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Name:	Fipronil
CAS No:	120068-37-3

PRODUCT DESCRIPTION

【Name】: Fipronil

【Iupac name】: 5-amino-1-[2,
6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)
pyrazole-3-carbonitrile

【CAS Registry number】: 120068-37-3

【Synonyms】: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrazole-3-carbonitrile
MB 46030
RM 1601
Fipronil (JAN)
1H-Pyrazole-3-carbonitrile, 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-
Fluocyanobenpyrazole
Fipronil 95%TC

【EINECS(EC#)】: 424-610-5

【Molecular Formula】: C₁₂H₄Cl₂F₆N₄OS (Products with the same molecular formula)

【Molecular Weight】: 437.15

【Inchi】: 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

【InChIKey】: ZOCSXAVNDGMNBV-UHFFFAOYSA-N

【Canonical SMILES】: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)S(=O)C(F)(F)F)N)Cl)C(F)(F)F

【MOL File】
120068-37-3.mol

Chemical and Physical Properties

【Appearance】: yellow powder

【Density】: 1.477-1.626

【Melting Point】: 200-201℃

【Boiling Point】: 510.1 oC at 760 mmHg

【Vapour】: 1.61E-10mmHg at 25°C

【Refractive Index】: 1.617

【Flash Point】: 262.3 oC

【Solubilities】: Insoluble

【Color/Form】: White solid

【Stability】: Stable at normal temperatures and pressures.

【Storage temp】: 0-6°C

【Computed Properties】: Molecular Weight:437.147779 [g/mol]
Molecular Formula:C₁₂H₄Cl₂F₆N₄OS
XLogP3-AA:4.5
H-Bond Donor:1
H-Bond Acceptor:10
Rotatable Bond Count:2
Tautomer Count:3
Exact Mass:435.938706
MonoIsotopic Mass:435.938706
Topological Polar Surface Area:104
Heavy Atom Count:26
Formal Charge:0
Complexity:599
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:1
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:4
Conformer Sampling RMSD:0.8
CID Conformer Count:5

Safety and Handling

【Hazard Codes】: N: Dangerous for the environment;T: Toxic;

【Risk Statements】: R23/24/25

【Safety Statements 】: S26

【HazardClass】: 6.1(b)

【Safety】: Hazard Codes:?NT
Risk Statements: 23/24/25-48/25-50/53-55-57?
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
R48/25: Toxic: danger of serious damage to health by prolonged exposure if swallowed?
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R55: Toxic to fauna
R57: Toxic to bees
Safety Statements: 26-36/37/39-45-60-61?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S60: This material and its container must be disposed of as hazardous waste
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
RIDADR: 2588
RTECS: UQ4430250
HazardClass: 6.1(b)
PackingGroup: III

【PackingGroup 】: III

【Skin, Eye, and Respiratory Irritations】: ... Slightly irritating to eyes.

【Transport】: 2588

【Formulations/Preparations】: USEPA/OPP Pesticide Code 129121; Trade Names: Fipronil 1.6 MP Insecticide for Manuf. Use, Fipronil 90 MP Insecticide, Fipronil technical (96.5% fipronil), Fipronil 1.5% granular soil insecticide, Icon 6.2 FS (56% fipronil), Icon 6.2SC Insecticide (56% fipronil), Icon 80WG Insecticide (80% fipronil), Regent 1.5G Insecticide (1.5% fipronil), Regent 4SC Insecticide (39.4% fipronil), Regent 80WG Insecticide (80% fipronil), BES 602 (0.0143% fipronil), BES-603 (0.0001% fipronil), Chipco Brand 60818A Fipronil Insecticide (0.1% fipronil), Chipco Brand 61442A Fipronil Insecticide (0.0001% fipronil), Chipco Brand 61748A End User Fipronil Insecticide (0.0143% fipronil), Chipco Brand 61748A Service Fipronil Insecticide (0.0143% fipronil), Chipco Brand Choice Insecticide (0.1% fipronil), H&G 61743A Fipronil Insecticide (0.05% fipronil), H&G 61748A Fipronil Insecticide (0.0103% fipronil), Maxforce ABF4 (0.001% fipronil), Maxforce ABF5 (0.0005% fipronil), Maxforce Ant Bait F1 (0.01% fipronil), Maxforce Ant Bait F2 (0.001% fipronil), Maxforce Ant Bait F3 (0.0001% fipronil), Maxforce Large Roach Bait F.03 (0.03% fipronil), Maxforce Roach Bait F.05 (0.05% fipronil), Product:RBF5 (0.01% fipronil), Termidor 80 WG Insecticide (80% fipronil), Termidor SC Insecticide (9.1% fipronil), Combat ABF5 (0.0005% fipronil), Combat ABF7 (0.001% fipronil), Combat Ant Bait F1 (0.01% fipronil), Combat Ant Bait F3 (0.001% fipronil), Combat Gold (0.05% fipronil), Combat Large Roach Bait F.03 (0.03% fipronil), Combat Small Roach Bait F.03 (0.03% fipronil), Frontline Plus for Cats (9.8% fipronil), Frontline Plus for Dogs (9.8% fipronil), Frontline Spray Treatment (0.29% fipronil), Frontline Top Spot for Cats (9.7% fipronil), Frontline Top Spot for Dogs (9.7% fipronil).
Suspension concentrate, granule, flowable concentrate for seed treatment, emulsifiable concentrate, water dispersable granules, ultra low volume liquid.

【Other Preventative Measures】: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

【Protective Equipment and Clothing】: ... Slightly irritating to eyes.

【Specification】: Product Categories: PHARMACEUTICALS;Ectoparasiticide;API;INSECTICIDE;Baby Food Directives 13/2003 EC&14/2003 ECPesticides&Metabolites;AcaricidesMethod Specific;Alpha sort;E-GAlphabetic;European Community: ISO and DIN;F;FA - FLPesticides;Insecticides;Pesticides;Pesticides&Metabolites;Pyrazoles.
Personal Protection:Compatible chemical-resistant gloves. Chemical safety goggles.
Fire Fighting:Extinguish using Water spray. Carbon dioxide, dry chemical powder, or appropriate foam. Wear self-contained breathing apparatus and protective clothing to prevent contact with skin and eyes.
?

【Octanol/Water Partition Coefficient】: log Kow= 4.0 (shake flask method)

【Disposal Methods】: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】: Methods of Manufacturing

I.G Buntain et al., EP 295117 (1988 to May & Baker); L.R. Hatton et al., US 5232940 (1993)

【Usage】: The material is used as a pesticide.

Biomedical Effects and Toxicity

【Pharmacological Action】: - Drugs used to treat or prevent parasitic infections.
- Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

【Biomedical Effects and Toxicity】: To investigate the localization of fipronil in dog skin, (14)C-fipronil was topically applied to a male beagle dog (spot-on administration) at the therapeutic dose of 10 mg/kg. By means of autohistoradiography, the radioactivity was precisely detected in the skin and appendages at various intervals after application. Radioactivity was predominantly observed within the stratum corneum, the viable epidermis, and in the pilo-sebaceous units (mainly in the sebaceous glands and epithelial layers). (14)C-fipronil was significantly detected in these structures up to 56 days post-treatment, in the application zone (neck) but also in the lumbar zone, thus indicating the mechanical displacement of fipronil. No radioactivity was detected in either the dermal or the hypodermal layers, confirming the low percutaneous passage of fipronil. [Cochet P et al; Eur J Drug Metab Pharmacokinet 22 (3): 211-6 (1997)] PubMed Abstract
With oral dosing /in the rat using 14C labeled or unlabeled fipronil/, the rate and extent of absorption appeared similar among all dose groups, but may have been decreased at the high dose. There were no significant sex-related differences in excretion. Feces appeared to be the major route of excretion for fipronil derived radioactivity, where 45-75% of an administered dose was excreted. Excretion in urine was between 5-25%.
Absorption of 14C-fipronil through epidermal membranes of humans, rabbits, and rats was measured in vitro in horizontal glass diffusion cells. ...The epidermal membranes were set up as a barrier between the two halves of the diffusion cells, and the absorption rates of a neat suspension of fipronil (200 g/L) as a formulation in EP60145A (a formulation base) and of two aqueous dilutions of the formulation containing 0.2 and 4 g/L of fipronil suspended in EP 60145A were determined... . Fipronil at doses of 4 and 200 g/L penetrated rabbit and rat epidermal membranes to a greater extent than those of humans, whereas at 0.2 g/L the extent of penetration was similar through human and rat skin. The extent of penetration increased with time across species. The % of the applied dose that had penetrated the different membranes after 8 hr was 0.08% through rat epidermal membranes, 0.07% through rabbit membranes, and 0.01% through human membranes for the neat formulation; 0.14, 0.67, and 0.07% of the dose of 4.0 g/L active ingredient; and 0.9, 13.9, and 0.9% of the dose of 0.2 g/L active ingredient, respectively. At the dose of 4.0 g/L, fipronil penetrated the skin of all three species more slowly than either testosterone or hydrocortisone. These two reference permeants were selected because their intrinsic rates of dermal penetration differ by two orders of magnitude, that of testosterone being faster. On the basis of the results for these two compounds, fipronil was considered to be a slow penetrant when applied as a formulation in EP 60145A.
In a study of the absorption, distribution, metabolism, and excretion of fipronil in ruminants, [phenyl(U)-14C]-fipronil (19.2 mCi/mmol) was administered orally by capsule twice daily before feeding to three lactating goats at a dose of 0.05, 2, or 10 ppm for 7 days; assuming a daily intake of 2.0 kg dry matter, these doses are approx equivalent to nominal daily doses of 0.1, 4, and 20 mg, respectively. Milk was collected twice daily. The animals were killed about 24 hr after admin of the final dose and tissues obtained for analysis. The recovery of radiolabel in urine, milk, and tissues indicated that the min absorption of test material was about 19% at 0.05 ppm, 33% at 2 ppm, and 15% at 10 ppm. Of the administered radiolabel, 18-64% was recovered in feces, 1-5% in the milk, and 8-25% in the tissues. Total recovery was similar at the low (83%) and high doses (77%) but was somewhat lower at the intermediate dose (50%). The greatest contributor to the difference in recovery between the animals at the low and high doses and those at the intermediate dose was the amount of radiolabel excreted in the feces: 18% of the total radiolabel administered at 2 ppm, 64% at 0.05 ppm, and 61% at 10 ppm. The reason for this difference is not clear. The greatest total tissue residues were observed in omental and renal fat (about 1.9 ppm at the 10 ppm dose), followed by liver (0.86 ppm) and much lower concns in kidney, milk (0.17 ppm), and skeletal muscle.
[phenyl(U)-14C]-Fipronil (19.2 mCi/mmol) was administered orally in capsules daily before feeding to groups of 5 laying hens at doses of 0.05, 2, or 10 ppm for 28 days; assuming a daily intake of 150 g dry matter, these doses were equivalent to nominal daily intakes of 0.0075, 0.3, and 1.5 mg, respectively. Eggs were collected twice daily. The animals were killed about 24 hr after admin of the final dose, and tissues were obtained. Of the administered radiolabel, 28-42% was recovered in excreta, 15-18% in eggs, and 1-5% in tissues; the total recovered was 52-58%. The greatest total tissue residues after admin of the highest dose were found in peritoneal fat (56 ppm). The levels in eggs were also high (30 ppm in yolks) after this dose and had not plateaued by the end of the study. The levels were lower in skin (17 ppm) and much lower in liver, egg white, and muscle.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】: TERRESTRIAL FATE: An experimental Koc range of 1,086-6,863(SRC) was determined for fipronil based on its log Kom range of 2.8-3.6(4), and a conversion equation(5). According to a classification scheme(1), the Koc values of 500 to 2,000 are low and values >5,000 indicate immobility in soil. Volatilization of fipronil from moist soil surfaces is not expected to be an important fate process(3) given an estimated Henry's Law constant of 8.4X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.78X10-9 mm Hg(2), and water solubility, 1.9 mg/l(2). Fipronil is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.78X10-9 mm Hg(2). The photolytic rate constant for the photodegradation of fipronil in soils ranges from 0.0047/hr to 0.0032/hr(4). The corresponding range for the half-lives of the reaction are 147 hours to 217 hours, respectively(4). Studies have shown that the extent of photodegradation is inversely proportional to the concentration of organic matter in the soil(4). The nitrile group of fipronil may undergo hydrolysis to the corresponding amide metabolite by chemical or biological processes. It has been reported that in acidic soil, the amide metabolite results more from biological activity rather than chemical hydrolysis(5). Studies also indicate that a sulfone and sulfide metabolite may occur from oxidative and reductive degradation processes in soils(5). Oxidation of fipronil to the corresponding sulfone can result from biological or chemical processes, however, studies indicate that the major degradation process was probably a chemical transformation(5).
AQUATIC FATE: Based on a classification scheme(1) and an experimental Koc range of 1,086-6,863(SRC), determined from its log Kom values of 2.8-3.6(7), and a conversion equation(2), fipronil is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 8.4X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 2.78X10-9 mm Hg(5), and water solubility, 1.9 mg/l(6). According to a classification scheme(3), an estimated BCF of 240(SRC), from its log Kow of 4.0(5) and a regression-derived equation(4), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Fipronil is stable to hydrolysis under acidic (pH 5.5) and neutral (pH 7) conditions. The rate of hydrolysis of fipronil under alkaline conditions was measured and it was found that degradation increased proportionally with an increase in pH; the corresponding half-life for the hydrolysis reaction is 770 hours at pH 9, 114 hours at pH 10, 11 hours at pH 11, and 2.4 hours at pH 12(6). Fipronil in acidic (pH 5.5) aqueous solution exposed to light from a xenon lamp revealed two parallel photodegradation reactions with the appearance of the trifluoromethylpyrazole derivative and the pyrazole-4-sulfonic acid derivative(6). The photolytic rate constants for the reactions are 0.11/hr and 0.05/hr(6), respectively. The corresponding half-lives for the reactions are 6.3 hours(SRC) and 13.86 hours(SRC), derived from the experimental rate constants and a conversion equation(4).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fipronil, which has a vapor pressure of 2.78X10-9 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fipronil may be removed from the air by wet and dry deposition(SRC).

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PRODUCT DESCRIPTION

Chemical and Physical Properties

Safety and Handling

Use and Manufacturing

Biomedical Effects and Toxicity

Environmental Fate and Exposure Potential

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