{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,5]],"date-time":"2026-08-05T00:41:18Z","timestamp":1785890478817,"version":"3.56.0"},"reference-count":43,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2024,6,8]],"date-time":"2024-06-08T00:00:00Z","timestamp":1717804800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22077070"],"award-info":[{"award-number":["22077070"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21772103"],"award-info":[{"award-number":["21772103"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2024,7]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>The design of novel agrochemicals starting from bioactive natural products is one of the most effective ways in the discovery and development of new pesticidal agents. In this paper, a series of novel butenolide\u2010containing methylxanthine derivatives (<jats:bold>Ia\u2010Ir<\/jats:bold>) were designed based on natural methylxanthine caffeine and stemofoline, and the derivatized insecticide flupyradifurone of the latter. The structures of the synthesized compounds were confirmed <jats:italic>via<\/jats:italic> <jats:sup>1<\/jats:sup>H\u2010NMR, <jats:sup>13<\/jats:sup>C NMR, HRMS and X\u2010ray single crystal diffraction analyses. The biological activities of the compounds were evaluated against a variety of agricultural pests including oriental armyworm, bean aphid, diamondback moth, fall armyworm, cotton bollworm, and corn borer; the results indicated that some of them have favorable insecticidal potentials, particularly toward diamondback moth. Among others, <jats:bold>Ic<\/jats:bold> and <jats:bold>Iq<\/jats:bold> against diamondback moth possessed LC<jats:sub>50<\/jats:sub> values of 6.187\u2005mg\u2009\u22c5\u2009L<jats:sup>\u22121<\/jats:sup> and 3.269\u2005mg\u2009\u22c5\u2009L<jats:sup>\u22121<\/jats:sup>, respectively, \u2013 2.5\u2010 and 4.8\u2010fold of relative insecticidal activity respectively to that of flupyradifurone (LC<jats:sub>50<\/jats:sub>=15.743\u2005mg\u2009\u22c5\u2009L<jats:sup>\u22121<\/jats:sup>). Additionally, both the DFT theoretical calculation and molecular docking with acetylcholine binding protein were conducted for the highly bioactive compound\u2005(<jats:bold>Ic<\/jats:bold>). <jats:bold>Ic<\/jats:bold> and <jats:bold>Iq<\/jats:bold> derived from the integration of caffeine (natural methylxanthine) and butenolide motifs can serve as novel leading insecticidal compounds for further optimization.<\/jats:p>","DOI":"10.1002\/cbdv.202400823","type":"journal-article","created":{"date-parts":[[2024,4,30]],"date-time":"2024-04-30T14:13:47Z","timestamp":1714486427000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Novel Insecticidal Butenolide\u2010Containing Methylxanthine Derivatives: Synthesis, Crystal Structure, Biological Activity Evaluation, DFT Calculation and Molecular Docking"],"prefix":"10.1002","volume":"21","author":[{"given":"Lei","family":"Wang","sequence":"first","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University  Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wenqi","family":"Fan","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University  Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Na","family":"Yang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University  Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lixia","family":"Xiong","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University  Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0748-3861","authenticated-orcid":false,"given":"Baolei","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory of Elemento-Organic Chemistry College of Chemistry Nankai University  Tianjin 300071 China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2024,6,8]]},"reference":[{"key":"e_1_2_10_1_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4457"},{"key":"e_1_2_10_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.5598"},{"key":"e_1_2_10_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.3c01809"},{"key":"e_1_2_10_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.heliyon.2018.e00829"},{"key":"e_1_2_10_5_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00018-003-3269-3"},{"key":"e_1_2_10_6_1","doi-asserted-by":"publisher","DOI":"10.1038\/nrd1983"},{"key":"e_1_2_10_7_1","doi-asserted-by":"publisher","DOI":"10.3390\/nu5104159"},{"key":"e_1_2_10_8_1","doi-asserted-by":"publisher","DOI":"10.7150\/ijbs.11127"},{"key":"e_1_2_10_9_1","doi-asserted-by":"publisher","DOI":"10.2174\/1389200013338270"},{"key":"e_1_2_10_10_1","doi-asserted-by":"publisher","DOI":"10.3748\/wjg.v20.i5.1127"},{"key":"e_1_2_10_11_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.6207592"},{"key":"e_1_2_10_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.4777"},{"key":"e_1_2_10_13_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms8618"},{"key":"e_1_2_10_14_1","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-9063(199612)48:4<375::AID-PS501>3.0.CO;2-#"},{"key":"e_1_2_10_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/agronomy12040885"},{"key":"e_1_2_10_16_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13592-018-0583-1"},{"key":"e_1_2_10_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.6834"},{"key":"e_1_2_10_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.2c03876"},{"key":"e_1_2_10_19_1","doi-asserted-by":"publisher","DOI":"10.1021\/np050361y"},{"key":"e_1_2_10_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf0205615"},{"key":"e_1_2_10_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02373"},{"key":"e_1_2_10_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/ps.3932"},{"key":"e_1_2_10_23_1","volume":"20","author":"Jerez A. 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