Prometon

225.29

225.29

216-548-0

DY7SQ0399L

163048

DTXSID6022341

Colorless powder|White, crystalline|Crystalline solid

29336990

72

2.99

1.088 at 20 deg C (units not specified)

91-92 °C

366.8°C (rough estimate)

124.6±22.6 °C

1.7610 (estimate)

In water, 750 mg/L at 20 deg C

0-6°C

2.3X10-6 mm Hg at 20 deg C

Oral-Rat LD50: 503 mg/kg; Oral-Mouse LD50: 2160 mg/kg

Combustion produces toxic nitrogen oxide gas

Henry's Law constant = 9.09X10-10 atm-cu m/mol at 25 °C (est)

pKa = 4.3 at 21 °C

HEATING PROMETONE @ 260 °C PRODUCES ISOMERIZATION & DISMUTATION PRODUCTS|Stable to hydrolysis at 20 °C in neutral, slightly acidic or slightly alkaline media. Hydrolyzed by acids or alkalis on warming. Decomposed by u.v. irradiation.|Relatively stable at neutral pH, but hydrolyzes in strong acid or base; Decomposed by UV light.|Hydroxyl radical reaction rate constant = 3.79X10-11 cu cm/molec-sec at 25 °C (est)

Non-corrosive under common application conditions

UN2763 Triazine pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.UN2763

22-36/37/38

26-36

XY4200000

Xn

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

Shelf life of at least 3 to 5 yr when stored in dry place at minimum storage temperatures (Pramitol 25E > 32 deg F).

P261-P305 + P351 + P338

H302-H315-H319-H335

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.|PESTICIDE DISPOSAL: Wastes resulting from use of this product may be disposed of on site or at an approved waste disposal facility. CONTAINER DISPOSAL: Triple rinse (or equivalent) and offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill, or by incineration, or by burning, if allowed by state and local authorities. If burned, keep out of smoke. /Pramitol 4RR/|Do not contaminate water used for irrigation or domestic purposes. ... Do not contaminate water when disposing of equipment washwaters ./Pramitol 4RR/|Safe Disposal of Pesticides. An empty pesticide container can be as hazardous as a full one because of residues left inside. Never reuse such a container. When empty, a pesticide container should be rinsed carefully three times and the rinsewater thoroughly drained back onto the sprayer or the container previously used to mix the pesticide. Use the rinsewater as a pesticide, following label directions. Replace the cap or closure securely. Dispose of the container according to label instructions. Do not puncture or burn a pressurized container like an aerosol - it could explode. Do cut or puncture other empty pesticide containers made of metal or plastic to prevent someone from reusing them. Wrap the empty container and put it in the trash after you have rinsed it.

Fry DM; Environ Health Perspect 103 (Suppl 7): 165-71 Oct 1995. Reproductive effects in birds exposed to pesticides and industrial chemicals.|Loosli R; Toxicology 91 (1): 59-62 1994. Health surveillance of pesticide workers: a manual for occupational health professionals triazines|Barcelo D; J Chromatogr 643 (1-2): 117-143 1993. Environmental Protection Agency and other methods for the determination of priority pesticides and their transformation products in water.|Lintelmann J et al; Fresenius' J Anal Chem 346 (10-122): 988-994 1993. Behavior of polycyclic aromatic hydrocarbons (PAHs) and triazine herbicides in water and aquifer materials of a drinking water recharge plant: I. The are of investigation and the determination methods for PAHs and triazine herbicides in the aqueous matrix.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 197 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Causes substantial but temporary eye injury. Harmful if swallowed, inhaled, or absorbed through skin. Do not get in eyes or on clothing. Wear protective eyewear (goggles, face shield, or safety glasses). Avoid contact with skin. Avoid breathing vapor or spray mist. Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash clothing before reuse. /Pramitol 3.75%/|The use of personal protective equipment such as glasses, synthetic gloves & ... /NIOSH approved breathing apparatus/ is important. /Herbicides/

Nonflammable.

Extinguish fire using agent suitable for type of surrounding fire. ... Use water in flooding quantities as fog. Use "alcohol foam" ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticide (compounds and preparations), solid (insecticides, agricultural, not elsewhere classified, other than liquid)/|Avoid breathing dusts & fumes from burning material. Keep upwind. /Triazine pesticide, solid, not otherwise specified, (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/

For minor spills. leaks, etc.. follow all precautions indicated on /the pesticide/ label and clean up immediately. Take special care to avoid contamination of equipment and facilities during cleanup procedures and disposal of wastes. In the event of a major spill, fire, or other emergency, call 1-800-535-5053 (INFOTRAC). day or night. /Pramitol 4RR/|After Applying a Pesticide, Indoors or Outdoors. To remove pesticide residues, use a bucket to rinse tools or equipment three times, including any containers or utensils that you used when mixing the pesticide. Then pour the rinsewater into the pesticide sprayer and reuse the solution by applying it according to the pesticide product label directions. After applying any pesticide wash your hands and any other parts of your body that may have come in contact with the pesticide..To prevent tracking pesticides inside, remove or rinse your boots or shoes before entering your home. Wash any clothes that have been exposed to a lot of pesticide separately from your regular wash.

Avoid inhalation of dust. Avoid contact with skin.|Only clean clothing ... should be worn & clothing should be changed daily ... Adequate sanitary facilities & 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/|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, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/ Not elsewhere classified.|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, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/|For more Preventive Measures (Complete) data for PROMETON (8 total), please visit the HSDB record page.

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.

A skin and eye irritant.

The major hazards encountered in the use and handling of prometone stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this colorless to white, crystalline substance may occur from its manufacture, formulation, and 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 prometone does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving prometone, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Prometone may be shipped domestically via air, rail, road, and water, in containers bearing the label "Poison". Prometone should be stored in cool, dry areas, away from sparks, flames, and other sources of ignition. Small dry spills of prometone 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 prometone from entering water sources and sewers. Before implementing land disposal of prometone, consult with regulatory agencies for guidance.

Prometon was detected, not quantified, in the secondary effluent of a municipal treatment plant in Illinois that received industrial discharges(1).

SOIL: Prometon was detected 20.4 m below surface level at an effluent-irrigated citrus grove site in Israel at a concn of 0.03 mg/L(1). Prometon was detected in 28 of 822 soil samples collected from 49 agrichemical facilities located throughout IL at a median concn of 151 ug/kg, range 45 to 1605 ug/kg(2).

Prometon was not detected in the atmosphere of the Mississippi River valley(1). Samples collected from 1,700 Mississippi River miles from New Orleans, LA, June 1st to St Paul, MN, June 10th 1994 contained no prometon with a detection limit of 0.90 ng/cu m(2).

moderately toxic

LD50 Rat oral 2980 mg/kg /Technical/|LD50 Rabbit percutaneous > 2000 mg/kg /Technical/|LC50 Rat inhalation > 3.26 mg/l/4 hr /Technical/|LD50 Rat oral 2276 mg/kg /Pramitol 25E/|For more Non-Human Toxicity Values (Complete) data for PROMETON (10 total), please visit the HSDB record page.

It is slightly toxic to birds & practically nontoxic to honeybees.|/PLANTS/ A photosynthetic inhibitor but may have additional effects.

Prometon's production may result in its release to the environment through various waste streams; its use as a non-selective systemic herbicide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 305(2) to 572(3), indicate that prometon is expected to have low to moderate mobility in soil(SRC). Volatilization of prometon from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.1X10-10 atm-cu m/mole(SRC) based upon its vapor pressure, 2.3X10-6 mm Hg(4), and water solubility, 750 mg/L(4). Prometon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Prometon exhibits a photodegradation half-life of 46.8 days on soil(5). Several soil bacteria and fungi are reported to attack prometon(6). However, it is not known whether biodegradation is the primary degradation process in soil(6). Average soil half-life is reported as 932 days(7).|AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 305(2) to 572(3), indicate that prometon is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 9.1X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 2.3X10-6 mm Hg(5), and water solubility, 750 mg/L(5). According to a classification scheme(6), an estimated BCF of 19(SRC), from its log Kow of 2.99(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Prometon is stable to photodegradation in water(9). Based upon degradation studies done in soil, it is not known whether biodegradation is the primary degradation process in water(10).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), prometon, which has a vapor pressure of 2.3X10-6 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase prometon 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 10 hours(SRC), calculated from its rate constant of 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase prometon may be removed from the air by wet or dry deposition(SRC). A 100 ppm prometon solution exposed to artificial sunlight in a photo reactor resulted in 1% loss in 135 minutes(4), suggesting a potential for direct photolysis(SRC).

The rate constant for the vapor-phase reaction of prometon with photochemically-produced hydroxyl radicals has been estimated as 3.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Prometon degraded very little in sterilized San Joaquin sandy loam soil with a 20% water content(2). 1,3,5-Triazines, such as prometon, have UV absorption bands whose tail extends beyond 290 nm(3), suggesting a potential for direct photolysis(SRC). Prometon is stable in water at 25 °C under sunlight but does exhibit a photodegradation half-life on sandy loam soil of 46.8 days, producing 6-methoxy-N-(1-methylethyl)-1,3,5-triazine-2,4-diamine(4). When a 100 ppm prometon solution at 50 °C was exposed to artificial sunlight in a photo reactor, 1% loss occurred in 135 minutes(5). The addition of 0.2% Tergitol TMN-10 surfactant had no significant effect on the photodegradation while Triton X-100 enhanced it(5). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(6). Catalyzed hydrolysis of prometon has been observed on montmorillonite clay(7). After the prometon is adsorbed on the calcium-saturated montmorillonite, protonation and hydrolysis readily occur(7).

An estimated BCF of 19 was calculated in fish for prometon(SRC), using a log Kow of 2.99(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).

398.11 L/kg|A mean Koc of 524.3 was reported for prometon in 29 soils(1). The Freundlich adsorption constant, K, and exponent, 1/n, for prometon on San Joaquin sandy loam (0.72% organic carbon, 9.7% clay, pH 6.2) at 25 °C were 2.94 and 0.81, respectively; the corresponding Koc is 408 at a concn of 1 ppm and 305 at a concn of 10.3 ppm(2). Koc values of 572 and 395 were determined in Hanford sandy loam (0.43% organic C, pH 6.05, 7.1% clay, 25.8% silt, 67.1% sand) and Tujunga loamy sand (0.33% organic C, pH 6.3, 4.5% clay, 13.5% silt, 82.0% sand), respectively(3). According to a classification scheme(4), these Koc values suggest that prometon is expected to have low to moderate mobility in soil(SRC). Only 0.1% of prometon applied to a 30.5 cm column and leached under unsaturated flow conditions with 1.2 cm of water/day, was found in leachate at the end of 30 days(5). Prometon was included in mobility class 3, on a scale from 1 (immobile) to 5 (very mobile)(6). Prometon is adsorbed onto soil humic acid, forming stable complexes(7). Ionic, hydrogen bonding, electron donor-acceptor, and covalent forces contribute to the binding. The fact that the basicity of several s-triazines, and hence their tendency to form ionic bonds, is not correlated with adsorptivity indicate that ionic bonding is not the primary factor governing adsorption(7). Data on the free radical content of humic acid adducts, demonstrate that electron donor-acceptor forces are particularly important in the binding of prometon to soil(7). The Freundlich adsorption constant, K, and exponent, 1/n, for prometon on Volcay bentonite at 25 °C was 150 and 0.64, respectively(8). The mean sorption coefficient (Kd) of 4.86 was given for 59 measured values(9). A pKa of 4.3 at 21 °C(10) indicates prometon will exist predominately in the unionized form under environmental pHs(SRC). Max adsorption of prometon onto soil organic matter occurred in the pH range 4.2 to 5.2; the addition of HCl or NaOH decreased adsorption(11). Approximately 52% of the prometon adsorbed by organic matter was desorbed with two extractions of 0.1 N NaCl(11).

ALTHOUGH INSUFFICIENT DATA ... /WERE/ OBTAINED TO PERMIT DEFINITE CONCLUSIONS ON THE RELATION BETWEEN SOIL PROPERTIES & LOSS BY VOLATILIZATION, PROMETONE LOSSES APPEARED TO BE DIRECTLY RELATED TO SAND CONTENT & INVERSELY RELATED TO PERCENTAGE OF CLAY & ORGANIC MATTER IN SOIL. PROMETONE DID NOT VOLATILIZE IN APPRECIABLE AMT FROM ... SHARKEY CLAY & DUNDEE SILT LOAM ... THE EFFECT OF MOISTURE ON VOLATILITIES OF SEVEN S-TRIAZINES WAS DETERMINED AT 45 °C ON TIFTON LOAMY SAND. ON WET SOIL THE ORDER OF LOSS OF HERBICIDES WAS TRIETAZINE > ATRAZINE > AMETRYN APPROX EQUAL TO PROPAZINE APPROX EQUAL TO PROMETRYN APPROX EQUAL TO PROMETONE > SIMAZINE, WHEREAS ON DRY SOIL THE LOSSES WERE NOT AS EXTENSIVE. THE ORDER WAS TRIETAZINE > PROPAZINE > ATRAZINE APPROX EQUAL TO SIMAZINE APPROX EQUAL TO PROMETONE > AMETRYN APPROX EQUAL TO PROMETRYN. ADSORPTION AND WATER SOLUBILITY WERE SUGGESTED AS FACTORS THAT CAN AFFECT THE RATE OF VAPORIZATION OF THESE HERBICIDES.|The Henry's Law constant for prometon is estimated as 9.1X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 2.3X10-6 mm Hg(1), and water solubility, 750 mg/L(1). This Henry's Law constant indicates that prometon is expected to be essentially nonvolatile from water surfaces and moist soil(2). Prometon is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

SURFACE WATER: In a survey of 11 agricultural watersheds in Ontario, prometon was found in 0.2% and 1.5% of samples in 1975-6 and 1976-7, respectively, with a mean concn of 0.02 ppb(1). Prometon was detected in selected streams feeding into Lakes Ontario, Erie, Huron and Lake St. Clair(2). Prometon was detected in the Mississippi River and its tributaries between July and Aug 1991 at concns ranging from not detected to 68 ng/L; the highest concn was detected in the Illinois River at Hardin, IL(3). Prometon was detected in 42% of water samples collected from the Susquehanna River Fall line at concns of 2-19 ng/L, mean 9 ng/L; max concn occurred in May(4). Prometon was detected in 60% of water samples collected from the Potomac River Fall line at concns of 8-17 ng/L, mean 14 ng/L; max concn occurred in June(4). Prometon was detected in 25% of water samples collected from the James River Fall line at concns of 2-18 ng/L, mean 6 ng/L; max concn occurred in April(4). From samples taken April 1993 to April 1994 in CO, prometon was detected in 100% of samples collected from a small agricultural area and in >90% of the samples collected from an urban area; median (max) concns were 0.0066 (0.11) and 0.063 (0.17) ug/L, respectively(5). Median (max) prometon concns in rivers and streams of the Midwestern US were <0.05 (<0.05), <0.05 (0.93), and <0.05 (0.24) ug/L in water samples collected prior to planting in March and April, after planting in May and June, and at harvest in Oct and Nov 1989, respectively(6). Mean prometon concns in water samples from five locations in the Yakima River Basin collected in Sept 1988, ng/L: 5.9 in Sulfur Creek; 5.1 in Granger Drain; 3.9 in Moxee Drain; 2.4 in Yakima River at Umtanum; and 4.6 in Yakima River at Kiona(7). Prometon was detected in 15 of 98 surface water samples from the Yakima River Basin, WA in 1999-2000(8).|SURFACE WATER: Prometon was detected in 12% of 339 samples collected from 150 Midwestern streams between 1989 and 1990, in 8.8% of 230 samples collected from the Mississippi River at Baton Rouge, LA between 1991 and 1994, and in 10% of 456 water samples collected from 76 reservoirs in 1992 and 1993(1). 53 Rivers in the Midwest, covering 9 states were analyzed for prometon, 13 of the 50 samples taken in 1989, 8 of the 52 samples in 1990, 4 of the 52 samples in 1994, and 19 of the 50 samples taken in 1995 contained prometon but at concns <0.05 ug/L(2). Propazine occurrences in midwestern streams were greater in 1995 than in 1989 and average concentrations were the same in 1995 and 1989(3). At least 75% of the surface water samples from a small central Indiana watershed tested positive for prometon(4). Prometon was detected in 40 of 142 samples taken from 4 sites in the San Joaquin river basin in 1993(5). Prometon was detected in 70.7% of samples taken in 8 urban and agricultural streams across the US in 1990 including Winnipauk, CT, Denver and Greeley, CO, Annandale, VA, Bridgeport, MD, Tallahassee and Hawkinsville, FL, Marietta and Cobb, GA, Las Vegas, NV, Niskayuna and Canajoharie, NY, Durham and Mt. Angel, OR(6). Prometon was detected in 16% of 70 agricultural streams in the upper midwest in August 1997(7).|GROUNDWATER: Between 1968 and 1978, only one well out of 237 in Ontario, Canada, analyzed because of suspected contamination, was found to contain prometon(1). In a survey of 303 wells conducted in the summer of 1991 in the corn- and soybean-producing region of the midcontinental US, prometon was detected more frequently (5%) than any other herbicide except atrazine; it was detected in 19 wells at a max concn of 0.60 ug/L(2). Prometon was detected in 44% of 78, 1% of 78, and 3% of 76 samples taken at Davis Spring, Blue Hole and Burns Cave, WV, respectively, in 1991(3). It was detected in water samples from the lower zone of the southern San Joaquin Valley in the summer of 1986 at a concn of 0.1 ug/L; in the summer of 1987, it was detected in the eastern San Joaquin valley at a concn of 1.0 ug/L(4). Prometon was detected in 100% of groundwater samples collected from alluvial wells in the Denver, CO metropolitan area at a max concn of 1.4 ug/L(5). Groundwater samples collected from domestic wells and springs in the Ozark Plateaus Province, April- Sept 1993, contained prometon at concns of 0.001-0.13 ug/L(6). Of 7,848 samples taken from 1991 to 1996 in the Nebraska management system evaluation area 126 samples contained prometon at > 0.05 ug/L(7). Prometon was detected in 15.1% of 106 municipal wells in IA tested during the summer of 1995(8). Prometon was found in 18.3% of 131 wells in IA, sampled 1995-1998(9). Prometon was found in a stream bed well and 1 of 9 ground water field blanks in a small central Indiana watershed(10). Prometon was found in 26.4% of 208 wells in 9 urban land use studies(11). Prometon was found in 49 of 4086 wells sampled as of Dec 1999 in CA(12).|DRINKING WATER: In a nationwide survey of pesticides in drinking water wells, prometon was detected in community water system wells (0.5%) and rural domestic wells (0.2%)(1). Prometon was detected in 8 wells in 6 CA counties out of 668 wells sampled in 32 counties; concn ranged form 0.05 to 0.55 ppb(2). Prometon was detected in 22 drinking water wells in the state of CA, sampled between 1975 to 1991, at a max concn of 1 ug/L(3). It was detected in Texas wells during 1987 and 1988 at concns ranging from 1.9 to 29.6 ug/L(4).|RAIN/SNOW: Prometon was detected in 0.3% of 1,056 rainwater samples collected in 10 Midwestern states in 1990 and 1991(1). Prometon was detected in urban and agricultural rainwater, Apr-Sep 1995 in MS(2). Prometon was found in 2 of 16, 4 of 16, 2 of 18, 4 of 18, 1 of 15, and 2 of 15 rainwater samples in Jackson, MS, Rolling Fork, MS, Iowa City, IA, Cedar Rapids, IA, Lake Harriet, MN and Princeton, MN, respectively, Apr-Sep 1995(3).

Prometon was identified in Florida orange oil(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 1,566 workers (114 of these are female) are potentially exposed to prometon in the US(1). The NOES Survey does not include farm workers. Occupational exposure to prometon may occur through inhalation of dust particles and spray mists, and dermal contact with this herbicide during and after its application and at workplaces where prometon is produced. Monitoring data and use indicate that the general population may be exposed to prometon via ingestion of drinking water, and dermal contact with this compound in herbicides where it is used(SRC).

When the rate of excretion of various s-triazines was determined, the time required for excretion of 50% of applied dose in lab animals was 12-26 hr, whereas corresponding figures for ruminants ranged from 1-2 days. The 2-methoxy-s-triazines seem to be the most rapidly eliminated derivatives as shown with prometone ...|Mono- & didealkylated parent compounds ... were identified in urine of rats & rabbits after application of several hundred mg/kg of nonlabeled simazine, atrazine, propazine, prometone and prometryn.|/Prometone is/ absorbed through both foliage & roots. /It is/ translocated from roots & stems acropetally.|/In the rat/ 2-methoxy-4,6-diamino-s-triazine & ammeline represented about 11 & 31%, respectively, of the 92% of radioactivity excreted with the urine.

Replacement of the methoxy group by a hydroxy group & oxidation of isopropyl groups to yield alcohol & carboxy derivatives gave rise to various minor metabolites /in urine of rats/.|Rats were administered (14)c-ring-prometone. Urine was collected and analyzed & eight metabolites were identified ... the major metabolites ... were ammeline (31.5%) & 2,4-diamino-6-methoxy-s-triazine (10-14%). other metabolites included: 2-amino-4-(1-carboxyethylamino)-6-methoxy-s-triazine; 2-amino-4-(1-carboxyethylamino)-6-hydroxy-s-triazine; 2-amino-4-methoxy-6-(2-propan-1-ol)amino-s-triazine; 2-amino-4-hydroxy-6-(2-propan-1-ol)amino-s-triazine; & 2-amino-4-hydroxy-6-isopropylamino-s-triazine.

In analyzing whether the triazines share a common mechanism of toxicity, /the EPA Office of Pesticide Programs/ OPP first examined the pesticides, atrazine, simazine, and cyanazine for inclusion in the initial common mechanism group. ... Toxicologically, the pesticides are positive for mammary gland tumors in female Sprague-Dawley (SD) rats, and atrazine and simazine have data suggesting that they interfere with the pituitary luteinizing hormone (LH) pre-ovulatory surge. OPP then examined whether any other 1,3,5-triazines or other pesticides or metabolites containing s-triazine rings shared these characteristics. A subset of eight pesticides containing the triazine moiety -- atrazine, simazine, propazine, cyanazine, terbutylazine, terbumeton, terbutryn, tribenuron methyl (Express) -- from this larger group were found to cause the similar toxic effect of inducing mammary gland tumors in only female rats but not male rats or both sexes of mice. Several triazine-containing pesticides do not cause that carcinogenic profile -- ametryn, prometryn, prometon, metsulfuron methyl, trisulfuron, chlorsulfuron, and DPXM6316 (Harmony). It should be pointed out that there is no known common mechanism of toxicity to group ametryn, prometryn, prometon, metsulfuron methyl, trisulfuron, chlorsulfuron, or DPX-M6316 (Harmony) with the other eight pesticides.|Simazine, as well as other triazines, appears to act on metabolism of plant hormones, particularly plant growth regulation hormones. This conclusion results from studies in which triazines (including simazine), when applied at low rates, resulted in more vigorous and healthy plants than controls, yet at higher rates of application, resulted in growth inhibition. /Simazine & other 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/|... 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 disappearance of sucrose & glyceric acid with the formation of aspartic & malic acids. /s-Triazines/

SAMPLES OF 2-METHOXY-4,6-BIS(ISOPROPYLAMINO)-1,3,5-TRIAZINE WERE SCREENED FOR VOLATILE NITROSAMINE CONTAMINATION & NO NITROSAMINE WAS DETECTED OVER 1 PPM.

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

/LABORATORY ANIMALS: Acute Exposure/ A skin and eye irritant.|/LABORATORY ANIMALS: Acute Exposure/ Causes substantial but temporary eye injury. Harmful if swallowed, inhaled, or absorbed through skin. /Pramitol 3.75%/|/OTHER TOXICITY INFORMATION/ No cases of poisoning in man have been reported from prometone ingestion.|/OTHER TOXICITY INFORMATION/ Moderately toxic by inhalation, ingestion, and skin contact.

2-methoxy-4,6-bis(isopropylamino)-s-triazine

BONIDE PROMETON 3.75% LIQUID VEGETATION KILLER Active Ingredient 3.75% Prometon; TOTAL WEED KILLER Active Ingredient 1.60% Prometon; BONIDE TOTAL VEGETATION KILLER CONCENTRATE Active Ingredient 2.20% Prometon|DEXOL WEEDSOL NON SELECTIVE WEED AND GRASS KILLER Active Ingredient 1.50% Prometon|RIVERDALE PROMETON 1.5 READY TO USE VEGETATION KILLER Active Ingredient 1.50% Prometon; RIVERDALE PROMETON 5E VEGETATION KILLER Active Ingredient 5.00% Prometon; RIVERDALE PROMETON 3.73E VEGETATION KILLER Active Ingredient 3.73% Prometon|TRIOX VEGETATION KILLER Active Ingredient 1.86% Prometon|For more Formulations/Preparations (Complete) data for PROMETON (25 total), please visit the HSDB record page.

1,3,5-Triazine-2,4-diamine, 6-methoxy-N2,N4-bis(1-methylethyl)-: ACTIVE|The WHO Recommended Classification of Pesticides by Hazard identifies Prometone (technical grade) as unlikely to present an acute hazard in normal use; Main Use: herbicide.|INTRODUCED BY JR GEIGY SA (NOW CIBA-GEIGY AG) (SWISS PATENT 337,019; BRITISH PATENT 814,948) AS CODE NUMBER G 31,435 ...|APPLICATION OF SPRAYS OR GRANULES CAN BE MADE EITHER BEFORE OR AFTER WEEDS EMERGENCE. SINCE MUCH OF ITS ACTIVITY IS THROUGH ROOTS, ADEQUATE RAINFALL IS REQUIRED TO MOVE CHEMICAL INTO ROOT ZONE. ... USUAL CARRIER: WATER AT 470 TO 940 L/HA (50 TO 100 GAL/ACRE) OR DIESEL OIL, FUEL OIL, OR WEED OIL AT 940 TO 1870 (100 TO 200 GAL/ACRE) ARE THE USUAL CARRIERS. AGITATION IN SPRAY TANK IS NECESSARY TO KEEP CHEMICAL IN SUSPENSION. ... COMPATIBLE WITH MOST OTHER PESTICIDES WHEN USED @ NORMAL RATES. ... GLASSWEAR AND SPRAY EQUIPMENT MAY BE CLEANED BY WASHING WITH WATER.|... PROMETONE ... /IS/ USED WIDELY FOR INDUSTRIAL AREA WEED CONTROL AT RATES THAT GIVE CONTROL OF MANY WEED SPECIES FOR ONE OR MORE YEARS. THE MOST WIDESPREAD USE ... /IS/ ON CORN. MAIZE IS ABLE TO METABOLIZE /IT/ ... & IS THEREFORE TOLERANT TO EXTREMELY HIGH DOSAGES ...|Ring labelled triazine herbicides can be synthesized by successive replacement of the chlorine, normally twice with amine and if required, then with alcohol or thiol, in the presence of an acid scavenger. The reactivity of the chlorine atoms decreases with substitution so there is little tendency for multiple reaction to mixed products to occur if the calculated molecular ratios are used. An example was the syntheses of (14)carbon propazine and (14)carbon prometon.

Product analysis by glc with FID or by acidimetric titration. Residues determined by glc with ECD by gc with FID.|/DETERMINATION OF/ PROMETON IN PESTICIDES BY GAS CHROMATOGRAPHY. USE INSTRUMENT EQUIPPED WITH FLAME IONIZATION DETECTOR & 4 MM ID GLASS COLUMN (1.8 M) PACKED WITH 3% CARBOWAX 20M ON 80-100 MESH GAS-CHROM Q. ... CONDITION 24 HR @ 240 °C WITH NITROGEN OR HELIUM AT ABOUT 40 ML/MIN. ... OPERATE @ FOLLOWING CONDITIONS: TEMP INLET 240 °C, COLUMN 200 + OR - 20 °C ... NITROGEN OR HELIUM GAS, 80-100 ML/MIN; AIR & HYDROGEN, 80-100 ML/MIN; ATTENUATION VARIED SO THAT PEAK HEIGHTS OF PESTICIDE & INTERNAL STD /DIELDRIN IN CHLOROFORM/ ARE 60-80% FULL SCALE. RETENTION TIMES: PROMETON 3-5 MIN, INTERNAL STANDARD 9-15 MIN. WT SAMPLE: 1 G LIQ FORMULATION|SUBSTITUTED S-TRIAZINES INCL PROMETONE WERE DETERMINED BY GAS CHROMATOGRAPHIC, SPECTROPHOMETRIC, & ELECTROCHEMICAL METHODS. INDIVIDUAL S-TRIAZINES CAN BE DIFFERENTIATED CHIEFLY ON BASIS OF THEIR RETENTION INDICES.|THE SEPARATION & BEHAVIOR OF S-TRIAZINE DERIVATIVES, ONE OF WHICH WAS PROMETONE, ON A NH2-CHEMICAL BONDED STATIONARY PHASE WERE STUDIED. PENTANE & HEPTANE MOBILE PHASES WERE USED. THE NH2-PHASE PROVIDES A BETTER SEPARATION OF S-TRIAZINES DIFFERING IN THE SUBSTITUENT AT POSITION 2 COMPARED WITH THE FORMERLY USED CHEM BONDED CN- & REVERSED C18 PHASES.|For more Analytic Laboratory Methods (Complete) data for PROMETON (16 total), please visit the HSDB record page.

Analytical methodology for the separation and characterization of s-triazine residues in urine was developed. In the sample preparation procedure developed, a urine sample at pH 12 was extracted with hexane 3 times, using sodium chloride as an emulsion inhibitor. The combined hexane extract was dried by passing it through a sodium sulfate column and concentrated by rotary evaporation. The sample was transferred to a graduated centrifuge tube and further concentrated to 0.5 ml under a stream of dry nitrogen. The sample was analyzed by gas chromatography using the Hall electrolytic conductivity detector in the nitrogen-specific mode. Prometone was one of the triazines.

Pharmaceuticals|Pesticides -> Herbicides -> Triazine herbicides -> Methoxytriazine herbicides

Prometon has known environmental transformation products that include Atrazine-desethyl-2-hydroxy and Propazine-2-hydroxy.