Cyfluthrin CAS 68359-37-5
Introduction：Basic information about Cyfluthrin CAS 68359-37-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cyfluthrin Basic informationDescription References
| Product Name: | Cyfluthrin |
| Synonyms: | Sofac;SOLFAC;SOLFAC(R);tempo 2;(r,s)-alpha-cyano-4-fluoro-3-phenoxybenzyl-(1r,s)-cis,trans-3-(2,2-dichlorovin;(rs)-alpha-cyano-4-fluoro-3-phenoxybenzyl(1rs,3rs:1rs,3sr)-3-(2,2-dichloro;2-(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylicaciesterwith(4;2-(2,2-dichlorovinyl)-3,3-dimethyl-cyclopropanecarboxylicaciesterwith(4-fluoro-3-phenoxyphenyl)hydroxyacetonitrile |
| 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 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 |
| form | Oil |
| Water Solubility | 0.002-0.003 mg l-1 (20 °C) |
| color | Light yellow to yellow |
| Merck | 13,2785 |
| BRN | 2788149 |
| 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 | Cyfluthrin (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 |
| 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) |
| 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 |
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| Description | Cyfluthrin 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 Properties | In pure form this chemical may be colorlesscrystalline solid or powder. Commercial is a yellowishpaste or viscous, yellowish-brown oil. Aromatic odor. |
| Uses | Insecticide |
| Uses | Cyfluthrin is used to control a wide range of insects, especiallyLepidoptera, in cereals, fruit, vegetables and cotton. It is also used againstmigratory locusts and grasshoppers, in stored products, in public healthsituations and in animal health. |
| 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. |
| 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. |
| 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 |
| 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 isalso 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 isalso a nitrile. |
| Metabolic pathway | The non-enzymatic hydrolyzed products of 14C-cyfluthrin are isolated and identified by the incubationreaction mixture of a buffer solution. The products arederived from the hydrolysis of the ester linkage ofcyfluthrin via cyanhydrin. This results in thecorresponding aldehyde which undergoes bothoxidation and reduction to give rise to carboxylic acidand benzyl alcohol, respectively. |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName 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-Poisonousmaterials, Technical Name Required. |
| Degradation | Cyfluthrin is a stable compound but it is hydrolysed at high pH. DT50values in water at 22 °C at pH 4, 7 and 9 were 25-117, 11-20, and 3-7days, respectively (PM). Under aqueous photolysis conditions (but usingUV light and acetonitrile in the solution), its half-life was 12 days. Thebenzldehyde (3, 3%) (Scheme 1) and the benzoic acid (5, 9%) weredetected 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 soilsurface in the dark. |
| Incompatibilities | May react violently with strong oxidi-zers, bromine, 90% hydrogen peroxide, phosphorustrichloride, silver powders, or dust. Incompatible with silvercompounds. Mixture with some silver compounds formsexplosive salts of silver oxalate. Nitriles may polymerize inthe presence of metals and some metal compounds. Theyare incompatible with acids; mixing nitriles with strongoxidizing acids can lead to extremely violent reactions.Nitriles are generally incompatible with other oxidizingagents such as peroxides and epoxides. The combination ofbases and nitriles can produce hydrogen cyanide. Nitrilesare hydrolyzed in both aqueous acid and base to give car-boxylic acids (or salts of carboxylic acids). These reactionsgenerate heat. Peroxides convert nitriles to amides. Nitrilescan react vigorously with reducing agents. Acetonitrile andpropionitrile are soluble in water, but nitriles higher thanpropionitrile have low aqueous solubility. They are alsoinsoluble in aqueous acids. |
| Waste Disposal | Incineration would be aneffective disposal procedure where permitted. If an efficientincinerator is not available, the product should be mixedwith large amounts of combustible material and contactwith the smoke should be avoided. In accordance with40CFR165, follow recommendations for the disposal ofpesticides and pesticide containers. |
| References | [1] JIN-SUNG CHOI David M S. Structure–activity relationships for the action of 11 pyrethroid insecticides on rat Nav1.8 sodium channels expressed in Xenopus oocytes[J]. Toxicology and applied pharmacology, 2006, 211 3: Pages 233-244. DOI: 10.1016/j.taap.2005.06.022 [2] MOHANA KRISHNAN BASKAR Prakhya B M. In vitro evaluation of pyrethroid-mediated changes on neuronal burst parameters using microelectrode arrays[J]. Neurotoxicology, 2016, 57: Pages 270-281. DOI: 10.1016/j.neuro.2016.10.007 [3] KYU-SIK CHANG. Susceptibility and Resistance of Field Populations of Anopheles sinensis (Diptera: Culicidae) Collected from Paju to 13 Insecticides[J]. Osong Public Health and Research Perspectives, 2013, 4 2: Pages 76-80. DOI: 10.1016/j.phrp.2013.02.001 [4] CAITLIN J OLIVER. Pyrethroids and Nectar Toxins Have Subtle Effects on the Motor Function, Grooming and Wing Fanning Behaviour of Honeybees (Apis mellifera).[J]. PLoS ONE, 2015: e0133733. DOI: 10.1371/journal.pone.0133733 |
Cyfluthrin Preparation Products And Raw materials
| 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 |
