Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether
A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The...
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| Veröffentlicht in: | Journal of heterocyclic chemistry 2019-12, Vol.56 (12), p.3206-3214 |
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| container_issue | 12 |
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| container_title | Journal of heterocyclic chemistry |
| container_volume | 56 |
| creator | Li, Lizhong Zhou, Chunge Liu, Minhua Zhang, Ping Zhang, Ning Li, Jianming Li, Tao Liu, Xingping Cheng, Shufen Li, Qianhe Liu, Aiping |
| description | A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure‐activity relationships indicated that both an ethyl group on the 4‐position of the pyrimidine ring and alkyl chain as a para‐substituent group of the benzene ring showed good biological activity. |
| doi_str_mv | 10.1002/jhet.3710 |
| format | Article |
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Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure‐activity relationships indicated that both an ethyl group on the 4‐position of the pyrimidine ring and alkyl chain as a para‐substituent group of the benzene ring showed good biological activity.</description><identifier>ISSN: 0022-152X</identifier><identifier>EISSN: 1943-5193</identifier><identifier>DOI: 10.1002/jhet.3710</identifier><language>eng</language><publisher>Hoboken: Wiley Subscription Services, Inc</publisher><subject>Benzene ; Biological activity ; Derivatives ; Imidacloprid ; Insecticides ; Insects ; NMR ; Nuclear magnetic resonance</subject><ispartof>Journal of heterocyclic chemistry, 2019-12, Vol.56 (12), p.3206-3214</ispartof><rights>2019 Wiley Periodicals, Inc.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2970-a1420c5fdb4f4bc0f7a38f1821592cad3dac0cd7499974365f55a8cff105258e3</citedby><cites>FETCH-LOGICAL-c2970-a1420c5fdb4f4bc0f7a38f1821592cad3dac0cd7499974365f55a8cff105258e3</cites><orcidid>0000-0002-0225-4093 ; 0000-0001-5594-7080 ; 0000-0003-3487-9829 ; 0000-0002-0238-0030</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%2Fjhet.3710$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fjhet.3710$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids></links><search><creatorcontrib>Li, Lizhong</creatorcontrib><creatorcontrib>Zhou, Chunge</creatorcontrib><creatorcontrib>Liu, Minhua</creatorcontrib><creatorcontrib>Zhang, Ping</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Li, Jianming</creatorcontrib><creatorcontrib>Li, Tao</creatorcontrib><creatorcontrib>Liu, Xingping</creatorcontrib><creatorcontrib>Cheng, Shufen</creatorcontrib><creatorcontrib>Li, Qianhe</creatorcontrib><creatorcontrib>Liu, Aiping</creatorcontrib><title>Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether</title><title>Journal of heterocyclic chemistry</title><description>A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure‐activity relationships indicated that both an ethyl group on the 4‐position of the pyrimidine ring and alkyl chain as a para‐substituent group of the benzene ring showed good biological activity.</description><subject>Benzene</subject><subject>Biological activity</subject><subject>Derivatives</subject><subject>Imidacloprid</subject><subject>Insecticides</subject><subject>Insects</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><issn>0022-152X</issn><issn>1943-5193</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kE1LAzEQhoMoWKsH_0HAk9Bt87Hpbo5Sq1UKXip4C2k-2pRtdk22lfXXm7pePc07zDPzMi8AtxiNMUJkstuadkwLjM7AAPOcZgxzeg4GaUYyzMjHJbiKcZdaTItiAL4fTXQbP4Kx8-026TiCzkejWqecltUISq-hVDL0fZKtO7rWmQhrC319NBVsuuD2Tjsv984bqE1wR5mwxKjat9J55zdQwrVrtsZ3FTTJKlyDCyuraG7-6hC8P81Xs0W2fHt-mT0sM0V4gTKJc4IUs3qd23ytkC0kLS0uCWacKKmplgopXeSc8yKnU2YZk6WyFiNGWGnoENz1d5tQfx5MbMWuPgSfLAWhhFLOGZ0m6r6nVKhjDMaKJj0lQycwEqdoxSlacYo2sZOe_XKV6f4Hxetivvrd-AEpB32u</recordid><startdate>201912</startdate><enddate>201912</enddate><creator>Li, Lizhong</creator><creator>Zhou, Chunge</creator><creator>Liu, Minhua</creator><creator>Zhang, Ping</creator><creator>Zhang, Ning</creator><creator>Li, Jianming</creator><creator>Li, Tao</creator><creator>Liu, Xingping</creator><creator>Cheng, Shufen</creator><creator>Li, Qianhe</creator><creator>Liu, Aiping</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0225-4093</orcidid><orcidid>https://orcid.org/0000-0001-5594-7080</orcidid><orcidid>https://orcid.org/0000-0003-3487-9829</orcidid><orcidid>https://orcid.org/0000-0002-0238-0030</orcidid></search><sort><creationdate>201912</creationdate><title>Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether</title><author>Li, Lizhong ; Zhou, Chunge ; Liu, Minhua ; Zhang, Ping ; Zhang, Ning ; Li, Jianming ; Li, Tao ; Liu, Xingping ; Cheng, Shufen ; Li, Qianhe ; Liu, Aiping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2970-a1420c5fdb4f4bc0f7a38f1821592cad3dac0cd7499974365f55a8cff105258e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Benzene</topic><topic>Biological activity</topic><topic>Derivatives</topic><topic>Imidacloprid</topic><topic>Insecticides</topic><topic>Insects</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Lizhong</creatorcontrib><creatorcontrib>Zhou, Chunge</creatorcontrib><creatorcontrib>Liu, Minhua</creatorcontrib><creatorcontrib>Zhang, Ping</creatorcontrib><creatorcontrib>Zhang, Ning</creatorcontrib><creatorcontrib>Li, Jianming</creatorcontrib><creatorcontrib>Li, Tao</creatorcontrib><creatorcontrib>Liu, Xingping</creatorcontrib><creatorcontrib>Cheng, Shufen</creatorcontrib><creatorcontrib>Li, Qianhe</creatorcontrib><creatorcontrib>Liu, Aiping</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of heterocyclic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Lizhong</au><au>Zhou, Chunge</au><au>Liu, Minhua</au><au>Zhang, Ping</au><au>Zhang, Ning</au><au>Li, Jianming</au><au>Li, Tao</au><au>Liu, Xingping</au><au>Cheng, Shufen</au><au>Li, Qianhe</au><au>Liu, Aiping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether</atitle><jtitle>Journal of heterocyclic chemistry</jtitle><date>2019-12</date><risdate>2019</risdate><volume>56</volume><issue>12</issue><spage>3206</spage><epage>3214</epage><pages>3206-3214</pages><issn>0022-152X</issn><eissn>1943-5193</eissn><abstract>A series of original pyrimidinamine derivatives containing a biphenyl ether moiety were designed and synthesized. Their structures were confirmed by 1H NMR, MS, and elemental analyses. Their insecticidal activities against lepidopteran and hemiptera insects and acaricidal activities were tested. The results of bioassay demonstrated that 9k showed the best activity (LC50 = 2.08 mg/L) against Tetranychus urticae, which is comparable with the positive control, spirotetramat (LC50 = 2.27 mg/L), and 9g showed better activity (LC50 = 0.52 mg/L) against Aphis fabae than the positive control, imidacloprid (LC50 = 1.02 mg/L), and relatively good activity (LC50 = 2.49 mg/L) against T urticae. Their structure‐activity relationships indicated that both an ethyl group on the 4‐position of the pyrimidine ring and alkyl chain as a para‐substituent group of the benzene ring showed good biological activity.</abstract><cop>Hoboken</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/jhet.3710</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-0225-4093</orcidid><orcidid>https://orcid.org/0000-0001-5594-7080</orcidid><orcidid>https://orcid.org/0000-0003-3487-9829</orcidid><orcidid>https://orcid.org/0000-0002-0238-0030</orcidid></addata></record> |
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| subjects | Benzene Biological activity Derivatives Imidacloprid Insecticides Insects NMR Nuclear magnetic resonance |
| title | Design, synthesis, insecticidal, and acaricidal activities of novel pyrimidinamine derivatives containing a biphenyl ether |
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