Deltamethrin

Base Information

• Chemical Name: Deltamethrin
• CAS No.: 52918-63-5
• Deprecated CAS: 55700-96-4,62229-77-0
• Molecular Formula: C22H19Br2NO3
• Molecular Weight: 505.206
• Hs Code.: 29269090
• European Community (EC) Number: 258-256-6
• ICSC Number: 0247
• UN Number: 3349
• UNII: 2JTS8R821G
• DSSTox Substance ID: DTXSID8020381
• Nikkaji Number: J10.082J
• Wikipedia: Deltamethrin
• Wikidata: Q422257
• NCI Thesaurus Code: C83658
• Metabolomics Workbench ID: 49588
• ChEMBL ID: CHEMBL1593566
• Mol file: 52918-63-5.mol

Synonyms:Deltagran;FMC 45498;[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-1-carboxylate;New Musigie;NRDC 161;Suspend;DeltaGard;Butox;Cyclopropanecarboxylic acid,3-(2,2-dibromoethenyl)-2,2-dimethyl-,(S)-cyano(3-phenoxyphenyl)methyl ester,(1R,3R)-;Phagase 1;K-Obiol;Crackdown;Decis;RU 22974;[cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-(2,2-dibromoethenyl)-2,2-dimethyl-cyclopropane-1-carboxylate;K-Othrin;Cislin;RUP 987;α-cyano-3-phenoxybenzyl [1R-[1α(S*),3α]]-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate;JMC 45498;

Chemical Property of Deltamethrin

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.49E-11mmHg at 25°C
• Melting Point: 98 °C
• Refractive Index: 1.653
• Boiling Point: 535.8 °C at 760 mmHg
• Flash Point: 277.8 °C
• PSA: 59.32000
• Density: 1.595 g/cm³
• LogP: 6.49018
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml)
• Water Solubility.: <0.0002 mg l-1 (25 °C)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 504.97112
• Heavy Atom Count: 28
• Complexity: 643

Purity/Quality:

98% ^*data from raw suppliers

Deltamethrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N, Xn, F
• Hazard Codes: T,N,Xn,F
• Statements: 23/25-50/53-67-65-38-11
• Safety Statements: 24-28-36/37/39-38-45-60-61-62-16

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(=CC=C2)OC3=CC=CC=C3)C=C(Br)Br)C
• Isomeric SMILES: CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=C(Br)Br)C
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached.
• 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. The effects may be delayed. Exposure through the skin could cause local effects, including sensations such as tingling, itching or burning.
• Description: Deltamethrin is a kind of synthetic pyrethroids insecticide used worldwide in agriculture for home pest control and protection of foodstuff and disease vector control. Deltamethrin belongs to the type II pyrethroids, which is hydrophobic in nature. It kills the insects through producing severe delay in sodium channel inactivation, leading to a persistent depolarization of the nerve membrane without repetitive discharge. However, this pesticide can be contained in contaminated food and water, and is readily absorbed by the oral route. Recent studies have shown that it can have certain toxicity through inducing oxidative stress. Vitamin can be used to alleviate its toxicity. Deltamethrin is a type II pyrethroid insecticide and a modulator of voltage-gated sodium channels (Nav). It binds to Drosophila para Nav channels in a use-dependent manner following brief depolarizing prepulses and with increasing concentrations of 1 to 5 nM, indicating that it preferentially binds to the channel in the open state. It slowly activates Nav1.8 channels, delays inactivation by longer than 40 ms, and induces persistent tail currents for channels expressed in X. laevis oocytes. Deltamethrin decreases proliferation of MCF-7 cells and inhibits androgen receptor transactivation when used at concentrations of 10 and 20 μM or greater, respectively. However, it is not cytotoxic to MCF-7 and CHO cells at concentrations of 25 and 100 μM, respectively, and does not induce transactivation of the estrogen receptor. Deltamethrin is lethal to mice with an LD50 value of 50 mg/kg and at low sublethal doses of 0.05 and 0.1 mg/kg it induces histopathological changes in the liver, kidney, spleen, and testes, including a loss of spermatozoa and Sertoli cells.
• Uses: Synthetic pyrethroid insecticide, which acts as a potent inhibitor of calcineurin (protein phosphatase 2B) and has an IC50 of about 100pM. This inhibition action results in cellular hyperexcitability by causing non-mutated calcium channels to remain open for an extended period of time allowing an abundance of Ca2+ to enter the cell. A Type II pyrethroid insecticide that potently inhibits calcineurin Insecticide. Deltamethrin is effective against a wide range of insects in fruit, cereals, vegetables, cotton, soyabeans and oilseed rape. It is also used for the control of crawling and flying insects indoors, in stored grain and timber and for ectoparasite control on animals.

Technology Process of Deltamethrin

There total 7 articles about Deltamethrin 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:

2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-2H-5-chlorobenzotriazole (3896-11-5,85497-36-5) → deltametrin (52918-63-5)

Guidance literature:

Reference yield:

→ deltametrin (52918-63-5)

Guidance literature:

Reference yield:

→ (+-)-R,S-alcohol (1R,cis)-acid ester + (S)-(cyano)(3-phenoxyphenyl)-methyl 1R,cis-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate (52820-00-5,52918-63-5,55700-99-7,64363-96-8,64363-97-9,64364-01-8,64364-02-9,64364-03-0,80845-12-1,106454-65-3,120710-23-8,120710-24-9,120710-25-0)

Guidance literature:

upstream raw materials:

2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-2H-5-chlorobenzotriazole

Downstream raw materials:

3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid

2-hydroxy-2-(3-phenoxyphenyl)acetonitrile

2,2-dimethyl-3R-(2',2'-dibromovinyl)-cyclopropane-1R-carboxylic acid

C₂₅H₂₁Br₂F₃O₃

Refernces

• 1、 -. "Cis-Alkoxyspiro-Substituted Tetramic Acid Derivatives". . . Retrieved 2008/06/13.
• 2、 -. "Aryl-substituted heterocyclic enaminones". . . Retrieved 2008/06/13.