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Home > Encyclopedia > Cyromazine

Cyromazine

Cyromazine structure

Cyromazine 

structure
  • CAS No:

    66215-27-8

  • Formula:

    C6H10N6

  • Chemical Name:

    Cyromazine

  • Synonyms:

    1,3,5-Triazine-2,4,6-triamine,N2-cyclopropyl-;1,3,5-Triazine-2,4,6-triamine,N-cyclopropyl-;N2-Cyclopropyl-1,3,5-triazine-2,4,6-triamine;Vetrazin;Vetrazine;Vetrazin (pesticide);2-Cyclopropylamino-4,6-diamino-s-triazine;CGA 72662;Larvadex;Cyclopropylmelamine;Cyromazine;N-Cyclopropyl-1,3,5-triazine-2,4,6-triamine;Trigard;2,4-Diamino-6-(cyclopropylamino)-s-triazine;Neporex;Citation;Vetrazin Liquid;Patron;Cyromazin;2,4-Diamino-6-cyclopropylamino-1,3,5-triazine

  • Categories:

    Agrochemicals  >  Insecticides

Description

Cyromazine is a triazine insect growth regulator used as an insecticide and an acaricide. It is a cyclopropyl derivative of melamine. Cyromazine works by affecting the nervous system of the immature larval stages of certain insects.


Solid


Cyromazine is a triamino-1,3,5-triazine. It has a role as a triazine insecticide and a mouse metabolite.

Cyromazine Basic Attributes

166.18

166.18

266-257-8

CA49Y29RA9

759268

DTXSID6023999

Colorless crystals|White crystalline solid

29336990

Characteristics

103

-0.06 (pH 7.0)

Solid

1.35 g/cm3 @ Temp: 20 °C

219-222 °C

480.6±28.0 °C at 760 mmHg

100 °C

1.851

In water, 1.1% at 20 deg C (pH 7.5); methanol 1.7%

0-6°C

4.5 x l0 -7 Pa (25 °C)

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)

Henry's Law constant = 5.65X10-14 atm-cu m/mole at 25 °C (est)

pKa = 5.22 (weak base)

133.23 Ų [M+H]+ [CCS Type: TW]

Stable up to 310 °C. Stable to hydrolysis for 28 days at up to 70 °C|Hydroxyl radical reaction rate constant = 1.26X10-12 cu cm/molec-sec at 25 °C (est)

Safety Information

NONH for all modes of transport

2

36/37/38

26-36

XZ1056500

Xi

No hydrolysis was observed < or = 70 deg C for 28 days. Stable <310 deg C.

P261-P305 + P351 + P338

H315-H319-H335

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/

|Warning|H315 (21.57%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 204 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

Dry chemical, foam or carbon dioxide

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/

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/|For more Preventive Measures (Complete) data for CYROMAZINE (7 total), please visit the HSDB record page.

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.

Toxicity

LD50 Mouse (M, F) oral 2029 mg/kg|LD50 Rabbit (M,F) oral 1467 mg/kg|LD50 Rat oral 3387 mg/kg /Technical cyromazine/|LC50 Rat inhalation >2.720 mg/L air/4 hr|LD50 Rat percutaneous >3100 mg/kg

/BIRDS and MAMMALS/ Acute oral and dietary avian toxicity studies suggest that cyromazine is no more than slightly toxic to birds. Chronic toxicity effects on birds have been domonstrated with two species. Cyromazine significantly reduced the number of normal mallard duck hatchlings at 300 ppm (NOAEC = 75 ppm). In another study, there may have been a slight treatment related increase in the number of male bobwhite quail that exhibited regressing testes at 300 ppm (NOAEC = 75 ppm).|/AQUATIC SPECIES/ Cyromazine has been shown to be practically non-toxic to freshwater fish (e.e., rainbow trout, bluegill sunfish, channel catfish) and freshwater invertebrated (i.e., water flea) on an acute basis. Chronic toxicity studies are also available for freshwater animals. Cyromazine significantly reduced fathead minnow length and weight at 36 mg/L (NOAEC - 14 mg/L) in a fish early life stage toxicity test. A freshwater invertebrate lifecycle test concluded that cyromazine significantly affected daphnid growth and reproduction at 0.64 mg/L (NOAEC = 0.31 mg/L). ... Given that cyromazine acts as a chitin synthesis inhibitor, there is a potential for chronic effects to estuariine/marine invertebrate survivorship, growth, and/or reproduction.|/OTHER TERRESTRIAL SPECIES/ Cyromazine is practically non-toxic to honey bees based on an acute contact toxicity study. However, given that cyromazine is an insecticide and acts as a chitin synthesis inhibitor, there is a potential for adverse effects to non-target terrestrial invertebrate.|/PLANTS/ There are no aquatic or terrestrial plant toxicity data available for cyromazine. However, risks to plants are presumed to be minimal given the mode of action.|For more Ecotoxicity Excerpts (Complete) data for CYROMAZINE (7 total), please visit the HSDB record page.

Cyromazine's production may result in its release to the environment through various waste streams; its use as an insect growth regulator(1) will result in its direct release to the environment(SRC).

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 °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 °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).

The rate constant for the vapor-phase reaction of cyromazine with photochemically-produced hydroxyl radicals has been estimated as 1.26X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12.7 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyromazine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Cyromazine is reported to be stable to aqueous hydrolysis for 28 days at up to 70 °C(3). Cyromazine is stable in aqueous solution exposed to sunlight(4). A photolysis rate constant of 0.0116 per day has been reported for cyromazine on soil surfaces exposed to artificial light(4); this corresponds to a half-life of 60 days(SRC), however, the UV spectrum nor intensity of the artificial light was not reported for comparison to natural sunlight(SRC).

An estimated BCF of 3 was calculated in fish for cyromazine(SRC), using an experimental log Kow of -0.06(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

199.53 L/kg|Based upon a variety of measured Koc values in different soils (range of 81 to 1,800), cyromazine has a recommended Koc of 765(1). According to a classification scheme(2), this recommended Koc value suggests that cyromazine is expected to have low mobility in soil. 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. Anilines (aromatic amines) are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower than predicted in some soils(SRC).

The Henry's Law constant for cyromazine is estimated as 5.65X10-14 atm-cu m/mole(SRC) derived from its vapor pressure, 3.36X10-9 mm Hg(1), and water solubility, 13,000 mg/L(2). This Henry's Law constant indicates that cyromazine is expected to be essentially nonvolatile from water surfaces(2). Cyromazine is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 3.36X10-9 mm Hg at 25 °C(1).

Occupational exposure to cyromazine may occur through inhalation and dermal contact with this compound at workplaces where cyromazine is produced or used. (SRC)

Drug Information

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.

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. (See all compounds classified as Insecticides.)

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.|For more Absorption, Distribution and Excretion (Complete) data for CYROMAZINE (10 total), please visit the HSDB record page.

Cyromazine was well absorbed after oral administration /to rats/. ... 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.|Urine from a female rat given a single oral dose of 14C-cyromazine (uniformly triazine ring labeled) of 0.5 mg/kg bw was analyzed using TLC and a cation exchange column chromatography system. With both systems the majority of the urinary radioactivity was determined to be in the form of unchanged parent compound. Unchanged parent compound in urine accounted for about 80% of the administered dose. Three metabolites were detected with each system and were presumed to be the same compounds. These metabolites accounted for 2.2-3.2%, 3.0-5.5%, and 4.6-5.3% of the administered dose, respectively, but no identification was made. Fecal material from a male rat given the same dose as the above female was found to contain little unchanged parent compound: <0.1% of the administered dose. The same three metabolites as observed in urine were found and represented 0.1, 0.1 and 4.1% of the administered dose, respectively.|One male and one female albino Sprague-Dawley rats were given diet containing 3000 ppm of 14C-cyromazine for 10 days. In the male the liver was found to contain 31.3 ppm cyromazine and 0.96 ppm melamine and the kidney 62.4 ppm cyromazine and 1.3 ppm melamine. In the female liver residues were 13.2 ppm and 0.51 ppm and kidney residues 22.2 and 0.68 ppm of cyromazine and melamine, respectively. This study indicated that there was some conversion of cyromazine to melamine in vivo.|Urine from male and female monkeys (Macaca fasicicula) given single oral doses of 14C-cyromazine (uniformly triazine ring labeled) of 0.05 or 0.5 mg/kg bw by capsule was found to have the majority of the radioactivity present in the form of unchanged parent compound. Regardless of dose 93.6-96.1% of the urinary radioactivity was present as unchanged cyromazine. Additionally, 2.9-6.4% of the radioactivity as identified as melamine ... In a second study with the same strain of monkey given the same dose levels, urine collected during the first 24 hours after dosing had 95-100% of the recovered radioactivity in the form of unchanged cyromazine. In one male dosed at 0.05 mg/kg bw, no melamine was detected in the urine. In one female at 0.05 mg/kg bw and one monkey of each sex given 0.5 mg/kg bw 3.0-3.9% of the urinary radioactivity was in the form of melamine.|For more Metabolism/Metabolites (Complete) data for CYROMAZINE (9 total), please visit the HSDB record page.

Insect growth regulator with contact action, which interferes with moulting and pupation. When used on plants, action is systemic.|Cyromazine is an effective insecticide used to control dipteran insects. Its precise mode of action is yet to be determined, although it has been suggested that it interferes with the hormone system, sclerotization of the cuticle, or nucleic acid metabolism. To understand the way in which cyromazine acts, /the authors/ positionally cloned a cyromazine resistance gene from Drosophila melanogaster. Six cyromazine resistance alleles had previously been generated by ethyl methanasulfonate treatment. Two of these failed to complement each other and here /the authors/ identify them as having independent non-sense mutations in CG32743, which is an ortholog of Smg1 of worms and mammals and encodes a phosphatidylinositol kinase-like kinase (PIKK). RNAi experiments confirm that cyromazine resistance can be achieved by knocking down CG32743. These are the first cyromazine resistant mutations identified at the nucleotide level. In mammals Smg1 phosphorylates P53 in response to DNA damage. This finding supports the hypothesis that cyromazine interferes with nucleic acid metabolism.

/SRP:/ Basic Treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Encourage patient to take deep breaths. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . /Irritating materials/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation at the first sign of upper airway obstruction may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... Use proparacaine hydrochloride to assist eye irrigation ... . /Irritating materials/|Gastrointestinal decontamination. If a large amount of the fungicide has been ingested in the last few hours, and if copious vomiting has not already occurred, it may be reasonable to consider GI decontamination. Activated charcoal can be used along with the addition of the cathartic sorbitol to the charcoal slurry. If sorbitol is given separately, it should be diluted with an equal volume of water before administration. No more than one dose of sorbitol is recommended and it should be used with caution in children and the elderly. If contact with the toxicant has been minimal (for example, oral contamination only, promptly flushed out of the mouth), administration of charcoal without a cathartic, followed by careful observation of the patient, probably represents optimal management. /Substituted benzenes/|Skin decontamination. Dermal contamination should be washed off with soap and water. Flush contamination from the eyes with copious amounts of water. If irritation persists, specialized medical care should be obtained. /Substituted benzenes/

/OTHER TOXICITY INFORMATION/ EPA has concluded that only residues of the parent compound cyromazine need to be regulated and used for risk assessment and is proposing that melamine, a metabolite of cyromazine, be removed from the tolerance expression as a residue of toxicological concern. ... EPA has reassessed the weight-of-the evidence for both cyromazine and melamine with particular reference to their carcinogenic potential. Cyromazine is classified as a group ``E'' carcinogen (no evidence of carcinogenicity) with an chronic RfD of 0.0075 mg/kg/day with an uncertainty factor (UF) of 100 using a no observed adverse effect level (NOAEL) of 0.75 mg/kg/day and a lowest observed adverse effect level (LOAEL) of 7.5 mg/kg/day. ... Melamine produced bladder tumors only in the male rat urinary bladder at very high doses i.e., at a threshold effect >10,000 ppm in the diet. These tumors were due to the accumulation of stones (hard crystalline solids) which caused irritation and secondarily resulted in the formation of tumors; therefore melamine is not considered to be a direct carcinogen by the Agency. In addition, only about 10% of cyromazine is converted to melamine in vivo...

2-cyclopropylamino-4,6-diamino-s-triazine

Cyromazine Use and Manufacturing

Methods of Manufacturing

By reacting cyanuric chloride with cyclopropylamine to produce 2-cyclopropylamino-4, 6-dichloro-s-triazene, and then reacting with ammonia to produce 2-cyclopropylamino-4-chloro-6-amino-s-triazene , And finally reacted with ammonia to produce cyromazine.

Uses

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. Agricultural uses of cyromazine - 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.

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.

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|For more Formulations/Preparations (Complete) data for CYROMAZINE (7 total), please visit the HSDB record page.

EPA has begun to implement a new Registration Review program intended to make sure that, as the ability to assess risk evolves and as policies and practices change, all registered pesticides continue to meet the statutory standard of no unreasonable adverse effects. The Agency plans to review each registered pesticide every 15 years. EPA has created the following estimated timeline for completion of the cyromazine registration review: Public comment period for Cyromazine Docket March-June 2007. Final Workplan through Public comment on Final Work Plan: August 2007-December 2011; Public comment period for proposed regulatory review decision: March 2012; Final Decision September 2012. First approved in the U.S. as a registered product in 1985, cyromazine is not subject to reregistration (no Reregistration Eligibility Document (RED)).

Analysis of products and residues is by HPLC and by GLC.|Determination of cyromazine residues in crops using gas HPLC on a LiChrosorb-NH2 column with acetonitrile-water (9+1) as the mobile phase and UV detection at 214 nm. Recoveries ranged from 64.7 to 92.8% for duplicate lettuce samples fortified at the 4.02 and 8.04 ppm levels.|Cyromazine was separated from melamine using high performance liquid chromatography.

Determination of cyromazine residues in animal tissues and eggs using a HPLC on a Zorbax-NH2 column with acetonitrile water (19+1) as the mobile phase and UV detection at 214 nm. Recoveries of 108.7 and 101.3% for duplicate samples of chicken liver fortified at the 0.3 ppm level; recoveries were 68.7 and 64.3% for duplicate egg samples fortified with cyromazine at the same level. Flow rate is 0.7 ml/min. Detection limit is 0.05 ppm.

Agrochemicals -> Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Cyromazine has known environmental transformation products that include Melamine and NOA 435343.

Computed Properties

Molecular Weight:166.18
XLogP3:-0.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:166.09669434
Monoisotopic Mass:166.09669434
Topological Polar Surface Area:103
Heavy Atom Count:12
Complexity:148
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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