Tetflupyrolimet
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| Preferred IUPAC name
(3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carboxamide | |
Other names
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3D model (JSmol)
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CompTox Dashboard (EPA)
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| Properties | |
| C19H16F4N2O2 | |
| Molar mass | 380.343 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetflupyrolimet is an anilide herbicide for controlling grass weeds. It was launched in 2020,[1] and its novel mode of action makes it the first HRAC Group 28 herbicide, and the first new herbicidal mode of action discovered in some 30 years,[2] after Group 27 and Group 10.
Discovery
[edit]New effort to research herbicides has taken place recently, following a decades dearth of development, and growing problems with herbicide resistance. Mitsui developed cyclopyrimorate, the first Group 33, at around the same time.[3]
Tetflupyrolimet was discovered by high-volume screening in greenhouse testing. One vendor-supplied chemical, 4-phenylpyrrolidinone-5-anilide, looked promising. It made no chlorotic symptoms, but suppressed grass growth. Known modes of action were ruled out. The vendor however, supplied the wrong chemical. The promising sample had was -3-anilide, not -5-anilide. The 'correct' chemical, when re-created, had no herbicidal activity. The incorrect chemical sparked a slew of new experiments.[3]
Candidate pyrrolidinone amides were studied; generally stronger against grasses than broadleaf weeds, and had more effect preёmergently than post. Initial efforts focused on additions to the phenyl rings, with fluorine tested in several positions, analogs with other halogens like methyl and trifluoromethyl being generally less potent than fluorine on the 3-anilide ring. On the 4-phenul ring the analogs had pronounced, varied effects, with trifluoromethyl, trifluoromethoxy and halogen substitution at the 3 or 4 positions boosting efficacy. The free NH group by the anilide group proved crucial; its hydrogen being methyl-substituted negated activity. Selective control in rice drew researchers to the 4-phenyl trifluoromethyl analog, with the fluorine still in the ortho position on the anilide ring, as it was efficacious and crop-safe. Testing revealed a racemic mixture was inefficient, one enantiomer was providing all the activity. Methylating the lactam-ring isomer also strengthened activity. The central pyrrolidinone ring was replaced experimentally, but all were less effective (some completely ineffective) and some caused crop-damage.[3]
Field trials in Japan, Indonesia, India, Vietnam, Brazil and the USA came back promising for rice use.[3]
Mechanism
[edit]Tetflupyrolimet's mode of action is inhibition of the enzyme dihydroorotate dehydrogenase (DHODH), disrupting the de novo pyrimidine biosynthesis pathway. Plant cells also make pyrimidine through a salvage process of cellular components (like RNA), and this is energetically cheap, but when the plant needs large amounts of pyrimidine, such as when growing or rapidly dividing, it must use the de novo process, so by targeting this, tetflupyrolimet is most active against seedlings. Blocking pyrimidine formation then, halts growth and emergence.[2] Despite halted growth, there are no symptoms of chlorosis or eventual necrosis.[3]
DHODH converts dihydroorotate to orotate, and is mediated by ubiquinone. Tetflupyrolimet's effects can be undone by adding orotate, or the later product uridine monophosphate, directly.[3]
Tetflupyrolimet is rapidly absorbed by roots and shoots, is mobile in xylem and remains chemically stable in the plant.[2]
Usage
[edit]Tetflupyrolimet has been used on rice, sugarcane and citrus crops.[1]
Tetflupyrolimet has been sold under the tradenames "Innovader"[1] and "Dodhylex".[2]
References
[edit]- ^ a b c Hertfordshire, University of. "Tetflupyrolimet -- Pesticide Properties Database". sitem.herts.ac.uk.
- ^ a b c d "Dodhylex™ active | FMC Corp". www.fmc.com. Retrieved 3 May 2025.
- ^ a b c d e f Selby, Thomas P.; Satterfield, Andrew D.; Puri, Atul; Stevenson, Thomas M.; Travis, D. Andrew; Campbell, Matthew J.; Taggi, Andrew E.; Hughes, Kenneth A.; Bereznak, James (29 November 2023). "Bioisosteric Tactics in the Discovery of Tetflupyrolimet: A New Mode-of-Action Herbicide". Journal of Agricultural and Food Chemistry. 71 (47). American Chemical Society: 18197–18204. Bibcode:2023JAFC...7118197S. doi:10.1021/acs.jafc.3c01634. PMID 37285594.
External links
[edit]- Tetflupyrolimet in the Pesticide Properties DataBase (PPDB)