Cypermethrin

Base Information

• Chemical Name: Cypermethrin
• CAS No.: 52315-07-8
• Deprecated CAS: 69865-47-0,86752-99-0,86753-92-6,88161-75-5,97955-44-7,139203-31-9,137497-61-1,142443-95-6,146909-55-9,159940-28-0,186554-45-0,137497-61-1,139203-31-9,142443-95-6,146909-55-9,159940-28-0,186554-45-0,727730-89-4,86752-99-0,86753-92-6,88161-75-5,97955-44-7
• Molecular Formula: C22H19Cl2NO3
• Molecular Weight: 416.304
• Hs Code.: 2926.90 SYNONYMS
• European Community (EC) Number: 276-458-2,257-842-9,619-306-6,686-889-1,936-368-2
• ICSC Number: 0246
• NSC Number: 760420
• UN Number: 3352
• UNII: 1TR49121NP
• DSSTox Substance ID: DTXSID1023998
• Nikkaji Number: J9.674A
• Wikipedia: Cypermethrin
• Wikidata: Q412024
• NCI Thesaurus Code: C76869
• Metabolomics Workbench ID: 143628
• ChEMBL ID: CHEMBL373204
• Mol file: 52315-07-8.mol

Synonyms:alpha-cypermethrin;alphacypermethrin;alphamethrin;beta-cipermetrina;Cymbush;cypermethrin;cypermethrin, (1alpha(S*),3alpha)-(+-)-isomer;cypermethrin, (1R-(1alpha(R*),3beta))-isomer;cypermethrin, (1R-(1alpha(S*),3beta))-isomer;Fastac 50EC;Fendona;NRDC 149;supercypermethrin;supermethrin;WL 85871;WL-85871

Chemical Property of Cypermethrin

Chemical Property:

• Appearance/Colour: Viscous semisolid
• Vapor Pressure: 2.03E-27mmHg at 25°C
• Melting Point: 60-80 °C
• Refractive Index: n20/D 1.57
• Boiling Point: 511.3 °C at 760 mmHg
• Flash Point: 263 °C
• PSA: 59.32000
• Density: 1.329 g/cm³
• LogP: 6.17798
• Storage Temp.: −20°C
• Water Solubility.: insoluble
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 415.0741989
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

Cypermethrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N, F
• Hazard Codes: Xn,N,F
• Statements: 20/22-37-50/53-43-37/38-22-36-20/21/22-11-52/53
• Safety Statements: 24-36/37/39-60-61-2-36-26-16-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Pyrethrins/Pyrethroids
• Canonical SMILES: CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Cl)Cl)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the nervous system. This may result in facial sensation such as tingling, itching or burning.
• Description: Cypermethrin is a synthetic pyrethroid derivative of natural pyrethrins with a good insecticidal action. In vertebrates and invertebrates, cypermethrin acts mainly on the nervous system. It is both a stomach poison and a contact insecticide. Cypermethrin is used as an insecticide in large-scale commercial agricultural applications as well as in consumer products for domestic purposes. Cypermethrin is used to control pests in soybean, leeks, onions, carrots, turnips, swedes, parsnips, viola spp., spinach, black currant, gooseberries, sunflowers, linseeds, groundnuts, barley, and mushrooms. Cypermethrin is a type II pyrethroid insecticide. It prolongs opening of sodium channels resulting in membrane depolarization and a conductance block of the insect nervous system, and point mutations in sodium channels induce cypermethrin-resistance in house flies, cockroaches, and mosquitos. Cypermethrin (1-1.5 mg) reduces survival of ticks (H. anatolicum) in vitro in a concentration-dependent manner. Topical administration of cypermethrin reduces the number of ticks on infested cattle. Cypermethrin (5 and 10 ppm) reduces survival of lice (D. ovis) in sheep fleece and prevents re-infestation in contact-challenged sheep for 7 and 19 weeks, respectively. It induces developmental neurotoxicities in zebrafish, increasing mortality and edema and inducing body-axis curvature when used at concentrations ranging from 50 to 200 μg/L. Cypermethrin (15 mg/kg twice weekly for 24 weeks) also induces Parkinson''s disease-like neurodegeneration in rats, decreasing locomotor activity, dopamine production, and the number of tyrosine hydroxylase positive (TH+) neurons in the substantia nigra. Form: Odorless crystals (pure); yellow-brown viscous semisolid at ambient temperatures (technical grade).Cypermethrin is a pyrethroid insecticide. It was first synthesized in 1974.Cypermethrin is a synthetic chemical similar to the pyrethrins in pyrethrum extract (which comes from the chrysanthemum plant). Pyrethroids, including cypermethrin were designed to be effective longer than pyrethrins.
• Uses: Cypermethrin is a synthetic pyrethroid which is highly used pesticide in agriculture, household and animal husbandry mainly to crack, crevice and spot treatment for control of insects. Cypermethrin is commonly used to kill household insect pests. In California, it is the fourth most commonly-used insecticide: only chlorpyrifos, pyrethrins, and diazinon have more reported applications. It is also used in agriculture to control cotton, fruit and vegetable pests. About 90% of cypermethrin is manufactured for cotton crops (WHO, 1998). A potent inhibitor of calcineurin Zeta-cypermethrin is used for the control of Lepidoptera, beetles and aphids in cotton, fruit, vegetables, field crops, ornamentals and forestry. It is also used in public health. Synthetic pyrethroid insecticide, usually exists as a mixture of cis and trans isomers. Ectoparasiticide

Technology Process of Cypermethrin

There total 24 articles about Cypermethrin 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: 99.0%

alpha-cyano-3-phenoxybenzyl p-toluene sulphonate + 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid (55701-05-8) → cypermethrine (52315-07-8)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; In water; toluene;

Reference yield: 95.5%

permethric acid chloride (52314-67-7) + 3-Phenoxybenzaldehyde (39515-51-0) → cypermethrine (52315-07-8)

Guidance literature:

In tetrahydrofuran; dichloromethane; water;

Reference yield: 93.1%

sodium cyanide (773837-37-9) + permethric acid chloride (52314-67-7) + 3-Phenoxybenzaldehyde (39515-51-0) → cypermethrine (52315-07-8)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; at 35 - 40 ℃; for 4h;

upstream raw materials:

permethric acid chloride

3-phenoxy-benzoyl chloride

sodium cyanide

3-Phenoxybenzaldehyde

Downstream raw materials:

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

[(S)-cyano-(3-phenoxyphenyl)methyl](1R,3S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate

(R)-α-cyano-3-phenoxybenzyl (1R,3R)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate

4-{[2-[3-(2,2-Dichloro-vinyl)-2,2-dimethyl-cyclopropanecarbonyloxy]-2-(3-phenoxy-phenyl)-acetylamino]-methyl}-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester

Refernces

• 1、 Reddy, Ch. Venkateshwar,Mahesh,Raju,Reddy, V.V. Narayana. "A new phase transfer catalyst and its applications in organic transformations". . p. 2797 - 2802. Retrieved 2007/10/03.
• 2、 -. "Fungicidal active compound combinations". . . Retrieved 2008/06/13.