cis-Cyfluthrin

Names

[ Name ]:
cis-Cyfluthrin

[Synonym ]:
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, (R)-cyano(4-fluoro-3-phenoxyphenyl)methyl ester, (1R,3R)-
CYFLUTHRIN, (1R,3R,αR)-
Cyfluthrin
(Ξ)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1Ξ,3Ξ)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate
cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Tempo 2
Cyfluthrine
1RS,3SR)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
BAY-VI 1704
(1R,3R,αR)-Cyfluthrin
BAY FCR 1272
EINECS 269-855-7
Baythroid H
(RS)-α-cyano-4-fluoro-3-phenoxybenzyl (1RS,3RS
(R)-cyano(4-fluoro-3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylate
Responsar
β-Cyfluthrin
Solfac
MFCD00078636
Eulan SP
(R)-Cyano(4-fluoro-3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Baythroid
Cyfluthin
(RS)-α-cyano-4-fluoro-3-phenoxybenzyl (1RS)-cis-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
Cyfoxylate

Biological Activity

[Description]:

Cyfluthrin is a type II pyrethroid and has effects on various insects. Cyfluthrin is a modulator of Nav1.8 sodium channels by repetitive stimulation. Cyfluthrin can be applied in agriculture,veterinary, insecticide,pyrethroid and stored product[1][2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel

Research Areas >> Infection

[In Vitro]

Cyfluthrin (0-50 μM; 24 hours) is against SH-SY5Y cell growth with an IC50 and an IC30 of 19.39 μM and 4.81 μM, respectively[1].

[References]

[1]. Jin-Sung Choi,et al.Structure-activity Relationships for the Action of 11 Pyrethroid Insecticides on Rat Na v 1.8 Sodium Channels Expressed in Xenopus Oocytes.Toxicol Appl Pharmacol. 2006 Mar 15;211(3):233-44

[2]. María-Aránzazu Martínez, et al. Oxidative Stress and Related Gene Expression Effects of Cyfluthrin in Human Neuroblastoma SH-SY5Y Cells: Protective Effect of Melatonin. Environ Res. 2019 Oct;177:108579.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
496.3±45.0 °C at 760 mmHg

[ Melting Point ]:
60ºC

[ Molecular Formula ]:
C₂₂H₁₈Cl₂FNO₃

[ Molecular Weight ]:
434.288

[ Flash Point ]:
253.9±28.7 °C

[ Exact Mass ]:
433.064789

[ PSA ]:
59.32000

[ LogP ]:
6.29

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.611

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GZ1253000

CHEMICAL NAME :: Cyclopropanecarboxylic acid, 2-(2,2-dichlorovinyl)-3,3-dimethyl-, ester with (4-fluoro-3- phenoxyphenyl)hydroxyacetonitrile

CAS REGISTRY NUMBER :: 68359-37-5

LAST UPDATED :: 199710

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C22-H18-Cl2-F-N-O3

MOLECULAR WEIGHT :: 434.31

WISWESSER LINE NOTATION :: L3TJ A1 A1 B1UYGG CVOYCN&R DF COR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C39,1991

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 469 gm/m3/4H

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85KYAH "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989 Volume(issue)/page/year: 11,432,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - domestic

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - food intake (animal) Behavioral - muscle contraction or spasticity

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0555484

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - domestic

DOSE/DURATION :: 250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,198,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - chicken

DOSE/DURATION :: 69993 ug/kg/21D-I

TOXIC EFFECTS :: Endocrine - hypoglycemia Blood - pigmented or nucleated red blood cells Nutritional and Gross Metabolic - changes in chlorine

REFERENCE :: JJATDK JAT, Journal of Applied Toxicology. (John Wiley & Sons Ltd., Baffins Lane, Chichester, W. Sussex PO19 1UD, UK) V.1- 1981- Volume(issue)/page/year: 7,367,1987

Safety Information

[ Symbol ]:

GHS06, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H331-H410

[ Precautionary Statements ]:
P261-P264-P273-P301 + P310-P311-P501

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
T:Toxic;N:Dangerousfortheenvironment;

[ Risk Phrases ]:
R26/28;R50/53

[ Safety Phrases ]:
S1/2-S36/37/39-S45-S60-S61

[ RIDADR ]:
UN 2588

[ RTECS ]:
GZ1253000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
29269090

Precursor & DownStream

Precursor

DownStream

Articles

Development of a multi-residue method in a fetal matrix: analysis of meconium.

Anal. Bioanal. Chem 406(30) , 7785-97, (2014)

Meconium is the earliest stool of newborns. It is a complex matrix that reflects the degree of fetal exposure to environmental pollutants. To investigate exposure to xenobiotics, an analytical method ...

Atmospheric pressure gas chromatography-time-of-flight-mass spectrometry (APGC-ToF-MS) for the determination of regulated and emerging contaminants in aqueous samples after stir bar sorptive extraction (SBSE).

Anal. Chim. Acta 851 , 1-13, (2014)

This work presents the development, optimization and validation of a multi-residue method for the simultaneous determination of 102 contaminants, including fragrances, UV filters, repellents, endocrin...

Differential induction of cytochrome P450 isoforms and peroxisomal proliferation by cyfluthrin in male Wistar rats.

Toxicol. Lett. 220(2) , 135-42, (2013)

Cyfluthrin effects on in vivo drug metabolizing enzymes were evaluated using the oxidative substrate antipyrine. Antipyrine pharmacokinetics in plasma and urinary excretion of its major metabolites wi...