic><topic>Insecta - drug effects</topic><topic>insecticidal activity</topic><topic>Insecticides - chemical synthesis</topic><topic>Insecticides - chemistry</topic><topic>Insecticides - pharmacology</topic><topic>Molecular Structure</topic><topic>Pest control</topic><topic>Pesticides</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Protozoa. Invertebrates</topic><topic>pyrazole amide derivatives</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wu, Jian</creatorcontrib><creatorcontrib>Song, Bao-An</creatorcontrib><creatorcontrib>Hu, De-Yu</creatorcontrib><creatorcontrib>Yue, Min</creatorcontrib><creatorcontrib>Yang, Song</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><collection>Chemoreception Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Pest management science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wu, Jian</au><au>Song, Bao-An</au><au>Hu, De-Yu</au><au>Yue, Min</au><au>Yang, Song</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures</atitle><jtitle>Pest management science</jtitle><addtitle>Pest. Manag. Sci</addtitle><date>2012-05</date><risdate>2012</risdate><volume>68</volume><issue>5</issue><spage>801</spage><epage>810</epage><pages>801-810</pages><issn>1526-498X</issn><eissn>1526-4998</eissn><coden>PMSCFC</coden><abstract>BACKGROUND: Pyrazole and hydrazone derivatives possess good insecticidal activities; their substructural units are widely used in pesticide design. In an effort to discover new molecules with good insecticidal activities, a series of pyrazole amide derivatives containing hydrazone substructures were synthesised and bioassayed.
RESULTS: Bioassays demonstrated that some of the title compounds exhibited notable control of Plutella xylostella (Linnaeus), Helicoverpa armigera (Hübner), Culex pipiens pallens, Laphygma exigua (Hübner), Spodoptera litura (Fabricius), Nilaparvata lugens (Stål) and Rhopalosiphum maidis (Fitch) at 5, 10, 0.25, 200, 20, 100 and 500 mg L−1 respectively. Comparative molecular field analysis (CoMFA) based on the bioactivities for P. xylostella was studied; the values of q2 and r2 for the CoMFA model were 0.701 and 0.964 respectively.
CONCLUSION: Some of the title compounds displayed good and broad‐spectrum insecticidal activities against different insect species; the CoMFA model revealed that a bulky and negatively charged group at the 4‐position of benzene could enhance insecticidal activity. These results could provide useful information for the design of novel insecticide containing substructural units of pyrazole amide and hydrazone. Copyright © 2011 Society of Chemical Industry</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>22190278</pmid><doi>10.1002/ps.2329</doi><tpages>10</tpages></addata></record> |
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| ispartof | Pest management science, 2012-05, Vol.68 (5), p.801-810 |
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| source | MEDLINE; Wiley Online Library Journals Frontfile Complete |
| subjects | Amides - chemistry Amides - pharmacology Animals Bioassays Biological and medical sciences Butterflies & moths Chemical compounds CoMFA Control Drug Design Fundamental and applied biological sciences. Psychology hydrazone Hydrazones - chemistry Hydrazones - pharmacology Insecta - drug effects insecticidal activity Insecticides - chemical synthesis Insecticides - chemistry Insecticides - pharmacology Molecular Structure Pest control Pesticides Phytopathology. Animal pests. Plant and forest protection Protozoa. Invertebrates pyrazole amide derivatives Pyrazoles - chemistry Pyrazoles - pharmacology synthesis |
| title | Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures |
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