fipronil
fipronil
CAS: 120068-37-3
Molecular Formula: C12H4Cl2F6N4OS
fipronil - Names and Identifiers
| Name | fipronil |
| Synonyms | PRINCE Regent REGENT fipronil FIPRONIL Goliath gel 4-((trifluoromethyl)sulfinyl)- 5-Amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile |
| CAS | 120068-37-3 |
| EINECS | 424-610-5 |
| 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 |
fipronil - Physico-chemical Properties
| Molecular Formula | C12H4Cl2F6N4OS |
| Molar Mass | 437.15 |
| Density | 1.477-1.626 |
| Melting Point | 200-201°C |
| Boling Point | 510.1±50.0 °C(Predicted) |
| Flash Point | 262.3°C |
| Water Solubility | 1.9-2.4 mg 1l-1 (20 °C） |
| Solubility | Insoluble in water |
| Vapor Presure | 3.7×10-7 Pa (25 °C) |
| Appearance | Yellow powder |
| Color | White to Light yellow |
| Maximum wavelength(λmax) | ['208nm(H2O)(lit.)'] |
| Merck | 14,4085 |
| BRN | 8090115 |
| pKa | -5.86±0.20(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,2-8°C |
| Refractive Index | 1.617 |
| MDL | MFCD00867812 |
| Physical and Chemical Properties | The pure product is a white solid, m.p.200.5 ~ 201 ℃, relative density 1.48~1.63, vapor pressure 3.73 × 10-7Pa (2.8 × 10-7Pa) (20 ℃). Solubility: acetone 54.6g/100mL, dichloromethane 2.23g/100mL, methanol 13.75g/100mL, hexane and toluene 0.3g/mL, water 1.9mg/L. Partition coefficient (N-octanol/water) 4.0. Stable under normal storage conditions, the half-life of 135d in water, photolysis half-life of 8H in water. |
| Use | Mainly used in rice, sugar cane, potatoes and other crops, animal health is mainly used to kill cats and dogs on fleas and lice and other parasites |
fipronil - Risk and Safety
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R48/25 - 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 R36 - Irritating to the eyes |
| Safety Description | 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. S36/37 - Wear suitable protective clothing and gloves. S28 - After contact with skin, wash immediately with plenty of soap-suds. |
| UN IDs | 2588 |
| WGK Germany | 3 |
| RTECS | UQ4430250 |
| HS Code | 29331990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 in rats (mg/kg): 100 orally; >2000 dermally (Colliot); in mice (mg/kg): 32 i.p. (Cole) |
fipronil - Reference
| Reference Show more | 1. Wu Huan, Dong Sheying, Guo Jingjun. Magnetic solid phase extraction of phenyl organic pesticides in water [J]. Modern Chemical Industry, 2021,41(04):224-228 233. 2. Bai Junhui, Liu Aichun, He Xin. Determination of Fipronil and Its Metabolites Residues in Eggs [J]. Zhejiang Agricultural Sciences, 2020,61(10):2142-2144. 3. Qu, Fei, Han Wang, and Jinmao You. "Dual lanthanide-probe based on coordination polymer networks for ratiometric detection of glyphosate in food samples." Food chemistry 323 (2020): 126815.https://doi.org/10.1016/j.foodchem. 2020.126815 4. [IF=4.821] Jiahao Yin et al."Quenched electrochemiluminescence sensor of ZnO@g-C3N4 modified glassy carbon electrode for fipronil determination."Microchem J. 2019 Mar;145:295 5. [IF=7.514] Fei Qu et al."Dual lanthanide-probe based on coordination polymer networks for ratiometric detection of glyphosate in food samples."Food Chem. 2020 Sep;323:126815 |
fipronil - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | Fipronil (Fipronil), chemical name 5-amino -1-(2,6 dichloro-4-trifluorotolyl)-4-Trifluoromethyl-sulfinyl pyrazole -3-nitrile, is the first benzyrazole used for pest control. Since its discovery in 1987, it has been widely used in many fields such as agriculture and veterinary medicine, and has become an important pesticide variety. Fepperoni, the trade name is Ruijin, is a new type of benzyrazole insecticide, which is compared with traditional insecticides (organophosphorus, pyrethroids, carbamates), It has the advantages of broad spectrum and high efficiency. It has been widely used in many agricultural fields and is a commonly used insecticide for pest control. |
| pharmacological effects | fipronil mainly induces Cl-flow by blocking the Cl-channel of the nerve membrane controlled by γ-aminobutyric acid receptor, causing extreme excitement of the nervous system and leading to death of worms, thus achieving the prevention and control effect on various economic pests. |
| Preparation | 4-trifluoromethylaniline reacts with hydrochloric acid in hydrogen peroxide to generate 2,6-dichloro-4-trifluoromethylaniline; it is diazotized with sodium nitrite and hydrochloric acid to form diazonium salt, and is condensed with ethyl 2, 3-dicyanopropionate to form a condensate, and a pyrazole ring is formed in a closed loop in ammonia; then it is condensed with trichloromethyl sulfinyl chloride, the reaction product of perchloromethyl mercaptan oxidation by hydrogen peroxide, to obtain sulfide, and then undergo a replacement reaction with hydrogen fluoride to obtain non-prednis. The chemical reaction formula is as follows: |
| toxicity | acute oral LD50 in rats is 100 mg/kg, and acute percutaneous LD50 in rats is> 2000 mg/kg. Acute inhalation of LC50 in rats was 0.682mg/L. No irritation to rabbit skin, no irritation to eye mucosa. Ames test was negative and had no teratogenic effect. The LC50 of carp is 0.34mg/L (96h), and the oral LD50 of wild ducks is> 2150mg/kg. |
| Uses | Fluoropyrazole-containing broad-spectrum insecticides have high activity and wide application range. They are very sensitive to Hemiptera, Thysanoptera, Coleoptera, Lepidoptera and other pests, as well as pyrethroid and carbamate insecticides. It can be used for rice, cotton, vegetables, soybeans, rape, tobacco leaves, potatoes, tea, sorghum, corn, fruit trees, forests, public health, animal husbandry, etc., to control rice borers, brown planthoppers, rice weevil, cotton bollworm, armyworm, Plutella xylostella, Cabbage worm, Cabbage armyworm, armyworm, beetle, caterpillar, fruit tree mosquito, wheat aphid, coccidia, trichomonas, etc. The recommended dosage is 12.5~150g/hm2. China has approved field efficacy tests on rice and vegetables. The preparation is 5% gum suspension and 0.3% granules. Mainly used in rice, sugar cane, potatoes and other crops, animal health is mainly used to kill parasites such as fleas and lice on cats and dogs |
| production method | preparation of 5-amino -3-cyano -1-(2, 6-dichloro-4-trifluoromethyl phenyl) pyrazole suspension prepared from 7g sodium nitrite and 27.5mL concentrated sulfuric acid is diluted with acetic acid, and 21.2 g2 is added dropwise at 25~32 ℃, the acetic acid solution of 6-dichloro -4-trifluoromethylaniline is 50mL, the temperature is raised to 55 ℃, the temperature is heated for 20min, the solution of acetic acid (60mL) and water (125mL) of ethyl 2,3-dicyanopropionate is poured into, after stirring for 15min, water is added, the oil layer is separated, the dichloroethane is extracted, the oil layer is merged, the ammonia water is washed to pH 9, stratified, washed with water and dilute hydrochloric acid, dried, filtered and evaporated, the oil was recrystallized in toluene and hexane with 70.9% yield. Preparation of 5-Amino-3-cyano-1-(2, 6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylthiopyrazole A dichloromethane solution of trifluoromethyl sulfide (10.8g) was added dropwise to a methylene chloride solution containing 20g of the preceding product within 1h. Stir overnight at room temperature, wash, dry, filter, desolvate to obtain 26.3g of solid, recrystallize to obtain the product with 92% yield. Under the stirring of the synthesis of fipronil, the dichloromethane solution of 10g of the previous product was treated with 4.5g m-chloroperoxybenzoic acid. After stirring overnight, 2 parts of 1.6g m-chloroperoxybenzoic acid were added and placed for 2 days. Diluted with ethyl acetate, washed with sodium sulfite solution, sodium carbonate solution and water in turn, dried, filtered, desoluted, eluted and purified with dichloromethane on SiO2 chromatographic column to obtain fipronil 6.0g with 57.8% yield. Please refer to the synthesis of a new insecticidal type-fipronil, Issue 3 of Pesticide Magazine 2002. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 22:01:16
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