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Flumethrin

HCID 91702
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
69770-45-2
Standard SMILES
CC1(C)C(C=C(Cl)c2ccc(Cl)cc2)C1C(=O)OC(C#N)c1ccc(F)c(Oc2ccccc2)c1
InChIKey
YXWCBRDRVXHABN-UHFFFAOYSA-N
Molecular formula
C28H22Cl2FNO3
Average molar mass
510.4 g/mol
Monoisotopic mass
509.0960771

Names & identifiers

Preferred name
Flumethrin
IUPAC
[cyano-(4-fluoro-3-phenoxyphenyl)methyl] 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylate
English name
Flumethrin
Molecular formula
C28H22Cl2FNO3
Molecular weight
510.38

Names & synonyms

BayticolBayvarolFlumetrinDTXSID8058166FCR-2769BAY V1 6045BAY-V1-6045CHEBI:39361Cyano(4-fluoro-3-phenoxyphenyl)methyl 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylateRefChem:599351DTXCID4031934cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2-chloro-2-(4-chlorophenyl)ethenyl)-2,2-dimethylcyclopropanecarboxylate
Show more names
FlumioxazineFCR 2769Bay V1-6045FlufenthrinFluorobenthrinFlumethrin 95%Flumethrin SolutionFlumethrin in Methanol
alpha-cyano-(4-fluoro-3-phenoxy)benzyl-3-(2-chloro-2-(4-chlorophenyl)ethenyl)-2,2-dimethylcyclopropanecarboxylate274-110-4cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2-chloro-2-(4-chlorophenyl)ethenyl)-2,2-dimethylcyclopropane-1-carboxylate2O051W13LH69770-45-2Flumethrin3-[2-Chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid cyano(4-fluoro-3-phenoxyphenyl)methyl ester; Bayticol; Bayticol Pour-on; Bayvarol; FCR 2769; FlumethrinBayticol; Bayticol Pour-on; Bayvarol; FCR 2769

Database identifiers

CAS
69770-45-2
PubChem CID
91702
DTXSID
DTXSID8058166
ChEMBL
CHEMBL2107248
EC Number
274-110-4

Properties

Computed structural propertiesFilling in

XLogP
7.6
Topological polar surface area
59.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
5
Rotatable bonds
8
Heavy atoms
35
Formal charge
0
Complexity
825

Physicochemical properties

Melting point
25 °C · <25 °C
Boiling point
593.6 · 593.6±50.0 °C(Predicted)
Density
1.342 · 1.342±0.06 g/cm3(Predicted)
refractive index
25 · nD25 1.5831
Flash point
104 °C · 104 °C
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly, Sonicated)
JECFA Number
85 · 85
Major Application
agricultureenvironmental
InChI
InChI=1S/C28H22Cl2FNO3/c1-28(2)21(15-22(30)17-8-11-19(29)12-9-17)26(28)27(33)35-25(16-32)18-10-13-23(31)24(14-18)34-20-6-4-3-5-7-20/h3-15,21,25-26H,1-2H3
InChIKey
YXWCBRDRVXHABN-JCMHNJIXSA-N
SMILES
C1(C(OC(C#N)C2=CC=C(F)C(OC3=CC=CC=C3)=C2)=O)C(C=C(Cl)C2=CC=C(Cl)C=C2)C1(C)C
CAS DataBase Reference
69770 · 69770-45-2(CAS DataBase Reference)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H300 (34.7%): Fatal if swallowed [Danger Acute toxicity, oral];H301 (65.3%): Toxic if swallowed [Danger Acute toxicity, oral];H310 (34.7%): Fatal in contact with skin [Danger Acute toxicity, dermal];H311 (41.6%): Toxic in contact with skin [Danger Acute toxicity, dermal];H315 (41.6%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (41.6%): May cause an allergic skin reaction [Warning Sensitization, Skin];H319 (76.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H330 (26.7%): Fatal if inhaled [Danger Acute toxicity, inhalation];H331 (38.6%): Toxic if inhaled [Danger Acute toxicity, inhalation];H335 (23.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H360 (34.7%): May damage fertility or the unborn child [Danger Reproductive toxicity];H370 (34.7%): Causes damage to organs [Danger Specific target organ toxicity, single exposure];H372 (34.7%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure];H400 (23.8%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard];H410 (58.4%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P308+P316, P316, P318, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 101 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Chemistry & industry

Pharmacology

ATC CodeQP - Antiparasitic products, insecticides and repellents;QP53 - Ectoparasiticides, insecticides and repellents;QP53A - Ectoparasiticides for topical use, incl. insecticides;QP53AC - Pyrethrins and pyrethroids;QP53AC05 - Flumethrin
Metabolism/Metabolites · 1 item

The highest concentration is found in the liver, but high concentrations were also found in the spleen, kidney, lung, adrenal cortex, cartilage, bone marrow, pineal gland, pituitary, and subcutaneous adipose tissue; the lowest concentrations are found in the central nervous system. Flumethrin is excreted in the urine or the feces as unchanged compound or the metabolite, 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropanecarboxylic acid, flumethrin acid. 3-(4'-hydroxy-phenoxy)-4-fluorobenzoic acid and 3-phenoxy-4-fluorobenzoic acid can further be found in the urine as well as their glycine conjugates. The phenyl ring may be hydroxylated and, following ester bond hydrolysis, the cyano group is converted to SCN- and carbon dioxide and 3-phenoxybenzaldehyde is oxidized to the carboxylic acid. The resultant acids and phenols can then conjugate with glucuronic acid, sulfate, and/or amino acids. (L885)

Uses & manufacturing

UsesPyrethroids are used as insecticides. (L857)
Household ProductsInformation on 3 consumer products that contain Flumethrin in the following categories is provided:;• Pet Care
Use ClassificationVeterinary Drug -> INSECTICIDE; Veterinary Drug -> -> JECFA Functional Classes
Applications · 3 items

DescriptionFlumethrin: an ectoparasiticide.Flumethrin is an ectoparasiticide that belongs to the group of α-cyano-pyrethroids and has been registered in EU member states for use on companion and food-producing animals since 1986. These chemicals have been combined in a slow-release matrix collar formulation incorporating 10% imidacloprid (w/w) and 4.5% flumethrin (w/w). The imidacloprid component of the collar is aimed at the treatment and control of fleas and lice, and the flumethrin component is aimed at the treatment and control of ticks and mites. The medicated collar is expected to provide sustained protection over eight months to dogs exposed to ticks, fleas and lice[1-2].

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Related reactions

1 records
New reaction record
HRID 2130171 reaction equation
HRID 2130171As productTraining data from https://doi.org/10.1039/C8SC04228D (4/10)

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
FDA UNII
2 O051W13LH · 2O051W13LH
EPA Substance Registry System
3 · Cyclopropanecarboxylic acid, 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl)methyl (69770-45-2)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
301 · H301+H311+H331-H315-H317-H319
Precautionary statements
261 · P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
T
Risk Statements
23 · 23/24/25-36/38-43
Safety Statements
28 · 28-36/37-45
RIDADR
2902 · 2902
WGK Germany
3 · 3
HazardClass
6.1 · 6.1(b)
PackingGroup
III
HS Code
29269090 · 29269090
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1
Regulatory InformationFlumethrin: HSNO Approval: HSR003432 Approved with controls
Other Safety Information · 1 item

IMAP assessments - Cyclopropanecarboxylic acid, 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl)methyl ester: Environment tier I assessment;IMAP assessments - Cyclopropanecarboxylic acid, 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl)methyl ester: Human health tier I assessment

Hazard Classes and Categories · 2 items

Acute Tox. 2 (34.7%);Acute Tox. 3 (65.3%);Acute Tox. 1 (34.7%);Acute Tox. 3 (41.6%);Skin Irrit. 2 (41.6%);Skin Sens. 1 (41.6%);Eye Irrit. 2 (76.2%);Acute Tox. 2 (26.7%);Acute Tox. 3 (38.6%);STOT SE 3 (23.8%);Repr. 1B (34.7%);STOT SE 1 (34.7%);STOT RE 1 (34.7%);Aquatic Acute 1 (23.8%);Aquatic Chronic 1 (58.4%)

Acute toxicity - category 3

Toxicology

Treatment · 1 item

Following oral exposure, the treatment is symptomatic and supportive and includes monitoring for the development of hypersensitivity reactions with respiratory distress. Provide adequate airway management when needed. Gastric decontamination is usually not required unless the pyrethrin product is combined with a hydrocarbon. Following inhalation exposure, move patient to fresh air. monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. In case of eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. If the contamination occurs through dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. Vitamin E topical application is highly effective in relieving parenthesis. (T36)

Health Effects · 1 item

At high doses, signs of poisoning attributable to flumethrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (L863)

Exposure RoutesInhalation (L857) ; oral (L857) ; dermal (L857) ; eye contact (L857).
Toxicity Summary · 1 item

Pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. (T18, L857)

Signs and Symptoms · 1 item

Following dermal exposure to flumethrin, feelings of numbness, itching, burning, stinging, tingling, or warmth may occur, that could last for a few hours. Dizziness, headache, nausea, muscle twitching, reduced energy, and changes in awareness can result from inhalation or ingestion of large amounts of flumethrin. Paralysis can occur after exposure. (L857)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Toxicity DataLD50: > 100 mg/kg (Oral, Rat) (L885) LD50: > 2000 mg/kg (Dermal, Rat) (L885) LD50: ~3000 mg/kg (Inhalation, Rat) (L885)

Regulatory information

Regulatory InformationFlumethrin: HSNO Approval: HSR003432 Approved with controls

Safety data

PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
ridadr
2902
hs_code
29269090
risk_code
23/24/25-36/38-43
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T
safety_code
28-36/37-45
hazard_class
6.1(b)
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H301+H311+H331-H315-H317-H319
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralEye Irrit. 2Skin Irrit. 2Skin Sens. 1
Precautionary statements
P261-P280-P301+P310-P302+P352+P312-P304+P340+P311-P305+P351+P338

UsesFlumethrin is a synthetic pyrethroid insecticide used in the control of parasites, particularly ticks, on cattle, sheep, goats, horses, and dogs. Flumethrin is also used for control of mites in beehiv es.

UsesInsecticide; acaricide.

Additional notes

DefinitionChEBI: Flumethrin is an organochlorine acaricide, an organofluorine acaricide and a member of monochlorobenzenes. It has a role as a pyrethroid ester acaricide and a pyrethroid ester insecticide.