1-[3-(トリフルオロメチル)-2-ピリジニルスルホニル]-3-(4,6-ジメトキシ-2-ピリミジニル)尿素

Herbicides

Active substance -> EU Pesticides database: Approved

Herbicides

Environmental transformation -> Pesticides (parent, predecessor)

Pesticide (Flazasulfuron) -> USDA PDB

In octanol 0.2, methanol 4.2, acetone 22.7, dichloromethane 22.1, ethyl acetate 6.9, toluene 0.56, acetonitrile 8.7 (all in g/L, 25 °C); in hexane 0.5 mg/L at 25 °C

Solubility at 20 °C (w/w%): Acetone 1.2%; toluene 0.06%; at 25 °C (w/v%): acetic acid 0.67%

In water, 4.1 ppm (pH 1)

In water, 0.027 (pH 5), 2.1 (pH 7) (g/L, 25 °C)

164-166 °C

MP: 180 °C (99.7% purity)

Warning

H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Warning

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

P273, P391, and P501 (click each P-code to see the statement)

Commission Regulation No 844/2012

Flazasulfuron is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

04/30/EC, Reg. (EU) 2016/2016, Reg. (EU) 2017/805, Reg. (EU) No 540/2011, Reg. (EU) No 823/2012

Flazasulfuron: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Aquatic Acute 1 (100%)

Hazardous to the aquatic environment (acute) - category 1

Aquatic Acute 1

Keep out of reach of children and animals. Store in original containers only. Store in a cool, dry place and avoid excess heat. Carefully open containers. After partial use, fold and roll back bags, clamp and close tightly. Do not put concentrate or dilute material into food or drink containers. Do not contaminate other pesticides, fertilizers, water, food or feed by storage or disposal. /Katana Turf Herbicide/

In case of spill, avoid contact, isolate area and keep out animals and unprotected persons. Confine spills. To confine spill: Cover to prevent dispersal. Place damaged package in a holding container. Identify contents. /Katana Turf Herbicide/

Do not contaminate water when cleaning equipment or disposing of equipment wash waters or rinsate. /Katana Turf Herbicide/

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.

Nonrefilable container: Do not reuse or refill this container. Completely empty container into application equipment. Then offer for recycling if available or dispose of empty container ina sanitary landfill or by incineration, or, if allowed by Sate and Local authorities, by burning. If burned, stay out of smoke. /Katana Turf Herbicide/

Wastes resulting from the use of this product may be disposed of on site or at an approved waste disposal facility. /Katana Turf 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.

Use this product only in accordance with its labeling and with the Workers Protection Standard, 40 CFR part 170. /Katana Turf Herbicide/

Do not apply this product in a way that will contact workers or other persons either directly or through drift. Only protected handlers may be in the area during application. /Katana Turf Herbicide/

Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 4 hours. /Katana Turf Herbicide/

Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). if no such instructions for washables exist, use detergent and hot water. Keep and was PPE separately from other laundry. /Katana Turf Herbicide/

For more Preventive Measures (Complete) data for Flazasulfuron (9 total), please visit the HSDB record page.

Applicators and other handlers must wear: long-sleeved shirt and long pants, shoes plus socks. protective eyewear and chemical resistant gloves made of any waterproof material. /Katana Turf Herbicide/

Protective eyewear. Rubber 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 and shoes plus socks. Sod and seed farms are within the scope of the Worker Protect Standard. /Katana Turf Herbicide/

LD50; Species: Coturnix japonica (Japanese Quail) >2000 mg/kg /Conditions of bioassay not specified in source examined/

LC50; Species: Colinus virginianus (Northern Bobwhite Quail) diet >5620 mg/kg /Conditions of bioassay not specified in source examined/

LC50; Species: Anas platyrhynchos (Mallard Duck) diet >5620 mg/kg /Conditions of bioassay not specified in source examined/

LC50; Species: Oncorhynchus mykiss (Rainbow Trout); Concentration: 22 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for Flazasulfuron (7 total), please visit the HSDB record page.

Flazasulfuron is expected to be relatively persistent in soil and water (half-life about one month) and persistence is likely to increase with increasing pH of the media(1).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a log Kow of 1.30(2) and a regression-derived equation(3), indicates that flazasulfuron is expected to have moderate mobility in soil(SRC). Sulfonylurea herbicides, such as flazasulfuron, are more mobile in alkaline soils and in soils with lower organic matter content(4). The pKa of flazasulfuron is 4.37(2), 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). Volatilization of flazasulfuron from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.1X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Flazasulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(7). Biodegradation data were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 290(SRC), determined from a log Kow of 1.30(2) and a regression-derived equation(3), indicates that flazasulfuron 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 6.1X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), an estimated BCF of 2(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC,2011). The half-life of flazasulfuron in water has been reported as 17.4 hrs (pH 4); 16.6 days (pH 7); and 13.1 days (pH 9)(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), flazasulfuron, which has an estimated vapor pressure of 1.81X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase flazasulfuron may be removed from the air by wet or dry deposition(SRC). Flazasulfuron does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

/AQUATIC SPECIES/ ...The effects of the sulfonylurea herbicide, flazasulfuron (formulated as Katana) /were/ investigated on the unicellular green alga Scenedesmus obliquus. The pigment content of the algal suspensions was followed as a biomarker of exposure to the herbicide. The results demonstrate that flazasulfuron induced a reduction in chlorophyll content at concentrations of 10 ug/L, while the increase of pigment content in the culture was reduced with the lowest concentration tested (0.1 ug/L). Among the three pigments tested, chlorophyll a appeared to be the most sensitive biomarker. In the algal medium, flazasulfuron was slowly degraded (DT(50) approximately 8 days) to a compound that was tentatively identified. The toxicity of this herbicide for the algae was comparable to that of older herbicides which are used at a much higher rate.

The Koc of flazasulfuron is estimated as 290(SRC), using a log Kow of 1.30(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that flazasulfuron is expected to have moderate mobility in soil(SRC) and has the potential to leach to ground water and/or reach surface water during runoff events(5). Sulfonylurea herbicides, such as flazasulfuron(6), are more mobile in alkaline soils and in soils with lower organic matter content. The pKa of flazasulfuron is 4.37(1), 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). The mobility of flazasulfuron is expected to increase with increasing pH. A potential transport route is the wind erosion of soil particulates containing flazasulfuron(5).

An estimated BCF of 2 was calculated in fish for flazasulfuron(SRC), using an estimated log Kow of 1.30(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). Flazasulfuron has low potential to bioaccumulate(4).

The Henry's Law constant for flazasulfuron is estimated as 6.1X10-12 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that flazasulfuron is expected to be essentially nonvolatile from water and moist soil surfaces(2,3). Flazasulfuron is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-10 mm Hg(SRC), determined from a fragment constant method(4).

/LABORATORY ANIMALS: Acute Exposure/ Study Type: Acute dermal irritation (rabbit); Results: No erythema, edema, or dermal effects observed at application site.

/LABORATORY ANIMALS: Acute Exposure/ Study Type: Acute eye irriation (rabbit); Results: Minimal conjunctivitis through 48 hours. Free by 72 hours.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 90-day oral toxicity study, SL-160 (Flazasulfuron; 97.3% ai) was administered to 4 beagle dogs/sex/dose by capsule at dose levels of 0, 2, 10, 50, and 250 mg/kg/day for males and 0, 2, 10, 50, and 100 mg/kg/day for females. All animals survived to study termination with the exception of one male at 250 mg/kg/day (number 18) killed in extremis at Week 11 due to reduced spontaneous motor activity, poor health including weight loss, and a large decrease in food intake at Week 10. Clinical signs occurred sporadically in the study (regurgitation of feed, diarrhea, mucous in the stool, and swelling of the foreleg). Males of the high-dose group (250 mg/kg/day), had a decrease in mean body weight of about 5-6% (compared to controls) starting at Week 6. Hematology measurements were not statistically changed from control in either males or females. No adverse liver functions in either males or females were shown in the clinical chemistry. Absolute and relative liver weights were increased in the 250 mg/kg/day male group (173%, 181%) and the 100 mg/kg/day female group (122%, 122%). The histopathology of male dogs in the 250 mg/kg/day group included a slight increase in deposition of brown pigments, slight hepatocellular swelling, moderate atrophy of the thymus, and moderate atrophy/degeneration of the skeletal muscle. In the 50 mg/kg/day group, all male dogs had a slight increase in deposition of brown pigments, moderate inflammatory cell infiltration, hepatocellular degeneration/necrosis, and bile duct proliferation in the liver. The 10 mg/kg/day male group had a slight increase in the deposition of brown pigments, inflammatory cell infiltration and microgranulomas in the liver. The 100 mg/kg/day female group displayed increased deposition of brown pigments, inflammatory cell infiltration, hepatocellular degeneration/necrosis, bile duct proliferation, and microgranulomas in the liver. Atrophy/degeneration of the skeletal muscle was also observed in this group. In conclusion, the LOAEL was established in male dogs at 10 mg/kg/day and in female dogs at 50 mg/kg/day based on liver changes (hepatocellular swelling, hepatocellular degeneration/necrosis, inflammatory cell infiltration, hepatic microgranulomas, increased deposition of brown pigment) and atrophy/degeneration of the skeletal muscle. The NOAEL is 2 mg/kg/day for males and 10 mg/kg/day for females.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ In a 21-day dermal toxicity study, SL-160 (/flazasulfuron/ 96.3% ai) was applied to the shaved skin of five New Zealand white rabbits/sex/dose at dose levels of 0 (water), 250, 500, or 1000 mg/kg bw/day, 6 hours/day for 21 (males) or 22 (females) consecutive days. There were no treatment-related deaths, clinical observations, dermal reactions, or effects on body weight, food consumption, hematology, clinical chemistry, organ weight, or gross or histopathology. Based on the results of this study, the systemic and dermal LOAELs for Flazasufulron in male and female rabbits are not identified, and the systemic and dermal NOAELs are the limit dose of 1000 mglkglday.

For more Non-Human Toxicity Excerpts (Complete) data for Flazasulfuron (14 total), please visit the HSDB record page.

The half-life of flazasulfuron in water has been reported as 17.4 hrs (pH 4); 16.6 days (pH 7); and 13.1 days (pH 9)(1). Flazasulfuron has been reported to undergo base-catalyzed contraction rearrangement of the sulfonylurea bridge and its hydrolysis rate is faster in alkaline conditions than acidic conditions. Flazasulfuron degrades 10 to 100 times faster than some other sulfonylureas via an intermolecular nucleophilic addition and elimination reaction. Under alkaline conditions, this product can be further hydrolyzed to a pyridinyl-pyrimidinylamine(2). Chemical and enzyme-mediated hydrolysis is a major route of transformation of flazasulfuron in water, soil, and water-sediment systems. Both the half-life and mechanism of hydrolysis are pH dependent. There are four major hydrolytic and five metabolic products(3). Products formed from the sulfonylurea bridge contraction are biologically inactive(2). Flazasulfuron does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Flazasulfuron's production may result in its release to the environment through various waste streams; its use as a herbicide will result in its direct release to the environment. If released to air, an estimated vapor pressure of 1.8X10-10 mm Hg at 25 °C indicates flazasulfuron will exist solely in the particulate phase in the atmosphere. Particulate-phase flazasulfuron will be removed from the atmosphere by wet or dry deposition. Flazasulfuron does not contain chromophores that absorb at wavelengths >290 nm, and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, flazasulfuron is expected to have moderate mobility based upon an estimated Koc of 290. Sulfonylurea herbicides, such as flazasulfuron, are more mobile in alkaline soils and in soils with lower organic matter content. The pKa of flazasulfuron is 4.37, indicating that this compound will exist partially 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. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 6.1X10-12 atm-cu m/mole. Flazasulfuron may not volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data were not available. If released into water, flazasulfuron is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 2 suggests the potential for bioconcentration in aquatic organisms is low. The half-life of flazasulfuron in water has been reported as 16.6 days at pH 7. Occupational exposure to flazasulfuron may occur through inhalation and dermal contact with this compound at workplaces where flazasulfuron is produced or used. (SRC)

/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/

A series of studies were conducted to evaluate the absorption, distribution, metabolism, and excretion of (14)C-SL-160(P)/flazasulfuron/ in groups of 4 or 5 rats (CRL: CD BR VAF/Plus)/sex. In these studies, (14)C-SL-160(P) (CP-1385; 55.8 mCi/mMole; radiolabel purity variously reported as 97.29%, 97.5%. 98.49%., 99.2% and >98%) was administered orally by gavage at doses of 2 or 50 mg/kg or 2 mg/kg . In /one study/, rats had received daily oral gavage doses of nonlabeled SL-160 (Y-920205; 98.9% purity) for 14 days, prior to oral dosing with (14)C-SL-160(P) on Day 15. In the single and repeated dose studies, parent compound was the primary component in the metabolite profiles for urine (males: 19-40%; females: 51-67% of administered dose), with lesser amounts in feces (males and females: 2-5% of administered dose), and bile (males and females: 0.6-2% of administered dose). Including parent compound up to 11 fractions were detected among these matrices. The most prevalent metabolite (expressed as percent of administered dose) were HDTG+TPPG (approximately 6.5-12% in urine, approximately 0.4-2% in feces, and approximately 6.5-14% in bile), with minor amounts < 5%) of DTPU (N-(4,6-Dimethoxy-2-pyrimidinyl)-N-[3-(trifluoromethyl)-2-pyridinyl]urea), HDPU, 6-Methoxy-2-[[3-(trifluoromethyl)-2-pyridinyl]amino]-4-pyrimidinol, TPSA (3-Trifluoromethyl)-2-pyridinesulfonamide), and MTMG. Individually, unidentified fractions generally accounted for less than 2% of the administered dose in the urine and biliary metabolite profile. The fecal metabolite profile had up to 35% unidentified of the recovered dose.

Rapidly and extensively absorbed(90%), widely distributed and almost completely excreted (up to 90%) within 7 days, mainly in urine.

A series of studies were conducted to evaluate the absorption, distribution, metabolism, and excretion of (14)C-SL-160(P)/flazasulfuron/ in groups of 4 or 5 rats (CRL: CD BR VAF/Plus)/sex. In these studies, (14)C-SL-160(P) (CP-1385; 55.8 mCi/mMole; radiolabel purity variously reported as 97.29%, 97.5%. 98.49%., 99.2% and >98%) was administered orally by gavage at doses of 2 or 50 mg/kg or 2 mg/kg . In /one study/, rats had received daily oral gavage doses of nonlabeled SL-160 (Y-920205; 98.9% purity) for 14 days, prior to oral dosing with (14)C-SL-160(P) on Day 15. ... Differences were generally not noted between dose levels or between single versus repeated dose administration, but were noted between males and females. The studies demonstrated that 14C SL-160(P) is rapidly absorbed following a single oral dose of 2 or 50 mg/kg. By 48 hours post exposure, males and females absorbed 94% and 93% of the low dose, respectively, and 86% and 93% of the high dose, respectively. A similar pattern was observed when low- and high-dose animals were followed up to 168 hours with little difference noted between a single or repeated exposure. Elimination via the urine was the major route of excretion, accounting for 74-80% and 90-94% in males and females, respectively, following both low- and high-dose and single and repeated dose administration. Time course data revealed that a significant portion of the radioactivity in urine was excreted by 48-72 hours post exposure. Feces were the secondary route of elimination, accounting for 21-24% and 9-10% in males and females, respectively, following both low- and high-dose and single and repeated dose administration. The biliary excretion study determined that approximately 9.5% of the administered dose appeared in bile by 48 hours in low-dose males and females and high-dose females, with approximately 16.5% in high-dose males. Tissue distribution studies indicated that 14C-SL-160(P) is rapidly excreted from the system, with less than 4% (males) and 1% (females) of the administered radioactivity remaining in the tissues seven days after dosing. In general, the pattern of the radiolabel distribution in tissues was similar between the low- and high-dose groups in the single oral dose study and between the low-dose groups in the single and repeated dose groups. Pharmacokinetic studies confirmed the rapid absorption and elimination of 14C-SL-160(P). Following a single oral dose of (14)C-SL-160(P), tmax values (provided only for individual animals; mathematically determined value not provided) ranged from 30 minutes (3/5 animals/sex) or 4 hours (2/5 animals/sex) at 2 mg/kg, while the median tmax was 6 hours in males and 4 hours in females at the 50 mg/kg dose. At 2 and 50 mg/kg, males had slightly longer elimination half times for the blood than females (males: 27 and 36 hours, respectively; females: 18.8 and 33.8 hours, respectively). Likewise, males had a greater AUC (304 and 4440 ug-eq/g hr, respectively) than females (189 and 3080 ug-eq/g hr, respectively).

For flazasulfuron (USEPA/OPP Pesticide Code: 119011) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Herbicide

Flazasulfuron is registered for use on non-residential areas including golf courses and non-residential turf areas such as industrial parks, tank farms, sod farms, seed farms, sports fields and commercial lawns.

Flazasulfuron is /used/ for control of annual and perennial grasses, sedges, and broadleaf weeds.

Water dispersible granule

Wettable powder

Technical Flazasulfuron Herbicide (Isk Biosciences Corporation) Flazasulfuron 96.9%

Flazasulfuron 25WG (Isk Biosciences Corporation) Flazasulfuron 25%

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides