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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HCID 73674Generated: October 23, 2026

Thifensulfuron methyl

THIFENSULFURON-METHYL · PINNACLE · HARMONY · dpx-m6316 · ThifensuL · thiameturon · Harmony(TM) · furon MethyL

https://huagongshe.com/en/chemical/73674

Thifensulfuron methyl molecular structure

Identifiers & Physical Properties

CAS No.79277-27-3
Molecular formulaC12H13N5O6S2
Average molar mass387.4 g/mol
Monoisotopic mass387.03072514 g/mol
SMILESCOC(=O)c1sccc1S(=O)(=O)NC(=O)Nc1nc(C)nc(OC)n1
InChIKeyAHTPATJNIAFOLR-UHFFFAOYSA-N
PubChem CID73674
ChEMBLCHEMBL1904815
ChEBICHEBI:83453
EC No.616-673-4
DTXSIDDTXSID1024124

Chemical & Physical Properties

XLogP1.6
Topological polar surface area186
Hydrogen bond donors2
Hydrogen bond acceptors10
Rotatable bonds6
Heavy atoms25
Formal charge0
Complexity597
PesticidesPesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: ApprovedPesticides -> Herbicides, SulfonylureaEnvironmental transformation -> Pesticides (parent, predecessor)
LogP (partition coefficient)log Kow = -1.561.52
OdorOdorless
Density1.580 g/cu cm1.560±0.06 g/cm3(Predicted)
Color/FormOff-white solid
SolubilityIn water, 2.24X10+3 mg/L at 25 °CPractically insoluble in waterDMSO (Slightly, Heated), Methanol (Slightly, Heated)
Human DrugsPharmaceuticals
Endocrine DisruptorsPotential endocrine disrupting compound
Melting point186 °C176°C
Vapor pressure1.28X10-10 mm Hg at 25 °C
Physical DescriptionWhite solid[Merck Index] Off-white odorless solid[HSDB]
Stability/Shelf LifeAqueous hydrolysis DT50 4-6 days (pH 5), 180 days (pH 7), 90 days (pH 9).
Storage conditionsSealed in dry,Room Temperature
pKa (acidity coefficient)pKa at 25°: 4.0
Physical stateSolid
ColorWhite to Almost white
λmax280nm(Acidic aq.)(lit.)
Merck14,9316
BRN7448062
Henry's law constant3.4×108 mol/(m3Pa) at 25℃, HSDB (2015)
Major applicationsagricultureenvironmental
InChI1S/C12H13N5O6S2/c1-6-13-10(16-12(14-6)23-3)15-11(19)17-25(20,21)7-4-5-24-8(7)9(18)22-2/h4-5H,1-3H3,(H2,13,14,15,16,17,19)
InChIKeyAHTPATJNIAFOLR-UHFFFAOYSA-N
SMILESCOC(=O)c1sccc1S(=O)(=O)NC(=O)Nc2nc(C)nc(OC)n2
LogP (partition coefficient)1.560
CAS DataBase Reference79277-27-3(CAS DataBase Reference)
EWG's Food Scores1
FDA UNII5VFH25ES6F
Pesticides Freedom of Information Act (FOIA)Harmony
EPA Substance Registry SystemThifensulfuron-methyl (79277-27-3)
UNSPSC Code41116107
NACRESNA.24
GHS pictogramGHS09
Signal wordWarning
GHS hazard statementsH410
GHS precautionary statementsP273-P391-P501
Personal protective equipment (PPE)Eyeshields, Gloves
Hazard symbolsN
Risk statements (R)50/53
Safety statements (S)60-61
UN transport numberUN3077 9/PG 3
Water hazard class (WGK)2
RTECS numberXM8463000
Hazard class9Aquatic Acute 1Aquatic Chronic 1
Packing groupIII
Customs code29350090
Storage class11 - Combustible Solids
Hazardous substances data79277-27-3(Hazardous Substances Data)
ToxicityLC50 (96-hour) for both bluegill sunsh and rainbow trout >100 mg/LLC50 (48-hour) for Daphnia magna >1,000 mg/L (Humburg et al., 1989)acute oral LD50 for rats >5,000 mg/kg (Hartley and Kidd, 1987).

Safety & Regulations

GHS classificationWarningH400: 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)H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
Regulatory informationCommission Regulation (EU) No 1141/2010Thifensulfuron 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 540/2011Thifensulfuron-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.
Hazards summaryHigh-dose animal studies: In a 24-month feeding study at 125 mg/kg/day, rats had weight loss, and decreased serum sodiumNo evidence of carcinogenicity in a study of miceDecreased mean fetal weight in a developmental study[HSDB] An irritant[MSDSonline]
FIFRA requirementsTolerances 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, grainbarley, strawcanola, seedcorn, field, foragecorn, field, graincorn, field, stovercotton, gin byproductscotton, undelinted seedflax, seedoat, grainoat, strawsoybeanwheat, grainand 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: 128845Type of Pesticide: conventional - herbicideUse Site: food useYear: 1986.
Hazard Classes and CategoriesAquatic Acute 1 (100%)Hazardous to the aquatic environment (acute) - category 1Skin corrosion/irritation - Category 3
Storage conditionsStore 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.
Cleanup methodsIf 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.
Disposal methodsSafe 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Preventive Measures/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 cracksdon'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.
Allowable TolerancesTolerances 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 ppmbarley, straw, 0.10 ppmcanola, seed, 0.02 ppmcorn, field, forage, 0.10 ppmcorn, field, grain, 0.05 ppmcorn, field, stover, 0.10 ppmcotton, gin byproducts, 0.02 ppmcotton, undelinted seed, 0.02 ppmflax, seed, 0.02 ppmoat, grain, 0.05 ppmoat, straw, 0.10 ppmsoybean, 0.10 ppmwheat, grain, 0.05 ppmand wheat, straw, 0.10 ppm.
Ecotoxicity valuesLD50 Anas platyrhynchos (Mallard duck) oral >2510 mg/kg[USEPA, Office of Pesticide ProgramsPesticide Ecotoxicity Database (2000) on 3-[[[LC50 Anas platyrhynchos (Mallard duck, 10 day old) diet >5620 ppm/8 days[USEPA, Office of Pesticide ProgramsLC50 Colinus virginianus (Northern bobwhite, 13 day old) diet >5620 ppm/8 days[USEPA, Office of Pesticide ProgramsLD50 Apis mellifera (Honey bee) topical 12.5 ug/bee/48 hr[USEPA, Office of Pesticide ProgramsFor more Ecotoxicity Values (Complete) data for THIFENSULFURON-METHYL (7 total), please visit the HSDB record page.
Environmental fateTERRESTRIAL 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).
Ecotoxicity excerpts/OTHER TERRESTRIAL SPECIES/ Treated cereals may experience a temporary inhibition of growth and color changes in the leaves, but these have no ultimate effect on the yield.
Effluent ConcentrationsThifensulfuron 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).
EPA IRIS InformationHarmony1.3 x 10 ^-2 mg/kg-day
Soil Adsorption/MobilityKoc 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).
Artificial Pollution SourcesThifensulfuron methyl's production may result in its release to the environment through various waste streamsit's use as an herbicide(1) will result in its direct release to the environment(SRC).
Environmental BiodegradationAEROBIC: 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).
Environmental BioconcentrationAn 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).
Volatilization from Water/SoilThe 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).
Non-Human Toxicity Excerpts/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.
Environmental Abiotic DegradationHalf-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.
Personal protective equipment (PPE)Eyeshields, Gloves
Water hazard class (WGK)2
RTECS numberXM8463000
UN transport numberUN3077 9/PG 3
Customs code29350090
ToxicityLC50 (96-hour) for both bluegill sunsh and rainbow trout >100 mg/LLC50 (48-hour) for Daphnia magna >1,000 mg/L (Humburg et al., 1989)acute oral LD50 for rats >5,000 mg/kg (Hartley and Kidd, 1987).
Risk statements (R)50/53
Signal wordWarning
GHS pictogramGHS09
Hazard symbolsN
Safety statements (S)60-61
Hazard class9Aquatic Acute 1Aquatic Chronic 1
Storage class11 - Combustible Solids
Packing groupIII
GHS hazard statementsH410
GHS precautionary statementsP273-P391-P501
Hazardous substances data79277-27-3(Hazardous Substances Data)

Applications & Uses

Uses

Postemergence herbicide used to control wild garlic and many broad-leaved weeds in barley and spring wheat.

Uses

Herbicide.