3-[[3-(4-メトキシ-6-メチル-1,3,5-トリアジン-2-イル)ウレイド]スルホニル]チオフェン-2-カルボン酸メチル

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Approved

Pesticides -> Herbicides, Sulfonylurea

Environmental transformation -> Pesticides (parent, predecessor)

Herbicides

log Kow = -1.56

1.52

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 (EU) No 1141/2010

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

01/99/EC, 2010/77/EU, Reg. (EU) 2015/1885, Reg. (EU) 2016/1424, Reg. (EU) 2016/549, Reg. (EU) No 540/2011

Thifensulfuron-methyl: 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.

High-dose animal studies: In a 24-month feeding study at 125 mg/kg/day, rats had weight loss, and decreased serum sodium; No evidence of carcinogenicity in a study of mice; Decreased mean fetal weight in a developmental study; [HSDB] An irritant; [MSDSonline]

Tolerances are established for residues of the herbicide thifensulfuron methyl (methyl-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino] carbonyl] amino] sulfonyl]-2-thiophene carboxylate) in or on the following raw agricultural commodities: barley, grain; barley, straw; canola, seed; corn, field, forage; corn, field, grain; corn, field, stover; cotton, gin byproducts; cotton, undelinted seed; flax, seed; oat, grain; oat, straw; soybean; wheat, grain; and wheat, straw.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128845; Type of Pesticide: conventional - herbicide; Use Site: food use; Year: 1986.

Aquatic Acute 1 (100%)

Hazardous to the aquatic environment (acute) - category 1

Skin corrosion/irritation - Category 3

Hazardous to the aquatic environment (Acute) - Category 1

Aquatic Acute 1

Store in original container only, away from other pesticides, fertilizers, food, or feed. Do not contaminate water, food or feed.

Safe Storage of Pesticides. Always store pesticides in their original containers, complete with labels that list ingredients, directions for use, and first aid steps in case of accidental poisoning. Never store pesticides in cabinets with or near food, animal feed, or medical supplies. Do not store pesticides in places where flooding is possible or in places where they might spill or leak into wells, drains, ground water, or surface water.

If a spill occurs, clean it up promptly. Don't wash it away. Instead, sprinkle the spill with sawdust, vermiculite, or kitty litter. Sweep it into a plastic garbage bag, and dispose of it as directed on the pesticide product label.

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.

Safe Disposal of Pesticides. The best way to dispose of small amounts of excess pesticides is to use them - apply them - according to the directions on the label. If you cannot use them, ask your neighbors whether they have a similar pest control problem and can use them. If all of the remaining pesticide cannot be properly used, check with your local solid waste management authority, environmental agency, or health department to find out whether your community has a household hazardous waste collection program or a similar program for getting rid of unwanted, leftover pesticides. These authorities can also inform you of any local requirements for pesticide waste disposal.

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.

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.

/For applying the product/ wear the items of protective clothing the label requires: for example, non-absorbent gloves (not leather or fabric), rubber footwear (not canvas or leather), a hat, goggles, or a dust-mist filter. If no specific clothing is listed, gloves, long-sleeved shirts and long pants, and closed shoes are recommended. You can buy protective clothing and equipment at hardware stores or building supply stores.

Indoor Applications. If the label directions permit, leave all windows open and fans operating after the application is completed. If the pesticide product is only effective in an unventilated (sealed) room or house, do not stay there. Put all pets outdoors, and take yourself any your family away from treated areas for at least the length of time prescribed on the label. Apply most surface sprays only to limited areas such as cracks; don't treat entire floors, walls, or ceilings. Don't let pesticides get on any surfaces that are used for food preparation. Wash any surfaces that may have pesticide residue before placing food on them.

Indoor Applications. When using total release foggers to control pests, use no more than the amount needed and to keep foggers away from ignition sources (ovens, stoves, air conditioners, space heaters, and water heaters, for example). Foggers should not be used in small, enclosed places such as closets and cabinets or under tables and counters.

Outdoor Applications. Never apply pesticides outdoors on a windy day (winds higher than 10 mph). Position yourself so that a light breeze does not blow pesticide spray or dust into your face.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Tolerances are established for residues of the herbicide thifensulfuron methyl (methyl-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino] carbonyl] amino] sulfonyl]-2-thiophene carboxylate) in or on the following raw agricultural commodities: barley, grain, 0.05 ppm; barley, straw, 0.10 ppm; canola, seed, 0.02 ppm; corn, field, forage, 0.10 ppm; corn, field, grain, 0.05 ppm; corn, field, stover, 0.10 ppm; cotton, gin byproducts, 0.02 ppm; cotton, undelinted seed, 0.02 ppm; flax, seed, 0.02 ppm; oat, grain, 0.05 ppm; oat, straw, 0.10 ppm; soybean, 0.10 ppm; wheat, grain, 0.05 ppm; and wheat, straw, 0.10 ppm.

LD50 Anas platyrhynchos (Mallard duck) oral >2510 mg/kg[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 3-[[[

LC50 Anas platyrhynchos (Mallard duck, 10 day old) diet >5620 ppm/8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 3-[[[

LC50 Colinus virginianus (Northern bobwhite, 13 day old) diet >5620 ppm/8 days[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 3-[[[

LD50 Apis mellifera (Honey bee) topical 12.5 ug/bee/48 hr[USEPA, Office of Pesticide Programs; Pesticide Ecotoxicity Database (2000) on 3-[[[

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

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 13-55(2), indicate that thifensulfuron methyl is expected to have very high to high mobility in soil(SRC). Volatilization of thifensulfuron methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.9X10-14 atm-cu m/mole(SRC), calculated from its vapor pressure, 1.28X10-10 mm Hg(3), and water solubility, 2.24X10+3 mg/L(3). Thifensulfuron methyl is not expected to volatilize from dry soil surfaces(SRC) based upon the vapor pressure. Thifensulfuron methyl is expected to biodegrade in soil based on half-lives of 1.6, 2, 25, and 37 days for this substance in different non-sterile soils compared with half-lives of 27, 25, 53, and 102 days in different sterile soils(4,5). The half-life for the microbial degradation of thifensulfuron methyl to thifensulfuron in soil has been reported as 2-3 days(6,7).

TERRESTRIAL FATE: Half-lives reported for this substance in Saint-Nazaire soil (pH 6.7, organic matter 2%, clay 22%, sand 24.3%) were 22, 41.7, 52.8, and 89 hours at initial concentrations of 1, 10, 40, and 120 mg/kg, respectively(1).

AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 13-55(2), indicate that thifensulfuron methyl 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 2.92X10-14 atm-cu m/mole(SRC), derived from its vapor pressure, 1.28X10-10 mm Hg(4), and water solubility, 2.24X10+3(4). The pKa of thifensulfuron methyl is 4.0(4), indicating that the urea nitrogens in this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). According to a classification scheme(6), an estimated BCF of 0.04(SRC), from its log Kow of -1.56(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Thifensulfuron methyl may undergo direct photolysis in the environment based on a measured half-life of 15 hours for the structurally similar compound metsulfuron methyl(9). Thifensulfuron methyl is expected to undergo hydrolysis in the environment based on measured half-lives of 1.05, 7.07, 4.90, and 3.26 days at 25 °C and pH 5, 6.5, 7.5, and 8.5, respectively(10). Thifensulfuron methyl is expected to biodegrade in water based on half-lives of 1.6, 2, 25, and 37 days for this substance in different non-sterile soils compared with half-lives of 27, 25, 53, and 102 days in different sterile soils(10,12).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thifensulfuron methyl, which has a vapor pressure of 1.28X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase thifensulfuron methyl may be removed from the air by wet or dry deposition(SRC). Thifensulfuron methyl may undergo direct photolysis in the environment based on a measured half-life of 15 hours for the structurally similar compound metsulfuron methyl(4).

Thifensulfuron methyl was measured in surface water runoff from farming systems on field-scale coastal plain watersheds in Maryland(1). The samples were collected during the first runoff event following the application of this herbicide(1). The average (maximum) concentrations of thifensulfuron methyl in runoff samples from a two-year crop rotation system were <0.05 (0.24), 0.01 (0.83), and 0.06 (0.34) ug/L at applications of 11.0, 3.30, and 5.50 g/ha, respectively. These concentrations correspond to losses of 0.02, 0.5, and 2.22% of applied thifensulfuron methyl, respectively(1). The average (maximum) concentrations of thifensulfuron in runoff samples from a three-year crop rotation system were 0.04 2.54), <0.05 (0.12), and <0.05 (0.07) ug/L at applications of 11.0, 3.30, and 5.50 g/ha, respectively(1). These concentrations correspond to losses of 0.41, 0.04, and 0.21% of applied thifensulfuron methyl, respectively(1). Thifensulfuron methyl was not detected in soil-pore water from either system(1).

Harmony

1.3 x 10 ^-2 mg/kg-day

Koc values of thifensulfuron methyl range from 13-55(1). According to a classification scheme(2), this range of Koc values suggests that thifensulfuron methyl is expected to have very high to high mobility in soil. The pKa of thifensulfuron methyl is 4.0(3), indicating that the nitrogens in this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(4).

AEROBIC: Half-lives measured for thifensulfuron methyl at an initial concentration of 20 mg/kg in sterile and non-sterile St Nazaire soil (pH 6.7, organic matter 2%, clay 22%, sand 24.3%) were 27 and 1.6 days, respectively(1). Half-lives measured for thifensulfuron methyl at an initial concentration of 20 mg/kg in sterile and non-sterile Salanque soil (pH 7.8, organic matter 1.5%, clay 19.6%, sand 19%) were 25 and 2 days, respectively(1). The half-life for the microbial degradation of thifensulfuron methyl to thifensulfuron in soil has been reported as 2-3 days(2,3).

ANAEROBIC: Pseudo-first-order rate constants of 2.72X10-2 and 1.32X10-2 per day were determined for thifensulfuron methyl in native and sterile anaerobic sediment, respectively from a stagnant, slow-moving stream. These rate constants correspond to half-lives of 25 days in the native sediment and 53 days in the sterile sediment(1). Pseudo-first-order rate constants for thifensulfuron methyl in native and sterile anaerobic sediment from a eutrophic pond were 1.89X10-2 and 0.68X10-2 per day, respectively(1). These rate constants correspond to half-lives of 37 days in the native sediment and 102 days in the sterile sediment(1).

An estimated BCF of 0.04 was calculated for thifensulfuron methyl(SRC), using a log Kow of -1.56(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).

The Henry's Law constant for thifensulfuron methyl is estimated as 2.92X10-14 atm-cu m/mole(SRC) derived from its vapor pressure, 1.28X10-10 mm Hg(1), and water solubility, 2.24X10+3 mg/L(1). This Henry's Law constant indicates that thifensulfuron methyl is expected to be essentially nonvolatile from moist soil or water surfaces(2). Thifensulfuron methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ /In a/ 90 day oral toxicity /study using/ rodents: NOAEL= 7 and 9 mg/kg/day males and females, respectively. LOAEL= 177 (males) and 216 (females) mg/kg/day based on decreased body weight, body weight gain and organ weight. /from table/

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ /In a/ 90 day oral toxicity /study using/ nonrodents: NOAEL= 37.5 mg/kg/day. LOAEL= 187.5 mg/kg/day based on decreased body weight and actual weight in high dose males. /from table/

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Harmony was administered at dietary levels of 0, 25, 500, and 2500 ppm (0, 1.25, 25, 125 mg/kg/day) to 62 rats/sex/group for 24 months. There was an interim sacrifice of 10 animals/sex/group at 12 months. The following parameters were evaluated: mortality, physical signs, body weights, food consumption, hematology, clinical chemistry, urinalysis, macroscopic and microscopic pathology. A slight but significant body weight reduction was seen in high dose males, body weight gains were significantly lower at the two highest doses. Serum sodiums were sporadically lower at 500 and 2500 ppm throughout the study. Sodium levels in the rat are normally around 144 mg% and vary only slightly from animal to animal and over time. However, with administration of harmony, both the mid- (500 ppm) and high-dose (2500 ppm) groups showed a consistent decrease in serum sodium levels. Given the powerful homeostatic mechanisms that must be affected to change serum sodium levels from 144 mg%, the results appear to be a clearly compound-related.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ /In a/ chronic toxicity /study using/ dogs: NOAEL= 18.75 mg/kg/day. LOAEL= 18.75 mg/kg/day based on increased liver weight in high dose males and increased thyroid/parathyroid-to-body weight ratios in females at the high dose, and decreased body weight and body weight gain in females after week 22. /from table/

For more Non-Human Toxicity Excerpts (Complete) data for THIFENSULFURON-METHYL (8 total), please visit the HSDB record page.

Half-lives reported for the aqueous hydrolysis of thifensulfuron methyl are 4-6 days at pH 5, 180 days at pH 7, and 90 days at pH 9(1). Hydrolysis half-lives measured for thifensulfuron methyl at 29 °C and pH 5, 6, 8, 9, and 10 were 346, 1950, 739, 130, and 12 days, respectively(2). Hydrolysis half-lives measured for thifensulfuron methyl in aqueous buffer solutions at 28 °C and pH 4, 5, 9, and 10 were 1.7, 17, 6, and 0.4 days, respectively(3). Half-lives corresponding to measured hydrolysis rate constants determined for thifensulfuron methyl in aqueous buffer solutions were 7.3 days at pH 4 and 22 °C, 0.03 days at pH4 and 40 °C, 1.1 days at pH 7 and 40 °C, 18 days at pH 10 and 22 deg, and 0.19 days at pH 10 and 40 °C(4). Hydrolysis half-lives reported for thifensulfuron methyl in aqueous solutions at 25 °C were 0.42 days at pH 4, 1.05 days at pH 5, 7.07 days at pH 6.5, 4.90 days at pH 7.5, and 3.26 days at pH 8.5(5). Under acidic conditions, hydrolysis takes place through the initial cleavage of the sulfonylurea bridge followed by O-demethylation of the triazine ring. Under basic conditions, thifensulfuron methyl undergoes ester hydrolysis(2,3,4,6,7). The structurally similar compound metsulfuron methyl was degraded by 50% and 76% in an aqueous solution (10 ug/mL, pH 6.2) after 15 and 36 hours exposure to uv irradiation (greater than or equal to 290 nm), respectively(8). Only 5% of metsulfuron methyl was degraded in a control kept in complete darkness over the same time period(8). Based on the behavior of these analogous compounds, thifensulfuron methyl is expected to undergo direct photolysis in the environment.

Tolerances are established for residues of the herbicide thifensulfuron methyl (methyl-3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino] carbonyl] amino] sulfonyl]-2-thiophene carboxylate) in or on the following raw agricultural commodities: barley, grain; barley, straw; canola, seed; corn, field, forage; corn, field, grain; corn, field, stover; cotton, gin byproducts; cotton, undelinted seed; flax, seed; oat, grain; oat, straw; soybean; wheat, grain; and wheat, straw.

New Active Ingredients ... includes pesticide active ingredients initially registered after November 1, 1984, that currently have active product registrations. By law, these newer pesticides are not subject to the reregistration program. They must, however, meet the new safety standard of the FQPA, and will be reviewed on a 15-year cycle under the registration review program. ... Active Ingredient Number: 128845; Type of Pesticide: conventional - herbicide; Use Site: food use; Year: 1986.

In the rat metabolism study, ...of the radioactivity eliminated in the urine and feces, most was parent compound with 5 minor metabolites. /from table/

The primary degradation mechanism involves hydrolysis of the methoxycarbonyl group, O-demethylation of the heterocyclic ring, and hydrolysis of the sulfonylurea group.

Used as post-emergence herbicide for control of broad-leaved weeds in food crops; [Merck Index]

Farming (Pesticides) [Category: Industry]

For thifensulfuron-methyl (USEPA/OPP Pesticide Code: 128845) 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./

Sulfonylurea herbicide for postemergence broadleaf weed control in food crops.

Herbicide /for/ postemergence weed control in soybeans.

Selected products: Harmony; Pinnacle; ...Prospect; Refine. Mixtures: Canvas (+metsulfuron-methyl, +tribenuron-methyl); ...Basis (+rimsulfuron); Calibre (+tribenuron-methyl); Concert (+chlorimuron-ethyl); Grid (+rimsulfuron); Harmony Express (+carfentrazone-ethyl); Harmony Extra (+tribenuron-methyl); Harmony M (+metsulfuron-methyl); Lexus Millenium (+flupyrsulfuron-methyl-sodium); MIllenium (+flupyrsulfuron-methyl-sodium); Reliance (+chlorimuron-ethyl); Scoop (+metsulfuron-methyl); Synchronyl STS (+chlorimuron-ethyl).

Discontinued products: Crackshot. Mixtures: DP 928 (+metsulfuron-methyl); DUK 110 (+tribenuron-methyl).

Formulations: Dry flowable.

Pharmaceuticals

Pesticides -> Herbicides -> Urea herbicides -> Sulfonylurea herbicides

Herbicides

Environmental transformation -> Pesticides (parent, predecessor)