Rimsulfuron

431.44

431.44

602-908-8

462J071RD7

DTXSID1032642

Colorless crystals

183

0.288(pH 5);-1.47(pH 7)

White crystal or light yellow powder

0.784 at 25 deg C

177 °C

760.1±70.0 °C at 760 mmHg

>200 °C

1.6460 (estimate)

In water, 10 mg/L at 25 deg C; <10 ppm in distilled water

0-6°C

1.5X10-3 mPa /1.13X10-8 mm Hg/ at 25 deg C

LD50 orally in rats: >5000 mg/kg; dermally in rabbits: >2000 mg/kg (Palm)

Henry's Law constant = 6.42X10-10 atm-cu m/mol at 25 °C (est)

pKa = 4.0

log Kow = 0.034 (pH 7)|Hydroxyl radical reaction rate constant = 2.10X10-10 cu cm/molec-sec at 25 °C (est)

UN3077(solid)

1

UT7900000

Stable at normal temperatures and pressures.

P305 + P351 + P338

H319

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.|Waste resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. /DuPont Matrix Herbicide/|Container disposal: Triple rinse (or equivalent) the container. Then offer for recycling or reconditioning, 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. /DuPont Matrix Herbicide/|Do not flush to surface water or sanitary sewer system. /DuPont Matrix Herbicide/|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|H319 (78.12%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P273, P280, P305+P351+P338, P337+P313, P391, and P501|Aggregated GHS information provided by 68 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Applicators and other handlers must wear: Long-sleeve shirt and long pants. Chemical resistant gloves made of any water proof material such as polyethylene or polyvinylchloride. Shoes plus socks. /DuPont Matrix Herbicide/|Waterproof gloves|... Restricted-entry interval (REI) of 4 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, Chemical resistant gloves made of any waterproof material such as polyethylene or polyvinyl chloride. Shoes plus socks. /DuPont Matrix Herbicide/

Evacuate personnel to a safe area. Wear self-contained breathing apparatus. Wear full protective equipment. Use water spray. Runoff from fire control may be a pollution hazard.|Extinguishing media: Water, foam, dry chemical, CO2.|Fire Extinguishing Media: Water, foam, CO2, dry chemical.

Do not contaminate water by cleaning of equipment or disposal of equipment washwaters or rinsate. /DuPont Matrix Herbicide/|Dike spill. Prevent material from entering sewers, waterways, or low areas. Shovel or sweep up.|Spill clean up: Shovel or sweep up. /DuPont Matrix Herbicide/|Initial containment: Dike spill. Prevent material from entering sewers, waterways, or low areas. /DuPont Matrix Herbicide/

Use this product only in accordance with its labeling and with the Worker Protection Standard, 40 CFR Part 170. /DuPont Matrix Herbicide/|Do not apply directly to water, or to areas where surface water is present, or to intertidal areas below the mean high water mark. /DuPont Matrix Herbicide/|Users should: Wash hands before eating, drinking, chewing gum, using tobacco or using toilet. /DuPont Matrix Herbicide/|Discard clothing and other absorbent material that have been drenched or heavily contaminated with this product. Follow manufacturer's instructions for cleaning/maintaining personal protective clothing (PPE). If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry. /DuPont Matrix Herbicide/|For more Preventive Measures (Complete) data for Rimsulfuron (10 total), please visit the HSDB record page.

LD50 Rabbit dermal >2000 mg/kg|LC50 Rat inhalation >5.4 mg/L/4 hr|LD50 Rat oral >5000 mg/kg|LD50 Mouse oral >5000 mg/kg

/AQUATIC SPECIES/ ...The ecotoxicity of /rimsulfuron, and the metabolites 1-(N-(4,6-dimethoxypyrimidin-2-yl)-N-(3-(ethylsulfonyl)-2-pyridinylurea)) and 2-(N-((3-(ethylsulfonyl)-2-pyridinyl)-4,6-dimethoxy-2-pyrimidineamine))/ was evaluated through their effect on Daphnia magna and Vibrio fischeri (Microtox bioassay). No effect was observed on D. magna with 24 and 48 hr acute toxicity tests. Similarly, no toxic effect was observed with the Microtox test for the three chemicals in the range of concentrations tested that included the field application dose. ...

Rimsulfuron'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), the Koc range of 13 to 76(2) indicates that rimsulfuron is expected to have very high to high mobility in soil(SRC). Sulfonylurea herbicides, such as rimsulfuron, are more mobile in alkaline soils and in soils with lower organic matter content(2). The pKa of rimsulfuron is 4.00(3), 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 rimsulfuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.4X10-10 atm-cu m/mole(SRC), derived from its vapor pressure, 1.13X10-8 mm Hg(3), and water solubility, 10 mg/L(5). Rimsulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation half-lives in soil of 24.5 days in the laboratory and 5.7 days under field conditions(6) suggest that biodegradation may be an important environmental fate process in soil(SRC).|TERRESTRIAL FATE: Rimsulfuron was not detected in monitoring wells at two sandy agricultural research fields in Jyndevad and Tylstrup, Denmark following pesticide application (per common agricultural practice of 0.003 g/sq m) to crops on May 23, 2003 and June 3, 2004, respectively. Rimsulfuron degradation products [N-(4,6-dimethoxypyrimidin-2-yl)-N-((3-ethylsulfonyl)-2-pyridinyl)urea] and [N-((3-ethylsulfonyl)-2-pyridinyl)-4,6-dimethoxy-2-pyrimidineamine] were detected in the vadose zone of the soil at Jyndevad during the 6-year monitoring following rimsulfuron application; the latter compound was detected in associated groundwater. Both degradation compounds were also detected in the vadose zone at the Tylstrup site for 2 years post-application but again, not in groundwater samples(1).|TERRESTRIAL FATE: A field study was undertaken in Tennessee in a surface soil to track the dissipation of rimsulfuron. Field plots were set up in 1997 and 1998 on Sequatchie silt loam (pH 5.7, cation exchange capacity 7.0 cmol/g, 1.3% organic matter, and sand/silt/clay was 27/59/14, respectively). Rimsulfulron was applied at 46 g/ha and in combination with nicosulfuron at 46 g/ha. First order rate constants and associated half-lives observed in 1997 were: 0.22/day, half-life 3.1 days (alone); 0.20/day, half-life 3.5 days (mixture). For 1998: 0.56/day, half-life 1.2 days (alone); 0.32/day, half-life 2.2 days (mixture). Under laboratory conditions, moist Sequatchie silt loam soil at 50% field capacity was employed. Rimsulfuron was added at a concentration of 50.0 ng/g soil, both alone and in combination with nicosulfuron and samples were incubated at 30 °C. First order rate constants and associated half-lives observed were: 1.15/day, half-life 0.6 days (alone); 1.53/day, half-life 0.45 days (mixture)(1).|TERRESTRIAL FATE: Pyridine-2-14C-labeled rimsulfuron added to Fullsington silt loam (Newark, DE; 13% sand, 65% silt, 22% clay, 1.4% organic matter, pH 6.0, 4.9 mequiv/100 g cation exchange capacity) degraded rapidly with an average half-life of 5.6 days based on the first 14 days of data(1).|For more Environmental Fate (Complete) data for Rimsulfuron (6 total), please visit the HSDB record page.

Rimsulfuron undergoes hydrolysis in the environment(1-4). Half-lives were as follows (days): 0.08, pH 2; 0.17, pH 3; 0.28, pH 4; 2.37, pH 5; 11.89, pH 6.5; 0.61, pH 7.5; and 0.23, pH 8.5 calculated from first-order rate constants of (/day): 8.33, 4.04, 2.48, 0.29, 5.82X10-2, 1.13, and 3.00, respectively(1). Hydrolysis is also influenced by temperature as indicated by half-lives of 2.09, 1.11, 0.27, 0.21, 0.11, 0.03, and 0.02 days at 15, 20, 25, 30, 35, 45, and 55 °C, respectively, at pH 4(1). Pure rimsulfuron was rapidly hydrolyzed in aqueous solution using freshwater, a rate of 0.35/day, and hydrolysis was instantaneous under alkaline conditions(2). Using an aqueous soil suspension (alluvial sand loamy from the Swiss Rhone valley; 7.8% clay, 30% silt, 62.2% sand, 1.1% organic matter, 0.64% organic carbon, pH <8.1), the hydrolysis rate was 1/day(2). The hydrolysis rate was as high as the rate of photolysis (one to nine days at pH 5 and 9 under simulated sunlight) but decreased with increasing water pH. The main metabolite identified in neutral and alkaline conditions was N-[(3-ethylsulfonyl)-2-pyridinyl]-4,6-dimethoxy-2pyridinamine. Under acidic conditions the main metabolite was N-(4,6-dimethoxy-2-pyrimidinyl)-N-[(3-ethylsulfonyl)-2-pyridinyl)]urea(3). Minor hydrolysis metabolites pyridine sulfonamide, pyrimidine amine, and pyrimidine urea have also been identified(4). Rimsulfuron absorbs light at wavelengths 216 nm, 249 nm, and 298 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC). Under simulated sunlight in water, the photolysis half-life ranged from one to nine days at pH 5 and 9(3). Photolysis half-lives of 0.9, 11.6, and 0.5 at pH 5, pH 7, and pH 9, respectively, have been reported; at pH 5 90% photodegradation was observed in 3 days(4). Rimsulfuron does not undergo soil photolysis as indicated by similar half-lives of 11 days in both irradiated and unirradiated experimental conditions(4).|Rimsulfuron hydrolysis half-lives at 25 °C were reported as 4.6 days at pH 5, 7.2 days at pH 7, and 0.3 days at pH 9(1).

An estimated BCF of 3 was calculated in fish for rimsulfuron(SRC), using a log Kow of 0.29(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).

51.29 L/kg|The Koc of rimsulfuron is reported to range from 13 to 76(1). According to a classification scheme(2), this Koc range suggests that rimsulfuron is expected to have very high to high mobility in soil. Sulfonylurea herbicides are more mobile in alkaline soils and in soils with lower organic matter content(1). Rimsulfuron, applied at 14.7 g/ha to a 9 hectare tile-drained field in Outlook, Saskatchewan, Canada followed by 300 mm of irrigation water over a 2-week period, was not detected in underlying groundwater. Soil characteristics were Dark Brown Chernozem, 30.9-59.4% sand, 1.6%-0.5% organic matter (decreasing with depth), pH 7.8 to 8.4, increasing with depth(1). Using a southern Italian soil from Sellata Mountain (organic content 4.78%; cation exchange capacity 12.4 cmol/kg, 19.6% sand, 39.4% silt, 41.0% clay), rimsulfuron was 70% sorbed within 60 hours when treated with 0.3 mmol/kg. Rimusulfuron exhibits ionic sorption to soils characterized by high fine fractions, exchange capacity, and organic matter content(3). The pKa of rimsulfuron is 4.0(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). Rimsulfuron was weakly adsorbed on Cecil sandy loam (Raleigh, NC: 61% sand, 21% silt, 18% clay, 2.1% organic matter, pH 6.5, 6.6 mequiv/100 g cation exchange capacity (CEC)) and Sassafras sandy loam (Penns Grove, NJ: 74% sand, 16% silt, 9% clay, 1.0% organic matter, pH 6.3, 3.5 mequiv/100 g CEC) with Freundlich Isotherem constant K = 0.23 and 0.32, respectively. It was moderately adsorbed on Fargo clay loam (Horace, ND: 22% sand, 44% silt, 34% clay, 4.3% organic matter, pH 7.7, 29.7 mequiv/100 g CEC) and Flannagan silt loam (Rochelle, IL: 2% sand, 81% silt, 17% clay, 4.3% organic matter, pH 5.4, 21.2 mequiv/100 g CEC) with Freundlich Isotherem constant K = 1.36 and 1.57, respectively(6).

The Henry's Law constant for rimsulfuron is estimated as 6.4X10-10 atm-cu m/mole(SRC) derived from its vapor pressure, 1.13X10-8 mm Hg(1), and water solubility, 10 mg/L(2). This Henry's Law constant indicates that rimsulfuron is expected to be essentially nonvolatile from water and moist soil surfaces(3). Rimsulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

GROUNDWATER: Rimsulfuron was not detected in monitoring wells at two sandy agricultural research fields in Jyndevad and Tylstrup, Denmark following pesticide application (per common agricultural practice of 0.003 g/sq m) to crops on May 23, 2003 and June 3, 2004, respectively(1).

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

In rats, rimsulfuron is excreted within the first 72 hours following dosing in the urine (64%) and the feces (30%). Low, but detectable amounts of radioactivity were found in the heart, lung, liver, kidney, and muscle...|The metabolism of (14)C-labeled rimsulfuron was studied in male and female rats. The low dose groups were treated once by oral gavage with 25 mg/kg (14)C -pyridine-labeled compound and the high dose groups with 250 mg/kg of either (14)C -pyridine- or (14)C-pyrimidine-labeled compound. The repeat dose groups were gavaged orally with unlabeled test compound (25 mg/kg) for 14 consecutive days, followed on the 15th day by 25 mg/kg of (14)C -pyridine-test compound. Excretion accounted for 93 to 96% of the administered radioactivity, with 58 to 67% appearing in the urine and 20 to 33% in the feces. Tissue distribution of labeled residues was low. Males showed slightly higher hepatic accumulation than females within each test group. Animals in the repeat dose groups also showed a slight accumulation in the spleen. ...

Metabolism of rimsulfuron in plants and other animals (poultry and ruminants) appears to be similar to its metabolism in rats. Metabolism involves either the contraction or cleavage of the sulfonylurea bridge. While the cleavage of the bridge to form the pyridinesulfonamide metabolite is expected, the contraction reaction is not. The major residue found in plants is the parent compound, rimsulfuron.|The metabolism of (14)C-labeled rimsulfuron was studied in male and female rats. The low dose groups were treated once by oral gavage with 25 mg/kg (14)C -pyridine-labeled compound and the high dose groups with 250 mg/kg of either (14)C -pyridine- or (14)C-pyrimidine-labeled compound. The repeat dose groups were gavaged orally with unlabeled test compound (25 mg/kg) for 14 consecutive days, followed on the 15th day by 25 mg/kg of (14)C -pyridine-test compound. ... The metabolic profiles were determined using pooled urinary and fecal samples. The highest percentage of the urinary (42 to 55%) and fecal (5 to 16%) radioactivity was attributed to unmetabolized parent compound. The parent compound is metabolized by cleavage or contraction of the sulfonylurea bridge, leading to the formation of 3- (ethylsulfonyl)-2-pyridinesulfonamide (IN-E9260) or N-(4, 6-dimethoxy-2-pyrimidinyl)-N-((3-ethylsulfonyl)-2-pyridinyl) urea (IN-70941). IN-70941 is deamidated to form IN-70942, which is sequentially demethylated and hydroxylated.

... Blocks branched-chain amino acid synthesis by inhibiting the plant enzyme, acetolactate synthase.

/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 a/ structural chromosome aberration /assay/, human Lymphocytes /were exposed to/ rimsulfuron (DPX-E9636-22, purity: 98.8%) /at concentrations of/ 0, 0.1, 0.6, 1.0, and 1.3 mg/mL (high dose based on peak solubility) 3 hr exposure. No change in the number of aberrations/cell, % aberrant cells, % of cells with greater than 1 aberration, or mitotic index was observed at any rimsulfuron concentration in the absence or presence of S9-mediated metabolic activation. /The/ positive controls, mitomycin C (-S9) increases the number of aberrations/cell over negative controls by 16.5-42-fold, the % abnormal cells by 10-32-fold, and the % of cells with greater than 1 aberration from 0 to 8-16%. Cyclophosphamide (+S9) generated increases in number of aberrations/cell of 8.7-26-fold, % of abnormal cells of 8-22-fold, and the % of cells with greater than 1 aberration from 0 to 2-8%. No effect on any type of aberration was detected /and/ both positive controls showed increases in various types of chromosomal aberrations (particularly chromatid gaps). Rimsulfuron does not elicit clastogenic changes under the conditions tested.

N-((4,6-dimethoxypyrimidin-2-yl)aminocarbonyl)-3-(ethylsulfonyl)-2-pyridine-sulfonamide

Dry flowable, soluble granule.|Premix Partners: Atrazine; Clopyralid; Dicamba; Flumetsulam; Isoxaflutole; Nicosulfuron; Thifensulfuron-methyl|Water dispersible granule|Dupont Rimsulfuron Technical (E. I. Du Pont De Nemours and Co., Inc.) Rimsulfuron 99%|For more Formulations/Preparations (Complete) data for Rimsulfuron (35 total), please visit the HSDB record page.

The WHO Recommended Classification of Pesticides by Hazard identifies rimsulfuron as unlikely to present an acute hazard in normal use; Main Use: herbicide.

Adequate enforcement methodology (high performance liquid chromatography with ultraviolet (HPLC/ UV) detection method AMR-1241-88) is available to enforce the tolerance expression.|Product by GLC. Residues in plants and in soil by HPLC/UV. ... Residues of sulfonylureas in soil and water may also be determined by immunoassay.

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

Rimsulfuron has known environmental transformation products that include 3-(ethylsulfonyl)-2-pyridinesulfonamide, N-(3-(ethylsulfonyl)-2-pyridinyl)-4,6-dimethoxy-2-pyrimidinamine, and N-(4,6-dimethoxy-2-pyrimidinyl)-N-(3-(ethylsulfonyl)-2-pyridinyl)urea.|Rimsulfuron has known environmental transformation products that include IN-70941, IN-70942, IN-E9260, S12 (N-(4,6-dimethoxypyrimidin-2-yl)urea, and S13 (2-amino-4,6-dimethoxypyrimidine).