Fipronil

Fipronil
Names
	Preferred IUPAC name 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
	Other names Fipronil; Fluocyanobenpyrazole; Taurus; Termidor
Identifiers
CAS Number	120068-37-3 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5063 ;
ChEMBL	ChEMBL101326 ;
ChemSpider	3235 ;
ECHA InfoCard	100.102.312
KEGG	D01042 ;
PubChem CID	3352;
UNII	QGH063955F ;
CompTox Dashboard (EPA)	DTXSID4034609 ;
	InChI InChI=1S/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2 Key: ZOCSXAVNDGMNBV-UHFFFAOYSA-N ; InChI=1/C12H4Cl2F6N4OS/c13-5-1-4(11(15,16)17)2-6(14)8(5)24-10(22)9(7(3-21)23-24)26(25)12(18,19)20/h1-2H,22H2 Key: ZOCSXAVNDGMNBV-UHFFFAOYAP;
	SMILES FC(F)(F)S(=O)c2c(C#N)nn(c1c(Cl)cc(cc1Cl)C(F)(F)F)c2N;
Properties
Chemical formula	C12H4Cl2F6N4OS
Molar mass	437.14 g·mol−1
Density	1.477-1.626 g/cm3
Melting point	200.5 °C (392.9 °F; 473.6 K)
Pharmacology
ATCvet code	QP53AX15 (WHO)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
NFPA 704 (fire diamond)	2 1 0
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	97 mg/kg (rat, oral)
LC50 (median concentration)	0.25 mg/L (rainbow trout, aquatic)
Safety data sheet (SDS)	Fipronil
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole chemical family. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABA_A receptor and glutamate-gated chloride (GluCl) channels. This causes hyperexcitation of contaminated insects' nerves and muscles. Fipronil's specificity towards insects is believed to be due to its greater binding affinity for the GABA_A receptors of insects than to those of mammals, and for its action on GluCl channels, which do not exist in mammals. As of 2017, there does not appear to be significant resistance among fleas to fipronil.

Because of its effectiveness on various pests, fipronil is used as the active ingredient in flea control products for pets and home roach baits as well as field pest control for corn, golf courses, and commercial turf. Its widespread use makes its specific effects the subject of considerable attention. Observations on possible harm to humans or ecosystems are ongoing as well as the monitoring of pesticide resistance development.

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