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3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester

Bifenthrin

CAS: 82657-04-3

Molecular Formula: C23H22ClF3O2

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  5. 3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Names and Identifiers

Name Bifenthrin
Synonyms Brookade
fmc58000
fmc54800
fmc-54800
Bifenthrin
[1alpha,3alpha(z)]-(+-)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl
2-methylbiphenyl-3-ylmethyl(z)-(1rs,3rs)-3-(2-chloro-3,3,3-trifluoroprop-1-en
2-methylbiphenyl-3-ylmethyl-(z)-(1rs)-cis-3-(2-chloro-3,3,3-trifluoroprop-1-en
(2-methyl[1,1'-biphenyl]-3-yl)methyl 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylate
(2-methylbiphenyl-3-yl)methyl 3-[(1Z)-2-chloro-3,3,3-trifluoroprop-1-en-1-yl]-2,2-dimethylcyclopropanecarboxylate
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
3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester
(2-methyl-3-phenyl-phenyl)methyl (1R,3R)-3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarboxylate
(2-methyl-3-phenyl-phenyl)methyl (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl]-2,2-dimethyl-cyclopropanecarboxylate
(1α,3α(Z))(±)(2-methyl(1,1′-biphenyl)-3-yl)methyl-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcy-clopropanecarhoxylate
3-(2-chloro-3,3,3-trifluoropropyl-1-alkenyl)-2,2-dimethyl cyclopropane carboxylic-methyl-3-methyl-3-phenyl benzyl ester
CAS 82657-04-3
EINECS 200-258-5
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
InChIKey OMFRMAHOUUJSGP-JHEGMOCKSA-N

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Physico-chemical Properties

Molecular FormulaC23H22ClF3O2
Molar Mass422.87
Densityd25 1.212 g/ml
Melting Point68-71°C
Boling Point453.2±45.0 °C(Predicted)
Flash Point165°C
Water Solubility0.01 g/100 mL
Solubility Soluble in acetone, chloroform, dichloromethane, ether, toluene, heptane, slightly soluble in pentane, methanol.
Vapor Presure2.4×10-5 Pa (25 °C)
AppearanceWhite solid
Merck13,1215
Storage Condition0-6°C
SensitiveSensitive to light
MDLMFCD00143694
Physical and Chemical PropertiesPure white solid, solubility in water 0.1mg/l, soluble in acetone, chloroform, dichloromethane, ether, toluene, heptane. Slightly soluble in pentane, methanol, the original drug at 25°C stable for more than 1 year, at room temperature storage, stability greater than 1 year. Stable for 21 days at PH5-9(21°C) and DT50-65-125 days in soil.
UsePrevention and Control of cotton bollworm, cotton red spider, peach caryoptera, pear caryophylla, Hawthorn spider mite, Citrus Red Spider, macular Midge, tea wing worm, vegetable aphids, rape worm, diamondback moth, eggplant Red Spider, tea moth and other more than 20 kinds of pests, whitefly, tea geworm, tea worms.

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Risk and Safety

Risk CodesR20/21/22 - 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 the eyes
R11 - Highly Flammable
R36/37/38 - Irritating to eyes, respiratory system and skin.
R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed.
R43 - May cause sensitization by skin contact
R40 - Limited evidence of a carcinogenic effect
R23/25 - Toxic by inhalation and if swallowed.
Safety DescriptionS13 - 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.
S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S38 - In case of insufficient ventilation, wear suitable respiratory equipment.
S24 - Avoid contact with skin.
S23 - Do not breathe vapour.
UN IDsUN 2588
WGK Germany3
RTECSGZ1227800
HS Code29162090
Hazard Class6.1(b)
Packing GroupIII
ToxicityLD50 orally in rats: 54.5 mg/kg; LD50 dermally in rabbits: >2000 mg/kg (Doel)

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Reference

Reference
Show more
1. [IF=4.192] Changsheng Wei et al."Bifenthrin Induces Fat Deposition by Improving Fatty Acid Uptake and Inhibiting Lipolysis in Mice."J Agr Food Chem. 2019;67(51):14048–14055
2. [IF=1.902] Pengfei Li et al."Residual levels and dietary risk assessment of bifenthrin, dinotefuran, and its major metabolites in open wheat conditions."Biomedical Chromatography. 2021 Oct 15

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Introduction

Solubility in water is 0.1mg/l, soluble in acetone, chloroform, dichloromethane, ether, toluene, heptane. Slightly soluble in pentane, methanol, the original drug is stable at 25 ℃ for more than 1 year, and the storage stability at room temperature is more than 1 year. Stable in PH5-9(21 ℃) for 21 days and in soil for DT50-65-125 days.
Last Update：2022-10-16 17:29:11

3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester - Reference Information

NIST chemical information information provided by: webbook.nist.gov (external link)
EPA chemical substance information information provided by: ofmpeb.epa.gov (external link)
Overview bifenthrin is one of the new varieties of pyrethroid insecticides developed rapidly from 70 to 80, which is widely used in the world. Bifenthrin moderate toxicity to humans and livestock, the drug has a high affinity in the soil, insecticidal activity is very high, the insect stomach poison, contact killing effect, used in a variety of crops to control aphids, mites, cotton bollworm, pink bollworm, peach caryolysin, leaf hopper and other pests.
toxicity Acute oral LD50 was 54.5mg/L in rats and acute percutaneous LD50>2000mg/kg in rabbits, the skin and eyes of rats and rabbits were not stimulated, and the skin of guinea pigs was not sensitized. Animals were fed two trials with no effect concentration of 50mg/kg. No carcinogenic, teratogenic or mutagenic effect was found in animal test, and no abnormality was found in the third generation reproductive test. It is highly toxic to fish, with LC50 of 0.35 μg/L (96H), l500.15 μg/L (96h) for rainbow trout and l500.16 μg/L (48h) for Daphnia. Wild duck acute oral LC50 concentration of 1280mg/kg feed (8d), quail LC504450mg/kg feed (8d).
Use pyrethroid insecticides and acaricides. With a knock-down effect of strong, broad-spectrum, efficient, fast, long residual effect in the characteristics, to kill the role of contact and stomach toxicity, no absorption effect. Can be used for the control of cotton bollworm, pink bollworm, tea geometrid, tea worms, Apple or Hawthorn Red Spider, peach Carina, vegetable aphid, cabbage, vegetable moth, citrus leaf moth. Such as the prevention and control of cotton bollworm, pink bollworm in the second and third generation of egg incubation period, young insects into the bud, before the Boll, or control of cotton Red Spider, in the formation, if the occurrence of mites, spray with 10% ~ 6mL/3.4 m 2 or 7.5~6mL/4.5 m 2 of water. And can also be treated cotton aphid, bridge worm, rolled leaf worm, thorn moth, thrips and so on. Control of tea geometrid, tea worms, tea moth, with 10% emulsifiable concentrate 4000~10000 times liquid spray.
it can kill both insects and mites, and has a good control effect on cotton, vegetables, fruit trees, tea tree and other pests
control cotton bollworm, cotton red spider, peach, pear, hawthorn spider mites, Citrus Red Spider, macular mists, tea wing mists, vegetable aphids, cabbage worms, diamondback moth, eggplant Red Spider, tea moth and other more than 20 kinds of pests, whitefly, tea geeerigeron, tea worms.
production method preparation method-2-phenylbenzoyl chloride is prepared by reacting 2-phenylbenzoic acid with socl2, the corresponding 2-phenyl benzamide is obtained by reaction with dimethylformamide, and 2-phenyl dimethyl benzylamine is obtained by reduction with lithium aluminum hydride. The corresponding ammonium salt was prepared by reacting 2-phenyldimethylbenzylamine with CH3I, and then reacted with ethyl chloroformate after isomerization to obtain 2-methyl-3-phenylchlorobenzyl chloride. Finally, Bifenthrin was prepared by refluxing the corresponding acid in acetonitrile for 16h in the presence of KOH. Preparation Method 2 is prepared from 3, 3-dimethyl-1-enopentanoic acid 2-methyl-3-phenylbromobenzyl by condensation, cyclization and dehydrochlorination.
category pesticide
toxicity grade highly toxic
Acute toxicity oral-rat LD50: 54.5 mg/kg
flammability hazard characteristics flammability; Toxic chloride and fluoride gases from combustion
storage and transportation characteristics The warehouse is ventilated and dried at low temperature; It is stored and transported separately from food raw materials
extinguishing agent dry powder, foam, sand
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov (external link)
Last Update：2024-04-09 21:01:54
3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester
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View History
3-[(1Z)-2-Chloro-3,3,3-trifluoro-1-propenyl]-2,2-dimethylcyclopropanecarboxylic acid (2-methylbiphenyl-3-yl)methyl ester
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ethyl 3-(5-methyl-1H-pyrazol-1-yl)propanoate
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