{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,20]],"date-time":"2026-08-20T16:36:41Z","timestamp":1787243801379,"version":"build-2736575974"},"reference-count":36,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2022,9,19]],"date-time":"2022-09-19T00:00:00Z","timestamp":1663545600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"National Natural Science Foundation of China","award":["22077137"],"award-info":[{"award-number":["22077137"]}]},{"name":"National Natural Science Foundation of China","award":["31972289"],"award-info":[{"award-number":["31972289"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Neonicotinoids are important insecticides for controlling aphids in agriculture. Growing research suggested that neonicotinoid insecticides are a key factor causing the decline of global pollinator insects, such as bees. Flupyrimin (FLP) is a novel nicotinic insecticide with unique biological properties and no cross-resistance, and is safe for pollinators. Using FLP as the lead compound, a series of novel compounds were designed and synthesized by replacing the amide fragment with a sulfonamideone. Their structures were confirmed by 1H NMR, 13C NMR and HRMS spectra. Bioassay results showed that compound 2j had good insecticidal activity against Aphis glycines with an LC50 value of 20.93 mg\/L. Meanwhile, compound 2j showed significantly lower acute oral and contact toxicity to Apis mellifera. In addition, compound 2j interacted well with the protein in insect acetylcholine binding protein (AChBP). The molecular docking on honeybee nicotinic acetylcholine receptor (nAChR) indicated that the sulfonamide group of compound 2j did not form a hydrogen bond with Arg173 of the \u03b2 subunit, which conforms to the reported low bee-toxicity conformation. In general, target compound 2j can be regarded as a bee-friendly insecticide candidate.<\/jats:p>","DOI":"10.3390\/molecules27186133","type":"journal-article","created":{"date-parts":[[2022,9,20]],"date-time":"2022-09-20T04:28:55Z","timestamp":1663648135000},"page":"6133","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Design, Synthesis and Bioactivity of Novel Low Bee-Toxicity Compounds Based on Flupyrimin"],"prefix":"10.3390","volume":"27","author":[{"given":"Xingxing","family":"Lu","sequence":"first","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Huan","family":"Xu","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoming","family":"Zhang","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tengda","family":"Sun","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yufan","family":"Lin","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yongheng","family":"Zhang","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Agro-Environment and Agro-Product Safety, Agricultural College, Guangxi University, Nanning 530004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Honghong","family":"Li","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Agro-Environment and Agro-Product Safety, Agricultural College, Guangxi University, Nanning 530004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1163-4140","authenticated-orcid":false,"given":"Xuesheng","family":"Li","sequence":"additional","affiliation":[{"name":"Guangxi Key Laboratory of Agro-Environment and Agro-Product Safety, Agricultural College, Guangxi University, Nanning 530004, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0118-402X","authenticated-orcid":false,"given":"Xinling","family":"Yang","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2516-854X","authenticated-orcid":false,"given":"Hongxia","family":"Duan","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yun","family":"Ling","sequence":"additional","affiliation":[{"name":"Innovation Center of Pesticide Research, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"539","DOI":"10.1016\/j.crvi.2010.03.009","article-title":"The Conflicting Relationships between Aphids and Men: A Review of Aphid Damage and Control Strategies","volume":"333","author":"Dedryver","year":"2010","journal-title":"Comptes Rendus Biol."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"516","DOI":"10.1016\/j.crvi.2010.03.007","article-title":"Compatible Plant-Aphid Interactions: How Aphids Manipulate Plant Responses","volume":"333","author":"Giordanengo","year":"2010","journal-title":"Comptes Rendus Biol."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"524","DOI":"10.1016\/j.crvi.2010.04.001","article-title":"Aphids as Transport Devices for Plant Viruses","volume":"333","author":"Brault","year":"2010","journal-title":"Comptes Rendus Biol."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Zeni, V., Baliota, G.V., Benelli, G., Canale, A., and Athanassiou, C.G. 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