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 | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.102.312 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| 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 | |
| QP53AX15 (WHO) | |
| Hazards | |
| GHS labelling: | |
| Danger | |
| NFPA 704 (fire diamond) | |
| 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).
Infobox references | |
Fipronil is a broad-spectrum insecticide that belongs to the phenylpyrazole insecticide class. Fipronil disrupts the insect central nervous system by blocking the ligand-gated ion channel of the GABAA receptor (IRAC group 2B) 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 GABAA 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.
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.