Deltamethrin CAS 52918-63-5
Introduction：Basic information about Deltamethrin CAS 52918-63-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Deltamethrin Basic information
| Product Name: | Deltamethrin |
| Synonyms: | (1r-(1-alpha(s*),3-alpha))-oxyphenyl)methyleste;(S).alpha.-Cyano-phenoxybenzyl(1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate;(s)-alpha-cyano-3-phenoxybenzyl-(1r)-cis-3-(2,2-dibromovinyl)-2,2-dimethyl-cyc;(s)-alpha-cyano-3-phenoxybenzyl(1r,3r)-3-(2,2-dibromovinyl)-2,2-dimethyl-cyc;(S)-α-cyano-3-phenoxybenzyl(1R)-cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylate;[1R-[1alpha(S*),3alpha]]-Cyano(3-phenoxyphenyl)methyl 3-(2,2-dibromomethenyl)-2,2-dimethylcyclopropanedicarboxylate;[1r-[1alpha(s*),3alpha]]-cyano(3-phenoxyphenyl)methyl3-[2,2-dibromoethenyl)-2,;2,2-dimethylcyclopropanecarboxylate) |
| CAS: | 52918-63-5 |
| MF: | C22H19Br2NO3 |
| MW: | 505.2 |
| EINECS: | 258-256-6 |
| Product Categories: | Aromatics;Chiral Reagents;Mutagenesis Research Chemicals;Aromatics Compounds;INSECTICIDE;Aromatics, Chiral Reagents, Mutagenesis Research Chemicals;Pesticide intermediates;Alpha sort;D;DA - DHMethod Specific;DAlphabetic;Insecticides;Oeko-Tex Standard 100;Pesticides&Metabolites;PesticidesPesticides;Pyrethroids;Alphabetic |
| Mol File: | 52918-63-5.mol |
Deltamethrin Chemical Properties
| Melting point | 98°C |
| Boiling point | 300°C |
| alpha | +56～+64°(20℃/D)(c=4,C6H6) |
| density | 1.5214 (rough estimate) |
| vapor pressure | 1.24×10-2Pa (25 °C) |
| refractive index | 1.6220 (estimate) |
| Fp | -18 °C |
| storage temp. | −20°C |
| solubility | Soluble in DMSO (up to 50 mg/ml) |
| form | Crystalline |
| Water Solubility | <0.0002 mg l-1 (25 °C) |
| color | Colorless |
| λmax | 278nm(Hexane)(lit.) |
| Merck | 14,2883 |
| BRN | 6746312 |
| Stability: | Stable. Incompatible with acids, alkalies, strong oxidizing agents. |
| Major Application | agriculture environmental |
| Cosmetics Ingredients Functions | SKIN CONDITIONING NOT REPORTED FRAGRANCE |
| InChI | 1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18+,20-/m0/s1 |
| InChIKey | OWZREIFADZCYQD-NSHGMRRFSA-N |
| SMILES | CC1(C)[C@@H](\C=C(\Br)Br)[C@H]1C(=O)O[C@H](C#N)c2cccc(Oc3ccccc3)c2 |
| LogP | 6.200 |
| NIST Chemistry Reference | Deltamethrin(52918-63-5) |
| IARC | 3 (Vol. 53) 1991 |
| EPA Substance Registry System | Deltamethrin (52918-63-5) |
Safety Information
| Hazard Codes | T,N,Xn,F |
| Risk Statements | 23/25-50/53-67-65-38-11 |
| Safety Statements | 24-28-36/37/39-38-45-60-61-62-16 |
| RIDADR | UN 2811 6.1/PG 2 |
| WGK Germany | 3 |
| RTECS | GZ1233000 |
| HazardClass | 6.1(a) |
| PackingGroup | II |
| HS Code | 29269090 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 52918-63-5(Hazardous Substances Data) |
| Toxicity | LD50 in female rats (mg/kg): 31 orally; 4 i.v. (Kavlock) |
| Description | 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. |
| 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. |
| Chemical Properties | White Powder |
| Chemical Properties | Colorless, white, or off-white crystalline solidor powder. Odorless. Combustible. |
| 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. |
| Uses | A Type II pyrethroid insecticide that potently inhibits calcineurin |
| Uses | Insecticide. |
| Uses | Deltamethrin is effective against a wide range of insects in fruit,cereals, vegetables, cotton, soyabeans and oilseed rape. It is also used forthe control of crawling and flying insects indoors, in stored grain andtimber and for ectoparasite control on animals. |
| Definition | ChEBI: A carboxylic ester obtained by formal condensation between 3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid and cyano(3-phenoxyphenyl)methanol. |
| Contact allergens | Pyrethroids, also called pyrethrinoids, are neurotoxicsynthetic compounds used as insecticides, with irritantproperties. Cypermethrin and fenvalerate have beenreported as causing positive allergic patch tests, butonly fenvalerate was relevant in an agricultural worker. |
| Potential Exposure | Deltamethrin is a synthetic pyrethroidinsecticide that kills insects on contact and through diges-tion. It is used to control a variety of chewing and suckinginsects that infest fruit, vegetables and field crops, includ-ing apples, pears and plums; peas, glasshouse cucumbers,tomatoes, peppers, potted plants, and ornamentals; hops,oats, cotton and other field crops. Deltamethrin is also usedto control residential and commercial insect pests. Someformulations are RUPs) |
| Environmental Fate | Deltamethrin is a type II pyrethroid, a functional neurotoxinslowing the inactivation of voltage-gated sodium channelsleading to a state of hyperexcitability which in turn causes finetremor, salivation, and choreoathetosis. Other proposedcontributory actions include antagonism of gammaaminobutyricacid A receptor inhibition and voltage-gatedchloride and calcium channels. |
| Metabolic pathway | After oral administration of 14C-deltamethrin tolactating dairy cows, deltamethrin is metabolized andexcreted in the bile and urine with very littleaccumulation in major edible tissues. The majorportion (78-82%) of the radioactivity in feces isdeltamethrin. Only 4-6% is eliminated in the urine and0.42 ? 1.62% is secreted in the milk. The primarybiotransformation is via the hydrolysis of the esterlinkage followed by oxidation of the geminal methylgroups of cyclopropane carboxylic acids and phenoxybenzaldehyde, resulting in dicarboxylic acid,lactonecarboxylic acid, or phenoxybenzoic acid derivatives. Deltamethrin is not metabolized withinalgae cells and mouse fibroblasts, but is partiallytransformed into less or not active isomers. In algaeand fibroblast culture media, many metabolites ofdeltamethrin resulting mostly from hydrolysis of themolecule are found. This metabolism seems to belinked with the release of enzymes by cells into theculture medium. |
| Shipping | UN2811 Toxic solids, organic, n.o.s., HazardClass: 6.1; Labels: 6.1-Poisonous materials, TechnicalName Required.UN3349 Pyrethroid pesticide, solid toxic,Hazard Class: 6.1; Labels: 6.1-Poisonous materials. |
| Toxicity evaluation | Deltamethrin is twofold more persistent in aquatic environmentsthan in soil. Depending on conditions the environmentalhalf-life ranges from 2 days (for hydrolysis at pH 9) to 80 days(for degradation in an aquatic environment). |
| Degradation | Deltamethrin is very stable as a solid but it is readily hydrolysed in solutionunder alkaline conditions with a DT50 of 2.5 days at pH 9 (25 °C). Byanalogy with cypermethrin, the rate-determining step in dilute solution isnucleophilic attack by OH-. Isomerisation has been shown to occur in natural waters under darkconditions, yielding the inactive 1 ScisaS isomer (Maguire, 1992). Aqueousphotolysis (sunlight) causes slow degradation but also isomerism to theinsecticidally active 1RtransaS form. These isomerisation reactions, whichare more rapid than those of cypermethrin, were reported much earlier byRuzo et al. (1977). This is due to the heavy atom effect (bromine).Similarly, the decreased bond strength of C-Br (ct C-Cl) leads to photocatalysedreductive debromination, with tans- favoured over cisdebrominationby a factor of 4. The DT50 on soil photolysis is 9 days (PM). Photolysis of the ester bond is the main reaction of deltamethrin.Solvent effects are important. cis-3-(2,2-Dibromovinyl)-2,2-dimethylcyclopropanecarboxylicacid (2) and 3PBA (4) are the major products inwater (Scheme 1). A minor product (5) was formed by decarboxylation.Deltamethrin is resistant to photo-oxidation. The mechanisms of photodegradation of the pyrethroids have been reviewed by Ruzo (1982). |
| 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. |
| Waste Disposal | ncineration 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 | Adams, A. J. "A review of the efficacy and uses of deltamethrin for wood preservation." Document - the International Research Group on Wood Preservation (Sweden) (1996). Sayeed, I, et al. "Oxidative stress biomarkers of exposure to deltamethrin in freshwater fish, Channapunctatus Bloch." Ecotoxicology & Environmental Safety 56.2(2003):295-301. Yousef, Mokhtar I., T. I. Awad, and E. H. Mohamed. "Deltamethrin-induced oxidative damage and biochemical alterations in rat and its attenuation by Vitamin E." Toxicology 227.3(2006):240-247. |
Deltamethrin Preparation Products And Raw materials
| Raw materials | Thionyl chloride-->Bromine-->Sodium cyanide-->EMULSIFIER-->Butyryl chloride-->HYDROGEN CYANIDE-->3-Phenoxybenzaldehyde-->Permethric acid-->3-Phenoxybenzyl alcohol-->Cyclopropanecarboxylic acid-->Chrysanthemoyl chloride-->1,2-DIBROMOETHYLENE-->VINYLCYCLOPROPANE-->UV Absorber 326 |
| Preparation Products | TRALOMETHRIN-->Sanitary pesticide-->Deltamethrin+Malathion,E.C.-->Synergistic deltamethrin E.C. |
