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  • 66215-27-8 Structure
  • Basic information

    1. Product Name: Cyromazine
    2. Synonyms: 2-cyclopropylamino-4,6-diamino-s-triazine;ARMOR;ARMOR(R);cyclopropyl-1,3,5-triazine-2,4,6-triamine;Cyclopropylmelamine;CYPROMAZINE;CYROMAZIN;CYROMAZINE
    3. CAS NO:66215-27-8
    4. Molecular Formula: C6H10N6
    5. Molecular Weight: 166.18
    6. EINECS: 266-257-8
    7. Product Categories: FINE Chemical & INTERMEDIATES;Active Pharmaceutical Ingredients;INSECTICIDE;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, insecticide;Bases & Related Reagents;Heterocycles;Nucleotides;Pharmaceutical intermediate;Acaricides;Analytical Standards;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Chromatography;Environmental Standards;Heterocyclic Building Blocks;Metabolites;Pesticides;Pesticides &Triazines;Pesticide intermediates;Pesticide
    8. Mol File: 66215-27-8.mol
    9. Article Data: 11
  • Chemical Properties

    1. Melting Point: 223-227 °C(lit.)
    2. Boiling Point: 284.39°C (rough estimate)
    3. Flash Point: 100 °C
    4. Appearance: Colorless crystal
    5. Density: 1.3196 (rough estimate)
    6. Vapor Pressure: 4.5 x l0-7 Pa (25 °C)
    7. Refractive Index: 1.8300 (estimate)
    8. Storage Temp.: 0-6°C
    9. Solubility: DMSO (Slightly), Methanol (Slightly)
    10. PKA: 5.2 (base)
    11. Water Solubility: 13 g l-1 (pH 7.1,25 °C)
    12. Stability: Hygroscopic
    13. Merck: 14,2775
    14. BRN: 882879
    15. CAS DataBase Reference: Cyromazine(CAS DataBase Reference)
    16. NIST Chemistry Reference: Cyromazine(66215-27-8)
    17. EPA Substance Registry System: Cyromazine(66215-27-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: UN3077 (solid)
    5. WGK Germany: 2
    6. RTECS: XZ1056500
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 66215-27-8(Hazardous Substances Data)

66215-27-8 Usage

Description

Cyromazine, also known as N-Cyclopropyl-2,4,6-triamino-1,3,5-triazine, is a triazine insect growth regulator (IGR) commonly used as an insecticide and an acarcide. It is a cyclopropylderivative of melamine and belongs to the family of aminotriazines, which are compounds consisting of an amino group attached to a triazine ring. Cyromazine has specific activity against dipterous larvae and is approved by the FDA for use in livestock. It is not a cholinesterase inhibitor and takes effect by affecting the nervous system of the immature larval stage of insects. It is a white crystalline powder with a solubility of 11,000 mg/L at 20°C and pH 7.5, and its hydrolysis is not significant at pH 5-9.

Uses

Used in Agricultural Industry:
Cyromazine is used as an insect growth regulator for controlling fly larvae in livestock and poultry manure. It can be fed directly to livestock or applied directly to fly breeding sites, providing a means to manage pest populations in agricultural settings.
Used in Insect Control:
Cyromazine is used as a foliar spray to control leaf miners in vegetables, potatoes, and other crops, as well as on mushrooms. It is a high-efficiency and low-toxicity insecticide, making it suitable for protecting crops from pests without causing significant harm to the environment or non-target organisms.
Used in Poultry Industry:
As an insecticide, cyromazine is fed to caged poultry and passes through the chickens, leaving a residue in the manure. This chemical controls the growth of fly larvae developing in the manure, helping to maintain cleanliness and hygiene in poultry farming.
Used in Animal Health:
Cyromazine is used to control leafminer pests and has a good control effect on Liriomyza, a type of leafminer that can cause significant damage to crops. It can also be used to control flies on animals, contributing to the overall health and well-being of livestock.

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

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.

Flammability and Explosibility

Notclassified

Trade name

ARMOR?; CITATION; CGA-72662?; LARVADEX?; PATRON?; TRIGARD?; VETRAZIN?

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 evaluation published by the Pesticide Safety Directorate (PSD, 1993). The major degradation pathway of cyromazine involves the N-dealkylation of the cyclopropyl moiety to yield melamine. Both cyromazine and melamine are quite stable to biotransformation. Deamination and the formation of N-methylcyromazine were observed as minor pathways.

Degradation

Cyromazine (1) is stable to hydrolysis at pH 5, 7 and 9 and 70 °C for up to 28 days. No degradation of cyromazine was observed when irradiated under mercury vapour lamp (>290 nm) at 25 °C for up to 168 hours.

Check Digit Verification of cas no

The CAS Registry Mumber 66215-27-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,2,1 and 5 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 66215-27:
(7*6)+(6*6)+(5*2)+(4*1)+(3*5)+(2*2)+(1*7)=118
118 % 10 = 8
So 66215-27-8 is a valid CAS Registry Number.
InChI:InChI=1/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)

66215-27-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (C2366)  Cyromazine  >98.0%(HPLC)(T)

  • 66215-27-8

  • 5g

  • 196.00CNY

  • Detail
  • TCI America

  • (C2366)  Cyromazine  >98.0%(HPLC)(T)

  • 66215-27-8

  • 25g

  • 590.00CNY

  • Detail
  • USP

  • (1161203)  Cyromazine  United States Pharmacopeia (USP) Reference Standard

  • 66215-27-8

  • 1161203-200MG

  • 4,449.51CNY

  • Detail
  • Aldrich

  • (551295)  N-Cyclopropyl-2,4,6-triamino-1,3,5-triazine  97%

  • 66215-27-8

  • 551295-25G

  • 730.08CNY

  • Detail

66215-27-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name cyromazine

1.2 Other means of identification

Product number -
Other names 2-N-cyclopropyl-1,3,5-triazine-2,4,6-triamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66215-27-8 SDS

66215-27-8Synthetic route

2-Chloro-4,6-diamino-1,3,5-triazine
3397-62-4

2-Chloro-4,6-diamino-1,3,5-triazine

Cyclopropylamine
765-30-0

Cyclopropylamine

cyromazine
66215-27-8

cyromazine

Conditions
ConditionsYield
With sodium hydroxide at 70 - 85℃; for 6h; pH=9.5; pH-value; Temperature;96.37%
With potassium carbonate In water at 95 - 100℃; for 4h; pH=7.5 - 8.5; Temperature; Reagent/catalyst;90.1%
With sodium hydroxide at -10 - 10℃; for 10h; Temperature;24.47 g
2,4-dichloro-6-cyclopropylamino-1,3,5-triazine
32889-45-5

2,4-dichloro-6-cyclopropylamino-1,3,5-triazine

cyromazine
66215-27-8

cyromazine

Conditions
ConditionsYield
With ammonia In water; toluene at 120℃; under 4500.45 Torr; for 10h;93.5%
1,4-dioxane
123-91-1

1,4-dioxane

6-chloro-N-cyclopropyl-[1,3,5]triazine-2,4-diamine
35516-73-5

6-chloro-N-cyclopropyl-[1,3,5]triazine-2,4-diamine

cyromazine
66215-27-8

cyromazine

Conditions
ConditionsYield
With ammonia
With ammonia
6-chloro-N-cyclopropyl-[1,3,5]triazine-2,4-diamine
35516-73-5

6-chloro-N-cyclopropyl-[1,3,5]triazine-2,4-diamine

cyromazine
66215-27-8

cyromazine

Conditions
ConditionsYield
With ammonia In 1,4-dioxane; water
cyromazine
66215-27-8

cyromazine

isobutyl chloroformate
543-27-1

isobutyl chloroformate

2-cyclopropylamino-4,6-bis-isobutoxycarbonylamino-s-triazine

2-cyclopropylamino-4,6-bis-isobutoxycarbonylamino-s-triazine

Conditions
ConditionsYield
With pyridine; dmap In chloroform
acetyl chloride
75-36-5

acetyl chloride

cyromazine
66215-27-8

cyromazine

2,4-bis-acetylamino-6-cyclopropylamino-1,3,5-triazine

2,4-bis-acetylamino-6-cyclopropylamino-1,3,5-triazine

Conditions
ConditionsYield
In pyridine
Methoxyacetyl chloride
38870-89-2

Methoxyacetyl chloride

cyromazine
66215-27-8

cyromazine

2,4-bis-methoxyacetylamino-6-cyclopropylamino-1,3,5-triazine

2,4-bis-methoxyacetylamino-6-cyclopropylamino-1,3,5-triazine

Conditions
ConditionsYield
In pyridine
cyromazine
66215-27-8

cyromazine

2-cyclopropylamino-4-acetylamino-6-amino-1,3,5-triazine

2-cyclopropylamino-4-acetylamino-6-amino-1,3,5-triazine

Conditions
ConditionsYield
With acetic anhydride; triethylamine In tetrahydrofuran; diethyl ether
Methoxyacetic anhydride
19500-95-9

Methoxyacetic anhydride

cyromazine
66215-27-8

cyromazine

2-cyclopropylamino-4-methoxyacetylamino-6-amino-1,3,5-triazine
99135-52-1

2-cyclopropylamino-4-methoxyacetylamino-6-amino-1,3,5-triazine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; diethyl ether
Chlorodiisopropylphosphane
40244-90-4

Chlorodiisopropylphosphane

cyromazine
66215-27-8

cyromazine

N-cyclopropyl-N,N-bis(diisopropylphosphaneyl)-1,3,5-triazine-2,4,6-triamine

N-cyclopropyl-N,N-bis(diisopropylphosphaneyl)-1,3,5-triazine-2,4,6-triamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 60℃; Inert atmosphere; Sealed tube;

66215-27-8Downstream Products

66215-27-8Relevant articles and documents

Synthesis method of cyromazine active compound with high yield

-

Paragraph 0040-0063, (2021/05/29)

The invention relates to a synthesis method of a cyromazine active compound with high yield, cyanuric chloride, cyclopropylamine and ammonia gas are used as raw materials, single toluene is used as a solvent to synthesize the cyromazine active compound, the purity is more than 98%, and the yield is as high as 93%. The method has the characteristics of simplicity in operation, high solvent utilization rate, high product yield, less environmental pollution and the like. The labor load of workers is reduced, the production cost is reduced, and the environmental pollution is reduced.

Preparation method of cyromazine

-

Paragraph 0023; 0026-0027; 003-0031; 0034-0035; 0038-0039; 0, (2020/09/16)

The invention discloses a preparation method of cyromazine. Melamine is used as an initial raw material; the preparation method comprises the following steps: carrying out an acidic hydrolysis reaction to obtain 4, 6-diamino-2-hydroxy-1, 3, 5-triazine, carrying out a chlorination reaction on 4, 6-diamino-2-hydroxy-1, 3, 5-triazine to obtain a toluene solution of 4, 6-diamino-2-chloro-1, 3, 5-triazine, and carrying out an amination reaction on 4, 6-diamino-2-chloro-1, 3, 5-triazine and cyclopropylamine so as to generate cyromazine. According to the method, toxic 2-cyclopropylamino-4, 6-dichloro-S-triazine is prevented from being generated, ammoniation pressurizing equipment is prevented from being used, reaction conditions are milder, cheaper materials are used, and the prepared cyclopropylamine is high in yield and good in quality.

Active agent combinations

-

, (2008/06/13)

The novel active compound combinations of extracts from seeds of the neem tree and the active compounds of groups (B) to (F) listed in the description have very good insecticidal and acaricidal properties.

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