Related Searches: Cyromazine

Cyromazine(CAS No. 66215-27-8)

Cyromazine C6H10N6 (cas 66215-27-8) Molecular Structure

66215-27-8 Structure

Identification and Related Records

【Iupac name】
【CAS Registry number】
1,3,5-Triazine-2,4,6-triamine,N-cyclopropyl- (9CI)
CGA 72662
【Molecular Formula】
C6H10N6 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

white crystals
1.622 g/cm3
【Melting Point】
【Boiling Point】
480.7 °C at 760 mmHg
【Flash Point】
244.5 °C
11 g/L (20 C)
Colorless crystals
White crystalline solid
No hydrolysis was observed < or = 70 C for 28 days. Stable < 310 C.
【Storage temp】
【Computed Properties】
Molecular Weight:166.1838 [g/mol]
Molecular Formula:C6H10N6
H-Bond Donor:3
H-Bond Acceptor:0
Rotatable Bond Count:2
Tautomer Count:10
Exact Mass:166.096694
MonoIsotopic Mass:166.096694
Topological Polar Surface Area:103
Heavy Atom Count:12
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:3
Feature 3D Cation Count:3
Feature 3D Ring Count:1
Effective Rotor Count:2.6
Conformer Sampling RMSD:0.6
CID Conformer Count:5

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
【Safety Statements 】

The Food Safety and Inspection Service (FSIS) of the United States Department of Agriculture (USDA) provides a test method for analyzing cyromazine and Melamine in animal tissues in its Chemistry Laboratory Guidebook which "contains test methods used by FSIS Laboratories to support the Agency's inspection program, ensuring that meat, poultry, and egg products are safe, wholesome and accurately labeled." In 1999, in a proposed rule published in the Federal Register regarding cyromazine residue, the United States Environmental Protection Agency (EPA) proposed "remov[ing] Melamine, a metabolite of cyromazine from the tolerance expression since it is no longer considered a residue of concern."
Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
WGK Germany: 2
RTECS: XZ1056500

【Skin, Eye, and Respiratory Irritations】
A primary eye irritation study in the rabbit ... showed no eye irritation. A primary dermal irritation study in the rabbit ... showed mild irritation. Toxicity Category IV. A dermal sensitization study in the guinea pig ... showed no sensitization.
【Cleanup Methods】
For minor spills, leaks, etc., follow all precautions indicated on /the product/ label and clean up immediately. Take special care to avoid contamination of equipment and facilities during cleanup procedures and disposal of wastes. /Technical cyromazine/
【Fire Fighting Procedures】
Dry chemical, foam or carbon dioxide
LARVADEX 1% PREMIX Active Ingredient 1.00% Cyromazine; LARVADEX 2SL Active Ingredient 2.00% Cyromazine; NOVARTIS CYROMAZINE TECHNICAL SPEC GROUND Active Ingredient 97.00% Cyromazine
FLYZINE 1% PREMIX Active Ingredient 1.00% Cyromazine; FLYZINE TECHNICAL Active Ingredient 96.80% Cyromazine
SERENE FLY CONTROL PRODUCTS Active Ingredient 2.12% Cyromazine
CYROMAZINE TECHNICAL Active Ingredient 97.00% Cyromazine; TRIGARD 75W Active Ingredient 75.00% Cyromazine; ARMOR INSECT GROWTH REGULATOR Active Ingredient 5.00% Cyromazine; CITATION INSECTICIDE Active Ingredient 75% Cyromazine; TRIGARD OMC Active Ingredient 75% Cyromazine
'Neporex', water soluble powder (500 g/kg), water soluble granules (20 g/kg); 'Trigard', suspension concentrate (100 g/kg), wettable powder (750 g/kg); 'Vetrazine' water soluble powder (500 g/kg).
Feed premix
Soluble concentrate
【Other Preventative Measures】
AGRICULTURAL USE REQUIREMENTS: Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR part 170. This Standard contains requirements for the protection of agricultural workers on farms, forests, nurseries, and greenhouses, and handlers of agricultural pesticides. It contains requirements for training, decontamination, notification, and emergency assistance. It also contains specific instructions and exceptions pertaining to the statements on this label about personal protective equipment (PPE) and restricted-entry interval. /Trigard 75W/
Causes moderate eye irritation. Harmful if swallowed, absorbed through the skin, or inhaled. Avoid contact with eyes, skin, or clothing. Avoid breathing dust. Wash thoroughly with soap and water after handling and before eating, drinking, chewing gum, or using tobacco. Remove and wash contaminated clothing before reuse. /Trigard 75W/
Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables, use detergent and hot water. Keep and wash PPE separately from other laundry. /Trigard 75W/
Users should: Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. /Trigard 75W/
Do not apply directly to water, to areas where surface water is present, or to intertidal areas below the mean high water mark. Do not contaminate water when disposing of equipment wash water. Do not apply when weather conditions favor drift from target area ... Do not apply this product through any type of irrigation system. /Trigard 75W
The outer protective container contains Trigard Insecticide in ... water-soluble packets. ... After opening outer container, immediately dump the required number of unopened packets into the partially filled sprayer or mix tank. Do not handle the soluble packets or expose them to moisture, since this may cause rupturing. /Trigard 75W/
FIRST AID. If Inhaled: Move person to fresh air. If person is not breathing, call 911 or an ambulance, then give artificial respiration ... Call a poison control center or doctor for treatment advice. If on skin or clothIng: Take oft contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. Call a poison control center or doctor for treatment advice. It swallowed: Call a poison control center or doctor immediately for treatment advice. Have person sip a glass of water if able to swallow. Do not induce vomiting unless told to do so by a poison control center or doctor. Do not give anything by mouth to an unconscious person. If in eyes: Hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. Call a poison control center or doctor for treatment advice. /Technical Cyromazine/
【Protective Equipment and Clothing】
Applicators and other handlers must wear: Long-sleeved shirt and long pants; Chemical-resistant gloves made of any waterproof material - Category A (e.g., barrier laminate, butyl rubber, nitrile rubber, neoprene rubber, polyethylene, polyvinylchloride [PVC] or viton); Chemical-resistant footwear plus socks /Trigard 75W/
When handlers use closed systems, enclosed cabs, or aircraft in a manner that meets the requirements listed in the Worker Protection Standard (WPS) for agricultural pesticides [40 CFR 170.240(d)(4-6)], the handler PPE requirements may be reduced or modified as specified in the WPS. /Trigard 75W/
Do not enter or allow worker entry into treated areas during the restricted-entry interval (REI) of 12 hours. PPE required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water is: Coveralls; Chemical-resistant gloves made of any waterproof material - Category A (e.g., barrier laminate, butyl rubber, nitrile rubber, neoprene rubber, polyethylene, polyvinylchloride [PVC] or viton); Chemical-resistant footwear plus socks /Trigard 75W/
Safety glasses or goggles, rubber gloves, waterproof boots, long-sleeved shirt, long pants and hat.

?Cyromazine , its cas register number is 66215-27-8. It also can be called N-cyclopropyl-1,3,5-triazine-2,4,6-triamine ; 2-Cyclopropylamino-4,6-diamino-s-triazine ; Diamino-6-(cyclopropylamino)-s-triazine ; Cyclopropyl-1,3,5-triazine-2,4,6-triamine ; Cyclopropylmelamine ; Larvadex ; OMS-2014 ; Trigard .It is a?crystals.It?works by affecting the nervous system of the immature larval stages of certain insects.

【Octanol/Water Partition Coefficient】
log Kow = -0.06 (pH 7.0)
【Disposal Methods】
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Container Disposal Do not reuse outer container. Dispose of the empty outer foil pouch and outer container In the trash, as long as water-soluble packets are unbroken. /Trigard 75W/
Pesticide: Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. Container: Completely empty container including any liner by shaking and tapping sides and bottom to loosen clinging particles. Empty residue into equipment, then dispose of any liner in a sanitary landfill, or by incineration, if allowed by state and local authorities. If drum is contaminated and cannot be reused to contain additional cyromazine technical, dispose of in the same manner as the liner. /Technical cyromazine/

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Production: cyanuric chloride plus cyclopropylamine plus ammonia (amine formation/amine formation)
Prepn: H.U. Brechbuhler et al., DE 2736876; eidem, US 4225598 (1978, 1980 to Ciba-Geigy).
Consumption Patterns

Approximately 13,000 pounds of cyromazine are used annually on agricultural crops, with the highest usage in terms of percent crop treated on celery, spinach and lettuce.

Insect growth regulator.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
【Therapeutic Uses】
MEDICATION (VET): ectoparasiticide
MEDICATION (VET): Cyromazine, a triazine derivative, is effective against blowfly larvae on sheep and lambs and also against other Diptera such as houseflies and mosquitos. At recommended dose rates, cyromazine shows only limited activity against established strikes and must therefore be used preventively. Blowflies usually lay eggs on damp fleece of treated sheep. Although larvae are able to hatch, the young larvae immediately come into contact with cyromazine, which prevents the molt to second instars. The efficacy of a pour-on preparation of cyromazine does not depend on factors such as weather, fleece length, and whether the fleece is wet or dry. Control can be maintained for up to 13 wk after a single pour-on application, or longer if cyromazine is applied by dip or shower.
【Biomedical Effects and Toxicity】
Dermal Absorption /in rats/ ... at 10 hrs = 13 %. Cyromazine /was/ apparently rapidly absorbed into the skin in an inverse dose related manner. The absorption into the skin is followed by a slower release into the body. The main route of excretion is apparently by the urine. There is no evidence that the compound is sequestered in the skin. Mean absorption based on blood, urinary/ fecal excretion, and carcass, ranged from 0.6 to 7% for animals sacrificed at the end of the exposure periods. For animals exposed for 10 and 24 hours and followed for 48 hours post-exposure, mean absorption ranged from 8 to 14.5%. Total radioactivity absorbed generally decreased as dose increased indicating saturation of absorption with increasing dose. Amounts remaining in/on the skin at termination ranged from 4.5% (10 mg dose/2 hr exposure) to 24% ( 0.1 mg dose/24 hr exposure). The majority of the absorbed radioactivity was found in the urine and carcass. Most of the unabsorbed radioactivity was found in the skin washes from each dose/ duration. /In another portion of the same study in rats/ absorption at 10 hrs = 10%. Mean total recoveries of applied radioactivity from all dose groups ranged from 85 to 101%. Mean absorption based on blood, urinary/ fecal excretion, and carcass, ranged from 2% to 11%. Total radioactivity absorbed generally increased with increasing exposure time but decreased with increasing dose indicating saturation of penetration with increasing dose. The majority of the absorbed radioactivity was found in the urine and carcass. Most of the unabsorbed radioactivity was found in the skin washes from each dose/duration (35-90%). However, based on measurements of skin absorption, a significant amount of radioactive dose was also found in the skin itself (9-40%). Mean absorption with inclusion of radioactivity in dissolved skin ranged from 10 to 45%. The ratio of the amount of radioactive dose in the skin wash to the radioactivity in the skin itself decreased with time indicating penetration into the subsurface of the skin with time after treatment.
Cyromazine was well absorbed after oral administration /to rats/. Excretion was rapid at the dose (3 mg/kg), but an apparent delay in excretion occurred at the high dose (300 mg/kg). Fecal elimination was equivalent among dose groups except the high dose males, where a greater percentage was eliminated by this route. The origin of fecal radioactivity was via biliary elimination. Residual radioactivity in tissues was minimal in all dose groups. Urinary and fecal metabolites of 14C-cyromazine were isolated and identified by TLC, HPLC, and GC/MS. The major compounds were the N-dealkylated product melamine, hydroxycyromazine, and unmetabolized cyromazine identified
A single dose of 0.5 mg/kg bw of 14C-cyromazine (uniformly triazine ring labeled) was given orally to two male and one female Charles River white rats (not further identified). By 72 hours after dosing, 95% of the administered dose had been excreted in urine, essentially all within the first 24 hours. About 3% was excreted in feces, again predominantly in the first 24 hours. Negligible amounts were excreted as volatiles or CO2 in another two males and one female given the same dose. Tissue residues were below the level of detection except in liver; however, liver levels were too low to permit accurate quantitation (about 0.007 ppm).
Two chickens (strain not indicated) were given daily oral doses of 14C-cyromazine (uniformly triazine ring labeled) of 0.75 mg/hen/day by capsule for seven days. By 24 hours after the last dose 99.1% of the administered radioactivity had been recovered in the excreta with essentially none in volatiles and CO2. Both egg whites and egg yolks contained about 0.12-0.15 ppm consistently. Tissue levels were: byproducts (i.e. head and feet) 0.047 ppm test material equivalents; reproductive tract 0.047 ppm; liver 0.032 ppm; all other tissues 0.008-0.019 ppm.
One sheep (strain not given) was given a daily dose of 14C-cyromazine (uniformly triazine ring labeled) of 0.15 mg/kg bw/day by capsule for nine days. By 24 hours after the last dose about 90% of the administered dose had been recovered in urine. A further 3.7% was recovered in feces. Only a trace was detected in CO2. Blood levels appeared to plateau at about 0.1% of the administered dose after five days. Tissue levels were: 0.174 ppm in liver, 0.164 ppm in the GI tract, 0.048 ppm in kidney, 0.012-0.013 ppm in muscle, brain and heart, and at or below the level of detection in fat.
One lactating goat/dose level was given a daily oral dose of 14C-cyromazine (uniformly triazine ring labeled) of 5 or 50 mg/goat/day by capsule for ten consecutive days. By 24 hours after the last dose 90.4% of the low dose and 82.1% of the high dose had been recovered in urine. Fecal excretion accounted for 7.5% of the low dose and 5.7% of the high dose. There was some evidence of plateauing of urinary and fecal excretion after 5 days. Blood levels changed little on days 2-10 and were in the range of 0.05-0.09% of the dose at both dose levels. Tissue levels were 0.01 ppm or less in the low dose goat and 0.14 ppm or less in the high dose goat except in liver (0.79 and 1.522 ppm, respectively), kidney (0.04 and 0.437 ppm) and GI tract (contents) (1.27 and 1.11% of the administered dose). Daily milk levels accounted for about 0.3% of the administered dose.
A single dose of 0.05 or 0.5 mg/kg bw of 14C-cyromazine (uniformly triazine ring labeled) was given by capsule to groups of two male and two female monkeys (Macaca fasicicula). Twenty four hours after dosing 62.9-96.1% of the low dose and 47-82.2% of the high dose had been recovered in urine. Only a small additional amount was excreted in urine in the period 24-96 hours after dosing. Excretion in feces accounted for 1.14-1.31% of the low dose and 1.42-1.92% of the high dose most of which was recovered in the first 24 hours after dosing ... Because of the low total recovery of radioactivity in the above study, a second study was undertaken using one male and one female of the same strain of monkey and at the same dose levels given by capsule. Greater recovery of radioactivity was not achieved. At the high dose the results were similar to those in the above study. Most of the recovered radioactivity was in urine excreted during the first 24 hours after dosing with only a small amount in feces again mainly in the first 24 hours. About 14% of the administered dose was excreted in feces mainly in the first 48 hours after dosing.
... Groups of three male Harlan Sprague-Dawley albino rats/dose/time period were exposed to 14C-cyromazine (uniformly triazine ring labeled) at 0.1, 1.0 or 100 mg/rat applied to a shaved area on the upper back. The rats were sacrificed 1, 2, 4 and 10 hours after treatment. The percent of the total dose applied which was absorbed was 4.5-11.0% at the low dose, 3.5-11.4% at the mid dose and 2.2-7.1% at the high dose with the amount absorbed increasing with duration of exposure at all dose levels. The amount of material bound in the skin also increased with time. ... The highest recovery of absorbed material was in the urine, followed by the carcass. Fecal and blood levels were very low.
... Groups of male Harlan Sprague-Dawley albino rats were exposed to 14C-cyromazine (uniformly triazine ring labeled) at dose levels of 0.1, 1.0 or 10.0 mg/rat applied to shaved areas on the upper back. The treated area was enclosed and covered by a nonocclusive bandage. The hind legs of the rats were shackled to prevent scratching of the treated area. Groups of four rats/dose were sacrificed 2, 4, 10 and 24 hours after treatment. Additionally, two groups of four rats/dose had the bandages removed and the treated area washed 10 or 24 hours after treatment and then were returned to metabolism cages for a 48 hour period prior to sacrifice. In all groups, 62-86% of the applied dose was recovered in skin and cage washings and bandages, thus was not absorbed. The amount bound in skin tended to increase with duration of exposure but was reduced during a post-exposure period. The amount absorbed (recovered in urine, carcass, feces and blood) appeared to be higher in the rats which were maintained for 48 hours post-treatment.
Cyromazine is a new insect growth regulator with specific activity against dipterous larvae of the Liriomyza genus, which have become resistant to other pesticides. An experiment has been carried out in order to study the residual behavior, in celery, of this active ingredient and of its metabolite melamine, a potentially carcinogenic compound. The initial residue of cyromazine, 5.27 ppm, degrade itself with a pseudo first order kinetics, with a half-life (t 1/2) of 7.84 days. Its degradation leads to melamine which shows a greater persistence due to a lower decay rate (t = 8.45 days). The residual aspects are discussed with respect to phytoiatric treatments.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), a recommended Koc value of 765, determined from a measured Koc range of 81 to 1,800(2), indicates that cyromazine is expected to have low mobility in soil(SRC). Cyromazine has also been reported to have moderate mobility in soil(3), which would correspond to the lower Koc values measured in some soils(SRC). An agricultural runoff study(4) found that cyromazine (applied to soil via chicken manure) was present in runoff waters with concentrations increasing as rainfall rates increased. Volatilization of cyromazine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant as 5.65X10-14 atm-cu m/mole(SRC) derived from its vapor pressure, 3.36X10-9 mm Hg(3), and water solubility, 13,000 mg/L(3). Cyromazine is not expected to volatilize from dry soil surfaces(SRC) based upon a measured vapor pressure of 3.36X10-9 mm Hg(3). Numerous studies conducted (laboratory and field) demonstrate the cyromazine is degraded by biological mechanisms(3); no rates or additional data were available(SRC). Field dissipation half-lives have been reported to range from 75-284 days with a median of 189 days(2). The aerobic half-life in sand and a sandy loam soil were observed to be 107 and 142 days, respectively(2). Cyromazine is reported to be stable in anaerobic soil(2).
AQUATIC FATE: Based on a classification scheme(1), a recommended Koc value of 765, determined from a measured Koc range of 81 to 1,800(2), indicates that cyromazine may adsorb to suspended solids and sediment(SRC). Cyromazine can be transported from soils treated with cyromazine via runoff from rainfall(4). Volatilization from water surfaces is not expected(4), with a Henry's Law constant estimated as 5.65X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 3.36X10-9 mm Hg(4), and water solubility, 13,000 mg/L(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from a measured log Kow of -0.06(4) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Cyromazine is reported to be stable to aqueous hydrolysis and stable in aqueous solution exposed to sunlight(2). Biodegradation data relevant to aquatic media were not available(SRC, 2007).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyromazine, which has a measured solid vapor pressure of 3.36X10-9 mm Hg at 25 deg C(2), that corresponds to a super-cooled vapor pressure of 3.2X10-7 mm Hg(3), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyromazine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12.7 days(SRC), calculated from its rate constant of 1.26X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(4). Particulate-phase cyromazine will be removed from the atmosphere by wet or dry deposition(SRC).

Supplier Location

Top Suppliers

Diamond member Hubei XinRunde Chemical Co., Ltd
Business Type:Manufacturer
Diamond member Hebei LuXi Bio-Technology Co.,Ltd
Business Type:Trading Company
Diamond member Nanjing Bangnuo Biotechnology Co., Ltd.
Business Type:Manufacturer
Diamond member Wuhan Fortuna Chemical Co., Ltd.
Business Type:Manufacturer
Diamond member Hangzhou Dayangchem Co., Ltd.
Business Type:Manufacturer
Diamond member AOPHARM
Business Type:Manufacturer
Diamond member Finetech Industry limited.
Business Type:Manufacturer
Diamond member Hangzhou J&H Chemical Co., Ltd
Business Type:Manufacturer
Hui Chem Company Limited
Business Type:Manufacturer
Jinan Jianfeng Chemical Co., Ltd
Business Type:Manufacturer

Quick Search

Cas    Name

Related products


Cyromazine-d4;N2-(Cyclopropyl-d4)-;CyroMazine-d4 (cyclopropyl--d4)