Cyfluthrin

Cyfluthrin Basic information
Description References
Product Name:Cyfluthrin
Synonyms:Baythroid 2;Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(4-fluoro-3-phenoxyphenyl)methyl ester;beta-cyflutrin (bsi,iso);cyfluthrin (bsi,e-iso,ban);cyfluthrine (f-iso);cyflutrin-beta (canada);β-Cyfluthrin suspension;CYFLUTHRINWP
CAS:68359-37-5
MF:C22H18Cl2FNO3
MW:434.29
EINECS:269-855-7
Product Categories:Alpha sort;C;CAlphabetic;CO - CZMethod Specific;Endocrine Disruptors (Draft)Method Specific;INSECTICIDE;EPA;Insecticides;Oeko-Tex Standard 100;Pesticides&Metabolites;PesticidesPesticides;Pyrethroids
Mol File:68359-37-5.mol
Cyfluthrin Structure
Cyfluthrin Chemical Properties
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. Sealed in dry,Room Temperature
solubility Chloroform: Slightly Soluble,Methanol: Heated
Water Solubility 0.002-0.003 mg l-1 (20 °C)
form neat
Merck 13,2785
BRN 2788149
InChIKeyQQODLKZGRKWIFG-UHFFFAOYSA-N
LogP5.950
NIST Chemistry ReferenceCyfluthrin(68359-37-5)
EPA Substance Registry SystemCyfluthrin (68359-37-5)
Safety Information
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
Hazardous Substances Data68359-37-5(Hazardous Substances Data)
ToxicityLD50 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)
MSDS Information
ProviderLanguage
FCR 1272 English
Cyfluthrin Usage And Synthesis
DescriptionCyfluthrin 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
DescriptionCyfluthrin is a pyrethroid insecticide and a modulator of voltage-gated sodium channels (Nav). It slowly activates rat recombinant Nav1.8 channels, delays inactivation by longer than 40 ms, and induces persistent tail currents in channels expressed in X. laevis oocytes. It also decreases the mean burst rate in rat primary neurons (IC50 = 0.99 μM, respectively). Cyfluthrin is toxic to various insects, including A. melinus, G. ashmeadi, E. eremicus, and E. formosa (LC50s = 7, 67, 96, and 63 ng/ml, respectively) and the A. sinensis mosquito (LC50 = 0.446 ppm). It is also toxic to A. mellifera honeybees (LD50 = 0.22 ppm), affecting locomotor activity and wing fanning behavior with an increase in the mean bout duration of time spent upside down, indicating disruption of the righting reflex, and a decrease in wing fanning behavior when administered at a dose of 10 ng/bee. Formulations containing cyfluthrin have been used for the control of insects in agriculture and for non-commercial purposes.
Chemical PropertiesIn pure form this chemical may be colorless crystalline solid or powder. Commercial is a yellowish paste or viscous, yellowish-brown oil. Aromatic odor.
UsesInsecticide
UsesCyfluthrin 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.
DefinitionChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (4-fluoro-3-phenoxyphenyl)(hydroxy)acetonitrile.
General DescriptionA viscous amber partly crystalline oil. Used as an insecticide.
Reactivity ProfileCyfluthrin is a pyrethrine derivative. Incompatible with azocyclotin, and perhaps other azo compounds and organometallics.
Agricultural UsesInsecticide: 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 nameAZTEC®; 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
Potential ExposureCyfluthrin 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.
Metabolic pathwayThe 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.
ShippingUN2811 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.
DegradationCyfluthrin 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.
IncompatibilitiesMay 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 .
Waste DisposalIncineration 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.
BETA-CYFLUTHRIN 5.7%EC Methyl Cyfluthrin and b-cyfluthrin (sum of isomers) BETA-CYFLUTHRIN 95%TC Cyfluthrin+Malathion,E.C. (1S,3S,αS)-Cyfluthrin,(1S,3R,αS)-Cyfluthrin,(1R,3R,αS)-Cyfluthrin Phenylacetone Cyfluthrin+Acephate,E.C.(25%) 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE Vinyl ester resin BETA-CYFLUTHRIN SOLUTION 100UG/ML IN ACETONITRILE 1ML Cyfluthrin+Phoxim,E.C. (1S,3S,αR)-Cyfluthrin,(1R,3S,αR)-Cyfluthrin,(1S,3R,αR)-Cyfluthrin,(1R,3R,αR)-Cyfluthrin BETA-CYFLUTHRIN SOLUTION 100UG/ML IN MTBE 1ML Cyfluthrin,92%Tc,5%Ec Cyano Vinyl resin fluoro jade

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