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)

Flash point:

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

InChIKey

LVQDKIWDGQRHTE-UHFFFAOYSA-N

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

Hazardous Substances Data

66215-27-8(Hazardous Substances Data)

Toxicity

LC50 (96-hour) for rainbow trout and carp >100 mg/L and bluegill sunfish >90 mg/L (Hartley and Kidd, 1987); acute oral LD50 for rats 3,387 mg/kg (Hartley and Kidd, 1987)

MSDS

• Language:English Provider:Larvadex
• Language:English Provider:SigmaAldrich

Cyromazine Usage And Synthesis

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

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 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.

References

[1] Patent: CN108084102, 2018, A. Location in patent: Paragraph 0033; 0034; 0037; 0041

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