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Thifensulfuron methyl

Thifensulfuron methyl structure

Thifensulfuron methyl 

structure
  • CAS No:

    79277-27-3

  • Formula:

    C12H13N5O6S2

  • Chemical Name:

    Thifensulfuron methyl

  • Synonyms:

    2-Thiophenecarboxylic acid,3-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-,methyl ester;DPX-M 6316;Harmony;Thiameturon-methyl;Thifensulfuron methyl ester;Harmony 75DF;Thifensulfuron methyl;Pinnacle;Refine;Refine DF;Pinnacle 25DF;Harmony GT-XP;Harmony GT;Harmony SX

  • Categories:

    Agrochemicals  >  Herbicides

Description

ChEBI: A methyl ester resulting from the formal condensation of the carboxy group of thifensulfuron with methanol. It is used as a post-emergence herbicide for the control of grass and broad-leaved weeds.


Thifensulfuron-methyl is a methyl ester resulting from the formal condensation of the carboxy group of thifensulfuron with methanol. It is used as a post-emergence herbicide for the control of grass and broad-leaved weeds. It has a role as an environmental contaminant, a xenobiotic, a herbicide and an agrochemical. It is a N-sulfonylurea, a member of thiophenes, a member of 1,3,5-triazines and a methyl ester. It derives from a thifensulfuron.

Thifensulfuron methyl Basic Attributes

387.39

387.39

1308068-626-2

5VFH25ES6F

DTXSID1024124

Off-white solid

29350090

Characteristics

186

-1.56

1.580 g/cu cm

176 °C

1.608

In water, 2.24X10+3 mg/L at 25 deg C

0-6°C

1.28X10-10 mm Hg at 25 deg C

Oral-Rat LD50:> 5000 mg/kg

Combustion produces toxic nitrogen oxide and sulfur oxide gas

Odorless

Henry's Law constant = 2.92X10-14 atm-cu m/mol at 25 °C (est)

pKa = 4.0 at 25 °C

Safety Information

9

UN30779/PG3

2

50/53

60-61

XM8463000

N

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Aqueous hydrolysis DT50 4-6 days (pH 5), 180 days (pH 7), 90 days (pH 9).

P273-P391-P501

H410

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.

|Warning|H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|H410: Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]|H316: Causes mild skin irritation [Warning Skin corrosion/irritation]|P332+P31, and 332+P313

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.

/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.

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).

Toxicity

practically nontoxic

LD50 Rat oral >5000 mg/kg|LD50 Rabbit percutaneous >2000 mg/kg|LC50 Rat inhalation >7.9 mg/L air/4 hr

/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.

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

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).

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.

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).

28.18 L/kg|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).

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).

SURFACE WATER: Thifensulfuron methyl was detected above 0.01 ug/L in 1 out of 130 samples collected from Midwestern streams and rivers during 1998 at a concentration of 0.015 ug/L(1). The concentration of thifensulfuron methyl measured in water collected from the Iowa River near Rowan, IA in the summer of 1997 was 0.06 ug/L(2).

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

Drug Information

In mammals, following oral administration of thifensulfuron-methyl, 70-75% of the unchanged material is excreted in the urine and feces.

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.

thifensulfuron methyl

Thifensulfuron methyl Use and Manufacturing

Methods of Manufacturing

Thifensulfuron-methyl is produced by reaction of 2-(methoxycarbonyl)-3-thiophenesulfonyl isocyanate with 2-amino-4,6-dimethoxypyrimidine.

Uses

Herbicide.

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.

Treated cereals may experience a temporary inhibition of growth and color changes in the leaves, but these have no ultimate effect on the yield.

Product and residue analysis by hplc/ms/ms.

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

Thifensulfuron-methyl has known environmental transformation products that include 2-Amino-4-methoxy-6-methyl-1,3,5 triazine.|Thifensulfuron-methyl has known environmental transformation products that include 2-Acid-3-sulfonamide (IN-L9223), 2-Acid-3-triuret, 2-ester-3-sulfonamide (IN-A5546), O-Desmethyl thifensulfuron acid (IN-JZ789), O-Desmethyl triazine amine (IN-B5528), O-demethyl-Thifensulfuron-methyl (IN-L9226), Thifensulfuron acid (IN-L9225), Thiophene sulfonimide (IN-W8268), Triazine amine (IN-A4098), Triazine urea (IN-V7160), and thiophene sulfonamide.

Computed Properties

Molecular Weight:387.4
XLogP3:1.6
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:6
Exact Mass:387.03072550
Monoisotopic Mass:387.03072550
Topological Polar Surface Area:186
Heavy Atom Count:25
Complexity:597
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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