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Fipronil
Common name: Fipronil
IUPAC name:
(±-5-amino-1-(2,6-dichloro-a,a,a-trifluoro-p-tolyl)-4-trifluoromethylsulfinylpyrazole-3-carbonitrile
Chemical Abstracts name:    
5-amino-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(1R,S)-(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile
CAS RN: [120068-37-3]
 
PHYSICAL CHEMISTRY
Mol. wt.: 437.2
Form: White solid.
M.p.: 200-201 ºC; (tech., 195.5-203 °C)
V.p.: 3.7×10-4 mPa (25 ºC)
Kow logP= 4.0 (shake flask method)
Henry:3.7×10-5 Pa m3 mol-1 (calc.)
S.g./density: 1.477-1.626 (20 °C)
Solubility In water 1.9 (pH 5), 2.4 (pH 9), 1.9 (distilled) (all in mg/l, 20 °C). In acetone 545.9, dichloromethane 22.3, hexane 0.028, toluene 3.0 (all in g/l, 20 °C).
Stability  Stable in water at pH 5 and 7; slowly hydrolysed at pH 9 (DT50 c. 28 d). Stable to heat. Slowly degrades in sunlight (c. 3% loss after 12 d continuous irradiation); rapidly photolysed in aqueous solution (DT50 c. 0.33 d). 
 
TOXICOLOGY
Oral Acute oral  LD50 for rats 97, mice 95 mg/kg.
Skin and eye Acute percutaneous  LD50 for rats >2000, rabbits 354 mg/kg. Not a skin or eye irritant (OECD criteria). Not a skin sensitiser.
Inhalation  LC50 (4 h) for rats 0.682 mg/l (tech.; nose only exposure).
NOEL (2 y) for rats 0.5 mg/kg diet; (18 mo) for mice 0.5 mg/kg diet; (52 w) for dogs 0.2 mg/kg b.w. daily (combined sexes).
ADI (JMPR) 0.0002 mg/kg b.w.
Toxicity class WHO (a.i.) II
EPA (formulation) II
 
ECOTOXICOLOGY
Birds Acute oral   LD50 for bobwhite quail 11.3, mallard ducks >2000, pheasants 31, red-legged partridges 34, house sparrows 1120, pigeons >2000 mg/kg. Dietary LC50 (5 d) for bobwhite quail 49, mallard ducks >5000 mg/kg diet.
Fish Acute LC50 (96 h) for bluegill sunfish 85, rainbow trout 248, European carp 430 mg/l.
Daphnia  LC50 (48 h) 0.19 mg/l; for D. carinata (48 h) 3.8 mg/l.
Algae  EC50 (96 h) for Scenedesmus subspicatus 0.068 mg/l; (120 h) for Selenastrum capricornutum >0.16, Anabaena flos-aquae >0.17 mg/l.
Bees Highly toxic to honeybees, both by direct contact and by ingestion. However, no risk to bees when used as a soil or seed treatment.
Worms   Non-toxic.

 
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