Fipronil

Fipronil Basic information
Product Name:Fipronil
Synonyms:4-((trifluoromethyl)sulfinyl)-;m&b46030;PRINCE;REGENT;FIPRONIL;5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile;FIPRONIL <)>97 % (HPLC, EFF.);Goliath gel
CAS:120068-37-3
MF:C12H4Cl2F6N4OS
MW:437.15
EINECS:424-610-5
Product Categories:Pesticides intermediate;Fipronil insecticidal spectrum is wide, and existing insecticide resistance without interaction;Agro-Products;Heterocycles;Pesticide intermediates;MYCODECYL;PHARMACEUTICALS;Baby Food Directives 13/2003 EC&14/2003 ECPesticides&Metabolites;AcaricidesMethod Specific;Alpha sort;E-GAlphabetic;European Community: ISO and DIN;F;FA - FLPesticides;Ectoparasiticide;API;INSECTICIDE;Insecticides;Pesticides;Pesticides&Metabolites;Pyrazoles;120068-37-3
Mol File:120068-37-3.mol
Fipronil Structure
Fipronil Chemical Properties
Melting point 200-201°C
Boiling point 510.1±50.0 °C(Predicted)
density 1.477-1.626
vapor pressure 3.7×10-7 Pa (25 °C)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility DMSO: 250 mg/mL (571.89 mM)
pka-5.86±0.20(Predicted)
Water Solubility 1.9-2.4 mg 1l-1 (20 °C)
form neat
color White to Light yellow
λmax208nm(H2O)(lit.)
Merck 14,4085
BRN 8090115
LogP4.000
CAS DataBase Reference120068-37-3(CAS DataBase Reference)
EPA Substance Registry SystemFipronil (120068-37-3)
Safety Information
Hazard Codes T,N
Risk Statements 23/24/25-48/25-50/53-55-57-36
Safety Statements 26-36/37/39-45-60-61-36/37-28
RIDADR 2588
WGK Germany 3
RTECS UQ4430250
HazardClass 6.1(b)
PackingGroup III
HS Code 29331990
Hazardous Substances Data120068-37-3(Hazardous Substances Data)
ToxicityLD50 in rats (mg/kg): 100 orally; >2000 dermally (Colliot); in mice (mg/kg): 32 i.p. (Cole)
Fipronil Usage And Synthesis
DescriptionFipronil is a white powder with a mouldy odour. It has a low solubility in water and is a slow-acting poison. It does not bind strongly with soil, and the half-life of fipronil– sulphone is 34 days. Fipronil is a broadspectrum insecticide of the phenylpyrazole group. Fipronil was first used extensively for the control of ants, beetles, cockroaches, fleas; ticks, termites, mole crickets, thrips, rootworms, weevils, flea of pets, field pest of corn, golf courses, and commercial turf, and other insects. Fipronil was first used in the United States in 1996. Fipronil is a topical insecticide. It kills adult fleas and larvae, ticks, and chewing lice. As a liquid, fipronil is applied on the back side skin of dogs and cats. Reports indicate that some animals do become hypersensitive (allergic) to fipronil.
Chemical PropertiesWhite crystalline solid.
Chemical PropertiesWhite SOlid
Usesantifungal
UsesPesticide.
UsesA broad spectrum insecticide which actively disrupts the CNS of contacted insects by blocking the passage of chloride ions through GABA receptors.
UsesFipronil is used for the control of a wide range of insect species in rice, cereals, corn, cotton, top fruit, sugar beet, sugar cane, oilseed rape, many vegetables and other high-value crops. It also has a veterinary use as an ectoparasiticide.
DefinitionChEBI: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile is a member of the class of pyrazoles that is 1H-pyrazole that is substituted at positions 1, 3, 4, and 5 by 2,6-dichloro-4-(trifluoromethyl)phenyl, cyano, (trifluoromethyl)sulfinyl, and amino groups, respectively. It is a nitrile, a dichlorobenzene, a primary amino compound, a member of pyrazoles, a sulfoxide and a member of (trifluoromethyl)benzenes.
Agricultural UsesInsecticide, Veterinary medicine: Not approved for use in EU countries. Fipronil was introduced into the U.S. in 1996 for use in animal health and indoor pest control. It is the constituent of many products for controlling a wide spectrum of domestic animal and residential pests.
Trade nameBES® 602; CEASEFIRE®; CHIPCO®; COMBAT®; FRONTLINE; MB-46030®; H&G®; ICON®; MAXFORCE® ANT STATION; MAXFORCE® ROACH STATION; REGENCY SOFION®; REGENT®; REGENT® 500-FS; TERMIDOR® L VI-NIL
PharmacologyFipronil is a phenylpyrazole, the mode of action of which is to inhibit nerve transmission in arthropods by blocking γ -aminobutyric acid-gated chloride channels. Fipronil is available as spray and spot-on formulations to control fleas and ticks on cats and dogs. The adulticidal activity of fipronil accounts for the majority of its activity, although additional activity against flea eggs and larvae results from the presence of fipronil on hairs and debris shed into the environment from treated pets.
Autohistoradiography studies (11) into the cutaneous distribution of 14C-fipronil in the cat and dog following spot-on administration demonstrated that radioactivity was restricted principally to the stratum corneum, the viable epidermis, and the pilosebaceous units. Following its slow release from sebaceous glands, fipronil migrates in the sebum covering the skin and hairs by passive diffusion and was shown to persist on hair for up to 2 months after treatment.
Potential ExposurePyrazole/phenylpyrazole/organofluor ine insecticide; veterinary medicine. Fipronil was intro duced into the United States in 1996 for use in animal health and indoor pest control. It is the constituent of many products for controlling a wide spectrum of domestic ani mal and residential pests. Banned for use in EU.
Metabolic pathwayThrough the abiotic degradation of fipronil in aqueous solution and on the soil surface, 5-amino-3- carbamoyl-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4- [(trifluoromethyl)sulfinyl]pyrazole is the only hydrolysis product detected. Fipronil in acidic aqueous solution exposed under a xenon lamp degrades with the concomitant appearance of 5-amino-3-cyano-1-[2,6- dichloro-4-(trifluoromethyl)-phenyl]-4- (trifluoromethyl)pyrazole and 5-amino-3-cyano-1-[2,6- dichloro-4-(trifluoromethyl)phenyl]pyrazole-4-sulfonic acid. Under field conditions, when fipronil is applied in formulation, four metabolites which include one product resulting from reduction on the sulfur atom of fipronil are detected.
ShippingUN2588 Pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN2902 Pesticide, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
DegradationFipronil is stable in water at pH 5 and 7 but is slowly hydrolysed at pH 9 (DT50 28 days) to the amide (2). It undergoes rapid aqueous photolysis with a DT50 of ﹤0.5 day. The major photodecomposition product in water and on soil surfaces is desulfinyl-fipronil(3) which is formed by extrusion of the SO group. A minor photoproduct in water, on soil and on plant surfaces is the sulfonic acid (4). The mechanisms of these reactions are discussed in a recent paper by Bobe et al. (1998).
Toxicity evaluationAcute oral LD50 for rats: 100 mg/kg
Waste DisposalIt is the responsibility of chemical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly identify its classification and certification as a haz ardous waste and to determine the disposal method. United States Environmental Protection Agency guidelines for the classification determination are listed in 40 CFR Parts 261.3. Additionally, waste generators must consult and fol low all regional, national, state and local hazardous waste laws to ensure complete and accurate classification and dis posal methods.
Xylene 5-AMINO-1-(4-METHYLPHENYL)-1H-PYRAZOLE-3-CARBONITRILE PHENYL RESIN ALTRENOGEST 4-Amino-3,5-dichlorobenzotrifluoride Diphenyl ether 6-Aminocaproic acid Glycine Dichloroacetic acid 4-Aminobenzonitrile PHENYL VALERATE Fipronil o-Tolunitrile AMINO ACIDS 3-Aminobenzotrifluoride Diaminomaleonitrile Phenyl salicylate Phenylacetic acid

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