Epyrifenacil

Last updated

Epyrifenacil
Epyrifenacil structure.png
Names
Preferred IUPAC name
ethyl 2-[[3-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]-2-pyridinyl]oxy]acetate
Identifiers
3D model (JSmol)
ChEBI
EC Number
  • 885-819-9
PubChem CID
UNII
  • InChI=1S/C21H16ClF4N3O6/c1-3-33-18(31)10-34-19-14(5-4-6-27-19)35-15-8-13(12(23)7-11(15)22)29-17(30)9-16(21(24,25)26)28(2)20(29)32/h4-9H,3,10H2,1-2H3
    Key: XPEVJXBWHXAUDR-UHFFFAOYSA-N
  • CCOC(=O)COC1=C(C=CC=N1)OC2=C(C=C(C(=C2)N3C(=O)C=C(N(C3=O)C)C(F)(F)F)F)Cl
Properties
C21H16ClF4N3O6
Molar mass 517.82 g·mol−1
Hazards
GHS labelling:
GHS-pictogram-pollu.svg
Warning
H410
P273, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Epyrifenacil is an herbicide from the pyrimidinedione class which acts as a protoporphyrinogen oxidase inhibitor. It is effective against grass weeds and some broadleaf weeds. [1] [2] It is hepatotoxic and carcinogenic in animal models but these effects are not considered likely to affect humans at relevant exposure levels. [3] [4] Concerns have been raised about the environmental breakdown of epyrifenacil to the "forever chemical" trifluoroacetic acid. [5]

See also

References

  1. ↑ Sada Y, Jin Y, Hikosaka M, Ido K (May 2025). "Epyrifenacil, a new systemic PPO-inhibiting herbicide for broad-spectrum weed control". Pest Management Science. 81 (5): 2463–2468. doi:10.1002/ps.8244. PMC   11981982 . PMID   38873996.
  2. ↑ Maienfisch P, Koerber K (May 2025). "Recent innovations in crop protection research". Pest Management Science. 81 (5): 2406–2418. doi:10.1002/ps.8441. PMC   11981984 . PMID   39344983.
  3. ↑ Matsunaga K, Abe J, Ogata K, Fukunaga S, Kitamoto S. "Elucidation of the species differences of epyrifenacil-induced hepatotoxicity between mice and humans by mass spectrometry imaging analysis in chimeric mice with humanized liver". The Journal of Toxicological Sciences. 46 (12): 601–609. doi: 10.2131/jts.46.601 . PMID   34853245.
  4. ↑ Fukunaga S, Ogata K, Eguchi A, Matsunaga K, Sakurai K, Abe J, et al. (December 2022). "Evaluation of the mode of action and human relevance of liver tumors in male mice treated with epyrifenacil". Regulatory Toxicology and Pharmacology. 136 105268. doi: 10.1016/j.yrtph.2022.105268 . PMID   36210011.
  5. ↑ "Trump officials set to approve 'forever chemical' as pesticide ingredient". The Guardian. 11 November 2025.


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