ChemicalBook--->CAS DataBase List--->68359-37-5

68359-37-5

68359-37-5 Structure

68359-37-5 Structure
IdentificationBack Directory
[Name]

Cyfluthrin
[CAS]

68359-37-5
[Synonyms]

Sofac
SOLFAC
BAYGON
tempo 2
Balecol
bulldock
eulan sp
FCR 1272
fcr 4545
LEVERAGE
CLINCHER
BAYTHROID
SOLFAC(R)
responsar
Cylathrin
DECATHLON
bay-vi1704
CYFLUTHRIN
Cyfoxylate
Baythroid H
bay-v1 1704
cyfluthrine
Baythroid 2
Cyfloxylate
CYFLUTHRINWP
CYFLUTHRINEW
Baythroid(R)
BAY FCR 1272
BAYTHROID (TM)
beta-Cyfluthri
Cyfluthrin E.C.
BETA-CYFLUTHRIN
cyfluthrin(beta)
cyfluthrine (f-iso)
BAYTHROID,250MG, NEAT
β-Cyfluthrin solution
cyflutrin-beta (canada)
β-Cyfluthrin suspension
beta-cyflutrin (bsi,iso)
cyfluthrin (bsi,e-iso,ban)
3-phenoxyphenyl)methylester
BETA-CYFLUTHRIN PESTANAL, 250 MG
Baythroid (TM) 250mg [68359-37-5]
beta-Cyfluthrin 250mg [68359-37-5]
CYFLUTHRIN MIXTURE OF ISOMERS, PESTANAL,
vinyl)-2,2-dimethylcyclopropanecarboxylate
-fluoro-3-phenoxyphenyl)hydroxyacetonitrile
Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(R,S)-alpha-Cyano-4-fluoro-3-phenoxybenzyl-(1R,S)-cis,trans-3-(2,2
2-(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylicaciesterwith(4
(rs)-alpha-cyano-4-fluoro-3-phenoxybenzyl(1rs,3rs:1rs,3sr)-3-(2,2-dichloro
2-dichloroethenyl)-2,2-diethylcyclopropanecarboxylicacidcyano(4-fluoro-3-(
cyano(4-fluoro-3-phenoxyphenyl)methyl3-(2,2-dichloroethenyl)-2,2-dimethyl-cyc
(r,s)-alpha-cyano-4-fluoro-3-phenoxybenzyl-(1r,s)-cis,trans-3-(2,2-dichlorovin
CYANO-(4-FLUORO-3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANE
alpha-cyano-4-fluoro-3-phenoxybenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate
(RS)-ALPHA-CYANO-4-FLUORO-3-PHENOXYBENZYL(1RS,3RS:1RS,3SR)-3-(2,2-DICLOROVINYL)-2,2-DIMETHYLCYCLOPR
CYANO(4-FLUORO-3-PHENOXYPHENYL)METHYL-3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYL CYCLOPROPANE CARBOXYLATE
3-(2,2-Dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid α-cyano-4-fluoro-3-phenoxybenzyl ester
α-cyano-4-fluoro-3-phenoxybenzyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate cyfluthrin
Cyclopropanecarboxylicacid,3(2,2-dichloroethenyl)-2,2-dimethyl-cyano(4-fluoro-3-phenoxyphenyl)methylester
α-cyano-4-fluoro-3-phenoxybenzyl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate beta-cyfluthrin
3-(2,2-DICHLOROETHENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLIC ACIDCYANO(4-FLUORO-3-PHENOXYPHENYL)METHYL ESTER
Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl)methyl ester
(R,S)α-cyano-(4-fuloro-3-phenoxybenzyl)(R,S) cis,trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate
-(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylicaciesterwith(4-fluoro-3-phenoxyphenyl)hydroxyacetonitrile
2-(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylicaciesterwith(4-fluoro-3-phenoxyphenyl)hydroxyacetonitrile
(RS)-ALPHA-CYANO-4-FLUORO-3-PHENOXYBENZYL(1RS,3RS)-(1RS,3SR)-3-(2,2-DICLOROVINYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE
Cyfluthrin,Cyclopropanecarboxylicacid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-,cyano(4-fluoro-3-phenoxyphenyl)methyl ester
[EINECS(EC#)]

269-855-7
[Molecular Formula]

C22H18Cl2FNO3
[MDL Number]

MFCD00078636
[MOL File]

68359-37-5.mol
[Molecular Weight]

434.29
Chemical PropertiesBack Directory
[Appearance]

In pure form this chemical may be colorless crystalline solid or powder. Commercial is a yellowish paste or viscous, yellowish-brown oil. Aromatic odor.
[Melting point ]

60°C
[Boiling point ]

496.3±45.0 °C(Predicted)
[density ]

1.3336 (estimate)
[vapor pressure ]

1-8×10-8 Pa (20 °C)
[refractive index ]

nD23 1.5511
[storage temp. ]

0-6°C
[solubility ]

Chloroform: Slightly Soluble,Methanol: Heated
[form ]

neat
[Water Solubility ]

0.002-0.003 mg l-1 (20 °C)
[color ]

Light yellow to yellow
[Merck ]

13,2785
[BRN ]

2788149
[Henry's Law Constant]

3.4×102 mol/(m3Pa) at 25℃, HSDB (2015)
[InChI]

1S/C22H18Cl2FNO3/c1-22(2)15(11-19(23)24)20(22)21(27)29-18(12-26)13-8-9-16(25)17(10-13)28-14-6-4-3-5-7-14/h3-11,15,18,20H,1-2H3
[InChIKey]

QQODLKZGRKWIFG-UHFFFAOYSA-N
[SMILES]

CC1(C)C(\C=C(\Cl)Cl)C1C(=O)OC(C#N)c2ccc(F)c(Oc3ccccc3)c2
[LogP]

5.950
[NIST Chemistry Reference]

Cyfluthrin(68359-37-5)
[EPA Substance Registry System]

Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2, 2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl) methyl ester(68359-37-5)
Safety DataBack Directory
[Hazard Codes ]

T;N,N,T,T+
[Risk Statements ]

26/28-50/53-28-23
[Safety Statements ]

1/2-36/37/39-45-60-61-28
[RIDADR ]

2588
[WGK Germany ]

3
[RTECS ]

GZ1253000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29269090
[Storage Class]

6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials
[Hazard Classifications]

Acute Tox. 2 Inhalation
Acute Tox. 2 Oral
Aquatic Acute 1
Aquatic Chronic 1
Lact.
STOT SE 1
[Hazardous Substances Data]

68359-37-5(Hazardous Substances Data)
[Toxicity]

LD50 in male, female rats, male, female mice (mg/kg): 500-800, 1200, 300, 600 orally in Lutrol (Behrenz); LC50 (96 hr) in rainbow trout: 0.0006 mg/l (Hammann)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

p-Toluenesulfonic acid-->Copper-->Isobutylene-->Chloral-->4-Chlorotoluene-->Permethric acid-->1-Hexene-->1,2-Dichloroethylene-->diazoacetic acid-->3-Methyl-2-buten-1-ol-->Trimethacrylate-->Methyl 3,3-dimethylpent-4-enoate-->Cyclopropane-->orthoacetic acid-->Cyclobutanone-->3-PENTEN-2-OL-->4-PENTEN-2-OL-->4-Methyl-1,3-pentadiene
Hazard InformationBack Directory
[General Description]

A viscous amber partly crystalline oil. Used as an insecticide.
[Reactivity Profile]

Cyfluthrin is a pyrethrine derivative. Incompatible with azocyclotin, and perhaps other azo compounds and organometallics.
[Potential Exposure]

Cyfluthrin is a synthetic pyrethroid, nonsystemic insecticide used to control a variety of chew- ing and sucking insects on cotton, hops, cereals, corn, pea- nuts, fruit, potatoes, and other crops and vegetables. It is also used to control structural pests such as termites. Cyfluthrin can be found in both Restricted Use Pesticides (RUP) and General Use Pesticides (GUP) category. It is also a nitrile.
[First aid]

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions) if breathing has stopped, and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.
[Shipping]

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3349 (pyrethroid pesticide, solid, toxic)/151 Pyrethroid pesticide, solid toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous material UN3439 Nitriles, solid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
[Incompatibilities]

May react violently with strong oxidi- zers, bromine, 90% hydrogen peroxide, phosphorus trichloride, silver powders, or dust. Incompatible with silver compounds. Mixture with some silver compounds forms explosive salts of silver oxalate. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give car- boxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids .
[Chemical Properties]

In pure form this chemical may be colorless crystalline solid or powder. Commercial is a yellowish paste or viscous, yellowish-brown oil. Aromatic odor.
[Waste Disposal]

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. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers.
[Uses]

Cyfluthrin is used to control a wide range of insects, especially Lepidoptera, in cereals, fruit, vegetables and cotton. It is also used against migratory locusts and grasshoppers, in stored products, in public health situations and in animal health.
[Uses]

Insecticide
[Definition]

ChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.
[Production Methods]

The commercial production of cyfluthrin involves a multi-step chemical synthesis that integrates several key intermediates to form its complex structure. The process begins with the preparation of the cyclopropane carboxylic acid derivative, which is then esterified with a fluorinated phenoxybenzyl alcohol containing a cyano group. This esterification step is crucial for forming the active cyfluthrin molecule.
[Agricultural Uses]

Insecticide: Cyfluthrin is a non-systemic insecticide used to control a variety of chewing and sucking insects on cotton, hops, cereals, corn, peanuts, fruit, potatoes and other crops and vegetables. It is also used o control structural pests such as termites.
[Trade name]

AZTEC®; ATTATOX®; BAY FCR 1272®; BAYTHROID®; BAYTHROID® H; BAYTHROID® TECHNICAL; BUG-B-GON®; CONTUR®; CYLATHRIN®; EULAN SP®; FCR 1272®; INTUDER®; INTUDER HPX®; LASER®; RENOUNCE®; RESPONSAR®; SOLFAC®; TEMPO®; TEMPO® H; TEMPO® 20WP
[Mechanism of action]

Non-systemic with contact and stomach action and rapid knock-down effect. Sodium channel modulator.
[Metabolic pathway]

The non-enzymatic hydrolyzed products of 14C- cyfluthrin are isolated and identified by the incubation reaction mixture of a buffer solution. The products are derived from the hydrolysis of the ester linkage of cyfluthrin via cyanhydrin. This results in the corresponding aldehyde which undergoes both oxidation and reduction to give rise to carboxylic acid and benzyl alcohol, respectively.
[Degradation]

Cyfluthrin is a stable compound but it is hydrolysed at high pH. DT50 values in water at 22 °C at pH 4, 7 and 9 were 25-117, 11-20, and 3-7 days, respectively (PM). Under aqueous photolysis conditions (but using UV light and acetonitrile in the solution), its half-life was 12 days. The benzldehyde (3, 3%) (Scheme 1) and the benzoic acid (5, 9%) were detected at 144 hours (PSD).
On a soil surface in light, the initial half-life was 2 days. At day 9, 62% of the radioactivity was recovered as: cyfluthrin (36%)) 3 (2%), 5 (4%) and unidentified components (PSD). The compound was stable on a soil surface in the dark.
[Pesticide Type]

Insecticide
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Cyfluthrin(68359-37-5).msds
Questions And AnswerBack Directory
[Description]

Cyfluthrin is a broad-spectrum synthetic pyrethroid insecticide with both contact and poison action. It is first registered by EPA in 1987 and found in both restricted use and general-use insecticides. Cyfluthrin is used for a wide array of pests in agriculture, in and around the home, and in food handling establishments. These pests include cutworms, ants, silverfish, cockroaches, termites, grain beetles, weevils, mosquitoes, fleas, flies, corn earworms, tobacco budworm, codling moth, European corn borer, cabbageworm, loopers, armyworms, boll weevil, alfalfa weevil, Colorado potato beetle, and many others. Cyfluthrin is also used in public health situations and for structural pest control. Cyfluthrin is neurotoxic. It could cause organ inflammation in many animal studies and induce skin paresthesia, as well as reproductive problems. Also, Cyfluthrin is highly toxic to fish, aquatic organisms and bees.
[References]

  1. https://www.beyondpesticides.org
  2. http://onlinelibrary.wiley.com
  3. http://pmep.cce.cornell.edu
  4. https://en.wikipedia.org/wiki/Cyfluthrin
  5. http://dissemination.echa.europa.eu
Spectrum DetailBack Directory
[Spectrum Detail]

Cyfluthrin(68359-37-5)MS
Cyfluthrin(68359-37-5)1HNMR
Cyfluthrin(68359-37-5)IR1
Cyfluthrin(68359-37-5)IR2
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