N-Cyclopropyl-1,3,5-triazin-2,4,6-triamin

Pesticide -> EPA IRIS

Insecticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Other Insecticides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Cyromazine) -> USDA PDB

log Kow = -0.06 (pH 7.0)

0.05

Colorless crystals

White crystalline solid

All in g/kg, 20 °C: In methanol 22, isopropanol, 2.5, acetone, 1.7, n-octanol 1.2, dichloromethane 0.25, toluene, 0.015, hexane 0.0002

In water, 1.30X10+4 mg/L at 25 °C, pH 7.1

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

1.30E+04 mg/L @ 25 °C (exp)

224.9 °C

219 - 222 °C

Colorless or white solid; [HSDB]

Solid

Positive

3.13

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

135.6 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID6023999]

133.23 Ų [M+H]+ [CCS Type: TW]

Warning

H315 (53.7%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 82 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Commission Regulation (EC) No 1490/2002

Cyromazine is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2009/77/EC, Reg. (EU) 2022/801, Reg. (EU) No 540/2011

Status: Active Update: 07-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/33022

Cyromazine: Does not have an individual approval but may be used under an appropriate group standard

TLV Basis: bodyweight effects; hematological effects; [ACGIH] No occupational adverse effects reported; Melamine, a metabolite, causes urinary bladder calculi (NOAEL = 150 mg/kg/day) and bladder cancer (NOAEL = 225 mg/kg/day); These bladder tumours are thus an effect that occurs at high doses, having a threshold that is well above the expected human exposure through residues. [WHO JMPR: Cyromazine]

Tolerances are established for residues of the insecticide cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) in or on the following raw agricultural commodities: [Table#6103]

The additive cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) may be safely used in accordance with the following conditions: (i) It is used as a feed additive only in feed for chicken layer hens and chicken breeder hens at the rate of not more than 0.01 pound of cyromazine per ton of poultry feed. (ii) It is used for control of flies in manure of treated chicken layer hens and chicken breeder hens. (iii) Feeding of cyromazine-treated feed must stop at least 3 days (72 hours) before slaughter. If the feed is formulated by any person other than the end user, the formulator must inform the end user, in writing, of the 3-day (72 hours) preslaughter interval. (iv) To ensure safe use of the additive, the labeling of the pesticide formulation containing the feed additive shall conform to the labeling which is registered by the U.S. Environmental Protection Agency, and the additive shall be used in accordance with this registered labeling. (v) Residues of cyromazine are not to exceed 5.0 parts per million (ppm) in poultry feed.

Tolerances are established for the indirect or inadvertent residues of cyromazine (N -cyclopropyl-1,3,5-triazine-2,4,6-triamine), in or on the raw agricultural commodities when present therein as a result of the application of cyromazine to growing crops listed in paragraph (a)(1) of this section. [Table#6104]

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 121301; Type of Pesticide: Conventional - Insecticide; Use Site: Food use, ornamentals; Year: 1985.

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.

Do not contaminate water, food, or feed by storage or disposal practices. Store in a cool, dry place. Do not store this product under wet conditions. /Technical cyromazine/

Store in well-ventilated, secure area out of reach of children and animals.

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/

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/

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.

Tolerances are established for residues of the insecticide cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) in or on the following raw agricultural commodities: [Table#6101]

The additive cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) may be safely used in accordance with the following conditions: (i) It is used as a feed additive only in feed for chicken layer hens and chicken breeder hens at the rate of not more than 0.01 pound of cyromazine per ton of poultry feed. (ii) It is used for control of flies in manure of treated chicken layer hens and chicken breeder hens. (iii) Feeding of cyromazine-treated feed must stop at least 3 days (72 hours) before slaughter. If the feed is formulated by any person other than the end user, the formulator must inform the end user, in writing, of the 3-day (72 hours) preslaughter interval. (iv) To ensure safe use of the additive, the labeling of the pesticide formulation containing the feed additive shall conform to the labeling which is registered by the U.S. Environmental Protection Agency, and the additive shall be used in accordance with this registered labeling. (v) Residues of cyromazine are not to exceed 5.0 parts per million (ppm) in poultry feed.

Tolerances are established for the indirect or inadvertent residues of cyromazine (N -cyclopropyl-1,3,5-triazine-2,4,6-triamine), in or on the raw agricultural commodities when present therein as a result of the application of cyromazine to growing crops listed in paragraph (a)(1) of this section. [Table#6102]

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.

LD50; Species: Anas platyrhynchos (Mallard duck) oral >2510 mg/kg for 14 days

LC50; Species: Anas platyrhynchos (Mallard duck) dietary >5620 ppm for 8 days

LD50; Species: Colinus virginianus (Northern bobwhite) oral 1785 mg/kg for 14 days (95% confidence interval: 1444-2206 mg/kg)

LC50; Species: Colinus virginianus (Northern bobwhite) dietary >5620 ppm for 8 days

For more Ecotoxicity Values (Complete) data for CYROMAZINE (9 total), please visit the HSDB record page.

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).

/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

Hematologic

7.5 x 10 ^-3 mg/kg-day

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).

/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...

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).

Tolerances are established for residues of the insecticide cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) in or on the following raw agricultural commodities: [Table#6103]

The additive cyromazine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) may be safely used in accordance with the following conditions: (i) It is used as a feed additive only in feed for chicken layer hens and chicken breeder hens at the rate of not more than 0.01 pound of cyromazine per ton of poultry feed. (ii) It is used for control of flies in manure of treated chicken layer hens and chicken breeder hens. (iii) Feeding of cyromazine-treated feed must stop at least 3 days (72 hours) before slaughter. If the feed is formulated by any person other than the end user, the formulator must inform the end user, in writing, of the 3-day (72 hours) preslaughter interval. (iv) To ensure safe use of the additive, the labeling of the pesticide formulation containing the feed additive shall conform to the labeling which is registered by the U.S. Environmental Protection Agency, and the additive shall be used in accordance with this registered labeling. (v) Residues of cyromazine are not to exceed 5.0 parts per million (ppm) in poultry feed.

Tolerances are established for the indirect or inadvertent residues of cyromazine (N -cyclopropyl-1,3,5-triazine-2,4,6-triamine), in or on the raw agricultural commodities when present therein as a result of the application of cyromazine to growing crops listed in paragraph (a)(1) of this section. [Table#6104]

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 121301; Type of Pesticide: Conventional - Insecticide; Use Site: Food use, ornamentals; Year: 1985.

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.

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.

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.

Used as insecticide (acts as insect growth regulator); as veterinary ectoparasiticide; [HSDB] A selective insecticide used on vegetable crops; {WHO JMPR: Cyromazine]

Farming (Pesticides) [Category: Industry]

For cyromazine (USEPA/OPP Pesticide Code: 121301) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Cyromazine is an insecticide used on a variety of crops such as beans, celery, onions, root crops, leafy vegetables, and vegetable cucurbits. Cyromazine is also used as an insecticide for landscape and greenhouse ornamentals, as a seed treatment in bulb onions. There are no residential uses of cyromazine.

Cyromazine is registered for fly control in mushroom houses, and as a feed-through fly control agent for horse and chicken manure, and for fly larvae control in manure and floor areas of chicken facilities. Cyromazine is registered for control of the Colorado potato beetle, a variety of fly pest, fly larvae, leafminers, and maggots. There is a pending registration application for use of cyromazine as a larvacide spray on manure in cattle and hog facilities.

Cyromazine is in the triazine family of pesticides. While most triazines have herbicidal qualities, cyromazine is an insect growth regulator.

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).

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)).