Fipronil CAS 120068-37-3
Introduction：Basic information about Fipronil CAS 120068-37-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
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;Pesticide intermediates;MYCODECYL;Agro-Products;Heterocycles;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;Insecticides;Pesticides;Pesticides&Metabolites;Pyrazoles;Ectoparasiticide;API;INSECTICIDE;120068-37-3;Fipronil insecticidal spectrum is wide, and existing insecticide resistance without interaction |
| Mol File: | 120068-37-3.mol |
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) |
| form | Solid |
| Water Solubility | 1.9-2.4 mg 1l-1 (20 °C） |
| color | White to Light yellow |
| λmax | 208nm(H2O)(lit.) |
| Merck | 14,4085 |
| BRN | 8090115 |
| Major Application | agriculture environmental |
| 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 |
| InChIKey | ZOCSXAVNDGMNBV-UHFFFAOYSA-N |
| SMILES | Nc1c(c(nn1-c2c(Cl)cc(cc2Cl)C(F)(F)F)C#N)S(=O)C(F)(F)F |
| LogP | 4.000 |
| CAS DataBase Reference | 120068-37-3(CAS DataBase Reference) |
| EPA Substance Registry System | Fipronil (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 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 STOT RE 1 Oral |
| Hazardous Substances Data | 120068-37-3(Hazardous Substances Data) |
| Toxicity | LD50 in rats (mg/kg): 100 orally; >2000 dermally (Colliot); in mice (mg/kg): 32 i.p. (Cole) |
| Description | Fipronil is a white powder with a mouldy odour. It has a low solubility in water and is aslow-acting poison. It does not bind strongly with soil, and the half-life of fipronil– sulphoneis 34 days. Fipronil is a broadspectrum insecticide of the phenylpyrazole group. Fipronilwas 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, andcommercial 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 aliquid, fipronil is applied on the back side skin of dogs and cats. Reports indicate that someanimals do become hypersensitive (allergic) to fipronil. |
| Chemical Properties | White crystalline solid. |
| Chemical Properties | White SOlid |
| Uses | antifungal |
| Uses | Pesticide. |
| Uses | A broad spectrum insecticide which actively disrupts the CNS of contacted insects by blocking the passage of chloride ions through GABA receptors. |
| Uses | Fipronil is used for the control of a wide range of insect species inrice, cereals, corn, cotton, top fruit, sugar beet, sugar cane, oilseed rape,many vegetables and other high-value crops. It also has a veterinary useas an ectoparasiticide. |
| Definition | ChEBI: 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 Uses | Insecticide, Veterinary medicine: Not approved for use in EU countries. Fipronilwas introduced into the U.S. in 1996 for use in animalhealth and indoor pest control. It is the constituent of manyproducts for controlling a wide spectrum of domestic animal and residential pests. |
| Trade name | BES® 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 |
| Pharmacology | Fipronil is a phenylpyrazole, the mode of action of whichis to inhibit nerve transmission in arthropods by blockingγ -aminobutyric acid-gated chloride channels. Fipronil isavailable as spray and spot-on formulations to controlfleas and ticks on cats and dogs. The adulticidal activity offipronil accounts for the majority of its activity, althoughadditional activity against flea eggs and larvae resultsfrom the presence of fipronil on hairs and debris shed intothe environment from treated pets. Autohistoradiography studies (11) into the cutaneousdistribution of 14C-fipronil in the cat and dog followingspot-on administration demonstrated that radioactivitywas restricted principally to the stratum corneum, theviable epidermis, and the pilosebaceous units. Followingits slow release from sebaceous glands, fipronil migrates inthe sebum covering the skin and hairs by passive diffusionand was shown to persist on hair for up to 2 months aftertreatment. |
| Synthesis | 120067-83-6 120068-37-3 Example 1: This example illustrates the synthesis of 5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-((trifluoromethyl)sulfinyl)-1H-pyrazole-3-carbonitrile. 100 g (0.23 mol) of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole (compound of formula (II)) was dissolved in a solvent mixture consisting of 900 g (6.97 mol) of dichloroacetic acid (DCAA) and 30 g (0.3 mol) of concentrated sulfuric acid. After stirring at 15°C for 30 min, 25 g (0.22 mol) of 30% w/w aqueous hydrogen peroxide solution was slowly added over 90 min. The reaction was continued until HPLC analysis showed a conversion of more than 95%. Upon completion of the reaction, the reaction mixture was quenched using sodium sulfite (Na2SO3). Subsequently, the separation and purification of the product was carried out by conventional methods, resulting in the target product in 98% yield and 97.5% HPLC purity. |
| Potential Exposure | Pyrazole/phenylpyrazole/organofluor ine insecticide; veterinary medicine. Fipronil was intro duced into the United States in 1996 for use in animalhealth and indoor pest control. It is the constituent of manyproducts for controlling a wide spectrum of domestic ani mal and residential pests. Banned for use in EU. |
| Metabolic pathway | Through the abiotic degradation of fipronil in aqueoussolution and on the soil surface, 5-amino-3-carbamoyl-1-[2,6-dichloro-4-(trifluoromethyl)-phenyl]-4-[(trifluoromethyl)sulfinyl]pyrazole is the only hydrolysisproduct detected. Fipronil in acidic aqueous solutionexposed under a xenon lamp degrades with theconcomitant 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-sulfonicacid. Under field conditions, when fipronil is applied informulation, four metabolites which include oneproduct resulting from reduction on the sulfur atom offipronil are detected. |
| Shipping | UN2588 Pesticides, solid, toxic, Hazard Class:6.1; Labels: 6.1-Poisonous materials, Technical NameRequired. UN2902 Pesticide, liquid, toxic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required. |
| Degradation | Fipronil 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 photolysiswith a DT50 of ﹤0.5 day. The major photodecomposition product in waterand on soil surfaces is desulfinyl-fipronil(3) which is formed by extrusionof the SO group. A minor photoproduct in water, on soil and on plantsurfaces is the sulfonic acid (4). The mechanisms of these reactions arediscussed in a recent paper by Bobe et al. (1998). |
| Toxicity evaluation | Acute oral LD50 for rats: 100 mg/kg |
| Waste Disposal | It is the responsibility ofchemical waste generators to determine the toxicity andphysical properties and of a discarded chemical and toproperly identify its classification and certification as a haz ardous waste and to determine the disposal method. UnitedStates Environmental Protection Agency guidelines for theclassification determination are listed in 40 CFR Parts261.3. Additionally, waste generators must consult and fol low all regional, national, state and local hazardous wastelaws to ensure complete and accurate classification and dis posal methods. |
| References | [1] Patent: WO2012/7938, 2012, A1. Location in patent: Page/Page column 9-10 [2] Patent: WO2007/122440, 2007, A1. Location in patent: Page/Page column 10-11 [3] Patent: US2009/30211, 2009, A1. Location in patent: Page/Page column 3 [4] Patent: WO2007/122440, 2007, A1. Location in patent: Page/Page column 11 [5] Patent: US2009/30211, 2009, A1. Location in patent: Page/Page column 3 |
Fipronil Preparation Products And Raw materials
| Raw materials | Ethyl acetate-->Sodium carbonate-->Sodium sulfate-->Ammonium hydroxide-->3-Chloroperoxybenzoic acid-->Dimethyl sulfide-->Chloromethane-->Pyrazole-->Tetrachlorvinphos-->4-Nitrobenzoyl chloride-->Ethyl 2,3-dicyanopropionate |
| Preparation Products | FIPRONIL-DESULFINYL |
