Bifenthrin CAS 82657-04-3
Introduction：Basic information about Bifenthrin CAS 82657-04-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Bifenthrin Basic informationDescription References
| Product Name: | Bifenthrin |
| Synonyms: | (1α,3α(Z))(±)(2-methyl(1,1′-biphenyl)-3-yl)methyl-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcy-clopropanecarhoxylate;[1alpha,3alpha(z)]-(+-)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl;2-methylbiphenyl-3-ylmethyl-(z)-(1rs)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-en;2-methylbiphenyl-3-ylmethyl(z)-(1rs,3rs)-3-(2-chloro-3,3,3-trifluoroprop-1-en;fmc54800;fmc-54800;fmc58000;Brookade |
| CAS: | 82657-04-3 |
| MF: | C23H22ClF3O2 |
| MW: | 422.87 |
| EINECS: | 200-258-5 |
| Product Categories: | BI - BZMethod Specific;A-BPesticides&Metabolites;AcaricidesAlphabetic;Alpha sort;B;Endocrine Disruptors (Draft)Pesticides;EPA;Insecticides;Pesticides;Pesticides&Metabolites;Pyrethroids;HERBICIDE;Pesticide;Aromatics;Chiral Reagents;Isotope Labelled Compounds;Mutagenesis Research Chemicals |
| Mol File: | 82657-04-3.mol |
Bifenthrin Chemical Properties
| Melting point | 68-71°C |
| Boiling point | 453.2±45.0 °C(Predicted) |
| density | d25 1.212 g/ml |
| vapor pressure | 2.4×10-5 Pa (25 °C) |
| Fp | 165 °C |
| storage temp. | 0-6°C |
| solubility | DMSO: 100 mg/mL (236.48 mM) |
| form | Solid |
| color | White to off-white |
| Water Solubility | 0.01 g/100 mL |
| Merck | 13,1215 |
| InChI | 1S/C23H22ClF3O2/c1-14-16(10-7-11-17(14)15-8-5-4-6-9-15)13-29-21(28)20-18(22(20,2)3)12-19(24)23(25,26)27/h4-12,18,20H,13H2,1-3H3/b19-12- |
| InChIKey | OMFRMAHOUUJSGP-JHEGMOCKSA-N |
| SMILES | CC1(C(C1/C=C(C(F)(F)F)\Cl)C(OCC2=C(C(C3=CC=CC=C3)=CC=C2)C)=O)C |
| LogP | 7.300 (est) |
| CAS DataBase Reference | 82657-04-3(CAS DataBase Reference) |
| NIST Chemistry Reference | Bifenthrin(82657-04-3) |
| EPA Substance Registry System | Bifenthrin (82657-04-3) |
Safety Information
| Hazard Codes | Xn;N,N,Xn,F,T |
| Risk Statements | 20/21/22-50/53-36-11-36/37/38-48/22-43-40-23/25 |
| Safety Statements | 13-60-61-36/37-16-36-26-45-38-24-23 |
| RIDADR | UN 2588 |
| WGK Germany | 3 |
| RTECS | GZ1227800 |
| HazardClass | 6.1(b) |
| PackingGroup | III |
| HS Code | 29162090 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 2 Oral Acute Tox. 3 Inhalation Aquatic Acute 1 Aquatic Chronic 1 Carc. 2 Skin Sens. 1 STOT RE 1 |
| Hazardous Substances Data | 82657-04-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 54.5 mg/kg; LD50 dermally in rabbits: >2000 mg/kg (Doel) |
| Description | Bifenthrin is synthetic pyrethroid insecticide with biochemical origins in the natural insecticide pyrethrum. It is a waxy solid with a color ranging from an off-white to a pale tan, and with a slightly sweet odor. It is almost insoluble in water. Bifenthrin is used for the control of borers and termites in timber, insect pests in agricultural crops (bananas, apples, pears, ornamentals) and turf, as well as for general pest control (spiders, ants, fleas, flies, mosquitoes). Due to its high toxicity to aquatic organisms, it is listed as a restricted use pesticide. It has a very low solubility in water and tends to bind to soil, which minimizes runoff into water sources. It is marketed as Talstar, Bifenthrine, Brigade, Capture, Torant, Zipak, FMC 54800, and OMS3024. |
| References | [1] http://ec.europa.eu/food/plant/pesticides/eu-pesticides-database/public/?event=activesubstance.detail&language=DE&selectedID=1026 [2] http://apvma.gov.au/node/12396 [3] http://www.ehrf.info/wp-content/uploads/2012/03/Bifenthrin-Feb-2012.pdf |
| Description | Bifenthrin is a synthetic pyrethroid insecticide/miticide/acaricide. Bifenthrin is off-whiteto pale tan waxy solid granules with a faint, musty odour and a slightly sweet smell.Bifenthrin is soluble in methylene chloride, acetone, chloroform, ether, and toluene andslightly soluble in heptane and methanol. It is slightly combustible and support combustionat elevated temperatures. Thermal decomposition and burning may form toxic byproductssuch as carbon monoxide, carbon dioxide, hydrogen chloride, and hydrogenfluoride. Bifenthrin treatment affects the nervous system and causes paralysis in insects. |
| Chemical Properties | Bifenthrin is a member of the pyrethroid chemical class. It is an insecticide and acaricide. Bifenthrin is off-white to pale tan waxy solid granules with a faint, musty odor and slightly sweet smell. Bifenthrin is soluble in methylene chloride, acetone, chloroform, ether, and toluene, and is slightly soluble in heptane and methanol. It is slightly combustible and support combustion at elevated temperatures. Thermal decomposition and burning may form toxic by-products, such as carbon monoxide, carbon dioxide, hydrogen chloride, and hydrogen fl uoride. Bifentrin treatment affects the nervous system and causes paralysis in insects. |
| Chemical Properties | White Solid |
| Chemical Properties | Off white to pale tan waxy substance. Faint,sweet odor. |
| Uses | Bifenthrin controls foliar insect pests and some mites on a range ofcrops including cereals, citrus, cotton, fruit and vegetables. |
| Uses | Third generation synthetic pyrethroid. Insecticide, acaricide. |
| Definition | ChEBI: A carboxylic ester obtained by formal condensation of cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylic acid and [(2-methyl-1,1'-biphenyl)-3-yl]methanol. |
| Health Hazard | Bifenthrin is moderately toxic to species of mammals when ingested. Exposures to large doses of bifenthrin cause poisoning with symptoms that include, but are not limited to, incoordination, tremor, salivation, vomiting, diarrhea, and irritability to sound and touch. Exposures to bifenthrin through skin absorption and/or inhalation of dust cause adverse health effects. On contact with bifenthrin, occupational workers develop adverse health effects that include skin sensations, rashes, numbness, and a burning and tingling type of effect. As a pyrethroid poison, bifenthrin disturbs the electrical impulses in nerves, over-stimulating nerve cells, causing tremors and eventually causing paralysis. The skin-related health effects were found to be reversible and subside after a brief period of time and stoppage of further exposures to bifenthrin. Although bifenthrin causes no infl ammation or irritation on human skin, it can cause a tingling sensation that lasts about 12 h. Bifenthrin has caused no symptoms of irritation to rabbits’ eyes. The US EPA has classifi ed bifenthrin as toxicity class II, meaning moderately toxic |
| Agricultural Uses | Insecticide, Acaricide: A broad-spectrum insecticide. Registered to controlcone worms, seed bugs, seed worms and other insects andmites on rangeland, forests and right-of-ways. It is alsoused to control household and lawn pests. A U.S. EPA restrictedUse Pesticide (RUP). |
| Trade name | BIFLEX®; BISTAR®; BRIGADE®;CAPTURE® Bifenthrin; DISCIPLINE®; DOUBLETHREAT®; EMPOWER®; FMC® 54800; FMC® 58000;TALSTAR®; TALSTAR LAWN & TREE®; TORANT®;ZIPAK® |
| Potential Exposure | A broad spectrum pyrethroid secticide/acaricide used to control cone worms, seed bugs, seedworms and other insects and mites in forests, on rangeland,and right-of-ways. It is also used to control household andlawn pests. A United States Environmental ProtectionAgency Restricted Use Pesticide (RUP). |
| Metabolic pathway | When mites are administered 14C-bifenthrin either byinjection or by contact, bifenthrin is efficientlymetabolized by the mites and the metabolitesidentified arise from the combination of ester cleavage,oxidation, and conjugation reactions and are the4'-hydroxy derivative of the ester, the primary estercleavage products, the acid, and its 4'-hydroxyderivative from the alcohol moiety, as well as severalunidentified metabolites. |
| storage | Bifenthrin should be kept stored in a cool, dry, well-ventilated place away from heat, open flame or hot surfaces. It should only be stored in its original containers and should not be contaminated with other pesticides, fertilizers, water, food, or feed by storage or disposal |
| Shipping | UN2588 Pesticides, solid, toxic, Hazard Class:6.1; Labels: 6.1—Poisonous materials, Technical NameRequired. UN3349 Pyrethroid pesticide, solid toxic, HazardClass: 6.1; Labels: 6.1—Poisonous material. |
| Degradation | Bifenthrin is stable for 21 days in the pH range 5-9 at 21°C but it is labileat higher pH. It has a DT50 of 225 days in natural daylight and can thereforebe regarded as relatively photochemically stable (PSD). |
| Toxicity evaluation | Thesolubility of bifenthrin in water is relatively low at 0.1 mg l-1.Furthermore, the water octanol coefficient (Kow) is 1×106 andresults in bifenthrin binding to organic substrates. The soilsorption coefficients range between 1.31×105 and 3.02×105,indicating relatively tight binding to soil particles. They also tendto bind to organic particulate materials in the water column. TheKow of bifenthrin may explain the bioconcentration factors(BCFs) observed in some animals, especially fish. For example,fathead minnows (Pimephales promelas) exposed to 0.0037 mg l1bifenthrin had BCFs of 21 000 after 127 days and 28 000 after254 days of exposure. Hydrolysis of bifenthrin in buffered wateroccurs between pH 5 and 9. Photolysis studies in water and soilfound that the half-lives were 408 and 96.9 days, respectively.The aerobic soil half-life was 96.3 days and the anaerobic halflife,425 days. |
| Incompatibilities | May react violently with strong oxidizers,bromine, 90% hydrogen peroxide, phosphorustrichloride, silver powders or dust. Incompatible with silvercompounds, lime, and ordinary soaps. Mixture with somesilver compounds forms explosive salts of silver oxalate. |
| Waste Disposal | Incineration would be aneffective disposal procedure where permitted. If an efficientincinerator is not available, the product should be mixedwith large amounts of combustible material and contactwith the smoke should be avoided. In accordance with40CFR165, follow recommendations for the disposal ofpesticides and pesticide containers. |
Bifenthrin Preparation Products And Raw materials
| Raw materials | N,N-Dimethylformamide-->Benzyl chloride-->Ethyl chloroformate-->Bromobenzene-->Benzoyl chloride-->Benzyl bromide-->Benzamide-->2-Methyl-3-biphenylmethanol-->7,12-DIMETHYLBENZ[A]ANTHRACENE-->2-Biphenylcarboxylic acid-->Allylacetic acid |
| Preparation Products | Aluminum chloride-->Chlorine-->Sulfur-->Ferric chloride-->Phosphorus pentoxide-->Zinc oxide-->Phosphorus oxybromide-->Potassium-->Melamine-->Methyl chloroformate-->Chlorothalonil-->Arsenic(III) oxide-->GOLD-->Bromine chloride-->polytetrafluoroethylene fluoroethylene polymer electret-->PHOSPHORUS PENTAFLUORIDE |
