Isocycloseram

Isocycloseram
Names
Preferred IUPAC name
4-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-N-[(4R)-2-ethyl-3-oxo-1,2-oxazolidin-4-yl]-2-methylbenzamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.340.824 Edit this at Wikidata
EC Number
  • 941-777-4
UNII
  • InChI=1S/C23H19Cl2F4N3O4/c1-3-32-21(34)18(10-35-32)30-20(33)14-5-4-12(6-11(14)2)17-9-22(36-31-17,23(27,28)29)13-7-15(24)19(26)16(25)8-13/h4-8,18H,3,9-10H2,1-2H3,(H,30,33)/t18-,22+/m1/s1
    Key: WLSQDEYDCAGPIR-GCJKJVERSA-N
  • CCN1C(=O)[C@@H](CO1)NC(=O)C2=C(C=C(C=C2)C3=NO[C@@](C3)(C4=CC(=C(C(=C4)Cl)F)Cl)C(F)(F)F)C
Properties
C23H19Cl2F4N3O4
Molar mass 548.32 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isocycloseram is a chemical compound discovered by Syngenta which acts as an insecticide. It acts as a noncompetitive antagonist of invertebrate γ-aminobutyric acid (GABA)-gated chloride channels, producing uncontrolled neuronal excitation leading to paralysis and death in various species of insects, but with high selectivity over mammalian GABA receptors. Unwanted toxicity to desirable non targeted insects such as pollinators can be an issue, requiring strategic application and use.[1][2][3][4]

Uses

Pesticide

In November 2025, the U.S. Environmental Protection Agency approved agricultural use of isocycloseram as a pesticide. Because the compound is defined as a PFAS by the European Union, OECD, and several U.S. states, concerns were raised about health and environment impacts of the approval.[5][6] The U.S. EPA does not consider chemicals with a single fluorinated carbon like isocycloseram to be PFAS and contends that "molecules with only one fluorinated carbon generally lack the persistence and bioaccumulation properties that are commonly associated with forever chemicals".[7]

References

  1. ^ Cassayre J, Smejkal T, Blythe J, Hoegger P, Renold P, Pitterna T, et al. (2021). "The discovery of isocycloseram: A novel isoxazoline insecticide". Recent Highlights in the Discovery and Optimization of Crop Protection Products. pp. 165–212. doi:10.1016/B978-0-12-821035-2.00008-5. ISBN 978-0-12-821035-2.
  2. ^ Blythe J, Earley FG, Piekarska-Hack K, Firth L, Bristow J, Hirst EA, et al. (October 2022). "The mode of action of isocycloseram: A novel isoxazoline insecticide". Pesticide Biochemistry and Physiology. 187 105217. Bibcode:2022PBioP.18705217B. doi:10.1016/j.pestbp.2022.105217. PMID 36127059.
  3. ^ van Herk WG, Vernon RS, Labun T, Spies J (October 2024). "Isocycloseram, a novel isoxazoline insecticide seed treatment for protection of wheat and barley and mortality of wireworms, Limonius californicus (Coleoptera: Elateridae)". Journal of Economic Entomology. 117 (5): 1926–1937. doi:10.1093/jee/toae170. PMID 39082981.
  4. ^ Saran RK, Hoppé M, Mayor S, Long C, Blakely B, Eppler L, et al. (February 2025). "Efficacy and utility of isocycloseram a novel isoxazoline insecticide against urban pests and public health disease vectors". Pest Management Science. 81 (2): 978–989. Bibcode:2025PMSci..81..978S. doi:10.1002/ps.8497. PMID 39535487.
  5. ^ Held L (2025-12-10). "What to Know About PFAS in Pesticides". Civil Eats. Retrieved 2026-01-17.
  6. ^ Kluger J. "EPA Is Embracing PFAS Pesticides. These Are The Health Risks". TIME. Archived from the original on 2025-12-10. Retrieved 2026-01-17.
  7. ^ US EPA O (2025-11-03). "Pesticides Containing a Single Fluorinated Carbon". www.epa.gov. Retrieved 2026-01-17.

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