Prallethrin CAS 23031-36-9
Introduction：Basic information about Prallethrin CAS 23031-36-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Prallethrin Basic informationChemical properties Application
| Product Name: | Prallethrin |
| Synonyms: | s-4068sf;trans-(+-)-ydroxy-3-methyl-2-(2-propynyl)-2-cyclopenten-1-on;(RS)-2-Methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl (1RS,3RS:1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate;2-methyl-4-oxo-3-prop-2-ynylcyclopent-2-enyl-2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropanecarboxylate;Pralle;2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)-1-cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propynyl)-2-cyclopenten-1-yl ester;2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic acid 2-methyl-4-oxo-3-(2-propynyl)-2-cyclopenten-1-yl ester;Rethrinpropargyl |
| CAS: | 23031-36-9 |
| MF: | C19H24O3 |
| MW: | 300.39 |
| EINECS: | 245-387-9 |
| Product Categories: | Agro-Products;INSECTICIDE |
| Mol File: | 23031-36-9.mol |
Prallethrin Chemical Properties
| Melting point | 25°C |
| Boiling point | 381.62°C (rough estimate) |
| density | d420 1.03 |
| vapor pressure | ﹤4.3×10-5 Pa (23.1 °C) |
| refractive index | 1.4200 (estimate) |
| Fp | 139 °C |
| storage temp. | 2-8°C |
| solubility | Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Sparingly) |
| Water Solubility | 8 mg l-1 (25 °C) |
| Stability: | Stable. Incompatible with strong oxidizing agents. |
| Major Application | agriculture environmental |
| InChI | 1S/C19H24O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h1,9,14,16-17H,8,10H2,2-6H3 |
| InChIKey | SMKRKQBMYOFFMU-UHFFFAOYSA-N |
| SMILES | C\C(C)=C/C1C(C(=O)OC2CC(=O)C(CC#C)=C2C)C1(C)C |
| CAS DataBase Reference | 23031-36-9(CAS DataBase Reference) |
| EPA Substance Registry System | Prallethrin (23031-36-9) |
Safety Information
| Hazard Codes | T,N |
| Risk Statements | 22-23-50/53 |
| Safety Statements | 45-60-61 |
| RIDADR | UN2811 6.1/PG 2 |
| WGK Germany | 3 |
| HS Code | 29162090 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 3 Inhalation Acute Tox. 4 Oral Aquatic Acute 1 Aquatic Chronic 1 |
| Hazardous Substances Data | 23031-36-9(Hazardous Substances Data) |
| Toxicity | mouse,LD50,oral,190mg/kg (190mg/kg),Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 228, 1989. |
| Chemical properties | The original medicine is an oil like liquid. At b.p.>313.5℃ , the relative density is 1.03. It is easy to dissolve in methanol and hexane. The solubility is >50% at normal temperature, The solubility in the water at 25 C is 8.03mg/L, The distribution coefficient is 30800. |
| Application | The product characteristics of fenvalerate are the same as those of fenpropathrin with strong contact toxicity. The knockdown and killing performance is 4 times higher than that of the right-handed trans pyrethrin, and has a prominent driving effect on cockroaches. It is mainly used for processing mosquito repellent incense, electric mosquito repellent incense, liquid mosquito repellent incense and spray to control household pests such as housefly, mosquito, louse, cockroach etc. The recommended amount of use is as follows: (with effective ingredients) mosquito repellent incense: The electric heat mosquito incense containing 0.05% of the product: Containing 10mg/ tablets of this product to control the temperature of the electric heater center at 125-135℃. Liquid mosquito repellent incense: containing 0.66% of this product, plus proper stabilizer; Sustained-release agent; Aerosols: 0.05 0.2% of this product with appropriate amount of lethal agent, synergist and emulsifier. |
| Chemical Properties | solid |
| Uses | Prallethrin is used for the control of insects in domestic and publichealth situations. |
| Uses | Prallethrin ia a synthetic pyrethroid; propynyl analog of allethrin. Prallethrin is used as an insecticide. |
| Definition | ChEBI: Prallethrin is a member of cyclopropanes and a terminal acetylenic compound. It has a role as a pyrethroid ester insecticide and an agrochemical. It is functionally related to a chrysanthemic acid. |
| Hazard | A poison by ingestion and inhalation. Lowtoxicity by skin contact. |
| Pharmacology | Prallethrin is a propynyl analog of allethrin, with2-methyl-4-oxo-3-(prop-2-ynyl)-cyclopent-2-enyl as thesecondary alcohol moiety that has been introduced againstpublic health pests (113–115). The ester of the (S)-alcoholwith (1R)-trans,cis-chrysanthemic acid resolved partiallyis commercialized on the strength of the assessment ofinsecticidal action of individual stereoisomers (116). Comparedwith d-allethrin, it is approximately four, six, andfive times more effective on Musca domestica (for killing),Blattella germanica (for killing), and Culex pipiens pallens(for knockdown), respectively (43). A lower level of resistanceto prallethrin than to phenoxybenzyl pyrethroidswas demonstrated in a kdr-resistant housefly strain (116). |
| Safety Profile | A poison by ingestionand inhalation. Low toxicity by skin contact.When heated to decomposition it emitsacrid smoke and irritating vapors. |
| Metabolic pathway | Prallethrin is stable under normal room temperature storage conditionsfor up to 36 months. It is labile to alkali at the ester linkage, forming 2and 3 (Scheme 1). Analogy with the allethrins (from which it differsonly in the degree of unsaturation in the side chain - propyne ratherthan propene) would suggest that the compound is very photolabile. |
| Degradation | The metabolism of prallethrin was studied following single oral administrationand subcutaneous injection of the cis- and trans-isomers to rats attwo dose levels and after repeated dosing. The compound was labelled inthe alcohol moiety (inferred from the results) (PSD, 1995). Absorption was rapid with maximum tissue residues being attained3 hours after the dosing of each isomer. Biphasic clearance of radioactivitythen occurred with half-lives of 3 and 14-23 hours (cis-isomer) and 3-5and 7-35 hours (trans-isomer). Urinary excretion accounted for 13-32%(cis-isomer) and 45-62% (trans-isomer) of the dose with most of the balance in the faeces. Less than 0.1% was exhaled as 14CO2 . Residuesin tissues were very low (0.3% of the dose at 7 days). Metabolism anddisposition were independent of dose and dose route but residues intissues were somewhat higher for the cis-isomer. Twenty-one metabolites were identified (taking account of stereochemistryand conjugates). The major pathways of metabolism involvedoxidation at a methyl group of the isobutenyl group in the acid moiety(giving 4 and 5), at the C1 and C2 positions of the propynyl group in thealcohol moiety (giving 6 and 9) and dihydroxylation (to 7 and 8). Theresulting hydroxy derivatives were conjugated with glucuronic acid andsulfate. Hydrolysis of prallethrin also occurred to afford the acid 2 (presumed)and the alcohol 3. Hydrolysis of the hydroxylated prallethrins and furtheroxidation of 3 afforded 10 and 11. Further oxidation of 10 to the cyclictertiary alcohol (12) was observed. When bluegill sunfish were exposed to a l4C-labelled (acid and alcoholgroups) prallethrin isomer (1Rtrans), more than 50% of the biliaryradioactivity recovered from the gall bladder was observed as one ester metabolite. This was identified as the taurine conjugate of carboxylic acidmetabolite 5 (Oshima et al., 1992). |
Prallethrin Preparation Products And Raw materials
| Raw materials | Ethanol-->Ethyl acetate-->N,N-Dimethylformamide-->Ethyl acetoacetate-->Sodium ethoxide-->Acetylacetone-->Methylglyoxal-->CHAMAZULEN-->1-Hexyne-->6-Heptynoic acid-->PROPARGYL BENZENESULFONATE |
