Isocycloseram

Chemical compound From Wikipedia, the free encyclopedia

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]

Quick facts Names, Identifiers ...
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).
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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

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