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Metsulfuron methyl(CAS No. 74223-64-6)

Metsulfuron methyl C14H15N5O6S (cas 74223-64-6) Molecular Structure

74223-64-6 Structure

Identification and Related Records

【Name】
Metsulfuron methyl
【CAS Registry number】
74223-64-6
【Synonyms】
Metsulfuron-methyl
Gropper
Benzoic acid,2-[[[[(4-methoxy-6-methyl-1,3,5- triazin-2-yl)amino]carbonyl]amino]sulfonyl]-,methyl ester
HCHA 92HA
Ally 20DF
Ally
Brush-off
methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate
Escort (pesticide)
metsulfuron methyl
2-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)carbonyl)amino)sulfonyl)benzoic acid methyl ester
DPX 6376
DPX-T 6376
ALLIE
Metsulfuron-menthyl
【Molecular Formula】
C14H15N5O6S (Products with the same molecular formula)
【Molecular Weight】
381.36
【Inchi】
InChI=1/C14H15N5O6S/c1-8-15-12(18-14(16-8)25-3)17-13(21)19-26(22,23)10-7-5-4-6-9(10)11(20)24-2/h4-7H,1-3H3,(H2,15,16,17,18,19,21)
【Canonical SMILES】
CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2C(=O)OC
【MOL File】
74223-64-6.mol

Chemical and Physical Properties

【Appearance】
faint, sweet ester-like white to pale yellow solid
【Density】
1.473 g/cm3
【Melting Point】
158℃
【Boiling Point】
647.2 °C at 760 mmHg
【Refractive Index】
1.593
【Flash Point】
345.2 °C
【Solubilities】
Solubility (mg/L at 25 deg C): hexane 5.84X10-1, ethyl acetate 1.11X10+4, methanol 7.63X10+3, acetone 3.7X10+4, dichloromethane 1.32X10+5, toluene 1.24X10+3.
In water, 9.50X10+3 mg/L at 25 deg C
【Color/Form】
White crytals
White to pale yellow solid
Colorless crystals
【Storage temp】
0-6°C
【Computed Properties】
Molecular Weight:381.3638 [g/mol]
Molecular Formula:C14H15N5O6S
XLogP3-AA:1.5
H-Bond Donor:2
H-Bond Acceptor:6
Rotatable Bond Count:6
Tautomer Count:9
Exact Mass:381.074304
MonoIsotopic Mass:381.074304
Topological Polar Surface Area:158
Heavy Atom Count:26
Formal Charge:0
Complexity:609
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:2
Feature 3D Cation Count:2
Feature 3D Ring Count:2
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:463

Safety and Handling

【Hazard Codes】
N:Dangerousfortheenvironment;
【Risk Statements】
R50/53
【Safety Statements 】
S60;S61
【Cleanup Methods】
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.
【Transport】
UN3077 9/PG 3
【Formulations/Preparations】
Dry flowable
Wettable powder (700 g sulfometuron-methyl/kg). Mixtures include: 'Finesse', water dispersible granules (metsulfuron-methyl + chlorsulfuron)
Technical is >96% /pure/.
Selected products: Allie; Ally; Escort; Gropper; Flumen; Metsulsun-M; Nicanor; Quit; Retador; Rosulfuron; Stretch; Timefron; ...Gaio; Gem 690; Jubilee; Lorate; Simba; Luger; Malban; Metgard; Pilarcort' Purestand; Fozar; Triticas; Valuron. Mixtures: Canvas (+thifensulfuron-methyl, +tribenuron-methyl); ...Allie Express (+carfentrazone-ethyl); Ally Express (+carfentrazone-ethyl); Almix (+chlorimuron-ethyl); Finesse (+chlorsulfuron); Harmony M (+thifensulfuron-methyl); Lexus XPE (+flupyrsulfuron-methyl-sodium); Scoop (+thifensulfuron-methyl); Sindax (+bensulfuron-methyl); Speleo (+flupyrsulfuron-methyl-sodium); Neptune (+mecoprop-P); Pasture MD (+2,4-D +dicamba); Sulfonil (+propanil).
Discontinued products: Alrip; PartiSan. Mixtures: DP 911 (+tribenuron-methyl); DP 928 (+thifensulfuron-methyl).
Brush-off
Trade name: Blade, Luger, Thodsulfuron, Ultimate, Wopro-metsulfuron
【Other Preventative 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 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.
【Specification】

The IUPAC name of?Metsulfuron-methyl is?methyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate. With the?CAS registry number 74223-64-6,?it is also named as 2-(((((4-Methoxy-6-methyl-1,3,5-triazin-2yl)amino)carbonyl)amino)sulfonyl)benzoic acid methyl ester;?Brush-off. The?product's categories?are?herbicide; brush controller; alphabetic; herbicides; urea structure; alpha sort; pesticides & metabolites; others chemical reagents.?It is white crystalline solid. Inaddition, the?solubility in organic solvents is: dichloromethane 121g / L, acetone 36g / L, methanol?7.3g / L, ethanol 2.3g / L, xylene 580mg / L.

The other characteristics of this product can be summarized as:?(1)ACD/LogP: 1.70; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -0.09; (4)ACD/LogD (pH 7.4): -0.3; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 3.27; (8)ACD/KOC (pH 7.4): 2.02; (9)#H bond acceptors: 11; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.593; (13)Molar Refractivity: 87.82 cm3; (14)Molar Volume: 258.8 cm3; (15)Polarizability: 34.81×10-24 cm3; (16)Surface Tension: 69.1 dyne/cm; (17)Enthalpy of Vaporization: 100.3 kJ/mol; (18)Vapour Pressure: 1.23E-17 mmHg at 25°C; (19)Rotatable Bond Count: 6; (20)Tautomer Count: 9; (21)Exact Mass: 381.074304; (22)MonoIsotopic Mass: 381.074304; (23)Topological Polar Surface Area: 158; (24)Heavy Atom Count: 26.

Preparation of Metsulfuron-methyl: Added 2-amino-4-methoxy-6-methyl triazine 1.4g, dichloromethane 30ml and 2-sulfonyl isocyanate benzoate 2.4g to the reaction flask, stirred at room temperature for 16h. Rmoved the solvent of?filtrate, the residue was ground?with?chlorobutane to get white crystal.

Uses of?Metsulfuron-methyl: It is an ultra-high sulfonylurea herbicides and?branched-chain amino acid synthesis inhibitors.?And it?has?efficient, broad-spectrum, the? systemic characteristic. This chemical is used to control broad-leaved annual and perennial weeds in wheat field.

When you are using this chemical, please be cautious about it as the following:
It is very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?This material and its container must be disposed of as hazardous waste ans avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES: O=C(OC)c1ccccc1S(=O)(=O)NC(=O)Nc2nc(nc(OC)n2)C;
2.?InChI: InChI=1/C14H15N5O6S/c1-8-15-12(18-14(16-8)25-3)17-13(21)19-26(22,23)10-7-5-4-6-9(10)11(20)24-2/h4-7H,1-3H3,(H2,15,16,17,18,19,21).

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
duck LD50 oral > 2510mg/kg (2510mg/kg) ? "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A669, Pg. 1984,
mouse LD50 oral > 5gm/kg (5000mg/kg) ? Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 19, Pg. S147, 1994.
rabbit LD50 skin > 2gm/kg (2000mg/kg) ? Farm Chemicals Handbook. Vol. -, Pg. C16, 1991.
rat LC50 inhalation > 5gm/m3/4H (5000mg/m3) ? "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A669, Pg. 1984,
rat LD50 oral > 5gm/kg (5000mg/kg) ? "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A669, Pg. 1984,

【Octanol/Water Partition Coefficient】
log Kow = 2.20
【Disposal Methods】
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.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation ... G. Levitt, EP 7687 (1980 to DuPont); idem, US 4383113 (1983 to DuPont).

Biomedical Effects and Toxicity

【Biomedical Effects and Toxicity】
Overall recovery of metsulfuron methyl among the treatment groups was acceptable (about 91.6-103.8%). The primary route of excretion /in rats/ was via the urine which accounted for approximately 71-95% (78-96% if cage wash radioactivity is considered) among the various treatment groups. Fecal elimination was 4.8-13.3%. Excretion was almost complete within 48 ours. Based on time course urinary and fecal excretion data, elimination half-lives (males and females) were estimated to be 13-16 hours for Group I (single low dose), 9-12 hours for Group II (21 day dietary exposure), and 23-29 hours for Group III single high dose) which affirmed notable alteration of absorption and/or excretion processes in the high-dose group. Tissue burdens were minimal (generally 0.03 ppm. In the high-dose group, females had somewhat higher tissue burdens (ranging from 0.8 ppm in brain to 7.1 ppm in liver and 8.0 ppm in kidneys) than did males (0.1 ppm in blood to 1.6 ppm in liver and 2.6 ppm in kidneys). No evidence for sequestration of the test article or its biotransformation products.
In mammals, following oral administration, metsulfuron-methyl is excreted predominantly unchanged. The methoxycarbonyl and sulfonylurea groups are only partly degraded, by O-demethylation and hydroxylation.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values ranging from 4-345(2,3), indicate that metsulfuron methyl is expected to have moderate to very high mobility in soil(SRC). Volatilization of metsulfuron methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.32X10-16 atm-cu m/mole(SRC), calculated from its vapor pressure 2.50X10-12 mm Hg(4) and water solubility of 9.50X10+3 mg/L(4). Metsulfuron methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Metsulfuron methyl is expected to biodegrade in soil based on half-lives of 27, 60, and 17-69 days for this substance in different non-sterile soils compared with half-lives of 54, 108, and 99-139 days in different sterile soils(5,6).
TERRESTRIAL FATE: The half-life of metsulfuran methyl (200 g/kg in an herbicide formulation) applied to a field was 33 days at an application rate of 20.0 g/ha and 23 days at an application rate of 10.0 g/ha(1). The half-life determined for metsulfuron methyl applied to spring barley fields was 6.5 days at each application rate (4, 8, and 6 g/ha)(2). Half-lives measured for 4.3 ug metsulfuron methyl in different flasks containing 50 g of Horitiu sandy loam were 36 days at 10 deg C; 22, 23, and 29 days at 22 deg C; and 8 days at 30 deg C(3). Half-lives of 10 and 11 days were measured for metsulfuron methyl applied to fields of Horitiu sandy loam at application rates of 30 and 60 g/ha, respectively(3). Metsulfuron methyl was dissipated by 50% after 16 days and by 90% after 54 days in a soil flow-through test system at both initial concentrations of 0.1 and 1.0 ppm(4). Half-lives corresponding to the degradation of 10 ug metsulfuron methyl applied to different samples containing 50 g of silt loam (pH 8, 22 g/kg organic carbon) that had been previously stored for 0, 3, and 6 months at 4 deg C were 45, 60, and 62 days, respectively(5). The half-lives measured in soil stored for 0, 3, and 6 months at 20 deg C were 45, 71, and 58 days, respectively(5).
AQUATIC FATE: Based on a classification scheme(1), Koc values ranging from 4-345(2,3) indicate that metsulfuron methyl is expected to have little to no adsorption to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 1.32X10-16 atm-cu m/mole(SRC), calculated from its vapor pressure of 2.50X10-12 mm Hg(5) and water solubility of 9.50X10+3 mg/L(5). The pKa of metsulfuron methyl is 3.8(6), 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(7). According to a classification scheme(8), measured BCF values ranging from 1-17(9), suggest the potential for bioconcentration in aquatic organisms is low(SRC). Mesulfuron methyl is expected to undergo hydrolysis in the environment based on measured half-lives of 4-9.6, 116, 99-139, and 87 days at pH 5.2, 7.1, 8.2, and 10.2 and temperatures of 25-28 deg C(10,11). Metsulfuron methyl is expected to biodegrade in water based on half-lives of 27, 60, and 17-69 days for this substance in non-sterile soil compared with half-lives of 54, 108, and 99-139 days in sterile soil(11,12).
AQUATIC FATE: Degradation of metsulfuron methyl was observed in an in-situ enclosure deployed in a mixed-wood/boreal forest lake(1). Half-lives were less than 84 days and approximately 30 days at initial concentrations of 1000 and 10,000 ug/L, respectively(1).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metsulfuron methyl, which has a vapor pressure of 2.50X10-12 mm Hg at 25 deg C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase metsulfuron methyl may be removed from the air by wet or dry deposition(SRC). Metsulfuron methyl may undergo direct photolysis based on 50 and 76% degradation of this substance 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(4). Only 5% of metsulfuron methyl was degraded in a control kept in complete darkness over the same time period(4).

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