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
CAS Number	1309959-62-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:191374;
ChemSpider	128919235;
ECHA InfoCard	100.340.824
EC Number	941-777-4;
PubChem CID	118261601;
UNII	2M3T3NFC78;
CompTox Dashboard (EPA)	DTXSID401337424;
	InChI 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;
	SMILES 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
Chemical formula	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). Infobox references

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 pest insects, but with high selectivity over mammalian GABA receptors. As with all insecticides, unwanted toxicity to desirable non targeted insects such as pollinators can be an issue, requiring strategic application and use.^[1]^[2]^[3]^[4]

References

^ 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.
^ 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.
^ 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.
^ 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.

[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.

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