Fipronil

Fipronil

Names
IUPAC name (RS)-5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
Other names Fipronil Fluocyanobenpyrazole Termidor
Identifiers
CAS Number	120068-37-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:5063 Y
ChEMBL	ChEMBL101326 Y
ChemSpider	3235 Y
ECHA InfoCard	100.102.312
KEGG	D01042 Y
PubChem	3352
UNII	QGH063955F Y
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 Y Key: ZOCSXAVNDGMNBV-UHFFFAOYSA-N Y 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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Fipronil is a broad-use insecticide that belongs to the phenylpyrazole chemical family. Fipronil is a broad-spectrum insecticide that disrupts the insect central nervous system by blocking GABA-gated chloride channels and glutamate-gated chloride (GluCl) channels, resulting in central nervous system toxicity. This causes hyperexcitation of contaminated insects' nerves and muscles. Specificity of fipronil on insects may come from a better efficacy on GABA receptor, but also because GluCl channels do not exist in mammals.

Fipronil is a slow acting poison. When used on dogs and cats, it kills virtually all fleas in 24–48 hours.

When used as bait, it allows the poisoned insect time to return to the colony or harborage. In cockroaches, the feces and carcass can contain sufficient residual pesticide to kill others in the same nesting site. In ants, the sharing of the bait among colony members assists in the spreading of the poison throughout the colony. With the cascading effect, the projected kill rate is about 95% in three days for ants and cockroaches. Fipronil serves as a good bait toxin not only because of its slow action, but also because most, if not all, of the target insects do not find it offensive or repulsive.

Toxic baiting with fipronil has also been shown to be extremely effective in locally eliminating German wasps (commonly called yellow jackets in North America). All colonies within foraging range are completely eliminated within one week.

Wildlife impacts include the following:

Fipronil is also used as the active ingredient in flea control products for pets, field pest control for corn, golf courses and commercial turf, although flea populations appear to be developing a genetic resistance to its effects.

Fipronil acts by binding to allosteric sites of GABA_A receptors and GluCl receptors (of insects) as an antagonist (a form of noncompetitive inhibition). This prevents the opening of chloride ion channels normally encouraged by GABA, reducing the chloride ions' ability to lower a neuron's membrane potential. This results in an overabundance of neurons reaching action potential and likewise CNS toxicity via over-stimulation.