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Bifenthrin(CAS No. 82657-04-3)

Bifenthrin C23H22ClF3O2 (cas 82657-04-3) Molecular Structure

82657-04-3 Structure

Identification and Related Records

【Name】
Bifenthrin
【Iupac name】
(2-methyl-3-phenylphenyl)methyl
3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,
2-dimethylcyclopropane-1-carboxylate
【CAS Registry number】
82657-04-3
【Synonyms】
Capture (pesticide)
(2-methyl-3-phenyl-phenyl)methyl 3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethyl-cyclopropane-1-carboxylate
Biflex
Biphenthrin
Brigade
Talstar
FMC 54800
Cyclopropanecarboxylic acid,3-[(1Z)-2-chloro-3,3,3-trifluoro-1- propenyl]-2,2-dimethyl-,(2-methyl[1,1'- biphenyl]-3-yl)methyl ester,(1R,3R)-rel-
(2-methyl-3-phenyl-phenyl)methyl 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropane-1-carboxylate
acaricide Bifenthrin
TALSTAR
CAPTURE
FMC 58000
CYCLOPROPANECARBOXYLIC ACID, 3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYL-, (2-METHYL(1,1′-BIPHENYL)-3-YL)METHYL ESTER, (Z)-
cyhalothrin
Binfenthrin
Bifenthrin 95%TC,2.5%%EC,10%EC,5%EW
BIFENTHRIN 95%
【Molecular Formula】
C23H22ClF3O2 (Products with the same molecular formula)
【Molecular Weight】
422.868
【Inchi】
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-UNOMPAQXSA-N
【Canonical SMILES】
CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)C=C(C(F)(F)F)Cl)C3=CC=CC=C3
【Isomers smiles】
CC1=C(C=CC=C1COC(=O)C2C(C2(C)C)/C=C(/C(F)(F)F)\Cl)C3=CC=CC=C3
【MOL File】
82657-04-3.mol

Chemical and Physical Properties

【Appearance】
white crystalline solid
【Density】
1.212 g/ml
【Melting Point】
68-71℃
【Boiling Point】
744.4°C at 760 mmHg
【Flash Point】
165 °C
【Water】
0.01 g/100 mL
【Solubilities】
0.01 g/100 mL in water
【Color/Form】
Light brown viscous oil
Viscous liquid; crystaline or waxy solid
Off-white to pale tan waxy solid
【Stability】
Stable for two years at 25 C and 50 C technical bifenthrin pyrethrins. Are stable for long periods in water-based aerosols where emulsifiers give neutral water systems. Stable 21 days at pH 5-9 (21 C).
【Storage temp】
0-6°C
【Computed Properties】
Molecular Weight:422.86779 [g/mol]
Molecular Formula:C23H22ClF3O2
XLogP3:6
H-Bond Donor:0
H-Bond Acceptor:5
Rotatable Bond Count:6
Exact Mass:422.126042
MonoIsotopic Mass:422.126042
Topological Polar Surface Area:26.3
Heavy Atom Count:29
Formal Charge:0
Complexity:622
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:1
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:2
Effective Rotor Count:7.6
Conformer Sampling RMSD:1
CID Conformer Count:258

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R20/21/22;R50/53
【Safety Statements 】
S13;S60;S61
【HazardClass】
6.1(b)
【Safety】

Hazard Codes:?HarmfulXn,?DangerousN,?FlammableF
Risk Statements: 20/21/22-50/53-36-11-36/37/38?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36:Irritating to eyes.?
R11:Highly flammable.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 13-60-61-36/37-16-36-26?
S13:Keep away from food, drink and animal foodstuffs.?
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.?
S16:Keep away from sources of ignition.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2588
RTECS: GZ1227800
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 82657-04-3(Hazardous Substances Data)

【PackingGroup 】
III
【Skin, Eye, and Respiratory Irritations】
Immediately irritating to the eye. /Pyrethrins/
The chief effect from exposure ... is skin rash particularly on moist areas of the skin. ... May irritate the eyes.
【Transport】
UN 2588
【Fire Fighting Procedures】
Use carbon dioxide, foam, or dry chemical /on fires involving pyrethroids/. /Pyrethrum/
Fire-fighting: Self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive-pressure mode. /Pyrethrum/
【Formulations/Preparations】
USEPA/OPP Pesticide Code 128825; Trade Names: FMC 54800, Capture, FMC 54800 technical, Talstar, Brigade, Biflex.
Emulsifiable concentrate; suspension concentrate; wettable powder; ultra-low volume liquid; granule.
Material contains greater than/equal to 97% cis-isomer and less than/equal to 3% trans-isomer.
【Reactivities and Incompatibilities】
Incompatibility: Strong oxidizers. /Pyrethrins/
... Incompatible with lime & ordinary soaps because acids & alkalies speed up processes of hydrolysis. /Pyrethrins/
【Other Preventative Measures】
Skin that becomes contaminated with /pyrethrum/ should be promptly washed or showered with soap or mild detergent and water. /Pyrethrum/
Clothing contaminated with /pyrethrum/ should be placed in closed containers for storage until provision is made for the removal of /pyrethrum/ from the clothing. /Pyrethrum/
Respirators may be used when engineering and work practice controls are not technically feasible, when such controls are in the process of being installed, or when they fail or need to be supplemented. Respirators may also be used for operations which require entry into tanks or closed vessels, and in emergency situations. /Pyrethrum/
Employees who handle /pyrethrum/ ... should wash their hands thoroughly with soap or mild detergent and water before eating, smoking, or using toilet facilities. /Pyrethrum/
Avoid contact with skin. Keep out of any body of water. Do not contaminate water by cleaning of equipment or disposal of waste. Do not reuse empty container. Destroy it by perforating or crushing. /Pyrethrum/
Workers should wash: Promptly when skin becomes contaminated. /Pyrethrins/
Work clothing should be changed daily: If it is reasonably probable that the clothing may be contaminated. /Pyrethrins/
Remove clothing: Promptly if it is non-impervious clothing that becomes contaminated. /Pyrethrins/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
Employees should be provided with and required to use dust- and splash-proof safety goggles where /pyrethroids/ ... may contact the eyes. /Pyrethroids/
Employees should be provided with and be required to use impervious clothing, gloves, and face shields (eight-inch minimum). /Pyrethroids/
Wear appropriate equipment to prevent: Repeated or prolonged skin contact. /Pyrethrum and pyrethrins/
Wear eye protection to prevent: Reasonable probability of eye contact. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 50 mg/cu m: Respirator Classes: Any chemical cartridge respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. Any supplied-air respirator. May require eye protection. Any self-contained breathing apparatus. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 125 mg/cu m: Respirator Classes: Any supplied-air respirator operated in a continuous flow mode. May require eye protection. Any powered, air-purifying respirator with organic vapor cartridge(s) in combination with a dust, mist, and fume filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 250 mg/cu m: Respirator Classes: Any chemical cartridge respirator with a full facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece. Any powered, air-purifying respirator with a tight-fitting facepiece and organic vapor cartridge(s) in combination with a high-efficiency particulate filter. May require eye protection. /Pyrethrins/
Recommendations for respirator selection. Max concn for use: 5,000 mg/cu m: Respirator Class: Any supplied-air respirator with a full facepiece and operated in a pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Emergency or planned entry into unknown concn or IDLH conditions: Respirator Classes: Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive pressure mode. Any supplied-air respirator with a full face piece and operated in pressure-demand or other positive pressure mode in combination with an auxiliary self-contained breathing apparatus operated in pressure-demand or other positive pressure mode. /Pyrethrins/
Recommendations for respirator selection. Condition: Escape from suddenly occurring respiratory hazards: Respirator Classes: Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister having a high-efficiency particulate filter. Any appropriate escape-type, self-contained breathing apparatus. /Pyrethrins/
【Specification】

?Bifenthrin (CAS NO.82657-04-3) is also named as (1alpha,3alpha(Z))-(+-)-(2-Methyl(1,1'-biphenyl)-3-yl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate ; (1alpha,3alpha(Z))-(+-)-3-(2-Chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid (2-methyl(1,1'-biphenyl)-3-yl)methyl ester ; 2-Methylbiphenyl-3-ylmethyl (Z)-(1RS,3RS)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate ; 2-Methylbiphenyl-3-ylmethyl-(Z)-(1RS)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxylate ;
Bifenthrine ; Bifenthrine [ISO-French] ; Biphenate ; Biphenthrin ; Biphentrin ; Brigade ; CCRIS 9249 ; Capture ; Caswell No. 463F ; EPA Pesticide Chemical Code 128825 ; FMC 54800 ; FMC 58000 ; HSDB 6568 ; Talstar?.?Pure product of Bifenthrin (CAS NO.82657-04-3) is?off-white solid. It can be dissolved in acetone (1.25kg / L), chloroform, dichloromethane, toluene, ethyl ether, slightly soluble in heptane and methanol and insoluble in water.

【Octanol/Water Partition Coefficient】
log Kow = >6.00
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Incineration would be an effective disposal procedure where permitted. ... /Pyrethrin products/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

2-Methyl-3-phenylbenzyl alcohol + 3-(2-chloro-3,3,3-thrifluoropropenyl)-2,2-dimethylcyclopropane carboxylic acid (esterification)
【Usage】

Third generation synthetic pyrethroid. Insecticide, acaricide.

Biomedical Effects and Toxicity

【Therapeutic Uses】
Pyrethrins with piperonyl butoxide are used for topical treatment of pediculosis (lice infestations). Combinations of pyrethrins with piperonyl butoxide are not effective for treatment of scabies (mite infestations). Although there are no well-controlled comparative studies, many clinicians consider 1% lindane to be pediculicide of choice. However, some clinicians recommend use of pyrethrins with piperonyl butoxide, esp in infants, young children, & pregnant or lactating women ... . If used correctly, 1-3 treatments ... are usually 100% effective ... Oil based (eg, petroleum distillate) combinations ... produce the quickest results. ... For treatment of pediculosis, enough gel, shampoo, or solution ... should be applied to cover affected hair & adjacent areas ... After 10 min, hair is ... washed thoroughly ... treatment should be repeated after 7-10 days to kill any newly hatched lice. /Pyrethrins/
【Biomedical Effects and Toxicity】
/PYRETHROIDS/ READILY PENETRATE INSECT CUTICLE AS SHOWN BY TOPICAL LD50 TO PERIPLANETA (COCKROACH) ... /PYRETHROIDS/
WHEN RADIOACTIVE PYRETHROID IS ADMIN ORALLY TO MAMMALS, IT IS ABSORBED FROM INTESTINAL TRACT OF THE ANIMALS & DISTRIBUTED IN EVERY TISSUE EXAMINED. EXCRETION OF RADIOACTIVITY IN RATS ADMIN TRANS-ISOMER: DOSAGE: 500 MG/KG; INTERVAL 20 DAYS; URINE 36%; FECES 64%; TOTAL 100%. /PYRETHROIDS/ [MIYAMOTO J; ENVIRON HEALTH PERSPECT 14: 15-28 (1976)] PubMed Abstract
Pyrethrins are absorbed through intact skin when applied topically. When animals were exposed to aerosols of pyrethrins with piperonyl butoxide being released into the air, little or none of the combination was systemically absorbed. /Pyrethrins/

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
The rate constant for the vapor-phase reaction of bifenthrin with photochemically-produced hydroxyl radicals has been estimated as 2.96X10-11 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 13 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of bifenthrin with ozone has been estimated as 1.62X10-18 cu cm/molecule-sec at 25 deg C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). A base-catalyzed second-order hydrolysis rate constant of 4.0X10-2 l/mole-sec(SRC) was estimated using a structure estimation method(3); this corresponds to half-lives of 5.5 years and 200 days at pH values of 7 and 8, respectively(3). Pyrethrins, eg bifenthrin, are expected to undergo photodegradation in the environmental UV spectrum (>290 nm)(4).

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