Cyromazine CAS 66215-27-8
Introduction：Basic information about Cyromazine CAS 66215-27-8, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Cyromazine Basic informationDescription References
| Product Name: | Cyromazine |
| Synonyms: | Vetrazin【pesticide】;Cyromazine, 2-Cyclopropylamino-4,6-diamino-s-triazine;N-Cyclopropyl;5-triazine-2,4,6-triamine,n-cyclopropyl-3;ai3-52713;cga72662;neoprex;Cyromazine (200 mg) |
| CAS: | 66215-27-8 |
| MF: | C6H10N6 |
| MW: | 166.18 |
| EINECS: | 266-257-8 |
| Product Categories: | Pharmaceutical intermediate;Pesticide;Acaricides;Analytical Standards;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Chromatography;Environmental Standards;Heterocyclic Building Blocks;Metabolites;Pesticides;Pesticides &Triazines;Pesticide intermediates;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, insecticide;Bases & Related Reagents;Heterocycles;Nucleotides;INSECTICIDE;FINE Chemical & INTERMEDIATES;Active Pharmaceutical Ingredients;66215-27-8 |
| Mol File: | 66215-27-8.mol |
Cyromazine Chemical Properties
| Melting point | 223-227 °C (lit.) |
| Boiling point | 284.39°C (rough estimate) |
| density | 1.3196 (rough estimate) |
| vapor pressure | 4.5 x l0-7 Pa (25 °C) |
| refractive index | 1.8300 (estimate) |
| Fp | 100 °C |
| storage temp. | 2-8°C |
| solubility | DMSO (Slightly), Methanol (Slightly) |
| pka | 5.2 (base) |
| Water Solubility | 13 g l-1 (pH 7.1,25 °C) |
| form | Solid |
| color | White to Off-White |
| Merck | 14,2775 |
| BRN | 882879 |
| Stability: | Hygroscopic |
| InChI | 1S/C6H10N6/c7-4-10-5(8)12-6(11-4)9-3-1-2-3/h3H,1-2H2,(H5,7,8,9,10,11,12) |
| InChIKey | LVQDKIWDGQRHTE-UHFFFAOYSA-N |
| SMILES | Nc1nc(N)nc(NC2CC2)n1 |
| LogP | -0.061 at 25℃ |
| CAS DataBase Reference | 66215-27-8(CAS DataBase Reference) |
| NIST Chemistry Reference | Cyromazine(66215-27-8) |
| EPA Substance Registry System | Cyromazine (66215-27-8) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36 |
| RIDADR | UN3077 (solid) |
| WGK Germany | 2 |
| RTECS | XZ1056500 |
| HS Code | 29336990 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Aquatic Chronic 2 |
| Hazardous Substances Data | 66215-27-8(Hazardous Substances Data) |
| Toxicity | LC50 (96-hour) for rainbow trout and carp >100 mg/L and bluegill sunfish >90mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 3,387 mg/kg (Hartley and Kidd,1987) |
| Description | Cyromazine is a triazine insect growth regulator that can be used as an insecticide and an acarcide. It is a kind of cyclopropylderivative of melamine, and also belongs to the family of aminotriazines which are compound consisting of an amino group attached to a triazine ring. It has specific activity against dipterous larvae, and has been approved by FDA for being applied to livestock. It is not a kind of cholinesterase inhibitor, and taking effect through affecting the nervous system of the immature larval stage of the insects. |
| References | https://pubchem.ncbi.nlm.nih.gov/compound/cyromazine#section=Top https://en.wikipedia.org/wiki/Cyromazine http://pmep.cce.cornell.edu/profiles/insect-mite/cadusafos-cyromazine/cyromazine/insect-prof-cyromazine.html |
| Chemical Properties | White crystalline powder. The solubility in water is 11,000 mg/L at 20°C and pH 7.5, and the hydrolysis is not obvious at pH 5-9. |
| Uses | Cypromazine is a high-efficiency and low-toxicity insecticide. It is mainly used to control leafminer pests, has a good control effect on Liriomyza, and can also be used to control flies. |
| Application | Cyromazine is an insect growth regulator, used to control fly larvae in livestock and poultry manure. It can be fed directly to livestock or applied directly to fly breeding sites. Cyromazine also exhibits systemic activity and is used as a foliar spray to control leaf miners in vegetables, potatoes, etc., and on mushrooms. |
| Definition | ChEBI: Cyromazine is a triamino-1,3,5-triazine. It has a role as a triazine insecticide and a mouse metabolite. |
| Preparation | Cyromazine is prepared by the reaction of cyanuric chloride and cyclopropylamine to obtain 2-Cyclopropylamino-4,6-dichloro-triazepine, and then reacts with ammonia to obtain 2-Cyclopropylamino-4-chloro-6-aminostriazepine, and then reacting with ammonia to produce. |
| General Description | N-Cyclopropyl-2,4,6-triamino-1,3,5-triazine, also known as cyromazine, is an insect growth regulator(IGR) that is commonly used as an insecticide. It undergoes metabolism in plants and animals to form melamine. Surface-enhanced Raman scattering (SERS) spectroscopic study indicates that it interacts with the surface of silver colloid through the lone pair on nitrogen. |
| Flammability and Explosibility | Not classified |
| Agricultural Uses | Insecticide (insect growth regulator): As an insect growth regulator, cyromazine is fed to caged poultry and is passed through the chicken, leaving a residue in the manure. The chemical controls the growth of the fly larvae developing in the manure. Used as a foliar spray to control leaf miners in vegetables, mushrooms, potatoes and ornamentals and to control flies on animals. |
| Trade name | ARMOR®; CITATION; CGA-72662®; LARVADEX®; PATRON®; TRIGARD®; VETRAZIN® |
| Synthesis | 3397-62-4 765-30-0 66215-27-8 2) Add 120 mL of deionized water to the intermediate obtained in step 1), followed by the addition of 7.2 g of cyclopropylamine, and the reaction system was heated to 95 °C. Slowly add the pre-prepared potassium carbonate aqueous solution (made by dissolving 7.8 g of potassium carbonate in 28 mL of deionized water) and adjust the pH of the reaction solution to 7.5-8.5. Maintain the reaction temperature at 100 °C and continuously stir the reaction for 4 h. After the reaction was completed, add 0.2 g of activated carbon. After the reaction was completed, 0.7 g of activated carbon was added and decolorized at 95 °C for 0.5 h. The activated carbon was subsequently removed by thermal filtration to obtain a clarified reaction solution. The reaction solution was cooled to 40 °C and left to crystallize for 2 h. It was further cooled to -2 °C to promote complete crystallization. The crystallized product was separated by filtration, washed with deionized water and finally dried at 90°C for 8 hours to give 15.2 g of cyromazine. The mass yield of cyromazine in this step was 90.1% and the product was a white crystalline powder, which was analyzed by high performance liquid chromatography (HPLC) and its purity was 99.4%. |
| Environmental Fate | Chemical/Physical. Cyromazine will react with mineral acids (e.g., hydrochloric acid,sulfuric acid) forming water-soluble salts |
| Metabolic pathway | Information presented in this summary is abstracted from the data evaluationpublished by the Pesticide Safety Directorate (PSD, 1993). The majordegradation pathway of cyromazine involves the N-dealkylation of thecyclopropyl moiety to yield melamine. Both cyromazine and melamine arequite stable to biotransformation. Deamination and the formation ofN-methylcyromazine were observed as minor pathways. |
| Degradation | Cyromazine (1) is stable to hydrolysis at pH 5, 7 and 9 and 70 °Cfor up to 28 days. No degradation of cyromazine was observed whenirradiated under mercury vapour lamp (>290 nm) at 25 °C for up to 168 hours. |
| References | [1] Patent: CN108084102, 2018, A. Location in patent: Paragraph 0033; 0034; 0037; 0041 |
Cyromazine Preparation Products And Raw materials
| Raw materials | Ammonium hydroxide-->Cyanuric chloride-->4-Chlorobenzaldehyde-->Cyclopropylamine-->CYPRAZINE-DESISOPROPYL-->2-CHLORO-4,6-DIAMINO-1,3,5-TRIAZINE-->Potassium carbonate |
