{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T20:16:21Z","timestamp":1792700181370,"version":"4.5.0"},"reference-count":117,"publisher":"MDPI AG","issue":"17","license":[{"start":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T00:00:00Z","timestamp":1787616000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100019648","name":"Kuban Science Foundation","doi-asserted-by":"crossref","award":["N-25.1\/27"],"award-info":[{"award-number":["N-25.1\/27"]}],"id":[{"id":"10.13039\/100019648","id-type":"DOI","asserted-by":"crossref"}]},{"award":["N-25.1\/27"],"award-info":[{"award-number":["N-25.1\/27"]}],"id":[{"id":"https:\/\/ror.org\/02avgf557","id-type":"ROR","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The aim of this work was to synthesize previously unknown thieno[2,3-b]pyridines bearing a \u03b2-ketoamide moiety, to study their structure, and to evaluate their agrochemical potential as 2,4-D herbicide safeners. A series of 3-(3-aminothieno[2,3-b]pyridine-2-yl)-3-oxo-N-phenylpropanamides were prepared via S-alkylation of readily available 2-thioxonicotinonitriles or 3-cyanopyridine-2-thiolates with \u03b3-bromoacetoacetanilide, followed by base-promoted Thorpe\u2013Ziegler cyclization. The structure of 4-[(3-cyano-4,6-dimethylpyridin-2-yl)thio]-3-oxo-N-phenylbutanamide was unambiguously established by single-crystal X-ray diffraction. Quantum chemical calculations (B3LYP-D3BJ\/6-311+G(2d,p)) revealed that the ketone form is significantly more stable than the enol tautomer with a calculated equilibrium constant in DMSO of 1.52 \u00d7 10\u22125, which is consistent with the absence of enol form signals in the NMR spectra. The calculated IR frequencies, after scaling, showed excellent agreement with experimental data. Additionally, we found that 4-[(3-cyano-4,6-dimethylpyridin-2-yl)thio]-3-oxo-N-phenylbutanamide undergoes intramolecular cyclization upon heating in AcOH or DMF, to give 4-hydroxy-7,9-dimethylthieno [2,3-b:4,5-b\u2032]dipyridin-2(1H)-one via aniline elimination, thus providing an alternative route to tricyclic thieno [2,3-b;4,5-b]dipyridine ensembles. Agrochemical screening demonstrated that some compounds exhibit pronounced antidote activity against the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) in sunflower seedlings, with root and hypocotyl protection reaching 119\u2013156% in laboratory tests. Field trials for the three most active compounds confirmed their efficacy, providing crop yield increases of 46\u201357% relative to the herbicide-only control. These results indicate that the newly synthesized thienopyridine \u03b2-ketoamides represent a promising class of 2,4-D herbicide safeners.<\/jats:p>","DOI":"10.3390\/molecules31172975","type":"journal-article","created":{"date-parts":[[2026,8,25]],"date-time":"2026-08-25T15:01:07Z","timestamp":1787670067000},"page":"2975","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":1,"title":["\u03b2-Ketoamides in Thieno[2,3-b]pyridine Series: Synthesis, Quantum Chemical Studies and 2,4-D Herbicide Safening Effects"],"prefix":"10.3390","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6846-8919","authenticated-orcid":false,"given":"Artem A.","family":"Amirkhanyan","sequence":"first","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7163-0497","authenticated-orcid":false,"given":"Victor V.","family":"Dotsenko","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"},{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9829-9674","authenticated-orcid":false,"given":"Alexandr","family":"Bespalov","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tatyana R.","family":"Hagur","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0007-8244-5925","authenticated-orcid":false,"given":"Eva S.","family":"Daus","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3435-4873","authenticated-orcid":false,"given":"Igor V.","family":"Yudaev","sequence":"additional","affiliation":[{"name":"Faculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9120-7637","authenticated-orcid":false,"given":"Yuliia V.","family":"Daus","sequence":"additional","affiliation":[{"name":"Faculty of Energetics, Kuban State Agrarian University, 13 Kalinina St., 350044 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7685-1448","authenticated-orcid":false,"given":"Darya Yu.","family":"Lukina","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry and Technologies, Kuban State University, 149 Stavropolskaya St., 350040 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Vladimir K.","family":"Vasilin","sequence":"additional","affiliation":[{"name":"Department of Biotechnology and Animal Product Technology, Kuban State Technological University, 2 Moskovskaya St., 350072 Krasnodar, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7125-9066","authenticated-orcid":false,"given":"Nicolai A.","family":"Aksenov","sequence":"additional","affiliation":[{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Inna V.","family":"Aksenova","sequence":"additional","affiliation":[{"name":"Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355017 Stavropol, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2026,8,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"929","DOI":"10.1080\/10426500307855","article-title":"Recent trends in the chemistry of thienopyridines","volume":"178","author":"Bakhite","year":"2003","journal-title":"Phosphorus Sulfur Silicon Relat. 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