Difethialone

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Difethialone
Difethialone.png
Names
Preferred IUPAC name
3-[3-(4′-Bromo[1,1′-biphenyl]-4-yl)naphthalen-1-yl]-4-hydroxy-2H-1-benzothiopyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.118.383 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C31H23BrO2S/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2 X mark.svgN
    Key: JHELOZJAKXYVBE-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C31H23BrO2S/c32-24-15-13-20(14-16-24)19-9-11-21(12-10-19)23-17-22-5-1-2-6-25(22)27(18-23)29-30(33)26-7-3-4-8-28(26)35-31(29)34/h1-16,23,27,33H,17-18H2
    Key: JHELOZJAKXYVBE-UHFFFAOYAX
  • O=c1c(C2CC(c3ccc(-c4ccc(Br)cc4)cc3)Cc3ccccc32)c(O)sc2ccccc12
Properties
C31H23BrO2S
Molar mass 539.49 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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Difethialone is an vitamin K antagonist anticoagulant used as a rodenticide. [1] It is considered a second generation agent. [2]

It belongs to the 4-thiochromenone or benzothiopyranone class of rodenticides, which differs from 4-hydroxycoumarins by the substitution of an oxygen atom with sulfur. It is especially similar to brodifacoum. It shares the same mechanism of inhibiting Vkorc1. It is effective for warfarin-resistant and warfarin-susceptible rodents. [1] Its high potency makes resistance harder to evolve, though a few populations of rodents have nevertheless managed to do so. [3]

In May 2008, the EPA added restrictions on the sale of difethialone in consumer-use rodenticide products and also for exterior use by commercial applicators. [4] [5]

References

  1. 1 2 Nahas K, Lorgue G, Mazallon M (1989). "Difethialone (LM-2219): a new anticoagulant rodenticide for use against warfarin-resistant and -susceptible strains of Rattus norvegicus and Mus musculus". Annales de Recherches Vétérinaires. 20 (2): 159–64. PMID   2751229.
  2. ↑ Saravanan K, Kanakasabai R, Thiyagesan K (June 2003). "Field evaluation of difethialone, a new second generation anticoagulant rodenticide in the rice fields". Indian Journal of Experimental Biology. 41 (6): 655–8. PMID   15266918.
  3. ↑ McGee, C.F.; McGilloway, D.A.; Buckle, A.P. (September 2020). "Anticoagulant rodenticides and resistance development in rodent pest species – A comprehensive review". Journal of Stored Products Research. 88: 101688. doi:10.1016/j.jspr.2020.101688.
  4. ↑ EPA, OCSPP, OPP, US (2014-03-04). "Restrictions on Rodenticide Products". www.epa.gov.
  5. ↑ "Regulations.gov". www.regulations.gov.


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