82657-04-3 Usage
Description
Different sources of media describe the Description of 82657-04-3 differently. You can refer to the following data:
1. 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.
2. Bifenthrin is a synthetic pyrethroid insecticide/miticide/acaricide. Bifenthrin is off-white
to 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 and
slightly soluble in heptane and methanol. It is slightly combustible and support combustion
at elevated temperatures. Thermal decomposition and burning may form toxic byproducts
such as carbon monoxide, carbon dioxide, hydrogen chloride, and hydrogen
fluoride. Bifenthrin treatment affects the nervous system and causes paralysis in insects.
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
Chemical Properties
Different sources of media describe the Chemical Properties of 82657-04-3 differently. You can refer to the following data:
1. 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.
2. White Solid
3. Off white to pale tan waxy substance. Faint,
sweet odor.
Uses
Different sources of media describe the Uses of 82657-04-3 differently. You can refer to the following data:
1. Third generation synthetic pyrethroid. Insecticide, acaricide.
2. Bifenthrin controls foliar insect pests and some mites on a range of
crops including cereals, citrus, cotton, fruit and vegetables.
3. 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 control
cone worms, seed bugs, seed worms and other insects and
mites on rangeland, forests and right-of-ways. It is also
used to control household and lawn pests. A U.S. EPA restricted
Use Pesticide (RUP).
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.
Check Digit Verification of cas no
The CAS Registry Mumber 82657-04-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,6,5 and 7 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 82657-04:
(7*8)+(6*2)+(5*6)+(4*5)+(3*7)+(2*0)+(1*4)=143
143 % 10 = 3
So 82657-04-3 is a valid CAS Registry Number.
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
82657-04-3Relevant articles and documents
Methods and Compositions for Use in Glued-Wood Products
-
, (2022/01/04)
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
Zhang, Ping,Yu, Qian,He, Xiulong,Qian, Kun,Xiao, Wei,Xu, Zhifeng,Li, Tian,He, Lin
, p. 420 - 431 (2018/01/04)
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.
Enantioselectivity in estrogenic potential and uptake of bifenthrin
Wang, Lumei,Liu, Weiping,Yang, Caixia,Pan, Zhiyan,Gan, Jianying,Xu, Chao,Zhao, Meirong,Schlenk, Daniel
, p. 6124 - 6128 (2008/02/12)
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.
