{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T13:49:10Z","timestamp":1791985750638,"version":"4.4.0"},"reference-count":43,"publisher":"Wiley","license":[{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"},{"start":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T00:00:00Z","timestamp":1791936000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["scijournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Pest Management Science"],"abstract":"Abstract<\/jats:title>\n \n BACKGROUND<\/jats:title>\n \n Nowadays, structural modifications of natural products have been one of procedures for research and development of new pesticide candidates. Here, by using a naturally tetracyclic quinolizidine alkaloid sophocarpine as the lead compound, a series of\n N<\/jats:italic>\n \u2010sulfonylpyrrolomatrine derivatives were explored by Van Leusen [3\u2009+\u20092] cycloaddition reaction as aphicidal agents.\n <\/jats:p>\n <\/jats:sec>\n \n RESULTS<\/jats:title>\n \n We prepared a series of\n N<\/jats:italic>\n \u2010sulfonylpyrrolomatrine derivatives (\n 3a<\/jats:bold>\n \u2013\n 3x<\/jats:bold>\n ) with the novel pyrrolomatrine skeleton, whose possible reaction mechanism was further proposed. Against\n Aphis citricola<\/jats:italic>\n Van der Goot,\n N<\/jats:italic>\n \u20102\u2010chlorobenzenesulfonyl pyrrolomatrine (\n 3k<\/jats:bold>\n ) and\n N<\/jats:italic>\n \u20103\u2010bromobenzenesulfonylpyrrolomatrine (\n 3o<\/jats:bold>\n ) showed 5.4\u2010 and 4.6\u2010fold pronounced aphicidal activity compared to sophocarpine; against\n Hyalopterus arundimis<\/jats:italic>\n Fabricius,\n N<\/jats:italic>\n \u20102\u2010fluorobenzenesulfonylpyrrolomatrine (\n 3h<\/jats:bold>\n ) and\n N<\/jats:italic>\n \u20102\u2010(trifluoromethyl)benzenesulfonylpyrrolomatrine (\n 3q<\/jats:bold>\n ) exhibited 9.2 and 7.1 times promising aphicidal activity compared to sophocarpine.\n <\/jats:p>\n <\/jats:sec>\n \n CONCLUSION<\/jats:title>\n \n Derivatives\n 3h<\/jats:bold>\n ,\n 3k<\/jats:bold>\n ,\n 3o<\/jats:bold>\n and\n 3q<\/jats:bold>\n can be investigated as the leads in the future as aphicidal agents. Meanwhile, it will pave the way for future structural optimization of complex natural products containing \u03b1,\u03b2\u2010unsaturated lactam skeleton by Van Leusen [3\u2009+\u20092] cycloaddition pyrrole synthesis reaction. \u00a9 2026 Society of Chemical Industry.\n <\/jats:p>\n <\/jats:sec>","DOI":"10.1002\/ps.71401","type":"journal-article","created":{"date-parts":[[2026,10,14]],"date-time":"2026-10-14T13:14:08Z","timestamp":1791983648000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["High value\u2010added use of natural plant products in crop protection: construction of novel\n \n N<\/i>\n <\/scp>\n \u2010sulfonylpyrrolomatrine derivatives from a naturally tetracyclic quinolizidine alkaloid sophocarpine via the Van Leusen reaction as aphicidal agents"],"prefix":"10.1002","author":[{"given":"Chaochao","family":"Wang","sequence":"first","affiliation":[{"name":"College of Plant Protection Northwest A&F University Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuqing","family":"Wu","sequence":"additional","affiliation":[{"name":"College of Plant Protection Northwest A&F University Yangling China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Min","family":"Lv","sequence":"additional","affiliation":[{"name":"College of Plant Protection Northwest A&F University Yangling China"},{"name":"School of Marine Sciences Ningbo University Ningbo China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3152-9922","authenticated-orcid":false,"given":"Hui","family":"Xu","sequence":"additional","affiliation":[{"name":"College of Plant Protection Northwest A&F University Yangling China"},{"name":"School of Marine Sciences Ningbo University Ningbo China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,10,14]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"crossref","first-page":"1112","DOI":"10.3390\/ijerph18031112","article-title":"Agriculture development, pesticide application and its impact on the environment","volume":"18","author":"Tudi M","year":"2021","journal-title":"Int J Environ Res Public Health"},{"key":"e_1_2_7_3_1","doi-asserted-by":"crossref","first-page":"6356","DOI":"10.1002\/ps.8364","article-title":"Plant natural product\u2010based pesticides in crop protection: semi\u2010synthesis, mono\u2010crystal structures and agrochemical activities of osthole ester derivatives, and study of their toxicology against Tetranychus cinnabarinus (Boisduval)","volume":"80","author":"Hao M","year":"2024","journal-title":"Pest Manag Sci"},{"key":"e_1_2_7_4_1","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1002\/fes3.108","article-title":"Pesticides, environment, and food safety","volume":"6","author":"Carvalho FP","year":"2017","journal-title":"Food Energy Secur"},{"key":"e_1_2_7_5_1","doi-asserted-by":"crossref","first-page":"10507","DOI":"10.1007\/s13762-023-04795-y","article-title":"Nanopesticides in agricultural pest management and their environmental risks: a review","volume":"20","author":"Kannan M","year":"2023","journal-title":"Int J Environ Sci Technol"},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","DOI":"10.1016\/j.scitotenv.2024.170113","article-title":"Pesticides: an alarming detrimental to health and environment","volume":"915","author":"Kaur R","year":"2024","journal-title":"Sci Total Environ"},{"key":"e_1_2_7_7_1","doi-asserted-by":"crossref","first-page":"1050","DOI":"10.3390\/nano15131050","article-title":"Nano\u2010enabled insecticides for efficient pest management: definition, classification, synergistic mechanism, and safety assessment","volume":"15","author":"Wei Y","year":"2025","journal-title":"Nanomaterials"},{"key":"e_1_2_7_8_1","doi-asserted-by":"crossref","DOI":"10.3390\/agriculture12050600","article-title":"Use of botanical pesticides in agriculture as an alternative to synthetic pesticides","volume":"12","author":"Ngegba PM","year":"2022","journal-title":"Agriculture (Basel)"},{"key":"e_1_2_7_9_1","doi-asserted-by":"crossref","DOI":"10.1016\/j.micpath.2022.105854","article-title":"Plant based natural products as potential ecofriendly and safer biopesticides: a comprehensive overview of their advantages over conventional pesticides, limitations and regulatory aspects","volume":"173","author":"Khursheed A","year":"2022","journal-title":"Microb Pathog"},{"key":"e_1_2_7_10_1","doi-asserted-by":"crossref","first-page":"5574","DOI":"10.1021\/acs.jafc.3c06681","article-title":"Discovery of pesticide candidates from natural plant products: semisynthesis and characterization of andrographolide\u2010based esters and study of their pesticidal properties and toxicology","volume":"72","author":"Hao M","year":"2024","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_11_1","doi-asserted-by":"crossref","first-page":"8324","DOI":"10.1021\/acs.jafc.1c02616","article-title":"Structure simplification of natural products as a lead generation approach in agrochemical discovery","volume":"69","author":"Sparks TC","year":"2021","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_12_1","doi-asserted-by":"crossref","DOI":"10.1016\/j.indcrop.2024.119785","article-title":"Non\u2010food bioactive products as pesticide candidates: preparation and agrochemical activities of novel nonivamide ether derivatives containing the isoxazole fragment","volume":"222","author":"Wen HP","year":"2024","journal-title":"Ind Crop Prod"},{"key":"e_1_2_7_13_1","doi-asserted-by":"crossref","first-page":"2711","DOI":"10.1002\/ps.5817","article-title":"Semi\u2010synthesis and characterization of some new matrine derivatives as insecticidal agents","volume":"76","author":"Cheng X","year":"2020","journal-title":"Pest Manag Sci"},{"key":"e_1_2_7_14_1","doi-asserted-by":"crossref","DOI":"10.3390\/molecules28083328","article-title":"Natural products for pesticides discovery: structural diversity derivation and biological activities of naphthoquinones plumbagin and juglone","volume":"28","author":"Wang KH","year":"2023","journal-title":"Molecules"},{"key":"e_1_2_7_15_1","doi-asserted-by":"crossref","first-page":"61","DOI":"10.3390\/medicina54040061","article-title":"Current research on the safety of pyrethroids used as insecticides","volume":"54","author":"Chrustek A","year":"2018","journal-title":"Medicina"},{"key":"e_1_2_7_16_1","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1021\/ar800131p","article-title":"Molecular recognition of neonicotinoid insecticides: the determinants of life or death","volume":"42","author":"Tomizawa M","year":"2009","journal-title":"Acc Chem 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pharmacology and experimental validation identify the potential mechanism of sophocarpine for COVID\u201019","volume":"71","author":"Zhang HX","year":"2022","journal-title":"J Med Microbiol"},{"key":"e_1_2_7_21_1","doi-asserted-by":"crossref","first-page":"3792","DOI":"10.3892\/etm.2017.4958","article-title":"Sophocarpine against enterovirus 71 in vitro","volume":"14","author":"Jin ZJ","year":"2017","journal-title":"Exp Ther Med"},{"key":"e_1_2_7_22_1","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1038\/aps.2010.207","article-title":"Electrophysiological mechanisms of sophocarpine as a potential antiarrhythmic agent","volume":"32","author":"Yang ZF","year":"2011","journal-title":"Acta Pharmacol Sin"},{"key":"e_1_2_7_23_1","doi-asserted-by":"crossref","DOI":"10.3390\/toxins15020105","article-title":"Insecticidal activities of Sophora flavescens alt. 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(Boisduval)","volume":"7","author":"Abdelhamid AA","year":"2022","journal-title":"ACS Omega"},{"key":"e_1_2_7_30_1","doi-asserted-by":"crossref","first-page":"9319","DOI":"10.1021\/acs.jafc.0c04157","article-title":"Synthesis, insecticidal evaluation, and 3D\u2010QASR of novel anthranilic diamide derivatives containing N\u2010arylpyrrole as potential ryanodine receptor activators","volume":"68","author":"Wu CC","year":"2020","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_31_1","doi-asserted-by":"crossref","first-page":"5397","DOI":"10.1021\/acs.jafc.7b01251","article-title":"Design, synthesis, and fungicidal evaluation of novel pyrazole\u2010furan and pyrazole\u2010pyrrole carboxamide as succinate dehydrogenase inhibitors","volume":"65","author":"Yao TT","year":"2017","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_32_1","doi-asserted-by":"crossref","first-page":"14211","DOI":"10.1021\/acs.jafc.3c03459","article-title":"Rational design of insecticidal isoxazolines containing sulfonamide or sulfinamide structure as antagonists of GABA receptors with reduced toxicities to honeybee and zebrafish","volume":"71","author":"Yang S","year":"2023","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_33_1","doi-asserted-by":"crossref","first-page":"4847","DOI":"10.1002\/ps.7686","article-title":"Green synthesis, characterization, and biochemical impacts of new bioactive isoxazoline\u2010sulfonamides as potential insecticidal agents against the Sphodroxia maroccana Ley","volume":"79","author":"El Mahmoudi A","year":"2023","journal-title":"Pest Manag Sci"},{"key":"e_1_2_7_34_1","doi-asserted-by":"crossref","first-page":"10790","DOI":"10.1021\/acs.jafc.1c01925","article-title":"Design, synthesis, and insecticidal activity of novel triazone derivatives containing sulfonamide or sulfonimide Moieties","volume":"69","author":"Yang Y","year":"2021","journal-title":"J Agric Food 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electron\u2010deficient compounds","volume":"23","author":"Ma ZN","year":"2018","journal-title":"Molecules"},{"key":"e_1_2_7_38_1","doi-asserted-by":"crossref","first-page":"1812","DOI":"10.1021\/acs.orglett.2c00240","article-title":"Silver\u2010catalyzed asymmetric desymmetrization of cyclohexadienones via Van Leusen pyrrole synthesis","volume":"24","author":"Abozeid MA","year":"2022","journal-title":"Org Lett"},{"key":"e_1_2_7_39_1","doi-asserted-by":"crossref","first-page":"12156","DOI":"10.1021\/acs.jafc.4c13297","article-title":"Discovery of cholesterol\u2010type oxime ester\/ether derivatives as aphicidal candidates against Aphis citricola Van der Goot and Hyalopterus arundimis Fabricius","volume":"73","author":"Li TZ","year":"2025","journal-title":"J Agric Food Chem"},{"key":"e_1_2_7_40_1","doi-asserted-by":"crossref","first-page":"1939","DOI":"10.1016\/S0960-894X(03)00312-3","article-title":"Novel pyrrolyllactone and pyrrolyllactam indolinones as potent cyclin\u2010dependent kinase 2 inhibitors","volume":"13","author":"Li XY","year":"2003","journal-title":"Bioorg Med Chem Lett"},{"key":"e_1_2_7_41_1","doi-asserted-by":"crossref","first-page":"2730","DOI":"10.1002\/slct.201800110","article-title":"Tandem synthesis of 3, 4\u2010disubstituted pyrroles from aldehydes, 1,3\u2010diketones and TosMIC under metal\u2010free conditions","volume":"3","author":"Manasa KL","year":"2018","journal-title":"ChemistrySelect"},{"key":"e_1_2_7_42_1","doi-asserted-by":"crossref","first-page":"305","DOI":"10.2174\/157017812800233778","article-title":"A novel synthesis of multisubstituted pyrroles via trisubstituted olefins and TosMIC derivatives","volume":"9","author":"Qiu FL","year":"2012","journal-title":"Lett Org Chem"},{"key":"e_1_2_7_43_1","doi-asserted-by":"crossref","DOI":"10.3390\/molecules22071131","article-title":"[3+2] Cycloaddition of tosylmethyl isocyanide with styrylisoxazoles: facile access to polysubstituted 3\u2010(isoxazol\u20105\u2010yl)pyrroles","volume":"22","author":"Zhang XM","year":"2017","journal-title":"Molecules"},{"key":"e_1_2_7_44_1","doi-asserted-by":"crossref","first-page":"7182","DOI":"10.1021\/acscatal.7b02682","article-title":"Site\u2010selective deuteration of N\u2010heterocycles via iridium\u2010catalyzed hydrogen isotope exchange","volume":"7","author":"Kerr WJ","year":"2017","journal-title":"ACS Catal"}],"container-title":["Pest Management 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