Cyprazine

Pesticides -> Herbicides, Triazine

Pesticide (Cyprazine) -> USDA PDB

log Kow= 3.06

3.06

31570.0 ppm in acetonitrile at 25 °C; 15470.0 ppm in toluene at 25 °C; 7280.0 ppm in benzene at 25 °C; 2230.0 ppm in carbon tetrachloride at 25 °C; 10.0 ppm in n-hexane at 25 °C; 233429.0 ppm in dimethylformamide at 25 °C; 190710.0 ppm in acetic acid @ 25 °C; 142430.0 ppm in acetone @ 25 °C; 94290.0 ppm in ethyl acetate @ 25 °C; 73820.0 ppm in chloroform @ 25 °C; 52860.0 ppm in ethanol @ 25 °C

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

325 °F (OPEN CUP)

156 °F (CLOSED CUP)

0.0000003 [mmHg]

3X10-7 mm Hg @ 20 °C

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Triazine herbicides disrupt photosynthesis in plants, but are generally not highly toxic in studies of laboratory animals; [HSDB] For the triazine herbicides, systemic toxicity unlikely unless large amounts are ingested; May cause irritation; [EPA Pesticides, p. 121]

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.

Under section 3(c)(2)(b) of FIFRA, the Data Call-In Program, existing registrants are required to provide EPA with needed studies. For cyprazine, responses to the data call-in have been evaluated and a chronic/tox decision has been made for suspension/cancellation.

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.

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/

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.

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/

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).

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)

Preliminary medical exam to detect chronic diseases of CNS, liver, heart, kidneys, lung & skin, as well as endocrinological or immunological disturbances, should ... /protect/ susceptible individuals. ... Periodical medical exam of internal organs, skin & eyes is important to avoid chronic occupational intoxications. It should include lab tests & patch tests if necessary. /Herbicides/

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.

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).

MOST OF THE TRIAZINES ARE VERY STABLE IN SOIL & DISSIPATE SLOWLY THROUGH ... DEGRADATION OF MOLECULAR SIDE CHAINS BY SOIL MICROORGANISMS. /TRIAZINES/

The presence of 2-chloro-4-amino-6-isopropylamino-1,3,5-triazine (the product of decyclopropanation of cyprazine and also the product of deethylation of atrazine) in tile-drain runoff water from a treated field may be due to biodegradation of cyprazine(2). However, at least some(2) of the 2-chloro-4-amino-6-ispropylamino-1,3,5-triazine, may have been present due to previous treatments of the field with atrazine(2). It has been reported that s-triazines which are similar in structure to cyprazine can be utilized by certain soil microorganisms as a source of energy(1).

Cyprazine is expected to biodegrade slowly based on biodegradation studies of simazine, which showed no degradation in 3.5 months(1) in soils. The half-life of cyprazine in unfiltered river water was 191 days (6 °C) and 190 days (22 °C)(2). The half-life of cyprazine in filtered river water was 160 days (6 °C) and 254 days (22 °C)(2). The half-life in seawater was 260 days (6 °C) and 184 days (22 °C)(2). No biodegradation was observed in ultrapure water(2).

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.

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).

SUBACUTE TOXICITY (ORAL INGESTION): A. TECHNICAL MATERIAL (1) ALBINO RATS 90 DAYS, 4 TO 50 MG/KG/DAY, NO DELETERIOUS EFFECTS. (2) BEAGLE DOGS, 90 DAYS, 2.5 MG/KG/DAY, NO DELETERIOUS EFFECTS; 12.5 MG/KG/DAY, DEPRESSED WT GAIN IN MALE BEAGLES; FEMALE BEAGLES NOT AFFECTED. (3) BEAGLE DOGS 18 DAYS, 50 MG/KG/DAY, FREQUENT VOMITING & DIARRHEA; HYPEREMIA OF SMALL INTESTINE.

A. SKIN (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL) FEMALE RABBITS (DUTCH BELTED STRAIN) WERE EXPOSED FOR SINGLE 24 HR PERIOD TO UNDILUTED EMULSIFIABLE CONCENTRATE DOSES OF 1.0-4.0 ML/KG WERE MODERATELY IRRITATING TO RABBIT SKIN. SKIN WAS NORMAL @ END OF 14 DAYS. B. EYES (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL). UNDILUTED EMULSIFIABLE CONCENTRATE WAS FOUND TO BE MILDLY IRRITATING TO RABBIT EYES (NEW ZEALAND STRAIN). SIGNS OF IRRITATION DISAPPEARED IN 5-7 DAYS FOLLOWING A SINGLE EXPOSURE. C. INHALATION (1) EMULSIFIABLE CONCENTRATE (1 LB AI/GAL). SINGLE 1 HR EXPOSURE OF RATS TO AEROSOLS OF THE EMULSIFIABLE CONCENTRATION (DILUTED WITH XYLENE) @ CONCN OF 1.8 & 7.78 MG EMULSIFIABLE CONCENTRATION /l OF AIR YIELDED FOLLOWING INFORMATION ON AUTOPSY 14 DAYS POST EXPOSURE: 1.78 MG/l- NO PHARMACOLOGICAL OR TOXICOLOGICAL SIGNS WERE OBSERVED ON AUTOPSY. 7.78 MG/L- 3 OUT OF 10 RATS HAD LUNGS CONTAINING NUMEROUS SMALL ABSCESSES.

CYPRAZINE, ATRAZINE & SIMAZINE WERE NOT MUTAGENIC IN 4 SALMONELLA TESTER STRAINS (TA98, TA100, TA1535, AND TA1538) AT UP 100 UG/PLATE IN PRESENCE OF AROCHLOR-INDUCED S9.

/TRIAZINES/ ... MAY EXERT ACTIVITY VIA EITHER FOLIAR UPTAKE OR SOIL APPLICATION OR BOTH. BROADER ACTIVITY APPEARS TO OCCUR VIA SOIL UPTAKE, WHILE THE FOLIAR ACTIVE CMPD ... TEND TO BE LIMITED IN THEIR ACTIVITY TO THE SIMPLE ANNUALS OR MERELY TO FOLIAGE KILL OF PERENNIALS. /TRIAZINES/

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).

Under section 3(c)(2)(b) of FIFRA, the Data Call-In Program, existing registrants are required to provide EPA with needed studies. For cyprazine, responses to the data call-in have been evaluated and a chronic/tox decision has been made for suspension/cancellation.

... 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 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.

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.

Used formerly as a herbicide; [HSDB]

Farming (Pesticides) [Category: Industry]

Herbicide /former use/

For cyprazine, responses to the data call-in have been evaluated and a chronic/tox decision has been made for suspension/cancellation.

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.