Sulfosulfuron

470.48

470.48

604-251-2

Y0XC20DL6D

DTXSID4034940

White crystals|White solid

2935009011

188

0.73 (pH 5)

1.5185 at 20 deg C

201.4 °C

1.696

Solubility in organic solvents (g/l at 20 °C) Acetone 0.71 Ethyl acetate 1.01 Dichloromethane 4.35 n‐Heptane <0.001 Methanol 0.33 Xylene 0.16;In water, 18 mg/L at 20 deg C, pH 5

0-6°C

6.61X10-10 mm Hg at 25 deg C

LD50 in rats (mg/kg): >5000 orally; >5000 dermally; LC50 (96 hr) in rainbow trout, carp (mg/l): >95, >91 (Parrish)

Odorless

Henry's Law constant = 2.5X10-13 atm-cu m/mol at 25 °C (est)

pKa = 3.51

Hydroxyl radical reaction rate constant = 2.12X10-10 cu cm/molec-sec at 25 °C (est)

UN30779/PG3

2

50/53

60-61

NJ5808500

N

Stable <54 deg C for 14 days. Hydrolysis DT50 7 days (pH 4), 48 days (pH 5), 168 days (pH 7), 156 days (pH 9) (all 25 deg C).

P273-P501

H410

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.|This product should not be dumped, spilled, rinsed or washed into sewers or public waterways.|Nonrefillable container. Do not reuse or refill this container. Triple rinse container (or equivalent) promptly after emptying. Triple rinse as follows: Empty the remaining contents into application equipment or a mix tank. Fill the container 1/4 full with water and recap. Shake for 10 seconds. Pour rinsate into application equipment or a mix tank or store rinsate for later use or disposal. Drain for 10 seconds after the flow begins to drip. Repeat this procedure two more times. Then offer for recycling if available or puncture and dispose of in a sanitary landfill, or by incineration, or, if allowed by State and local authorities, by burning. If burned stay out of smoke. /Maverick Herbicide/or|To avoid wastes, use all material in this container by application according to label directions. If wastes cannot be avoided, offer remaining product to a waste disposal facility or pesticide disposal program (often such programs are run by State or local governments or by industry). /Maverick Herbicide/or|SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|Aggregated GHS information provided by 136 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]|Not Classified

Applicators and other handlers must wear: long-sleeved shirt and long pants and shoes plus socks. /Maverick Herbicide/|Protective eyewear|... Restricted-entry interval (REI) of 12 hours. Personal protective equipment (PPE) required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water is: Coveralls, Shoes plus socks. Chemical resistant gloves, such as nitrile rubber, neoprene rubber or polyethylene. For more options, follow instructions for category A (dry- and water-based formulations) on an EPA chemical resistance category selection chart. /Maverick Herbicide/

Recommended: Water, foam, dry chemical, carbon dioxide (CO2). /Maverick Herbicide/|Fire Extinguishing Media: Water, dry chemical, CO2, alcohol foam.|Fire fighting equipment: Self-contained breathing apparatus. Equipment should be thoroughly decontaminated after use. /Maverick Herbicide/

Do not contaminate water when cleaning equipment disposing of washwaters or rinsate. /Maverick Herbicide/or|Sweep, scoop or vacuum and remove. Flush residual spill area with water.

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /Maverick Herbicide/|Avoid contact with eyes, skin, and clothing.|Long-sleeved shirt and long pants ... shoes plus socks.|This pesticide is highly toxic to non-target plants. Do not apply directly to water or to areas where surface water is present or to intertidal areas below the mean high water mark. Drift and runoff may be hazardous to plants in neighboring areas. /Maverick Herbicide/|For more Preventive Measures (Complete) data for Sulfosulfuron (10 total), please visit the HSDB record page.

LD50 Rat dermal >5000 mg/kg|LD50 Rat oral > 5000 mg/kg

/AQUATIC SPECIES/ ... Data presented here demonstrate that exposure to initial sulfosulfuron concentrations of 3.33 ug/L for up to 21 days was tolerated by /Glyceria maxima (Hartm) Holmb, Lagarosiphon major (Ridl) Moss and Myriophyllum spicatum L/ ... and that adverse effects were observed only when plants were exposed to initial concentrations of 3.33 and 10 ug/L for 70 days. As the occurrence of such high initial concentrations for long periods is unlikely in the aquatic environment, sulfosulfuron is not expected to have adverse effects on the growth of these species. ...

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

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 33(SRC), determined from a structure estimation method(2), indicates that sulfosulfuron is expected to have very high mobility in soil(SRC). Sulfonylurea herbicides, such as sulfosulfuron, are more mobile in alkaline soils and in soils with lower organic matter content(3). The pKa of sulfosulfuron is 3.51(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of sulfosulfuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.5X10-13 atm-cu m/mole(SRC), derived from its vapor pressure, 6.61X10-10 mm Hg(5), and water solubility, 1627 mg/L(6). Sulfosulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). Biodegradation data were not available(SRC, 2011).|TERRESTRIAL FATE: Using a simulated model wheat-crop ecosystem, sulfosulfuron applied at 25 and 50 g ai/ha dissipated with first-order rate constants resulting in half-lives of 3.50, 3.92, and 3.15 days in soil, plant, and water, respectively, for the 25 g/ai ha concentration. At a dosage of 50 g ai/ha, half-lives of 3.72, 4.02, and 3.28 days in soil, plant, and water, respectively, were observed. Under natural field conditions, half-lives of 3.00 and 2.94 days in soil and plant, respectively, were observed at the 25 g ai/ha dosage; 3.17 and 3.07 days in soil and plant, respectively, for the 50 g ai/ha dosage(1).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 33(SRC), determined from a structure estimation method(2), indicates that sulfosulfuron is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.5X10-13 atm-cu m/mole(SRC), derived from its vapor pressure, 6.61X10-10 mm Hg(4), and water solubility, 1627 mg/L(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from a log Kow of -0.77(5) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2011). Hydrolysis half-lives of 9.3, 40.6, 13.9 and 35.0 days at pH values of 4.0, 7.0, 9.2, and 6.8 (distilled water), respectively, were measured(8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfosulfuron, which has a vapor pressure of 6.61X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase sulfosulfuron may be removed from the air by wet or dry deposition(SRC). Sulfosulfuron exhibited a half-life of 9.1 days irradiated as an acetonitrile solution(4), suggesting that it may be susceptible to direct photolysis by sunlight(SRC).

Hydrolysis half-lives of 9.3, 40.6, 13.9 and 35.0 days at pH values of 4.0, 7.0, 9.2, and 6.8 (distilled water), respectively, were measured. Alkaline hydrolysis yielded 1-(2-ethylsulfonylimidazo[1,2-a]-pyridin-3-yl-3-(4,6-dimethoxypyrimidin-2-yl) amine(1). Hydrolysis half-lives of 7 (pH 4), 48 (pH 5), 168 (pH 7), and 156 days (pH 9) (all 25 °C) have also been reported(2). Under acidic conditions, 1-(2-ethylsulfonylimidazo[1,2-a]pyridin)-3-sulfonamide and 4,6-dimethoxy-2-aminopyrimidine were identified as hydrolytic degradation products(1). After irradiation for 11 days, the compound, present as an acetonitrile solution, decomposed with first-order rate kinetics, exhibiting a half-life of 9.1 days under sunlight. Photodegradation involved breaking of the sulfonylurea bridge as does acidic hydrolysis(1). Therefore sulfosulfuron may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 3 was calculated in fish for sulfosulfuron(SRC), using an estimated log Kow of -0.77(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). However, bioaccumulation studies of sulfosulfuron residues in catfish (Genus species not specified) exposed to 9 and 18 mg/L over 56 days showed the presence of high amounts of the herbicide (0.009 to 0.496 ug/g) and its metabolite aminopyrimidine in homogenized fish samples(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sulfosulfuron can be estimated to be 33(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulfosulfuron is expected to have very high mobility in soil. Sulfonylurea herbicides, such as sulfosulfuron, are more mobile in alkaline soils and in soils with lower organic matter content(3). The pKa of sulfosulfuron is 3.51(4), indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for sulfosulfuron is estimated as 2.3X10-11 atm-cu m/mole at pH 5(SRC) derived from its vapor pressure, 6.61X10-10 mm Hg(1), and water solubility, 18 mg/L(2). This Henry's Law constant indicates that sulfosulfuron is expected to be essentially nonvolatile from water and moist soil surfaces(3). Sulfosulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

DRINKING WATER: Sulfosulfuron was tested for in 206 surface drinking-water supplies of 15 communities in Manitoba, Saskatchewan, and Alberta, Canada in midsummer (July 2003). The source of drinking water in reservoirs was primarily from snowmelt runoff from crop lands. Sulfosulfuron was detected in 21 of 206 reservoir samples with a maximum concentration of 36.1 ng/L; detection limit = 1.0 ng/L. Positive detections were found in two of four reservoirs in Manitoba, exhibiting mean concentrations of 1.4 and 25 ng/L; it was not detected in six reservoirs in Saskatchewan and five reservoirs in Alberta(1).

Occupational exposure to sulfosulfuron may occur through inhalation and dermal contact with this compound at workplaces where sulfosulfuron is produced or used. Limited monitoring data indicate that the general population may be exposed to sulfosulfuron via inhalation of ingestion of contaminated drinking water. (SRC)

Extensively aborbed and rapidly excreted; at low doses, the major excretion route was the urine (77-87%), but at high doses, the feces (55-63%).|In a metabolism study, radiolabelled Sulfosulfuron (98% radiochemically pure a.i.), was administered to Sprague-Dawley rats. In the pilot study, 2-3 rats/sex/group were administered either (14)C-Pd Sulfosulfuron (radiolabel at the C-5 position of pyrimidine ring) or (14)C-Im Sulfosulfuron (label at the C-3 position of the imidazopyridine ring), each at 10 mg/kg or 1,000 mg/kg, by gavage. Rats dosed with Im or Pd Sulfosulfuron isotopes had similar metabolite profiles; therefore in the main study, 5 rats/sex/group were administered a mixture of (14)C-Pd, (14)C-Im, (13)C-Im and (12)C- Sulfosulfuron at single oral doses of 10 or 1,000 mg/kg, repeated oral doses of 10 mg/kg (14 consecutive daily unlabelled doses, followed by 1 radiolabelled dose), or a single intravenous dose of 10 mg/kg. More than 90% of the administered radioactivity was excreted by 72 hrs post-dosing (mean total recovery ranged from 97% to 101%). Between 77% to 87% of the administered radioactivity was excreted in the urine in all low dose groups (5-13% was excreted in the feces, low single and repeat oral dosing and low iv dosing), whereas feces was the major route of elimination at high dose (63%, males and 55%, females; urinary excretion 32%, males and 33%, females). Biliary excretion appeared to occur, as shown by fecal excretion in the intravenous dose group (9% and 5% of administered dose, males and females). ... In all dose groups, minimal radioactivity was retained in tissues (less than 0.07%) or carcass (less than 0.17%). In the pilot study, expiration of (14)CO2 was insignificant (<0.04% of administered dose, all groups) and therefore not measured in the main study. Absorption was essentially complete at low dose (95%, males and 91%, females) but markedly reduced at the high dose (36%, males and 39%, females); it was not determined whether this was a dose-dependent effect or was due to a dose-vehicle effect.

In a metabolism study, radiolabelled Sulfosulfuron (98% radiochemically pure a.i.), was administered to Sprague-Dawley rats. In the pilot study, 2-3 rats/sex/group were administered either (14)C-Pd Sulfosulfuron (radiolabel at the C-5 position of pyrimidine ring) or (14)C-Im Sulfosulfuron (label at the C-3 position of the imidazopyridine ring), each at 10 mg/kg or 1,000 mg/kg, by gavage. Rats dosed with Im or Pd Sulfosulfuron isotopes had similar metabolite profiles; therefore in the main study, 5 rats/sex/group were administered a mixture of (14)C-Pd, (14)C-Im, (13)C-Im and (12)C- Sulfosulfuron at single oral doses of 10 or 1,000 mg/kg, repeated oral doses of 10 mg/kg (14 consecutive daily unlabelled doses, followed by 1 radiolabelled dose), or a single intravenous dose of 10 mg/kg. ... Metabolism of Sulfosulfuron in all groups was minimal and most was excreted unmetabolized (for example, it represented more than 90% of the total radioactivity excreted in the urine). Sulfosulfuron was metabolized primarily via ring hydroxylation of a carbon of the pyrimidine ring, or demethylation of the methoxy group at the 4- or 6-position of the pyrimidine ring. In addition, a limited amount of cleavage of the sulfonamide bond into sulfonamide or other imidazopyridine compounds and pyrimidine compounds was observed. Major metabolites identified in urine and feces were desmethyl Sulfosulfuron (3.6% or greater of administered dose), 5-hydroxy Sulfosulfuron (1.9% or greater) and sulfonamide (2.6% or greater). A fourth, Feces 488 (ND-1.68%; feces only), was partially characterized as a desmethylated metabolite. Other minor metabolites, 1 imidazopyridine and 3 pyrimidine metabolites, were also found at low levels (<1%) in the feces. Metabolite profiles were qualitatively similar among animals given high vs. low doses, single vs. repeated doses, oral vs. intravenous doses, or between males and females (the percentages of different metabolites varied but due to the low levels present, variations were not considered biologically significant). It was noted that small amounts of white precipitates were observed in the urine of high dose rats at 12 and 24 hrs post-dosing. These were not characterized, but were probably unmetabolized Sulfosulfuron, based on the low level of biotransformation.

In a metabolism study, radiolabelled Sulfosulfuron (98% radiochemically pure a.i.), was administered to Sprague-Dawley rats. In the pilot study, 2-3 rats/sex/group were administered either (14)C-Pd Sulfosulfuron (radiolabel at the C-5 position of pyrimidine ring) or (14)C-Im Sulfosulfuron (label at the C-3 position of the imidazopyridine ring), each at 10 mg/kg or 1,000 mg/kg, by gavage. Rats dosed with Im or Pd Sulfosulfuron isotopes had similar metabolite profiles; therefore in the main study, 5 rats/sex/group were administered a mixture of (14)C-Pd, (14)C-Im, (13)C-Im and (12)C- Sulfosulfuron at single oral doses of 10 or 1,000 mg/kg, repeated oral doses of 10 mg/kg (14 consecutive daily unlabelled doses, followed by 1 radiolabelled dose), or a single intravenous dose of 10 mg/kg. ... Urinary excretion followed a biexponential pattern with half-lives of 2.2-5.8 hrs, initial phase, and 21.4-56.7 hrs, terminal phase (similar rates were observed for whole body elimination). ...

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as 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 ... . /Poisons A and B/

/GENOTOXICITY/ In an in vitro cytogenetic assay, cultured human lymphocytes, obtained from a single donor, were exposed to Sulfosulfuron in initial (3-hr exposure with and without S9 to Sulfosulfuron, followed by 17-hr incubation and then 2-hr exposure to colcemid) and confirmatory (-S9: 19.5- and 43.4-hr exposures to Sulfosulfuron, followed by colcemid; +S9: same as initial) assays. The S9 homogenate was derived from Aroclor 1254-induced rat livers and the test material was delivered to the test system as a solution in DMSO. The highest dose level evaluated (with and without S9) in all assays and harvest times was 1000 ug/mL. A precipitate was observed at this dose level. In addition, reductions (from 14.9 to 66.7%) were seen in mitotic indices at this dose level with and without S9. However, there were no indications of any increased incidence of cells with chromosomal aberrations and/or numbers of polyploid cells. The positive controls induced the expected high yields of metaphase spreads with chromosomal aberrations. Based on the these considerations, it is concluded that Sulfosulfuron did not induce a clastogenic response in human lymphocytes under the conditions of this assay either in the presence or absence of S9 at doses up to and including those associated with cytotoxicity and/or test material precipitation.

N-(((4,6-dimethoxy-2-pyrimidinyl)-amino)carbonyl)-2-ethylsulfonylimidazo(1,2-a)pyridine-3-sulfonamide

Premix Partners: Metsulfuron-methyl|Wettable granule|Water dispersible granule|Mon 37500 Technical (Monsanto Company) Sulfosulfuron 98%|For more Formulations/Preparations (Complete) data for Sulfosulfuron (9 total), please visit the HSDB record page.

Adequate enforcement methodology LC/MS/MS is available to enforce the tolerance expression.|Residues in soil by HPLC/UV. Residues of sulfonylureas in soil and water may also be determined by immunoassay.

Agrochemicals -> Herbicides|Pharmaceuticals|Herbicides|Environmental transformation -> Pesticides (parent, predecessor)

Sulfosulfuron has known environmental transformation products that include desmethyl sulfosulfuron, sulfosulfuron aminopyrimidine, sulfosulfuron guanidine, and sulfosulfuron sulfonamide.|Sulfosulfuron has known environmental transformation products that include Desmethyl sulfosulfuron, Guanidine, S13 (2-amino-4,6-dimethoxypyrimidine), Sulfonamide, Sulfonylbiuret, and Sulfonylurea.