{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,17]],"date-time":"2026-07-17T17:31:09Z","timestamp":1784309469573,"version":"3.55.0"},"reference-count":42,"publisher":"MDPI AG","issue":"18","license":[{"start":{"date-parts":[[2024,9,14]],"date-time":"2024-09-14T00:00:00Z","timestamp":1726272000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Ministerio de Ciencia, Innovacion y Universidades in Spain","award":["PID2023\u2013150717NB\u2013I00"],"award-info":[{"award-number":["PID2023\u2013150717NB\u2013I00"]}]},{"name":"Ministerio de Ciencia, Innovacion y Universidades in Spain","award":["PDC2021\u2013121203\u2013I00"],"award-info":[{"award-number":["PDC2021\u2013121203\u2013I00"]}]},{"name":"Ministerio de Ciencia, Innovacion y Universidades in Spain","award":["PID2022\u2013139874OR\u2013C21"],"award-info":[{"award-number":["PID2022\u2013139874OR\u2013C21"]}]},{"name":"Ministerio de Ciencia, Innovacion y Universidades in Spain","award":["Y2020\/EMT\u20136290"],"award-info":[{"award-number":["Y2020\/EMT\u20136290"]}]},{"name":"Comunidad Aut\u00f3noma de Madrid","award":["PID2023\u2013150717NB\u2013I00"],"award-info":[{"award-number":["PID2023\u2013150717NB\u2013I00"]}]},{"name":"Comunidad Aut\u00f3noma de Madrid","award":["PDC2021\u2013121203\u2013I00"],"award-info":[{"award-number":["PDC2021\u2013121203\u2013I00"]}]},{"name":"Comunidad Aut\u00f3noma de Madrid","award":["PID2022\u2013139874OR\u2013C21"],"award-info":[{"award-number":["PID2022\u2013139874OR\u2013C21"]}]},{"name":"Comunidad Aut\u00f3noma de Madrid","award":["Y2020\/EMT\u20136290"],"award-info":[{"award-number":["Y2020\/EMT\u20136290"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This study investigates the chemical structure of profoxydim, focusing on its E\u2013isomer, the main commercial form. The research aimed to determine the predominant tautomeric forms under various environmental conditions. Using proton and carbon\u201313 NMR spectroscopy alongside theoretical modeling, we examined tautomers and their conformers in different solvents (MeOD, DMSO, CDCl3, benzene) to mimic gas and aqueous phases. The findings reveal that the enolic form dominates in the gas phase, while the ketonic form prevails in aqueous environments, providing key insights into the herbicide\u2019s environmental behavior. We also observed an isomeric transition from E to Z under acidic conditions, which could affect profoxydim\u2019s reactivity in natural environments. The theoretical calculations indicated that in acidic conditions, the E and Z forms are nearly degenerate, with the E form remaining dominant in neutral environments. Additionally, QSAR models assessed the toxicity of various tautomers, revealing significant differences that could impact bioactivity and environmental fate. This research offers crucial insights into the structural dynamics of profoxydim, contributing to cyclohexanedione chemistry and the development of more effective herbicides.<\/jats:p>","DOI":"10.3390\/molecules29184371","type":"journal-article","created":{"date-parts":[[2024,9,16]],"date-time":"2024-09-16T10:56:57Z","timestamp":1726484217000},"page":"4371","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Profoxydim in Focus: A Structural Examination of Herbicide Behavior in Gas and Aqueous Phases"],"prefix":"10.3390","volume":"29","author":[{"given":"Mar\u00eda","family":"Cobos-Escudero","sequence":"first","affiliation":[{"name":"Unit of Plant Protection Products, Instituto Nacional de Investigaci\u00f3n y Tecnolog\u00eda Agraria y Alimentaria (INIA-CSIC), Carretera de La Coru\u00f1a Km. 7, 28040 Madrid, Spain"},{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, M13, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paula","family":"Pla","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, M13, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3215-6726","authenticated-orcid":false,"given":"\u00c1lvaro","family":"Cervantes-Diaz","sequence":"additional","affiliation":[{"name":"Unit of Plant Protection Products, Instituto Nacional de Investigaci\u00f3n y Tecnolog\u00eda Agraria y Alimentaria (INIA-CSIC), Carretera de La Coru\u00f1a Km. 7, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Luis","family":"Alonso-Prados","sequence":"additional","affiliation":[{"name":"Unit of Plant Protection Products, Instituto Nacional de Investigaci\u00f3n y Tecnolog\u00eda Agraria y Alimentaria (INIA-CSIC), Carretera de La Coru\u00f1a Km. 7, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0776-222X","authenticated-orcid":false,"given":"Pilar","family":"Sand\u00edn-Espa\u00f1a","sequence":"additional","affiliation":[{"name":"Unit of Plant Protection Products, Instituto Nacional de Investigaci\u00f3n y Tecnolog\u00eda Agraria y Alimentaria (INIA-CSIC), Carretera de La Coru\u00f1a Km. 7, 28040 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3753-5215","authenticated-orcid":false,"given":"Manuel","family":"Alcam\u00ed","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, M13, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Instituto Madrile\u00f1o de Estudios Avanzados en Nanociencias (IMDEA\u2013Nanociencia), 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1509-2513","authenticated-orcid":false,"given":"Al Mokhtar","family":"Lamsabhi","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica, Facultad de Ciencias, M13, Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"},{"name":"Institute for Advanced Research in Chemical Sciences (IAdChem), Universidad Aut\u00f3noma de Madrid, 28049 Madrid, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2024,9,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"367","DOI":"10.1071\/CH10366","article-title":"Cyclohexane\u20131,3\u2013dione Oxime Ether Grass\u2013Specific Herbicides and the Discovery of Butroxydim","volume":"64","author":"Watson","year":"2011","journal-title":"Aust. 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