Permethrin

Iupac Name：(3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

Molecular Weight：391.2877

Modify Date.: 2022-03-14 11:12

Introduction: Yellow-brown to brown liquid, which sometimes tends to crystallize at room temperature (technical grade). View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Permethrin
1.2 Synonyms: (±)-3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (+-)-,(cis,trans)-yleste (3-Phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl)methyl (1Ξ,3Ξ)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate (3-Phenoxyphenyl)methyl 3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarboxylate (3-Phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate (3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (3-Phenoxyphenyl)methyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl)methyl3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropanecarbox (3-Phenoxyphenyl)methyl-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl)methyl3-(2,2-dichloroethyl)-2,2-dimethylcyclopropane-carboxy (3-phenoxyphenyl)methyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-carboxy [3-(phenyloxy)phenyl]methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate -1-carboxylate 1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid (3-phenoxyphenyl)methyl ester 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid, (3-phenoxyphenyl)methyl ester 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid(3-phenoxyphen 3-(Phenoxyphenyl)methyl (±)-cis,trans-3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 3-Dichloroacetyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline 3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2- dimethylcyclopropanecarboxylate 3-Phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 3-phenoxybenzyl (1RS,3RS 3-Phenoxybenzyl 2,2-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate 3-Phenoxybenzyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate 3-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 3-Phenoxybenzyl-3-(2,2-dichlorethenyl)-2,2-dimethylcyclopropancarboxylat Acticin Ambush Ambushfog Anomethrin N Antiborer 3768 Bematin 987 BW-21-Z Chinetrin Cooper Coopex Corsair Cosair Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester Diffusil H Dragnet Dragnet FT Ecsumin Ectiban Efmethrin EINECS 258-067-9 Eksmin Exmin EXPAR Exsmin ICI-PP 557 Imperator Indothrin Insorbcid MP Ipitox Kafil Kaleait Kavil Kestrel kudos L3TJ A1 A1 BVO1R COR&& C1UYGG LE 79-519 Lyclear MFCD00041809 Mitin BC MP79 m-Phenoxybenzyl (±)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate m-Phenoxybenzyl (±)-cis,trans-3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate NIX Outflank Outflank-stockade Peregin Peregin W Perigen Perigen W Permanone 80 Permasect Permasect-25EC Permethrin (cis/trans) Permethrin (isomers) Perthrine Picket Picket G Pounce Pramex Pynosect Quamlin Ridect Pour-On SBP 15131TEC SBP-1513TEC SPARTAN Stomoxi Stomoxin Stomoxin P Stomozan Talcord

1.3 CAS No.: 52645-53-1

1.4 CID: 40326

1.5 EINECS(EC#): 258-067-9

1.6 Molecular Formula: C21H20Cl2O3 (isomer)

1.7 Inchi: InChI=1S/C21H20Cl2O3/c1-21(2)17(12-18(22)23)19(21)20(24)25-13-14-7-6-10-16(11-14)26-15-8-4-3-5-9-15/h3-12,17,19H,13H2,1-2H3

1.8 InChkey: RLLPVAHGXHCWKJ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

1.10 Isomers Smiles: CC1(C(C1C(=O)OCC2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C

2. Properties

2.1 Density: 1.19

2.1 Melting point: 34-35℃

2.1 Boiling point: 465.9°Cat760mmHg

2.1 Refractive index: 1.6500 (estimate)

2.1 Flash Point: 159.4°C

2.1 Precise Quality: 390.07900

2.1 PSA: 35.53000

2.1 logP: 6.11330

2.1 Appearance: colourless crystals (but the technical productis normally supplied as a pale brown liquid)

2.2 Chemical Properties: Crystalline Solid

2.3 Color/Form: Water white to pale yellow; colorless crystals to a viscous liquid

2.4 Contact Allergens: Pyrethroids, also called pyrethrinoids, are neurotoxicsynthetic compounds used as insecticides, with irritantproperties. Cypermethrin and fenvalerate have beenreported as causing positive allergic patch tests, butonly fenvalerate was relevant in an agricultural worker.

2.5 Corrosivity: Does not corrode aluminum

2.6 Decomposition: When heated to decomp it emits toxic fumes of /hydrogen chloride/.

2.7 Water Solubility: insoluble

2.8 Stability: Stable. Incompatible with strong oxidising agents.

2.9 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A cyclopropanecarboxylate ester in which the esterifying alcohol is 3-phenoxybenzyl alcohol and the cyclopropane ring is substituted with a 2,2-dichlorovinyl group and with gem-dimethyl groups.

3.2 General Description: Pale brown liquid. Relatively water insoluble. Used as an insecticide.

3.3 Usage: Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp. Permethrin is 26 times less toxic than lindane and 3 times less toxic than pyrethrins. A 1% permethrin cream rinse (Nix) preparation with a single application was determined to be more effective than treatment with RID. Permethrin-treated military uniforms are effective against human body lice. Apply the cream rinse for 10 minutes and rinse off with water. Localized pruritus may be reported with use of this product.

4. Safety and Handling

4.1 Symbol: GHS02, GHS07, GHS09

4.1 Hazard Codes: Xn; N; T; F

4.1 Signal Word: Danger

4.1 Risk Statements: R20/22

4.1 Safety Statements: 13-24-36/37/39-60-61-45-36/37-16-7-26

4.1 Octanol/Water Partition Coefficient: log Kow= 6.50

4.2 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: 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.

4.3 Hazard Declaration: H225-H302-H312-H319-H332-H411

4.3 DisposalMethods: 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. If an efficient incinerator is not available, the product should be mixed with large amounts of combustible material and contact with the smoke should be avoided. /Pyrethrin products/

4.4 RIDADR: UN1230 3/PG 2

4.4 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/

4.5 Safety Profile: Poison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl-. See also ESTERS

4.6 Caution Statement: P210-P273-P280-P305 + P351 + P338

4.6 Formulations/Preparations: USEPA/OPP Pesticide Code 109701; Trade Names: Permanone 10, Ambush. Permanone 40, pounce, Matadan, NRDC 143, PP 557, Ectiban, Indothrin, Pramex, AI-29158, Diffusil H, Anomethrin N, Kavil, Perigen.
Emulsifiable concentrate; wettable powder; ULV liquid; fumigant; aerosol; dustable powder; water-dispersible granules.
It is used as a broad-spectrum insecticide in a variety of formulations. The cis/trans ratio varies depending on conditions of manufacture and can also vary with time due to differential rates of hydrolysis and photolysis. A common ratio is 40:60 for agricultural use, with veterinary preparations having lower ratios.
Mixtures (permethrin +) dimethoate; pyrethrins; malathion; tetramethrin; heptenophos; bioallethrin + piperonyl butoxide; primiphos-methyl; chloropyrifos-methyl+pyrethrins; bioallethrins S-cyclopentenyl isomer; bioallethrin S-cyclopentenyl isomer + piperonyl butoxide.
Premixes: Pyra Perm (+ pyrethrins), Tetra Perm (+ tetramethrin), Per Super (+ S-bioallethrin), Tennin (+ tetramethrin), Chinetrin (+ piperonyl butoxide + tetrametrhin), Killout (+ piperonyl butoxide + tetramethrin), Mobeesol (+ piperonyl butoxide + tetramethrin) Duracide P, Super Duracide P (+ piperonyl butoxide + tetramethrin), Permethrin K (+ fenitrothion), Phinoco-T22 (+ piperonyl butoxide + tetramethrin)

4.7 WGK Germany: 3

4.7 RTECS: GZ1255000

4.7 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/

4.8 Skin, Eye, and Respiratory Irritations: Mild irritant to skin and eyes. /Technical permethrin/
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. /Pyrethroids/

4.9 Safety: Poison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl^?. See also ESTERS.
Hazard Codes:?Xn,N,T,F
Risk Statements: 20/22-43-50/53-39/23/24/25-23/24/25-11-51/53-36-20/21/22?
R20/22:Harmful by inhalation and if swallowed.?
R43:May cause sensitization by skin contact.?
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.?
R39:Danger of very serious irreversible effects.?
R11:Highly flammable.?
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36:Irritating to eyes.?
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 13-24-36/37/39-60-61-45-36/37-16-7-26?
S13:Keep away from food, drink and animal foodstuffs.?
S24:Avoid contact with skin.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
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.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36/37:Wear suitable protective clothing and gloves.?
S16:Keep away from sources of ignition.?
S7:Keep container tightly closed.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN1230 3/PG 2
RTECS: GZ1255000

4.10 Specification: ? Ambush (CAS NO.52645-53-1), its Synonyms are Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (3-phenoxyphenyl)methyl ester ; Cyclopropanecarboxylic acid, 3-(2,2-dichlorovinyl)-2,2-dimethyl-, 3-phenoxybenzyl ester, (+-)-, (cis,trans)- ; Permethrin ; m-Phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate ; Ambushfog ; Anomethrin N . It is crystalline solid.

4.11 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - domestic	LD50	oral	32gm/kg (32000mg/kg)	?	Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
chicken	LD50	oral	7gm/kg (7000mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: IRRITABILITY GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS	JAT, Journal of Applied Toxicology. Vol. 7, Pg. 367, 1987.
duck	LD50	oral	11300mg/kg (11300mg/kg)	?	Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
guinea pig	LD50	oral	4gm/kg (4000mg/kg)	?	"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
man	LD50	unreported	> 4gm/kg (4000mg/kg)	?	Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
man	TDLo	oral	2270mg/kg (2270mg/kg)	BEHAVIORAL: COMA GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Journal of Toxicology, Clinical Toxicology. Vol. 36, Pg. 57, 1998.
mouse	LC50	inhalation	685mg/m3 (685mg/m3)	?	Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse	LD50	intraperitoneal	429mg/kg (429mg/kg)	?	Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
mouse	LD50	intravenous	31mg/kg (31mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 66, Pg. 153, 1982.
mouse	LD50	oral	424mg/kg (424mg/kg)	?	Ecotoxicology and Environmental Safety. Vol. 18, Pg. 27, 1989.
mouse	LD50	skin	> 10gm/kg (10000mg/kg)	?	Yakkyoku. Pharmacy. Vol. 30, Pg. 1635, 1979.
mouse	LD50	subcutaneous	10gm/kg (10000mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA	Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
mouse	LD50	unreported	680mg/kg (680mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA BEHAVIORAL: ATAXIA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
mouse	LDLo	intracrebral	600ug/kg (0.6mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 66, Pg. 290, 1982.
quail	LD50	oral	13500mg/kg (13500mg/kg)	?	Defense des Vegetaux. Vol. 32, Pg. 168, 1978.
rabbit	LD50	oral	4gm/kg (4000mg/kg)	?	"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A316, Pg. 1984,
rabbit	LD50	skin	> 2gm/kg (2000mg/kg)	?	Farm Chemicals Handbook. Vol. -, Pg. C233, 1991.
rat	LC50	inhalation	485mg/m3 (485mg/m3)	?	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 55(12), Pg. 21, 1990.
rat	LD	intravenous	> 270mg/kg (270mg/kg)	?	Nature. Vol. 246, Pg. 169, 1973.
rat	LD50	oral	383mg/kg (383mg/kg)	?	National Technical Information Service. Vol. AD-A047-284,
rat	LD50	skin	1750mg/kg (1750mg/kg)	?	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.
rat	LD50	subcutaneous	6600mg/kg (6600mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: ATAXIA	Bochu Kagaku. Scientific Pest Control. Vol. 41, Pg. 143, 1976.
rat	LD50	unreported	537mg/kg (537mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA BEHAVIORAL: COMA	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 53(9), Pg. 69, 1988.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 4

Hazardous to the aquatic environment, short-term (Acute) - Category Acute 1

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H317 May cause an allergic skin reaction H332 Harmful if inhaled H410 Very toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P280 Wear protective gloves/protective clothing/eye protection/face protection. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

Mass spectrum (electron ionization)

7. Synthesis Route

52645-53-1Total: 8 Synthesis Route

60066-52-6

52645-53-1 233 Suppliers

Literatures:
Sagami Chemical Research Center Patent: US4214097 A1, 1980 ;
Yield: ~76%

13826-35-2 103 Suppliers

52645-53-1 233 Suppliers

Literatures:
Kuraray Co., Ltd. Patent: US4113968 A1, 1978 ;
Yield: null

52314-67-7 60 Suppliers

13826-35-2 103 Suppliers

52645-53-1 233 Suppliers

Literatures:
Nakatsuji, Hidefumi; Morita, Jun-Ichi; Misaki, Tomonori; Tanabe, Yoo Advanced Synthesis and Catalysis, 2006 , vol. 348, # 15 p. 2057 - 2062
Yield: ~95%

View all

8. Precursor and Product

precursor:

10361-82-7

53874-66-1

61976-18-9

60066-52-6

63142-59-6

60066-48-0

1310-73-2

61898-95-1

52314-67-7

100-44-7

13826-35-2

2304-30-5

546-68-9

View all

product :

13826-35-2

55701-05-8

9. Other Information

9.0 Merck: 13,7257

9.1 BRN: 5765325

9.2 Description: Yellow-brown to brown liquid, which sometimes tends to crystallize at room temperature (technical grade).

Permethrin, a pyrethroid insecticide with little mammalian toxicity, has been marketed as a tick repellent. Permethrin is the only synthetic pyrethroid that is used worldwide for head lice. The spray formulation is the most widely available form. Once applied to clothing, it is stable through several wash cycles. It is also suitable for treating sleeping bags, tents, and fabric used for insect screening. A liquid concentrate has been used to impregnate fabric for as long as the life of the garment. Permethrin is particularly helpful in the prevention of tick and chigger bites. These crawling arthropods must travel across the treated fabric, whereas flying insects tend to be attracted directly to exposed skin. The combination of a DEET-containing repellent and permethrin-treated clothing is generally highly ffective against a wide range of biting arthropods.

9.3 Chemical Properties: Crystalline Solid

9.4 Uses: Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp. Permethrin is 26 times less toxic than lindane and 3 times less toxic than pyrethrins. A 1% permethrin cream rinse (Nix) preparation with a single application was determined to be more effective than treatment with RID. Permethrin-treated military uniforms are effective against human body lice. Apply the cream rinse for 10 minutes and rinse off with water. Localized pruritus may be reported with use of this product.

9.5 Uses: Labelled Permethrin (P288500). Synthetic pyrethroid insectide, more stable to light and at least as active as the natural pyrethrins and with low mammalian toxicity.

9.6 Uses: For the treatment of infestation with Sarcoptes scabiei (scabies); antihyperlipidemic; cholesterol sequestrant.

9.7 Definition: ChEBI: A cyclopropanecarboxylate ester in which the esterifying alcohol is 3-phenoxybenzyl alcohol and the cyclopropane ring is substituted with a 2,2-dichlorovinyl group and with gem-dimethyl groups.

9.8 Indications: Permethrin is a synthetic pyrethroid active against lice, ticks, mites, and fleas. It acts on neural cellmembranes, delaying repolarization and causing paralysis. The compound has no reported adverse properties, is heat and light stable, has 70% to 80% ovicidal activity, and leaves an active residue on the scalp.
Permethrin 0.5% spray kills ticks and repels mosquitoes and stable flies. It is broken down when applied to skin and, hence, should be applied to clothing, shoes, tents, and so on. Spray only enough to moisten the material. Spray on clothing at least 2 hours before wearing. One treatment should last through a few washings.

9.9 Brand name: Elimite (Allergan); Nix (GlaxoSmithKline).

9.10 General Description: Pale brown liquid. Relatively water insoluble. Used as an insecticide.

9.11 Air & Water Reactions: Insoluble in water.

9.12 Reactivity Profile: A pyrethroid derivative.

9.13 Contact allergens: Pyrethroids, also called pyrethrinoids, are neurotoxic synthetic compounds used as insecticides, with irritant properties. Cypermethrin and fenvalerate have been reported as causing positive allergic patch tests, but only fenvalerate was relevant in an agricultural worker.

9.14 Pharmacology: Permethrin is a synthetic pyrethroid that interferes with the influx of sodium through cell membranes, leading to neurologic paralysis and death of the mite. There is minimal percutaneous absorption (<2%), which is rapidly hydrolyzed and excreted in the urine. Permethrin 5% dermal cream (Elimite) is applied for 8 to 12 hours to the entire body from the chin down and is then washed off.

9.15 Clinical Use: Permethrin is 3-(2,2-Dichloroethenyl)-2,2-dimethylcyclopropanecarboxylicacid (3-phenoxyphenyl)methylester or 3-(phenoxyphenyl)methyl (±)-cis, trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate(Nix). This synthetic pyrethrinoid compound is more stablechemically than most natural pyrethrins and is at least as activeas an insecticide. Of the four isomers present, the1(R),trans and 1(R),cis-isomers are primarily responsiblefor the insecticidal activity. The commercial product is amixture consisting of 60% trans and 40% cis racemic isomers.It occurs as colorless to pale yellow low-melting crystalsor as a pale yellow liquid and is insoluble in water butsoluble in most organic solvents.
Permethrin exerts a lethal action against lice, ticks, mites,and fleas. It acts on the nerve cell membranes of the parasitesto disrupt sodium channel conductance. It is used as apediculicide for the treatment of head lice. A single applicationof a 1% solution effects cures in more than 99% ofcases. The most frequent side effect is pruritus, which occurredin about 6% of the patients tested.

9.16 Safety Profile: Poison by inhalation, intravenous, and intracerebral routes. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. A skin irritant. When heated to decomposition it emits toxic fumes of Cl-. See also ESTERS

9.17 Veterinary Drugs and Treatments: Permethrin is synthetic pyrethroid that acts as an adulticide insecticide/miticide. It has knockdown activity against fleas, lice, ticks, and certain mites (e.g., Cheyletiella, Sarcoptes scabiei) and also has repellant activity. In small animal medicine, it is used primarily for fleas and ticks on dogs. In large animal and food animal medicine, there are many products (not listed below) available for pour-on, dusting, and spray use for flies, lice, mites, mosquitoes, ticks and keds.
Permethrin acts by disrupting the sodium channel current in arthropod nerve cell membranes, resulting in paralysis and death.

9.18 Environmental Fate: Soil. Permethrin biodegraded rapidly via hydrolysis yielding 3-(2,2-dichloroethenyl)- 2,2-dimethylcyclopropanecarboxylic acid and 3-phenoxybenzyl alcohol (Kaufman et al., 1981). The reported half-life in soil containing 1.3–51.3% organic matter and pH 4.2–7.7 is <38 days (Worthing and Hance, 1991)
In lake water, permethrin degraded more rapidly than in flooded sediment to transand cis-(dichlorovinyl)dimethylcyclopropanecarboxylic acid. The cis isomer was more stable toward biological and chemical degradation than the trans isomer (Sharom and Solom
Plant. Metabolites identified in cotton leaves included trans-hydroxypermethrin, 2′- hydroxypermethrin, 4′-hydroxypermethrin, dichlorovinyl acid, dichlorovinyl acid conjugates, hydroxydichlorovinyl acid, hydroxydichlorovinyl acid conjugates, phe
Dislodgable residues of permethrin on cotton leaves 0, 24, 48, 72 and 96 hours after application (1.1 kg/ha) were (cis:trans): 0.26:0.38, 0.24:0.34, 0.22:0.32, 0.16:0.24 and 0.15:0.21 μg/m2, respectively (Buck et al., 1980).
Photolytic. Photolysis of permethrin in aqueous solutions containing various solvents (acetone, hexane and methanol) under UV light (λ >290 nm) or on soil in sunlight initially resulted in the isomerization of the cyclopropane moiety and ester cl

9.19 Metabolic pathway: Permethrin was one of the first photostable pyrethroids suitable for field use.It served as a precursor for others such as its α-cyano analogue, cypermethrin. As it lacks the cyano group it has no chirality at the acarbon atom and therefore consists of a mixture of only four isomers. It is hydrolysed more readily than cypermethrin because it is an ester of a primary alcohol.
Much of the early research on the metabolism of the synthetic, photostable pyrethroids was conducted by Casida and co-workers on permethrin. The published results greatly assisted subsequent work on the analogues. This is stressed because some of the information reported below will draw on the metabolic schemes given in the cypermethrin entry.
The environmental fate of permethrin and its metabolism in plants, insects, animals and fish have been reported. The insecticide is metabolised by ester cleavage to its constituent acid and alcohol and subsequent conjugation of these. The primary metabolites are also subject to oxidation prior to conjugation. Permethrin itself is also subject to oxidation, the cisisomers more so than the trans-isomers because the former is more slowly hy droly sed.

9.20 Degradation: Permethrin is stable as a solid but it is readily hydrolysed in solution under alkaline conditions; it is most stable at pH 4. It is relatively resistant to photodegradation in the context of field use but it undergoes facile photoisomerism (Holmstead et al., 1978). It can be degraded under laboratory conditions affording DCVA (2) and 3-phenoxybenzyl alcohol (3PBAlc, 3). Under appropriate conditions, trans-permethrin affords 29% trans-DCVA and 13% cis-DCVA. The mechanisms of these reactions have been reviewed in detail by Ruzo (1982). Permethrin is resistant to photo-oxidation; other reactions, such as dechlorination, are of minor importance. The degradation products are shown in Scheme 1.

9.21 Toxicity evaluation: Acute oral LD₅₀ for rats: 430-4,000 mg/kg (cis:trans ca. 40:60); ca. 6,000 mg/kg (cis:trans ca. 20:80)

10. Computational chemical data

Molecular Weight: 391.2877g/mol
Molecular Formula: C₂₁H₂₀Cl₂O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 390.0789499
Monoisotopic Mass: 390.0789499
Complexity: 521
Rotatable Bond Count: 7
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 35.5
Heavy Atom Count: 26
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 2
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB4MAAGAAAAAAAAAAAAGAAAAAAAAAAwYAAAAAAAAAABQAAAGgIAAAAADwagmIIyDoAABACIAiDSCAACCAAgIAAIiAEGCIgMJjKEMRqCOCCkwBEIqAfIwDAPgAABAAAAAAAAAAIAAAAAAAAAAAAAAA==

11. Recommended Suppliers

Global228SuppliersView all >>

Hebei Bester Biotechnology Co., Ltd. Diamond member

1YR

Products:pmk powder ;pmk oil ;bmk powder ;bmk oil ;Protonitazene hcl ; Bromazolam ; Metonitazene; 2-Bromo-4'-methylpropiophenone ;
Tel:+8613073-165382-+8613102867802
Email:luly@chbbest.com

Permethrin cas 52645-53-1

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kg
Time: 2023/05/31

Inquire

Shandong Meichang New Material Technology Co., LTD Diamond member

2YRS

Products:Pharmaceutical intermediates, chemicals, fast delivery, safe arrival, high quality, 24-hour online service.
Tel:86-531-13273191718
Email:sales03@sd-lingwobio.com

Permethrin cas 52645-53-1