Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives
BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses.RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl der...
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| Veröffentlicht in: | Pest management science 2008-08, Vol.64 (8), p.863-872 |
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| creator | Paula, Vanderlúcia F Barbosa, Luiz Cláudio A Teixeira, Róbson R Picanço, Marcelo C Silva, Gerson A |
| description | BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses.RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 μg mg⁻¹ insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated.CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. Copyright |
| doi_str_mv | 10.1002/ps.1559 |
| format | Article |
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Their structures were confirmed on the basis of IR, NMR and MS analyses.RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 μg mg⁻¹ insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated.CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. Copyright</description><identifier>ISSN: 1526-498X</identifier><identifier>EISSN: 1526-4998</identifier><identifier>DOI: 10.1002/ps.1559</identifier><identifier>PMID: 18324641</identifier><identifier>CODEN: PMSCFC</identifier><language>eng</language><publisher>Chichester, UK: John Wiley & Sons, Ltd</publisher><subject>3-benzylfuran-2-yl N,N,N,N-tetraethyldiamidophosphate derivatives ; Animals ; Ascia monuste orseis ; Biological and medical sciences ; Chemical synthesis ; Coleoptera - drug effects ; Control ; Diaphania hyalinata ; Fundamental and applied biological sciences. Psychology ; furan-2-yl N ; Furans - chemical synthesis ; Furans - pharmacology ; furan‐2‐yl N,N,N′,N′‐tetraethyldiamidophosphates ; Hymenoptera - drug effects ; Insect control ; insect pests ; insecticidal properties ; Insecticides ; Insecticides - chemical synthesis ; Insecticides - pharmacology ; instars ; lactones ; Lepidoptera - drug effects ; Molecular Structure ; Mortality ; NMR ; Nuclear magnetic resonance ; N′-tetraethyldiamidophosphates ; organophosphates ; Organophosphorus Compounds - chemical synthesis ; Organophosphorus Compounds - pharmacology ; Phytopathology. Animal pests. Plant and forest protection ; Protozoa. Invertebrates ; Pyralidae ; Sitophilus zeamais ; Solenopsis saevissima ; Structure-Activity Relationship ; synthesis ; Toxicity</subject><ispartof>Pest management science, 2008-08, Vol.64 (8), p.863-872</ispartof><rights>Copyright © 2008 Society of Chemical Industry</rights><rights>2008 INIST-CNRS</rights><rights>Copyright John Wiley and Sons, Limited Aug 2008</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4309-fc2ae52950516618523deb87393c477e2ebff88641838838a56cbe72bc7c54c93</citedby><cites>FETCH-LOGICAL-c4309-fc2ae52950516618523deb87393c477e2ebff88641838838a56cbe72bc7c54c93</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.1559$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fps.1559$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20520161$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18324641$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Paula, Vanderlúcia F</creatorcontrib><creatorcontrib>Barbosa, Luiz Cláudio A</creatorcontrib><creatorcontrib>Teixeira, Róbson R</creatorcontrib><creatorcontrib>Picanço, Marcelo C</creatorcontrib><creatorcontrib>Silva, Gerson A</creatorcontrib><title>Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives</title><title>Pest management science</title><addtitle>Pest. Manag. Sci</addtitle><description>BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses.RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 μg mg⁻¹ insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated.CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. Copyright</description><subject>3-benzylfuran-2-yl N,N,N,N-tetraethyldiamidophosphate derivatives</subject><subject>Animals</subject><subject>Ascia monuste orseis</subject><subject>Biological and medical sciences</subject><subject>Chemical synthesis</subject><subject>Coleoptera - drug effects</subject><subject>Control</subject><subject>Diaphania hyalinata</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>furan-2-yl N</subject><subject>Furans - chemical synthesis</subject><subject>Furans - pharmacology</subject><subject>furan‐2‐yl N,N,N′,N′‐tetraethyldiamidophosphates</subject><subject>Hymenoptera - drug effects</subject><subject>Insect control</subject><subject>insect pests</subject><subject>insecticidal properties</subject><subject>Insecticides</subject><subject>Insecticides - chemical synthesis</subject><subject>Insecticides - pharmacology</subject><subject>instars</subject><subject>lactones</subject><subject>Lepidoptera - drug effects</subject><subject>Molecular Structure</subject><subject>Mortality</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>N′-tetraethyldiamidophosphates</subject><subject>organophosphates</subject><subject>Organophosphorus Compounds - chemical synthesis</subject><subject>Organophosphorus Compounds - pharmacology</subject><subject>Phytopathology. Animal pests. Plant and forest protection</subject><subject>Protozoa. Invertebrates</subject><subject>Pyralidae</subject><subject>Sitophilus zeamais</subject><subject>Solenopsis saevissima</subject><subject>Structure-Activity Relationship</subject><subject>synthesis</subject><subject>Toxicity</subject><issn>1526-498X</issn><issn>1526-4998</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10d9r1TAUB_AgiptT_A-0CLIHzcyPJk0eZeoU5xTuhuJLSNMTb2ZvW5PezfrXm0vL9UkSyHn4cE7yDUKPKTmhhLBXQzqhQug76JAKJnGptbq7r9W3A_QgpWtCiNaa3UcHVHFWypIeom41deMaUkiF7ZoidAncGFxobFvYXN2EcSp6X3RwW3BcQ_dnav022g4zPLXFxcu8jvPGI4zRwrie2ibYTWj6Yd2nYW1HKBqI4cbmXpAeonvetgkeLecRunr39vL0PT7_fPbh9PU5diUnGnvHLAimBRFUSqoE4w3UquKau7KqgEHtvVL5BYqrvK2QroaK1a5yonSaH6Fnc98h9r-2kEZz3W9jl0caxpiUSjKR0fGMXOxTiuDNEMPGxslQYnaxmiGZXaxZPlnabesNNP_ckmMGzxdgk7OtzwG5kPaOEcEIlTv3Yna3oYXpf_PMl9UyFs86pBF-77WNP42seCXM14szo79fstXHT28Mz_7p7L3tjf0R8w2uVnkwzx9PiRQl_wuZLqT8</recordid><startdate>200808</startdate><enddate>200808</enddate><creator>Paula, Vanderlúcia F</creator><creator>Barbosa, Luiz Cláudio A</creator><creator>Teixeira, Róbson R</creator><creator>Picanço, Marcelo C</creator><creator>Silva, Gerson A</creator><general>John Wiley & Sons, Ltd</general><general>Wiley</general><general>Wiley Subscription Services, Inc</general><scope>FBQ</scope><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></search><sort><creationdate>200808</creationdate><title>Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives</title><author>Paula, Vanderlúcia F ; Barbosa, Luiz Cláudio A ; Teixeira, Róbson R ; Picanço, Marcelo C ; Silva, Gerson A</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4309-fc2ae52950516618523deb87393c477e2ebff88641838838a56cbe72bc7c54c93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>3-benzylfuran-2-yl N,N,N,N-tetraethyldiamidophosphate derivatives</topic><topic>Animals</topic><topic>Ascia monuste orseis</topic><topic>Biological and medical sciences</topic><topic>Chemical synthesis</topic><topic>Coleoptera - drug effects</topic><topic>Control</topic><topic>Diaphania hyalinata</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>furan-2-yl N</topic><topic>Furans - chemical synthesis</topic><topic>Furans - pharmacology</topic><topic>furan‐2‐yl N,N,N′,N′‐tetraethyldiamidophosphates</topic><topic>Hymenoptera - drug effects</topic><topic>Insect control</topic><topic>insect pests</topic><topic>insecticidal properties</topic><topic>Insecticides</topic><topic>Insecticides - chemical synthesis</topic><topic>Insecticides - pharmacology</topic><topic>instars</topic><topic>lactones</topic><topic>Lepidoptera - drug effects</topic><topic>Molecular Structure</topic><topic>Mortality</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>N′-tetraethyldiamidophosphates</topic><topic>organophosphates</topic><topic>Organophosphorus Compounds - chemical synthesis</topic><topic>Organophosphorus Compounds - pharmacology</topic><topic>Phytopathology. Animal pests. Plant and forest protection</topic><topic>Protozoa. Invertebrates</topic><topic>Pyralidae</topic><topic>Sitophilus zeamais</topic><topic>Solenopsis saevissima</topic><topic>Structure-Activity Relationship</topic><topic>synthesis</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Paula, Vanderlúcia F</creatorcontrib><creatorcontrib>Barbosa, Luiz Cláudio A</creatorcontrib><creatorcontrib>Teixeira, Róbson R</creatorcontrib><creatorcontrib>Picanço, Marcelo C</creatorcontrib><creatorcontrib>Silva, Gerson A</creatorcontrib><collection>AGRIS</collection><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><jtitle>Pest management science</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Paula, Vanderlúcia F</au><au>Barbosa, Luiz Cláudio A</au><au>Teixeira, Róbson R</au><au>Picanço, Marcelo C</au><au>Silva, Gerson A</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives</atitle><jtitle>Pest management science</jtitle><addtitle>Pest. Manag. Sci</addtitle><date>2008-08</date><risdate>2008</risdate><volume>64</volume><issue>8</issue><spage>863</spage><epage>872</epage><pages>863-872</pages><issn>1526-498X</issn><eissn>1526-4998</eissn><coden>PMSCFC</coden><abstract>BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses.RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 μg mg⁻¹ insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl)furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2(5H)-ones evaluated.CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. Copyright</abstract><cop>Chichester, UK</cop><pub>John Wiley & Sons, Ltd</pub><pmid>18324641</pmid><doi>10.1002/ps.1559</doi><tpages>10</tpages></addata></record> |
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| ispartof | Pest management science, 2008-08, Vol.64 (8), p.863-872 |
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| subjects | 3-benzylfuran-2-yl N,N,N,N-tetraethyldiamidophosphate derivatives Animals Ascia monuste orseis Biological and medical sciences Chemical synthesis Coleoptera - drug effects Control Diaphania hyalinata Fundamental and applied biological sciences. Psychology furan-2-yl N Furans - chemical synthesis Furans - pharmacology furan‐2‐yl N,N,N′,N′‐tetraethyldiamidophosphates Hymenoptera - drug effects Insect control insect pests insecticidal properties Insecticides Insecticides - chemical synthesis Insecticides - pharmacology instars lactones Lepidoptera - drug effects Molecular Structure Mortality NMR Nuclear magnetic resonance N′-tetraethyldiamidophosphates organophosphates Organophosphorus Compounds - chemical synthesis Organophosphorus Compounds - pharmacology Phytopathology. Animal pests. Plant and forest protection Protozoa. Invertebrates Pyralidae Sitophilus zeamais Solenopsis saevissima Structure-Activity Relationship synthesis Toxicity |
| title | Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives |
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