Cyprazine

227.69

227.69

245-338-1

GAD00GI28B

DTXSID6040294

WHITE CRYSTALS

2933699011

62.7

3.06

1.24 g/cm³

167 °C

399ºC at 760mmHg

156 DEG F (CLOSED CUP)

1.674

6.9 ppm in water @ 25 deg C; 195.4 ppm @ 40 deg C

3X10-7 mm Hg @ 20 deg C

Oral-Rat LD50: 1200 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

ODORLESS

THE CHLORINE CAN BE REPLACED SLOWLY BY HYDROXYL BY REFLUX IN AQ ACIDS OR BASES

NONCORROSIVE UNDER NORMAL USE CONDITIONS

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

STABLE UNDER ORDINARY CONDITIONS

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.

The use of personal protective equipment such as glasses, synthetic gloves & /NIOSH approved breathing apparatus/ ... is important. /Herbicides/

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itslef does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol foam", dry chemical or carbon dioxide. /Triazine pesticide, solid NOS/

Only clean clothing ... should be worn & clothing should be changed daily ... Adequate sanitary facilites & washing water should be provided for workers to wash before meals. Smoking & consumption of alcoholic drinks before & during the handling of herbicides should be forbidden. Contaminated clothing should be removed immediately & a hot bath taken if possible. Personal hygiene should be encouraged. /Herbicides/|SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Triazine pesticide, solid NOS/|Personnel protection: Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Triazine pesticide, solid NOS/

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.

The major hazards encountered in the use and handling of cyprazine stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this odorless, white crystalline substance may occur from its use as an herbicide. Effects from exposure may include shortness of breath, muscle spasms, ataxia, and anorexia. In activities and situations where over exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. While cyprazine does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving cyprazine, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Cyprazine may be shipped domestically via air, rail, road, and water, in containers bearing the label "Poison". Small dry spills of cyprazine may be placed into a clean, dry, covered container for later disposal (liquid solutions are first absorbed in sand or other noncombustible absorbent). Large liquid spills should be diked far ahead to prevent cyprazine from entering water sources and sewers. Before implementing land disposal of cyprazine, consult with regulatory agencies for guidance.

The concn of cyprazine in tile-drain runoff water from corn fields treated post-emergence with cyprazine ranged <0.01 to 0.57 ug/l and <0.01 to 4.13 ug/l (detection limit 0.01 ug/l) for the first and second seasons of treatment, respectively(1)

moderately toxic

LD50 MOUSE MALE ORAL 1306 MG/KG|LD50 MOUSE FEMALE ORAL 1056 MG/KG|LD50 RAT MALE & FEMALE ORAL 516 MG/KG|LD50 RAT PERCUTANEOUS 3000 MG/KG|For more Non-Human Toxicity Values (Complete) data for CYPRAZINE (7 total), please visit the HSDB record page.

CYPRAZINE CAN ENTER THE WATER FROM ITS USE AS HERBICIDE ON CROPLAND.|Cyprazine's former production and use as a herbicide(1) resulted in its direct release to the environment(SRC).

TERRESTRIAL FATE: THE LONG SOIL PERSISTENCE OF THESE CMPD DOES ... CREATE THE PROBLEM OF SOIL CARRY OVER, WHICH CAN DAMAGE SUCCEEDING CASH CROPS. THEREFORE EXTREME CAUTION MUST BE TAKEN IN THEIR APPLICATION ON CROPLAND TO AVOID SUCH INJURY TO FOLLOWING CROPS. /TRIAZINES/|TERRESTRIAL FATE: DEGRADATION PRODUCTS OF CYPRAZINE & ATRAZINE WERE MONITORED OVER A 3 YEAR PERIOD IN SOIL (PREDOMINANTLY LOAMY SANDS & SAND CLAY LOAMS) IN FIELDS USED TO GROW MAIZE. THE LEVEL OF HYDROXYTRIAZINES IN SOIL SAMPLES RANGED FROM 0.05 TO 0.5 PPM & THEY WERE THE PREDOMINANT TRIAZINE RESIDUES IN THE FIELDS DURING SPRING & AUTUMN.|TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.06(2) and a regression-derived equation(3), indicates that cyprazine is expected to have low mobility in soil(SRC). Volatilization of cyprazine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.6X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Cyprazine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3X10-7 mm Hg(5). Cyprazine is expected to biodegrade slowly based on biodegradation studies of simazine in soil, which showed no degradation in 3.5 months(6).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.06(2) and a regression-derived equation(3), indicates that cyprazine is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.6X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Cyprazine may be subject to hydrolysis in water based on comparison with structurally similar compounds(SRC). The hydrolysis half-life of simazine was reported as 70 days at pH 5(5). According to a classification scheme(6), an estimated BCF of 22(SRC), from its log Kow(2)and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low. Cyprazine is expected to biodegrade slowly in water with half-lives of 160-260 days(8). The half-life of cyprazine was 37 days (river water) and 68 days (seawater)(8) when the test system was exposed to natural sunlight, suggesting that photolysis may be important in sunlit surface waters(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyprazine, which has a vapor pressure of 3X10-7 mm Hg at 20 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase cyprazine 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 20 hours(SRC), from its rate constant of 1.9X10-11 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3). Particulate-phase cyprazine may be removed from the air by wet and dry deposition(SRC). Cyprazine may be susceptible to photodegradation based upon photolysis data for s-triazines similar in structure to cyprazine such as simazine(4), but the kinetics of this reaction are unknown(SRC).

MOST OF THE TRIAZINES ARE VERY STABLE IN SOIL & DISSIPATE SLOWLY THROUGH CHEM CONVERSION TO HYDROXY FORM ... /TRIAZINES/|PHOTODECOMPOSITION APPEARS TO BE MINIMAL ON SOILS. /TRIAZINE HERBICIDES/|HYDROLYSIS & OXIDATION ARE THE GENERAL ROUTES OF SOIL METABOLISM FOR TRIAZINE HERBICIDES. /TRIAZINE HERBICIDES/|The rate constant for the vapor-phase reaction of cyprazine with photochemically-produced hydroxyl radicals has been estimated as 1.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 20 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Cyprazine may be subject to hydrolysis in water based on comparison with structurally similar compounds(SRC). The hydrolysis half-life of simazine was reported as 70 days at pH 5(2). Cyprazine may be susceptible to photodegradation based upon photolysis data for s-triazines similar in structure to cyprazine such as simazine(3), but the kinetics of this reaction are unknown(SRC). The half-life of cyprazine was reported as 190 days and 184 days in river and seawater, respectively in closed bottle tests conducted in the absence of sunlight(4). The half-lives decreased to 37 days (river water) and 68 days (seawater) when exposed to sunlight(4), suggesting that photolysis may occur in sunlit surface water(SRC).

An estimated BCF of 22 was calculated for cyprazine(SRC), using a log Kow of 3.06(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.

ADSORPTION OF TRIAZINES THROUGH AN EXCHANGE PROCESS TO ORGANIC MATTER & CLAY MINERALS IS DEPENDENT ON PH OF SOLN & ACIDITY OF ADSORBENT SURFACE. HYDROGEN BONDING & HYDROPHOBIC BONDING ARE OTHER MECHANISMS BY WHICH SOIL ORGANIC MATTER ADSORBS TRIAZINE HERBICIDES, ESP AT HIGHER PH LEVELS. ... TRANSPORT FROM SOIL TO WATER OCCURS IN SOLUTION AND IN SEDIMENTS. /TRIAZINE HERBICIDES/|The Koc of cyprazine is estimated as 1,100(SRC), using a log Kow of 3.06(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyprazine is expected to have low mobility in soil.

The Henry's Law constant for cyprazine is estimated as 2.6X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that cyprazine is essentially nonvolatile from water surfaces(2). Cyprazine's Henry's Law constant(1) indicates that volatilization from moist soil surfaces is not expected(SRC). Cyprazine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3X10-7 mm Hg(3).

CYPRAZINE WAS APPLIED POST-EMERGENCE TO CORN PRODUCTION PLOTS DRAINED BY TILE DRAINS (DEPTH 1.2-1.6 M). WATER SAMPLES WERE COLLECTED FROM THE TILE OUTLETS & ANALYZED. CONCN FROM TILE OUTLETS RANGED FROM 0.000 TO 0.57 UG/L.|SURFACE WATER: Cyprazine was detected, not quantified, in 0.3% of creek water samples from the Hillman Creek watershed in southwestern Ontario, Canada(1). Cyprazine was found in 0.9% of samples of waters collected from 11 agricultural watersheds in Ontario, Canada during 1975-1976 at a max concn of 0.3 ng/l(2). The avg concn ranged from not detected to 0.16 ng/l and from not detected to 0.04 ng/l during May 1975-April 1976 and May 1976-April 1977, respectively, and the overall averages were 0.04 and 0.02 ng/l, respectively(2).

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

BOTH FOLIAR & ROOT ABSORPTION OCCUR /IN PLANTS/. ... CHEMICAL MOVES ACROPETALLY BUT NOT BASIPETALLY.|RATS ADMIN SINGLE ORAL DOSES OF (14)CARBON-LABELED CYPRAZINE EXCRETED 97.6% WITHIN 72 HR (72.7% IN URINE & 24.9% IN FECES). LESS THAN 1% OF RADIOACTIVITY WAS DETECTED IN EXPIRED AIR AS (14)CARBON DIOXIDE. RATS CONTAINED 7.5% OF RADIOACTIVITY @ SACRIFICE, 72 HR AFTER DOSING.

CYPRAZINE WAS RAPIDLY METABOLIZED TO WATER SOL CMPD IN LEAVES OF TOLERANT CORN, SORGHUM, & SUGAR CANE & MORE SLOWLY IN SUSCEPTIBLE BARLEY, BY DISPLACEMENT OF 2-CHLORO GROUP BY GLUTATHIONE OR GAMMA-GLUTAMYLCYSTEINE. THE RESULTING SULFIDE CONJUGATES WERE AMONG THE MOST ABUNDANT WATER SOL METABOLITES PRESENT 6 HR AFTER TREATMENT.|CHLOROTRIAZINES REACTED /WITH A PLANT ENZYME RESPONSIBLE FOR THEIR CONJUGATION/ IN THE DECREASING ORDER OF GS-13529, ATRAZINE, CYPROZINE, PROPAZINE, & SIMAZINE WITH NO CORRELATION TO THEIR WATER SOLUBILITY OR PARTITION COEFFICIENTS. APPARENTLY, INTACT ALKYLAMINO SUBSTITUENTS @ BOTH C4 & C6 POSITIONS ARE PREFERRED STRUCTURES FOR CONJUGATION SINCE MOST OF THE ENZYME ACTIVITY WAS LOST WHEN ONE OF THE SIDE CHAIN ALKYL GROUPS WAS REMOVED.|IN CORN, RAPID CONJUGATION OF FOLIARLY APPLIED CYPROZINE ... WAS OBSERVED, BUT DECR DRASTICALLY IN COURSE OF 3 WK. AT THAT TIME THE INCR HYDROXY DERIVATIVES REACHED CONCN OF THE CONJUGATES.|IN RATS ADMIN SINGLE ORAL DOSES OF (14)CARBON LABELED CYPRAZINE, FOUR URINARY METABOLITES WERE IDENTIFIED: 2-HYDROXY-4,6-DIAMINO-S-TRIAZINE; 2-CHLORO-4,6-DIAMINO-S-TRIAZINE; 2-HYDROXY-4-AMINO-6-ISOPROPYLAMINO-S-TRIAZINE; & 2-CHLORO-4-AMINO-6-ISOPROPYLAMINO-S-TRIAZINE.|For more Metabolism/Metabolites (Complete) data for CYPRAZINE (6 total), please visit the HSDB record page.

... Their chief mode of action appears to involve carbohydrate metabolism. The chlorinated s-triazines inhibit starch accumulation by blocking the production of sugars. Similar behavior has been shown for the methoxy & methylthio-s-triazines. It has been reported that the s-triazines affect the tricarboxylic acid cycle with activation of phospho-phenyl pyruvate-carboxylase causing the disapperance of sucrose & glyceric acid with the formation of aspartic & malic acids. /s-Triazines/|THE MODE OF ACTION ... APPEARS TO BE RELATED TO THEIR EXTREMELY EFFECTIVE INHIBITION OF PHOTOSYNTHESIS BY BLOCKING THE HILL REACTION STEP, WHICH IS PROBABLY THEIR PRIMARY MECHANISM OF ACTION. /TRIAZINES/|SINCE CHLOROSIS IS THE FIRST SIGN OF THE EFFECT OF TRIAZINES ON PLANTS, INTERFERENCE WITH CARBON DIOXIDE ASSIMILATION & SUGAR FORMATION CAN BE EXPECTED. STUDIES SHOWING THAT HILL REACTION IS INHIBITED CONFIRMED THIS. /TRIAZINES/

cyprazine

Compounds were supplied as wettable powders & emulsifiable concentrates & in herbicidal mixtures with other triazines, but it has been largely superseded by other agents.|OUTFOX IS AN EMULSIFIABLE LIQ CONTAINING 12.8% OR 1.2 LB/IMPERIAL GAL OF CYPRAZINE. PREFOX IS AN EC CONTAINING 4 LB/US GAL OF S-ETHYL DIETHYLTHIOCARBAMATE & 3/4 LB/US GAL OF CYPRAZINE, CORRESPONDING TO 50.3% & 9.9% RESPECTIVELY, OF THE FORMULATION WEIGHT.|HERBICIDAL SYNERGISTIC MIXTURES CONTAINING 1-METHYL-4-PHENYLPYRIDINIUM CHLORIDE & CYPRAZINE, DICAMBA, OR 2,4-DB WERE ESPECIALLY EFFECTIVE FOR CONTROL OF NUTSEDGE.|CYPRAZINE MODIFIED SELECTIVITY OF LARGE NUMBER OF HERBICIDES. POSTEMERGENCE TREATMENT WITH MIXTURE 0.56 KG CYPRAZINE/HA & 0.14 KG BARBAN/HA GAVE HIGHER HERBICIDAL EFFECT & LOWER PHYTOTOXICITY TO RICE THAN DID BARBAN ALONE.

DISCOVERED IN 1965 AND DEVELOPED BY GULF RESEARCH & DEVELOPMENT COMPANY. INTRODUCED BY GULF OIL CORPORATION AS AN EXPERIMENTAL HERBICIDE IN 1969; US PATENTS 3,451,802 & 3,503,971. CODE NUMBER S-6115.

ELECTROLYTIC CONDUCTIVITY DETECTOR & A (63)NICKEL ELECTRON CAPTURE DETECTOR WERE USED TO DETERMINE NANOGRAM AMOUNTS OF TRIAZINE HERBICIDES SEPARATED BY GAS CHROMATOGRAPHY. CYPRAZINE WAS INCLUDED.|Five classes of triazine herbicides were studied by combined high performance liq chromatography mass spectrometry. Separations were performed on a reversed C8 column, using acetonitrile water as mobile phase, followed by in line UV & mass spectral analysis. Positive & negative ion spectra were recorded. Most of herbicides were more sensitive in the positive ion mode. Cyprazine was one the herbicides included in this study.|GAS CHROMATOGRAPHIC ANALYSIS OF SOIL SAMPLES CONTAINING TRIAZINE HERBICIDES WAS CARRIED OUT BY USE OF A HALL ELECTROLYTIC CONDUCTIVITY DETECTOR. RECOVERY STUDIES INDICATED THAT HYDROXY-CYPRAZINE COULD BE EXTRACTED MORE EFFICIENTLY FROM FORTIFIED SOIL SAMPLES THAN COULD N-DEALKYLATED HYDROXY-S-TRIAZINE.

HERBICIDES