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Cyanazine

Cyanazine structure

Cyanazine 

structure
  • CAS No:

    21725-46-2

  • Formula:

    C9H13ClN6

  • Chemical Name:

    Cyanazine

  • Synonyms:

    Propanenitrile,2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methyl-;Propionitrile,2-[[4-chloro-6-(ethylamino)-s-triazin-2-yl]amino]-2-methyl-;2-[[4-Chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropanenitrile;SD 15418;WL 19805;2-(4-Chloro-6-ethylamino-s-triazin-2-ylamino)-2-methylpropionitrile;2-Chloro-4-ethylamino-6-(1-methyl-1-cyanoethylamino)-s-triazine;DW 3418;2-Chloro-4-ethylamino-6-(α,α-dimethylcyanomethyl)amino-1,3,5-triazine;Bladex;Cyanazine;Bladex 80WP;2-[[4-Chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]-2-methylpropionitrile;Fortrol;Cyanazin;Bladex 50WP;Gramex;11096-88-1;12679-53-7

  • Categories:

    Agrochemicals  >  Herbicides

Description

Cyanazine is an off-white to tan crystalline solid. Molecular . Hazard identification (based on NFPA-704 M Rating System): Health 2, flammability 1, reactivity 0. Soluble in water. Physical properties may be altered by car- rier solvents used in commercial formulations.


Cyanazine appears as colorless crystals. Non corrosive when dry. Used as a selective systemic herbicide.|WHITE CRYSTALLINE POWDER.


Cyanazine appears as colorless crystals. Non corrosive when dry. Used as a selective systemic herbicide.|Cyanazine is a chloro-1,3,5-triazine that is 2-chloro-1,3,5-triazine substituted by an ethyl amino and a (2-cyanopropan-2-yl)amino group at positions 6 and 4 respectively. It has a role as a herbicide, an environmental contaminant and a xenobiotic. It is a 1,3,5-triazinylamino nitrile and a chloro-1,3,5-triazine.

Cyanazine Basic Attributes

240.69

240.69

244-544-9

W34C4P18WD

0391

2811|2763

DTXSID1023990

White crystals

2933699011

Characteristics

86.5

2.24

Off-white Granular Powder

129 g/cm3 @ Temp: 20 °C

167.5-169 °C

349.9±44.0 °C at 760 mmHg

100 °C

1.614

Solubility in water, g/100ml at 25°C: 0.02

APPROX 4°C

Vapour pressure at 20°C: negligible

Oral-Rat LD50: 149 mg/kg; Oral-Mouse LD50: 380 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Henry's Law constant= 2.57X10-10 atm-cu m/mole @ 25 °C

pKa = 0.87

155.79 Ų [M+H]+

White crystalline solid /Technical cyanazine (> or equal 95% pure)/

Stable at pHs between 5.0 and 9.0, but is hydrolyzed by strong acids and bases.

Amines, Phosphines, and Pyridines

A triazine derivative.

Formulated products are noncorrosive

Safety Information

III

6.1(b)

UN 2588/2811

3

22-50/53-39/23/24/25-23/24/25-36-20/21/22-11-52/53

37-60-61-45-36/37-36-26-16

UG1490000

Xn;N,N,Xn,T,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Very stable to heat and UV light. Stable between pH 5 and 9, but hydrolyzed by strong acids and alkalis.

P273-P501

H302-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. For electric vehicles or equipment, ERG Guide 147 (lithium ion batteries) or ERG Guide 138 (sodium batteries) should also be consulted. (ERG, 2016)|Not combustible. Liquid formulations containing organic solvents may be flammable.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Danger|H301 (18.75%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P363, P391, P405, and P501|Aggregated GHS information provided by 176 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P201, P202, P260, P264, P270, P273, P280, P281, P301+P312, P305+P351+P338, P308+P313, P309+P311, P314, P330, P337+P313, P391, P405, and P501

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: SMALL FIRE: Dry chemical, CO2 or water spray. LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. (ERG, 2016)|In case of fire in the surroundings, use appropriate extinguishing media.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)

Use with adequate ventilation. Avoid eye, skin contact, breathing dust, or contact with water, feed, or food.|SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Do NOT wash away into sewer. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Cool. Dry.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly.

Animal tests show that this substance possibly causes malformations in human babies.

AVOID EXPOSURE OF (PREGNANT) WOMEN! IN ALL CASES CONSULT A DOCTOR!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety spectacles.

In a study of two watersheds in GA, seasonal losses of cyanazine via field runoff have been reported to range from 0.07 to 1.0% of total field application(1). The daily flux of cyanazine to the Mississippi River and 6 of its tributaries from agricultural use was estimated for the period between May 1991 through March 1992; the estimated daily fluxes over the 11 month period were summed to produce the following total estimated discharges over the 11 month period: Minnesota River: 5.9 kg; White River: 1.6 kg; Illinois River: 23 kg; Platte River: 12 kg; Missouri River: 40 kg; Ohio River: 11 kg; Mississippi River at Clinton, IA: 9.1 kg; Mississippi River at Thebes, IL: 99 kg; Mississippi River at Baton Rouge, LA: 130 kg(2).

SEDIMENT: Cyanazine was not detected in sediment samples collected from a small agricultural catchment in Sweden between 1990-1991 (detection limit 20-100 ug/kg, dry weight); the average concentration of cyanazine in surface water within the catchment was 0.09 to 0.03 ug/l for 1990 and 1991, respectively(1). Cyanazine was found at 90 percent of the sites examined in a survey of 28 agrochemical dealerships in Iowa; the maximum concentration was 4,600 ppb(2).

Toxicity

highly toxic

LD50 Rat oral 288 mg/kg|LD50 Rabbit dermal <2000 mg/kg|LD50 Mouse oral 380 mg/kg|LD50 Rat dermal >1200 mg/kg|For more Non-Human Toxicity Values (Complete) data for CYANAZINE (16 total), please visit the HSDB record page.

Cyanazine's use as a pesticide for the control of annual grasses and broadleaf weeds(1) is expected to result in its direct release to the environment(SRC). However, in the US, registration is canceled as of January 1, 2000(2). Sale and distribution of existing stock may continue through September 30, 2002, and all use is prohibited after December 31, 2002(2).

TERRESTRIAL FATE: The half-life of cyanazine determined in field studies ranged from 6-30 days (1). The half-life of cyanazine measured under laboratory conditions range from 3-19 days at 30 and 5 degrees C, respectively (34% moisture content) to greater than 200 days at 20 degrees C and 8% moisture content(1). Based on a classification scheme(2) and measured Koc values of 182-372(3,4), cyanazine is expected to have moderate mobility in soil(SRC). Volatilization of cyanazine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 2.57X10-10 atm-cu m/mole(5). Cyanazine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.38X10-07 mm Hg(6). Photodegradation of cyanazine is not expected to be an important fate process(7).|AQUATIC FATE: Based on a classification scheme(1) and measured Koc values of 182-372(2,3), cyanazine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 2.57X10-10 atm-cu m/mole(4). Volatilization was not an important process in a model ecosystem study(5). According to a classification scheme(6), an estimated BCF of 5(SRC), from its log Kow of 2.22(7), suggests the potential for bioconcentration in aquatic organisms is low. A half-life of 30-40 days was measured for cyanazine in constructed wetlands; the cyanazine metabolites deethylcyanazine and cyanazine amide were detected in the constructed wetlands(8). At 25 °C and pH range 5.5-9, the un-catalyzed aqueous hydrolysis half-life is at least 200 days(9). Laboratory studies have suggested, however, that natural water constituents, such as humic and fulvic acid, may catalyze the chemical hydrolysis(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyanazine, which has a vapor pressure of 1.38X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyanazine 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 41 hours(SRC), calculated from its rate constant of 9.31X10-12 cu cm/molecule-sec at 25 °C(SRC), determined using a structure estimation method(3). Particulate-phase cyanazine may be removed from the air by wet and dry deposition(SRC). Cyanazine has been detected in widespread rainwater monitoring studies(4); degradation rates while associated with rainwater and clouds are unknown(SRC); these monitoring studies suggest that widespread atmospheric dispersal is possible(4).

When applied to soil, cyanazine degraded primarily to des-isopropyl atrazine. The anticipated amide, the initial hydrolysis product of the nitrile, was also seen.|The rate constant for the vapor-phase reaction of cyanazine with photochemically-produced hydroxyl radicals has been estimated as 9.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of approximately 41 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).|The aqueous hydrolysis of cyanazine was studied over a temperature range of 25-75 °C and a pH range of 1.5-12(1); at 25 °C and a pH range of 5.5-9.9, the hydrolysis half-life is at least 200 days(1); at 25 °C and pH 4 the half-life is 205 hr(1); an end-product of both base and acid-catalyzed hydrolysis was 2-hydroxy-4-carboxyisopropylamino-6-ethylamino-1,3,5-triazine(1); 2-chloro-4-amidoisopropylamino-6-ethylamino-1,3,5-triazine was isolated during alkaline hydrolysis(1). These half-lives indicate that hydrolysis will not be an important removal mechanism unless it is catalyzed by some agent in the environment(SRC). Hydrolysis studies conducted at 50 °C with a variety of acid catalysts have demonstrated that the second-order catalytic hydrolysis rate is related to the pKa of the acid catalyst (rate increases as pKa decreases)(2); the practical implications are that cyanazine may undergo some catalytic degradation in aqueous solutions of humic-fulvic acid constituents in the environment(2). In 1967 to 1970 field trials, the half-life of cyanazine ranged from 1.3 to 5 weeks(3); breakdown of cyanazine in soil occurred (at least partially) through hydrolysis of the nitrile group to the amide and then to the acid(4); some hydrolysis of the 2-chloro group also occurred(4); after 32 days, the major degradation product was the acid, together with small amounts of the hydroxy acid(4).

Using a system developed by R. Metcalf, (14)C-ring-labeled cyanazine was introduced into an aquatic model ecosystem. After 35 days, analyses of the components were conducted. In addition to unchanged cyanazine, N-deethylcyanazine, cyanazine amide, N-deethylcyanazine amide, and three unknowns were found in the water. Radioactivity did not increase in the food chain of algae to mosquitoes to fish (a decrease from 1.3 to 0.05 ppm was observed), indicating that this compound does not concentrate through the food chain.|An estimated BCF of 5 was calculated for cyanazine(SRC), using a log Kow of 2.22(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. In a model ecosystem study, cyanazine did not bioaccumulate in any of the organisms in the ecosystem that included algae, clam, crab, daphnia, elodea, fish, mosquito and snail(4).

190.55 L/kg|An experimentally determined Koc of 200 has been reported (soil type not given)(1). A Koc of 182 was measured in a silty soil(2). Using soil TLC, an intermediate mobility was measured in a silty clay loam (Rf of 0.39) and a high mobility was measured in a sandy loam (Rf of 0.74)(3); the avg Koc for these two soils was reported as 372(4). A Koc of 97 was measured for a silt loam soil from a corn field(5); in field studies using this soil (0.70% organic carbon), a max of 0.04% of surface application was lost through subsurface tile drains(5). In field studies, cyanazine did not leach below a 0.20 m depth in a sandy loam soil(6) or below a 0.30 m depth in a silt loam soil(7). However, cyanazine leached through 0.90 m of a soil composed of 29% clay, 49% silt and 22% sand(8). Cyanazine is reversibly adsorbed to soil particles(9); adsorption increases with increased organic matter content, decreasing soil water and decreasing pH(9). The adsorption of cyanazine by microbial biomass has been observed(10). According to a classification scheme(11), the measured Koc values suggest that cyanazine is expected to have moderate to high mobility in soil(SRC).

The Henry's Law constant for cyanazine is 2.57X10-10 atm-cu m/mole(1). This Henry's Law constant indicates that cyanazine is expected to be essentially nonvolatile from water surfaces(2). Cyanazine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.38X10-7 mm Hg(3).

GROUNDWATER: In a 1969 to 1978 monitoring analysis of well water from 237 wells from agricultural areas of Ontario, Canada, cyanazine was detected in only two wells at levels of 0.1-10 ug/l(1). Cyanazine was reportedly found at 1.1 ppb concn in one of 82 wells in a central PA study where the water level was about 75 below land surface(2); it was also detected at low levels (0.1-1.0 ppb) in three wells in Iowa during springtime(2,3). According to the USEPA's Groundwater Data Base, cyanazine has been detected in groundwaters from IA, IL, MD, MN, PA and VT and concentrations ranging from 0.01 to 80 ppb(4). Cyanazine was detected in 3 of 283 water samples collected between April 1991 and December 1992 from three springs and two streams located within an agricultural area with karst topography in southeast West Virginia; the low rate of detection may reflect the relatively high limit of detection of the analytical method used (20 ug/l)(5). Cyanazine was detected in groundwater samples collected between 1990-1992 at 4 of 5 sites in Arkansas, where the pesticide was mixed or loaded, at concentrations ranging from 0.5-1.8 ug/l(6). Cyanazine was detected in 7 of 303 monitoring wells located in 12 midwestern states of the U.S. that were sampled between 1991-1994(7). Cyanazine amide, a metabolite of cyanazine, was detected in 11 of 100 of the monitoring wells that were sampled for both cyanazine and cyanazine amide during the same time period(7). Cyanazine was found at 90 percent of the sites examined in a survey of 28 agrochemical dealerships in Iowa; the maximum concentration was 92 ppm(8).|DRINKING WATER: Drinking water samples collected in Dresden, Ontario between 1982 and 1987 contained annual mean cyanazine levels ranging from <0.05 to 4.6 ug/l(1); the highest reported level was 10 ug/l(1). In July 1986, 33 treated public water sources were analyzed for cyanazine following a rainstorm(2); cyanazine was detected in 30 of 33 waters at levels of 0.12-20 ug/l(2). Cyanazine was detected in 36 of 201 wells in rural Missouri between December 1987 and September 1989 at concentrations ranging from 0.3-1.1 ug/l; all of the detections were in samples collected from shallow wells (12-100 feet) and 16 of the 22 detections were in wells that were less than 60 feet deep(3). According to the USEPA Pesticides in Ground Water Database, which contains data gathered from 1971-1991, cyanazine was detected in 155 of 7,468 potable water wells at concentrations ranging from trace-29.0 ug/l(4).|SURFACE WATER: Between 1983 to 1991, the US Geological Survey collected and analyzed more than 4000 water samples collected at 8 monitoring stations located on rivers and tributaries of the Lake Erie basin(1); maximum cyanazine concentrations detected at the stations ranged from 1.36 to 24.77 ug/l(1); most samples were below detection limits (0.05 ug/l)(1); average concentrations of positive detections ranged from 0.05 to 0.40 ug/l(1); most detections occurred during agricultural use seasons indicating field runoff(1). During a Jan 1981 to Dec 1985 water monitoring analysis of the mouths of Grand, Saugeen and Thames Rivers (Ontario, Canada), cyanazine was detected at concentrations of the 1 ug/l magnitude in 8 of 96 Grand River samples, 5 of 143 Saugeen River samples, and 32 of 222 Thames River samples(2); during a Jan 1986 to Dec 1990 water monitoring analysis of the mouths of Grand, Saugeen and Thames Rivers (Ontario, Canada), cyanazine was detected in 2 of 250 Grand River samples, 2 of 154 Saugeen River samples, and 3 of 70 Thames River samples(3). Water samples collected from the Sydenham River (Dresden, Ontario) between 1982 and 1987 contained annual mean cyanazine levels ranging from 0.5 to 3.6 ug/l(4); the highest reported level was 10 ug/l(4).|SURFACE WATER: Monitoring of the Des Moines River (Iowa) and an associated reservoir during Sep 1977 to Nov 1978 found the highest cyanazine concentrations (71-457 ng/l) during the agriculturally active months of May through Aug(1); it was noted that agricultural runoff from the upstream watershed was a major source of river pollution(1); levels during Sep to Dec were 2-151 ng/l and below detection limits during Jan to Apr(1). Cyanazine was positively detected in 15 water samples collected from various Swedish streams during 1985-1987 with max concentrations of 0.7 ug/l(2). Cyanazine was detected in 4 of 31 NJ surface water samples at concentrations of 0.025 to 0.07 ppb (sampling dates and locations not reported)(3). Monitoring conducted by the US Geological survey at 17 sampling stations on the Mississippi River and its tributaries during May to Jun 1988 detected cyanazine levels ranging from 17 to 647 ng/l(4). Water samples collected from the Cedar River (IA) from May 1984 through Nov 1985 were found to contain cyanazine at levels below 1 ug/l(5). Twenty-five water samples were collected between April 1993 through April 1994 at the mouths of two tributaries of the South Platte River in Colorado: Lonetree Creek which drains an agricultural area and Cherry Creek which drains an urban area(6). The median and maximum concentrations of cyanazine detected were 0.058 and 5.9 ug/l in Lonetree Creek and <0.013 (method detection limit) and 0.045 in Cherry Creek, respectively(6). A total of 43 samples were collected from 43 locations within the Lower Susquehanna and the Potomac River Basins in June 1994. Concentrations of cyanazine in tributaries of the Susquehanna River ranged from <0.013 to 3.90 ug/l; the highest concentration was recorded after a storm event(7). Concentrations of cyanazine in tributaries to the Potomac ranged from <0.013 to 0.069 ug/l(7). Concentrations of cyanazine in the Susquehanna and Potomac Rivers ranged from <0.013 to 0.39 ug/l and <0.013 to 0.02 ug/l, respectively(7). Samples were collected from 59-62 lake, stream and river sites in Arkansas between 1989-1991 at times selected to coincide with times when pesticides are applied(8). Cyanazine was detected in 7.4% of 485 samples; percentiles of the detected concentrations were (ug/l): min, 0.1; 25th, 0.4; 50th, 0.9; 75th, 1.1; max, 16.6(8).|RAIN/SNOW/FOG: Collection of 14 to 24 rainwater samples at each of four US sites (West Lafayette, IN; Tiffin, OH; Parsons, WV; Potsdam, NY) in the spring and summer of 1985 resulted in cyanazine detections ranging from 0.1 (detection limit) to 1.0 ug/l(1); cyanazine was found in nearly 35% of all samples collected(1). Cyanazine was not detected in samples of rain collected in 1996 at a location in Hannover, Germany that was approximately 15 km away from any agricultural areas(2). Cyanazine was detected in 7.2% of 2085 samples collected between March 1990 and September 1991 from 81 National Atmospheric Deposition Program/National Trends Network Sites located throughout the U.S.; percentiles of the measured concentrations were (ug/l): 90th, <0.05; 95th, 0.07; 99th, 0.27; max, 2.0(3).

... Manufacture, formulation and application of /cyanazine/.|Occupational exposure to cyanazine occurs through dermal contact and inhalation of aerosols and dust, especially to workers applying the compound as a herbicide(1). Monitoring data indicate that the general population may be exposed to cyanazine via ingestion of contaminated drinking water(SRC).

Drug Information

Pesticides used to destroy unwanted vegetation, especially various types of weeds, grasses (POACEAE), and woody plants. Some plants develop HERBICIDE RESISTANCE. (See all compounds classified as Herbicides.)

Cyanazine is rapidly metabolized and eliminated from the body by rats and dogs (within 4 days). Research showed that after the oral administration of (14)C cyanazine the material was absorbed and metabolized rapidly; about 40% of the administered dose was excreted in the urine and 47% in the feces.|In rats and dogs, following oral administration, cyanazine is rapidly metabolized and eliminated within approximately 4 days.

The primary pathway for metabolism of cyanazine in rats is N-deethylation to yield an amine. In addition, N-acetylcysteinyl derivatives were found in the urine. Dechlorination resulting in a 2-hydroxy triazine was noted, as well as the cyano group hydrolyzed to an amide and then further to a carboxyl analog. The 2-hydroxy compound was a major metabolite in the feces. The bile contained glutathione conjugates.|Redroot pigweed did not hydroxylate cyanazine but did conjugate this compound. In corn, hydrolysis, N-dealkylation and glutathione /conjugation/ were observed. The hydroxy-acid and dealkylated hydroxy-acid were observed in corn. Presence of the carboxyl group on the isopropylamino side chain suppressed dealkylation of the ethylamino group.|Fall panicum and green foxtail contain water and chloroform soluble metabolites 5 days after foliar (14)C cyanazine application. The nitrile group was hydrolyzed and the triazine two position was hydroxylated.|Cyanazine degradation proceeds initially by hydrolysis of the nitrile group and slower hydrolysis of the 2-chloro group. 2-Hydroxycyanazine is the major metabolite found in rat feces. The rat also produces the 4-amino derivative and the N-acetylcysteinyl derivative and hydrolyzes the cyano group to the corresponding amide and carboxy derivatives.

A photosynthesis inhibitor.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. (ERG, 2016)|Teratogens

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)


Fresh air, rest. Refer for medical attention.


Remove contaminated clothes. Rinse and then wash skin with water and soap.


First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Skin decontamination: Skin contamination should he treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be, obtained without delay.|Gastrointestinal decontamination: Ingestion of these herbicides are likely to be followed by vomiting and diarrhea due to their irritant properties. Management depends on: (1) the best estimate of the quantity ingested, (2) time elapsed since ingestion, and (3) the clinical status of the subject. Activated charcoal is probably effective in limiting irritant effects and reducing absorption of most or all of these herbicides. Aluminum hydroxide antacids may be useful in neutralizing the irritant actions of more acidic agents. Sorbitol should be given to induce catharsis if bowel sounds are present and if diarrhea has not already commenced. Dehydration and electrolyte may be severe enough to require oral or intravenous fluids. There are no specific antidotes for poisoning by these herbicides. In the case of suicidal ingestions, particularly, the possibility must always be kept in mind that multiple toxic substances may have been swallowed. If large amounts of herbicide have been ingested and the patient is seen an hour of the ingestion, gastrointestinal decontamination should be considered. If the amount of ingested herbicides was small, if effective emesis has already occurred, or if treatment is delayed, administer activated charcoal and sorbitol mouth.|Intravenous fluids: If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and fluid balance and administer intravenous infusions of glucose, normal saline, Ringer's solution, or Ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained.|Treatment of poisoning with cyanazine would be symptomatic.

2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-s-triazine

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Cyanazine Use and Manufacturing

Methods of Manufacturing

The hydroxyisobutyronitrile is reacted with ammonia to prepare aminoisobutyronitrile, and then the acetone suspension of cyanuric chloride and aminoisobutyronitrile are cooled to 0°C, and 50% sodium hydroxide solution is added with stirring. After the reaction mixture is neutral, ethylamine and sodium hydroxide are added to prepare cyanotriazine.

Uses

Herbicide.

Approximately 23 million pounds of cyanazine were used annually for agricultural purposes in the U.S. between 1987-1989.

USEPA/OPP Pesticide Code 100101; Trade Names: Bladex; Payze; SD 15418; Bladex 80WP; Cyanazine SD 15418; DW 3418; fortol; Fortrol; WL 19805.|Available as a granular product, wettable powder, flowable concentrate, emulsifiable concentrate, and soluble concentrate. Sold in combination with atrazine, alachlor, metolachlor, paraquat, and butylate.|Dry flowable, liquid|Technical grade >95% pure|Suspension concentrate, wettable powder, granule, DF

Reported application rates vary, 0.54-4.8 lb/acre depending upon the crop.|U.S.: Registration is canceled as of January 1, 2000. Sale and distribution of existing stock may continue through September 30, 2002, and all use prohibited after December 31, 2002.

Product analysis is by ir or glc or hplc. ... Residues in plants determined by glc with ECD or FID ... and in soils by glc or hplc ... . In water by lc with uv detection ... .|AOAC Method 992.14. Pesticides and Metabolites in Finished Drinking Water by Liquid Chromatographic Method.|AOAC Method 991.32. Cyanazine in Technical Products and Pesticide Formulations by Liquid Chromatographic Method.|EMSLC Method 508.1. Determination of Chlorinated Pesticides, Herbicides, and Organohalides by Liquid-Solid Extraction and Electron Capture Gas Chromatography (Revision 1). Detection limit= 0.007 ug/l.|For more Analytic Laboratory Methods (Complete) data for CYANAZINE (6 total), please visit the HSDB record page.

Agrochemicals -> Herbicides|Health Hazards -> Teratogens|Pharmaceuticals|Herbicides|HERBICIDES

Computed Properties

Molecular Weight:240.69
XLogP3:2.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:240.0890221
Monoisotopic Mass:240.0890221
Topological Polar Surface Area:86.5
Heavy Atom Count:16
Complexity:272
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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