Cyfluthrin

Base Information

• Chemical Name: Cyfluthrin
• CAS No.: 68359-37-5
• Deprecated CAS: 85782-82-7,83855-46-3,80850-08-4,83855-46-3
• Molecular Formula: C22H18Cl2FNO3
• Molecular Weight: 434.294
• Hs Code.: 29269090
• European Community (EC) Number: 269-855-7
• ICSC Number: 1764
• UN Number: 3352,3349
• UNII: SCM2QLZ6S0
• DSSTox Substance ID: DTXSID5035957
• Nikkaji Number: J18.756I
• Wikipedia: Cyfluthrin
• Wikidata: Q61641151
• NCI Thesaurus Code: C80599
• Metabolomics Workbench ID: 144169
• ChEMBL ID: CHEMBL2104608
• Mol file: 68359-37-5.mol

Synonyms:beta-cyfluthrin;cyano(4-fluoro-3-phenoxyphenyl)methyl 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane carboxylate;cyfluthrin;OMS 2012;OMS-2012

Chemical Property of Cyfluthrin

Chemical Property:

• Appearance/Colour: viscous amber partly crystalline oil.
• Vapor Pressure: 1-8×10-8 Pa (20 °C)
• Melting Point: 60 °C
• Refractive Index: nD23 1.5511
• Boiling Point: 496.3 °C at 760 mmHg
• Flash Point: 253.9 °C
• PSA: 59.32000
• Density: 1.368 g/cm³
• LogP: 6.31708
• Storage Temp.: 0-6°C
• Water Solubility.: 0.002-0.003 mg l-1 (20 °C)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 433.0647770
• Heavy Atom Count: 29
• Complexity: 679
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

β-Cyfluthrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T;N,N,T,T+
• Statements: 26/28-50/53-28-23
• Safety Statements: 1/2-36/37/39-45-60-61-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC1(C(C1C(=O)OC(C#N)C2=CC(=C(C=C2)F)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the nervous system.
• Effects of Long Term Exposure: See Acute Hazards/Symptoms.
• 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. 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.
• 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.

Technology Process of Cyfluthrin

There total 2 articles about Cyfluthrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ cyfluthrin (68359-37-5,1820573-27-0,80850-08-4,85782-82-7)

Guidance literature:

Reference yield:

(S)-α-cyano-4-fluoro-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (1820573-27-0,80850-08-4,85782-82-7) → (R)-α-cyano-4-fluoro-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate (68359-37-5,1820573-27-0,80850-08-4,85782-82-7)

Guidance literature:

In water; acetone; at 21 ℃; Further Variations:; Temperatures; Solvents; Kinetics;

DOI:10.1021/jf048425i

Reference yield:

cyfluthrin (68359-37-5,1820573-27-0,80850-08-4,85782-82-7) → 2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyethanenitrile (76783-44-3) + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8) + α-cyano-4-fluorobenzyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Guidance literature:

With Trichoderma viride 5-2; In phosphate buffer; at 28 ℃; pH=6.5;

DOI:10.1021/jf0349580

upstream raw materials:

(S)-α-cyano-4-fluoro-3-phenoxybenzyl (1R)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

Downstream raw materials:

2-(4-fluoro-3-phenoxyphenyl)-2-hydroxyethanenitrile

3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid

4-fluoro-3-phenoxybenzaldehyde

Refernces

• 1、 Liu, Weiping,Qin, Sujie,Gan, Jianying. "Chiral stability of synthetic pyrethroid insecticides". . p. 3814 - 3820. Retrieved 2007/10/03.
• 2、 -. "Fungicidal active compound combinations". . . Retrieved 2008/06/13.