82657-04-3

Basic information

• Product Name: Bifenthrin
• Synonyms: [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;bifenthrine;biphenate;biphenthrin;biphentrin;brigade
• CAS NO: 82657-04-3
• Molecular Formula: C₂₃H₂₂ClF₃O₂
• Molecular Weight: 422.87
• EINECS: 200-258-5
• Product Categories: HERBICIDE;Pesticide;BI - BZMethod Specific;A-BPesticides&Metabolites;AcaricidesAlphabetic;Alpha sort;B;Endocrine Disruptors (Draft)Pesticides;EPA;Insecticides;Pesticides;Pesticides&Metabolites;Pyrethroids;Aromatics;Chiral Reagents;Isotope Labelled Compounds;Mutagenesis Research Chemicals;NULL
• Mol File: 82657-04-3.mol

Chemical Properties

• Melting Point: 68-71°C
• Boiling Point: 453.2 °C at 760 mmHg
• Flash Point: 165 °C
• Appearance: powder
• Density: d25 1.212 g/ml
• Vapor Pressure: 4.95E-22mmHg at 25°C
• Storage Temp.: 0-6°C
• Water Solubility: 0.01 g/100 mL
• Merck: 13,1215
• CAS DataBase Reference: Bifenthrin(CAS DataBase Reference)
• NIST Chemistry Reference: Bifenthrin(82657-04-3)
• EPA Substance Registry System: Bifenthrin(82657-04-3)

Safety Data

• Hazard Codes: Xn;N,N,Xn,F,T
• 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
• Hazardous Substances Data: 82657-04-3(Hazardous Substances Data)

Usage

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

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

Trade name

BIFLEX?; BISTAR?; BRIGADE?; CAPTURE? Bifenthrin; DISCIPLINE?; DOUBLE THREAT?; 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, seed worms and other insects and mites in forests, on rangeland, and right-of-ways. It is also used to control household and lawn pests. A United States Environmental Protection Agency Restricted Use Pesticide (RUP).

Metabolic pathway

When mites are administered 14C-bifenthrin either by injection or by contact, bifenthrin is efficiently metabolized by the mites and the metabolites identified arise from the combination of ester cleavage, oxidation, and conjugation reactions and are the 4'-hydroxy derivative of the ester, the primary ester cleavage products, the acid, and its 4'-hydroxy derivative from the alcohol moiety, as well as several unidentified 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 Name Required. UN3349 Pyrethroid pesticide, solid toxic, Hazard Class: 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 labile at higher pH. It has a DT50 of 225 days in natural daylight and can therefore be regarded as relatively photochemically stable (PSD).

Toxicity evaluation

The solubility of bifenthrin in water is relatively low at 0.1 mg l-1. Furthermore, the water octanol coefficient (Kow) is 1×106 and results in bifenthrin binding to organic substrates. The soil sorption coefficients range between 1.31×105 and 3.02×105, indicating relatively tight binding to soil particles. They also tend to bind to organic particulate materials in the water column. The Kow 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 l1 bifenthrin had BCFs of 21 000 after 127 days and 28 000 after 254 days of exposure. Hydrolysis of bifenthrin in buffered water occurs between pH 5 and 9. Photolysis studies in water and soil found 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, phosphorus trichloride, silver powders or dust. Incompatible with silver compounds, lime, and ordinary soaps. Mixture with some silver compounds forms explosive salts of silver oxalate.

InChI:InChI=1/2C23H22ClF3O2/c2*1-14-16(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/h2*4-12,18,20H,13H2,1-3H3/b2*19-12-/t2*18-,20-/m10/s1

Upstream product

• 354-58-5 1,1,1-Trichloro-2,2,2-trifluoroethane 
• 107489-30-5 (2-methyl[1,1'-biphenyl]-3-yl)methyl cis,trans-2,2-dimethyl-3-formylcyclopropanecarboxylate 
• 107686-51-1 (2-methyl-3-phenylphenyl)methyl (1RS,3SR)-3-(1-acetoxy-2,2-dichloro-3,3,3-trifluoropropyl)-2,2-dimethylcyclopropanecarboxylate 
• 107686-48-6 (2-methyl-3-phenylphenyl)methyl (1RS,3SR)-3-(2,2-dichloro-3,3,3-trifluoro-1-hydroxypropyl)-2,2-dimethylcyclopropanecarboxylate 
• 107686-57-7 (2-methyl-3-phenylphenyl)methyl 2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate 
• 7440-66-6 zinc 
• 850227-76-8 cis-3-(2-chloro-3,3,3-trifluoroprop-1-ene-1-yl)-2,2-dimethylcyclopropanecarboxylic acid 
• 84541-46-8 3-chloromethyl-2-methyl-[1,1'-biphenyl] 
• 94361-06-5 cyproconazol 
• 92880-79-0 bifenthrin 
• 78246-90-9 cyhalothrin chloride 
• 76350-90-8 (2-methyl-[1,1′-biphenyl]-3-yl)methanol 

Relevant articles and documents

Production process of bifenthrin

The invention discloses a production process of bifenthrin. The production process comprises the following steps: mixing 2-methyl-3-phenyl benzyl alcohol and a catalyst, putting in a reaction vessel,increasing the temperature to 10-60 DEG C to a molten state, dropwise adding 3-(2-chlorine-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane methyl halide under the condition of a certain negativepressure, absorbing negative-pressure tail gas by using tertiary water to obtain by-product acid; after the completion of dropwise adding, performing thermal-insulation reaction for 1-3 hours at a temperature of 10-60 DEG C, ending the reaction when the 2-methyl-3-phenyl benzyl alcohol is controlled to be less than 0.1 percent, performing product washing treatment, directly standing, layering andremoving water to obtain the bifenthrin. The production process disclosed by the invention has the beneficial effects that a solvent required for bifenthrin synthesis is cancelled, the subsequent treatment is simple, no re-crystallization treatment is required, by-product halogen acid is recovered, other three wastes are not generated, and the quality of the obtained bifenthrin is obviously improved. The production process disclosed by the invention has the advantages that the processes are simple, the product quality is high, the economy is improved through the by-product halogen acid, and the requirements for industrial clean production are met.

Methods and Compositions for Use in Glued-Wood Products

The present invention relates to biocide-composites providing high retention of biocides in glueline-treated glued-wood products that are hot-pressed or hot-pressed and block-stacked during manufacture.

Enantiomeric separation of type I and type II pyrethroid insecticides with different chiral stationary phases by reversed-phase high-performance liquid chromatography

The enantiomeric separation of type I (bifenthrin, BF) and type II (lambda-cyhalothrin, LCT) pyrethroid insecticides on Lux Cellulose-1, Lux Cellulose-3, and Chiralpak IC chiral columns was investigated by reversed-phase high-performance liquid chromatography. Methanol/water or acetonitrile/water was used as mobile phase at a flow rate of 0.8?mL/min. The effects of chiral stationary phase, mobile phase composition, column temperature, and thermodynamic parameters on enantiomer separation were carefully studied. Bifenthrin got a partial separation on Lux Cellulose-1 column and baseline separation on Lux Cellulose-3 column, while LCT enantiomers could be completely separated on both Lux Cellulose-1 and Lux Cellulose-3 columns. Chiralpak IC provided no separation ability for both BF and LCT. Retention factor (k) and selectivity factor (α) decreased with the column temperature increasing from 10°C to 40°C for both BF and LCT enantiomers. Thermodynamic parameters including ?H and ?S were also calculated, and the maximum Rs were not always obtained at lowest temperature. Furthermore, the quantitative analysis methods for BF and LCT enantiomers in soil and water were also established. Such results provide a new approach for pyrethroid separation under reversed-phase condition and contribute to environmental risk assessment of pyrethroids at enantiomer level.

Use of prochloraz for wood protection

The active compound prochloraz and fungicidal compositions based on prochloraz are highly suitable for protecting wood and timber products against attack and/or destruction by soft-rot fungi.

Enantioselectivity in estrogenic potential and uptake of bifenthrin

Despite the fact that the biological processes of chiral compounds are enantioselective, the endocrine disruption activity and uptake of chiral contaminants with respect to enantioselectivity has so far received limited research. In this study, the estrogenic potential and uptake of the enantiomers of a newer pyrethroid insecticide, bifenthrin (BF), were investigated. Significant differences in estrogenic potential were observed between the two enantiomers in the in vitro human breast carcinoma MCF-7 cell proliferation assay (i.e., the E-SCREEN assay) and the in vivo aquatic vertebrate vitellogenin enzyme-linked immunosorbent assay (ELISA). In the E-SCREEN assay, the relative proliferative effect ratios of 1S-cis-BF and 1R-cis-BF were 74.2% and 20.9%, respectively, and the relative proliferative potency ratios were 10% and 1%, respectively. The cell proliferation induced by the two BF enantiomers may be through the classical estrogen response pathway via the estrogen receptor (ER), as the proliferation induced by the enantiomers could be completely blocked when combined with 10-6 mol/L of the ER antagonist ICI 182,780. Measurement of vitellogenin induction in Japanese medaka (Oryzias latipes) showed that, at an exposure level of 10 ng/mL, the response to 1S-cis-BF was about 123 times greater than that to the R enantiomer. Significant selectivity also occurred in the uptake of BF enantiomers in the liver and other tissues of J. medaka. These results together suggest that assessment of the environmental safety of chiral insecticides should consider enantioselectivity in acute and chronic ecotoxicities such as endocrine disruption.

PESTICIDAL COMPOSITIONS

Composition for controlling insects and representatives of the order Acarina, which comprises a combination of variable amounts of one or more compounds of the formula in which A is an unsubstituted or, depending on the possibility of substitution on the ring system, mono- to tetrasubstituted, aromatic or non-aromatic monocyclic or bicyclic heterocyclic radical, in which the substituents of A can be chosen from the group consisting of C1-C3alkyl, C1-C3alkoxy, halogen, halo-C1-C3alkyl, cyclopropyl, halocyclopropyl, C2-C3alkenyl, C2-C3alkynyl, halo-C2-C3alkenyl, halo-C2-C3alkynyl, halo-C1-C3alkoxy, C1-C3alkylthio, Halo-C1-C3alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro; R is hydrogen, C1-C6alkyl, phenyl-C1-C4alkyl, C3-C6cycloalkyl, C2-C6alkenyl or C2-C6alkynyl; and X is N—NO2 or N—CN, in the free form or in salt form, if appropriate tautomers, in the free form or salt form, and one or more of the compounds (I) to (CLXXXIV) mentioned according to the invention and at least one auxiliary. A method of controlling pests, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compound of the formula (A) for the preparation of the composition, are described.

Macrocyclic plant acaricides

Compounds of the formula I STR1 in which either R is methyl and there is a double bond in the 9,10-position, or in which R is hydrogen and there is a single bond in the 9,10-position, are highly active against Acarina which damage plants.

2,2-Dimethylcyclopropane-carboxylic acid derivatives

A 2,2-dimethylcyclopropanecarboxylic acid derivative having the formula: STR1 wherein R1 is an alkyl group or an aryl group, R2 is a hydrogen atom, an acyl group, a sulfonyl group or an alkyl group, and each of X1 and X2 is a halogen atom.

PRACTICAL AND STEREOCONTROLLED SYNTHESES OF BOTH (1R*,3S*)- AND (1R*,3R*)-3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATES

The title compounds of (1R*,3S*) configuration were prepared from 3-formyl-2,2-dimethylcyclopropanecarboxylate by addition of CF3CCl2ZnCl, acetylation, and reductive β-elimination with zinc, whereas the (1R*,3R*) isomer was derived from Me2C=CHCH(OH)CCl2CF3 by diazoacetylation, Cu(II) catalyzed intramolecular cyclization, and the zinc reduction.