{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,2]],"date-time":"2026-06-02T05:45:13Z","timestamp":1780379113028,"version":"3.54.1"},"reference-count":30,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2022,5,31]],"date-time":"2022-05-31T00:00:00Z","timestamp":1653955200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>The crop loss caused by bacteria has increased year by year due to the lack of effective control agents. In order to develop efficient, broad-spectrum, and structurally simple agricultural bactericide, the structure of piperonylic acid was modified and a series of novel piperonylic acid derivatives containing a sulfonic acid ester moiety was synthesized. Bioassay results indicated the compounds exhibited significantly antibacterial activities. Among them, compound <jats:bold>41<\/jats:bold> exhibited excellent antibacterial activities against <jats:italic>Pseudomonas syringae pv. Actinidiae<\/jats:italic> (Psa), with inhibitory value 99 and 85% at 100\u00a0\u03bcg\/ml and 50\u00a0\u03bcg\/ml, respectively, which was higher than that of thiodiazole-copper (84 and 77%) and bismerthiazol (96 and 78%). In addition, some compounds also showed moderate insecticidal activity against <jats:italic>Spodoptera frugiperda.<\/jats:italic> The abovementioned results confirm the broadening of the application of piperonylic acid, with reliable support for the development of novel agrochemical bactericide.<\/jats:p>","DOI":"10.3389\/fchem.2022.913003","type":"journal-article","created":{"date-parts":[[2022,5,31]],"date-time":"2022-05-31T04:44:13Z","timestamp":1653972253000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":3,"title":["Synthesis and Bioactivities of Novel Piperonylic Acid Derivatives Containing a Sulfonic Acid Ester Moiety"],"prefix":"10.3389","volume":"10","author":[{"given":"Dandan","family":"Xie","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin","family":"Hu","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xiaoli","family":"Ren","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zaiping","family":"Yang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2022,5,31]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"8012","DOI":"10.1016\/j.arabjc.2020.09.031","article-title":"Phytochemical Profiling and Antimicrobial Activity of Ginger (Zingiber Officinale) Essential Oils against Important Phytopathogens","volume":"13","author":"Abdullahiab","year":"2020","journal-title":"Arab. J. Chem."},{"key":"B2","doi-asserted-by":"publisher","first-page":"2280","DOI":"10.1039\/d1ce01717a","article-title":"Thermal Method Usage Features for Multicomponent Crystal Screening","volume":"24","author":"Boycov","year":"2022","journal-title":"CrystEngComm"},{"key":"B3","doi-asserted-by":"publisher","first-page":"1103","DOI":"10.1001\/jamadermatol.2015.1745","article-title":"Cutaneous Toxic Effects of bRAF Inhibitors Alone and in Combination with MEK Inhibitors for Metastatic Melanoma","volume":"151","author":"Carlos","year":"2015","journal-title":"JAMA Dermatol"},{"key":"B4","doi-asserted-by":"publisher","first-page":"1305","DOI":"10.1007\/s10904-019-01094-3","article-title":"Effective Removal of Antibacterial Drugs from Aqueous Solutions Using Porous Metal-Organic Frameworks","volume":"29","author":"Chai","year":"2019","journal-title":"J. Inorg. Organomet. Polym."},{"key":"B5","doi-asserted-by":"publisher","first-page":"1","DOI":"10.3389\/fchem.2021.645876","article-title":"Synthesis and Bioactivities of Novel 1,3,4-thiadiazole Derivatives of Glucosides","volume":"9","author":"Chen","year":"2021","journal-title":"Front. Chem."},{"key":"B6","doi-asserted-by":"publisher","first-page":"030006052110161","DOI":"10.1177\/03000605211016146","article-title":"Apatinib Combined with Concurrent Chemoradiotherapy in Patients with Subglottic Small Cell Carcinoma: a Case Report","volume":"49","author":"Chen","year":"2021","journal-title":"J. Int. Med. Res."},{"key":"B7","doi-asserted-by":"publisher","first-page":"4666","DOI":"10.1002\/ejoc.200900719","article-title":"Convergent Synthesis of Pancratistatin from Piperonal and Xylose","volume":"2009","author":"Dam","year":"2009","journal-title":"Eur. J. Org. Chem."},{"key":"B8","doi-asserted-by":"publisher","first-page":"e19372","DOI":"10.1097\/md.0000000000019372","article-title":"Apatinib Combined with Chemotherapy or Concurrent Chemo-Brachytherapy in Patients with Recurrent or Advanced Cervical Cancer","volume":"99","author":"Guo","year":"2020","journal-title":"Medicine"},{"key":"B9","doi-asserted-by":"publisher","first-page":"24942","DOI":"10.1039\/c9ra05349b","article-title":"Biological Activity Evaluation and Action Mechanism of Chalcone Derivatives Containing Thiophene Sulfonate","volume":"9","author":"Guo","year":"2019","journal-title":"RSC Adv."},{"key":"B10","doi-asserted-by":"publisher","first-page":"123","DOI":"10.1080\/10426507.2019.1655418","article-title":"Biological Activity Evaluation and Action Mechanism of 1,4-Pentadien-3-One Derivatives Containing Thiophene Sulfonate","volume":"195","author":"Guo","year":"2020","journal-title":"Phosphorus, Sulfur, Silicon Relat. Elem."},{"key":"B11","doi-asserted-by":"publisher","first-page":"2057","DOI":"10.1080\/10826079208016325","article-title":"Determination of Miloxacin and its Metabolite in Fish by High Performance Liquid Chromatography with Fluorescence and UV Detection","volume":"15","author":"Horie","year":"1992","journal-title":"J. Liq. Chromatogr."},{"key":"B12","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1177\/1934578x20966191","article-title":"Simultaneous Determination of 6 Antiallergic Components in Asarum Sieboldii Using High-Performance Liquid Chromatography","volume":"15","author":"Jang","year":"2020","journal-title":"Nat. Prod. Commun."},{"key":"B13","first-page":"3166","article-title":"Design, Synthesis and In-Vitro Evaluation of Aryl Amides as Potent Inhibitors against Mycobacterium tuberculosis","volume":"11","author":"Joseph","year":"2019","journal-title":"J. Pharm. Sci. Res."},{"key":"B14","doi-asserted-by":"publisher","first-page":"4795","DOI":"10.1080\/07391102.2020.1782767","article-title":"Evaluation of the Interaction of Novel Tyrosine Kinase Inhibitor Apatinib Mesylate with Bovine Serum Albumin Using Spectroscopies and Theoretical Calculation Approaches","volume":"39","author":"Kou","year":"2021","journal-title":"J. Biomol. Struct. Dyn."},{"key":"B15","doi-asserted-by":"publisher","first-page":"1951786","DOI":"10.1155\/2019\/1951786","article-title":"Interaction of Anticancer Drugs with Human Organic Anion Transporter hOAT4","volume":"2019","author":"Liu","year":"2019","journal-title":"J. Oncol."},{"key":"B16","doi-asserted-by":"publisher","first-page":"4283","DOI":"10.3390\/molecules25184283","article-title":"In Vivo pharmacokinetic Analysis Utilizing Non-targeted and Targeted Mass Spectrometry and In Vitro Assay against Transient Receptor Potential Channels of Maobushisaishinto and its Constituent Asiasari Radix","volume":"25","author":"Matsumoto","year":"2020","journal-title":"Molecules"},{"key":"B17","doi-asserted-by":"publisher","first-page":"e0259134","DOI":"10.1371\/journal.pone.0259134","article-title":"Accelerative Action of Topical Piperonylic Acid on Mice Full Thickness Wound by Modulating Inflammation and Collagen Deposition","volume":"16","author":"Moreira","year":"2021","journal-title":"PLoS One"},{"key":"B18","doi-asserted-by":"publisher","first-page":"127869","DOI":"10.1016\/j.jhazmat.2021.127869","article-title":"Facile Fabrication of Tb3+-Functionalized COF Mixed-Matrix Membrane as a Highly Sensitive Platform for the Sequential Detection of Oxolinic Acid and Nitrobenzene","volume":"427","author":"Quan","year":"2022","journal-title":"J. Hazard. Mater."},{"key":"B19","doi-asserted-by":"publisher","first-page":"1035","DOI":"10.1021\/acs.cgd.9b01365","article-title":"Improving the Dissolution Rate of the Anticancer Drug Dabrafenib","volume":"20","author":"Rai","year":"2020","journal-title":"Cryst. Growth & Des."},{"key":"B20","doi-asserted-by":"publisher","first-page":"126774","DOI":"10.1016\/j.bmcl.2019.126774","article-title":"Design, Synthesis and Antifungal Activity of Amide and Imine Derivatives Containing a Kakuol Moiety","volume":"30","author":"Sui","year":"2020","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"B21","doi-asserted-by":"publisher","first-page":"1","DOI":"10.26434\/chemrxiv.12678488","article-title":"An Integrative Drug Repurposing Pipeline Using KNIME and Programmatic Data Access: a Case Study on COVID-19 Data","volume":"6","author":"Tuerkova","year":"2020","journal-title":"ChemRxiv"},{"key":"B22","doi-asserted-by":"publisher","first-page":"179","DOI":"10.1016\/0378-4347(96)00078-3","article-title":"High-performance Liquid Chromatographic Method for the Rapid and Simultaneous Determination of Sulfamonomethoxine, Miloxacin and Oxolinic Acid in Serum and Muscle of Cultured Fish","volume":"682","author":"Ueno","year":"1996","journal-title":"J. Chromatogr. B Biomed. Sci. Appl."},{"key":"B23","doi-asserted-by":"publisher","first-page":"11","DOI":"10.1016\/s0044-8486(00)00475-0","article-title":"Pharmacokinetics and Metabolism of Miloxacin in Cultured Eel","volume":"193","author":"Ueno","year":"2001","journal-title":"Aquaculture"},{"key":"B24","doi-asserted-by":"publisher","first-page":"5466","DOI":"10.1007\/s00044-013-0541-4","article-title":"Synthesis, Anticancer and Antibacterial Activities of Piperine Analogs","volume":"22","author":"Umadevi","year":"2013","journal-title":"Med. Chem. Res."},{"key":"B25","doi-asserted-by":"publisher","first-page":"443","DOI":"10.16438\/j.0513-4870.2016-0954","article-title":"Simultaneous Determination of Donafenib and its N-Oxide Metabolite in Human Plasma by Liquid Chromatography-Tandem Mass Spectrometry","volume":"52","author":"Wang","year":"2017","journal-title":"Yao Xue Xue Bao"},{"key":"B26","doi-asserted-by":"publisher","first-page":"2109","DOI":"10.1002\/jhet.4334","article-title":"Design, Synthesis, and Evaluation of New 4( 3 H )\u2010quinazolinone Derivatives Containing a Pyrazole Carboxamide Moiety","volume":"58","author":"Wang","year":"2021","journal-title":"J. Heterocycl. Chem."},{"key":"B27","doi-asserted-by":"publisher","first-page":"533","DOI":"10.1002\/jhet.4399","article-title":"Synthesis and Antibacterial Activity of Novel 1,4\u2010pentadien\u20103\u2010one Derivatives Bearing a Benzothiazole Moiety","volume":"59","author":"Wang","year":"2022","journal-title":"J. Heterocycl. Chem"},{"key":"B28","doi-asserted-by":"publisher","first-page":"4293","DOI":"10.1038\/s41467-021-24644-1","article-title":"A Novel RyR1-Selective Inhibitor Prevents and Rescues Sudden Death in Mouse Models of Malignant Hyperthermia and Heat Stroke","volume":"12","author":"Yamazawa","year":"2021","journal-title":"Nat. Commun."},{"key":"B29","doi-asserted-by":"publisher","first-page":"2841","DOI":"10.3390\/molecules25122841","article-title":"Synthesis and Spectroscopic Analysis of Piperine- and Piperlongumine-Inspired Natural Product Scaffolds and Their Molecular Docking with IL-1\u03b2 and NF-\u039ab Proteins","volume":"25","author":"Zazeri","year":"2020","journal-title":"Molecules"},{"key":"B30","doi-asserted-by":"publisher","first-page":"2158","DOI":"10.1111\/bcp.14583","article-title":"Case of Bullous Pemphigoid Induced by Apatinib Mesylate","volume":"87","author":"Zheng","year":"2021","journal-title":"Br. J. Clin. Pharmacol."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2022.913003\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,5,31]],"date-time":"2022-05-31T04:44:17Z","timestamp":1653972257000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2022.913003\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,5,31]]},"references-count":30,"alternative-id":["10.3389\/fchem.2022.913003"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2022.913003","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,5,31]]},"article-number":"913003"}}