Metsulfuron-methyl
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Metsulfuron-methyl
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CAS No:
74223-64-6
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Formula:
C14H15N5O6S
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Chemical Name:
Metsulfuron-methyl
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Synonyms:
Benzoic acid,2-[[[[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino]carbonyl]amino]sulfonyl]-,methyl ester;DPD 63760H;DPX 6376;Metsulfuron-methyl;DPX-T 6376;Gropper;Escort;Ally 20DF;Ally;T 6376;Brush-off;N-[(2-Methoxycarbonyl)phenyl]sulfonyl-N′-(6-methoxy-4-methyl-2-triazinyl)urea;HCHA 92HA;Escort (pesticide);Saber DF;Strech 60VP;Grench;Laren;Ally XP;Algrip;Cimarron;MSM Turf;Accurate 60VG;Allie SX;Zinger;Zinger WP;82197-07-7;860461-33-2
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CAS No:
Description
Light yellow solid White, off-white or pale yellow crystalline solid. Slight, sweet odor; ester-like.
Metsulfuron methyl is a N-sulfonylurea in which the sulfonyl group is attached to a 2-(methoxycarbonyl)phenyl group while a (4-methoxy-6-methyl-1,3,5-triazin-2-yl group replaces one of the amino hydrogens of the remaining urea group. It has a role as a herbicide, an environmental contaminant and a xenobiotic. It is a member of 1,3,5-triazines, a benzoate ester and a N-sulfonylurea.
Metsulfuron-methyl Basic Attributes
381.36
381.36
616-063-8
2589ET7417
DTXSID6023864
White crytals|White to pale yellow solid|Colorless crystals
2935009011
Characteristics
158
2.20
faint, sweet ester-like white to pale yellow solid
1.473 g/cm3
163-166 °C
647.2ºC at 760 mmHg
345.2ºC
1.593
In water, 9.50X10+3 mg/L at 25 deg C
0-6°C
2.5X10-12 mm Hg at 25 deg C
LD50 in male and female rats, in male and female rabbits (mg/kg): >5000, >2000 orally; LC50 (96 hour) in American perch, rainbow trout: 150 ppm; LD50 in wild ducks: 2510 mg/kg (Lefebvre)
Faint, sweet, ester-like
Henry's Law constant = 1.32X10-16 atm-cu m/mole at 25 °C (est)
pKa = 3.8 at 20 °C
Safety Information
UN30779/PG3
2
50/53
60-61
DH3563000
N
Stable in air to about 140 deg C. It is hydrolysed in acid solution, 50% loss (25 deg C) occurs in 15 hr at pH 2, 33 days at pH 5, > 41 days at pH 7 and pH 9, but is more rapid at 45 deg C.
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.
Blair AM, Martin TD; Pestic Sci 22 (3): 195-220 (1988). A review of the activity, fate and mode of action of sulfonylurea herbicides.
|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]
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.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Toxicity
LC50 Rat (male and female) inhalation >5 mg/L air/4 hr|LD50 Rat (male and female) oral >5000 mg/kg|LD50 Rabbit percutaneous >2000 mg/kg|LD50 Rabbit (male and female) oral >2000 mg/kg
/FIELD STUDIES/ The impact of two herbicides on the phytoplankton community of a typical forest lake was investigated using in situ enclosures. Chronic exposure to hexazinone resulted in concentration-dependent depression of /dissolved oxygen/ (DO), which mirrored reductions in biomass of all dominant phytoplankton groups (Cyanophyta, Chlorophyta, Chrysophyta, Cryptophyta, and Bacilliarophyceae). Although effects observed at the lowest treatment level of hexazinone (0.01 mg/L) were transient, no evidence of recovery in biomass was discernible at higher test concentrations within the 77 days of investigation. In contrast, metsulfuron methyl at concentrations as high as 1.0 mg/L (approximately 40x the worst-case expected environmental concentration [EEC]) induced only slight transient effects and only in the Cyanophyta. ...|/AQUATIC SPECIES/ Fingerlings of the silver catfish (Rhamdia quelen) were exposed to clomazone, quinclorac, and metsulfuron methyl. ... The LC50 value was 7.32 mg/L for clomazone and 395 mg/L for quinclorac, but was not obtained for metsulfuron-methyl since all fingerlings survived the highest concentration of 1200 mg/L. ... Clomazone significantly inhibited AChE activity, achieving maximal inhibition of about 83% in brain and 89% in muscle tissue. In contrast, quinclorac and metsulfuron methyl caused increases in enzyme activity in the brain (98 and 179%, respectively) and inhibitions in muscle tissue (88 and 56%, respectively).|... In the clay soil, bacterial populations decreased with increasing concentration of metsulfuron-methyl during the first 9 days of incubation but exceeded that of the control soil from day 27 onward. In the sandy loam soil, the herbicide reduced bacterial populations during the first 3 days after application, but these increased to the level of untreated controls after 9 days' incubation. Fungal populations in both soils increased with increasing metsulfuron-methyl concentrations, especially in the sandy loam soil. CO2 evolution was stimulated in both soils in the presence of the herbicide initially, but decreased during days 3 to 9 of the incubation period before increasing again afterward.
Metsulfuron methyl's production may result in its release to the environment through various waste streams; it's use as a herbicide(1) will result in its direct release to the environment(SRC).
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 °C; 22, 23, and 29 days at 22 °C; and 8 days at 30 °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 °C were 45, 60, and 62 days, respectively(5). The half-lives measured in soil stored for 0, 3, and 6 months at 20 °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 °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 °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).
First-order hydrolysis rate constants measured for metsulfuron methyl in aqueous buffer solutions at 25 °C and pH 5.2, 6.2, 7.1, 8.2, 9.4, and 10.2 were 0.072, 0.011, 0.006, 0.005, 0.007, and 0.008 per day, respectively, which correspond to half-lives of 9.6, 63, 116, 139, 99, and 87 days, respectively(1). Hydrolysis rate constants measured for this substance in soil solutions at 25 °C and pH 7.1, 9.4, and 10.2 were 0.006, 0.009, and 0.008 per day, respectively, which correspond to half-lives of 116, 99, and 87 days, respectively(1). The first-order hydrolysis rate constants measured for metsulfuron methyl in aqueous buffer solutions at pH 4 and temperatures of 20, 25, 35, 45, and 55 °C were 0.014, 0.37, 1.07, 3.09, and 7.95 per day, respectively, which correspond to half-lives of 4.98, 1.87, 0.64, 0.22, and 0.08 days, respectively(2). Hydrolysis half-lives for metsulfuron methyl at 28 °C in sterile soil were 139 days (pH 8.1, 90% water content), 99 days (pH 8.1, 50% water content), 5 days (pH 5.2, 90% water content), and 4 days (pH 5.2 and 50% water content)(3). The acidic hydrolysis of metsulfuron methyl has been reported to proceed via two steps(4). The first involves the breakdown of the sulfonylurea bridge which leads to 4-methyoxy-6-methyl-1,3,5-triazin-2-amine and o-carboxymethylphenylsulfonylcarbamic acid(4,5). The second involves the degradation of the carbamate to form methyl o-sulfamoylbenzoate(4,5). Base hydrolysis of this compound is reported to proceed via a single step involving the nucleophilic substitution of the methoxy group of the s-triazine by a hydroxide group(4,6). 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(7). Only 5% of metsulfuron methyl was degraded in a control kept in complete darkness over the same time period(7).
BCF values of 17, 14, and 1 were measured for metsulfuron methyl in freshwater microalga Chlorella fusca at pH 5, 5.3, and 6, respectively(1). According to a classification scheme(2), these BCF values suggests the potential for bioconcentration in aquatic organisms is low(SRC).
34.67 L/kg|Koc values ranging from 4-345 have been measured for metsulfuron methyl in various types of soil(1,2). According to a classification scheme(3), this range of Koc values suggests that metsulfuron methyl is expected to have moderate to very high mobility in soil. The pKa of metsulfuron methyl is 3.8(4), indicating that the urea nitrogens of 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).|Koc values measured for metsulfuran methyl in various types of soil were 14 in a clay loam (pH 7.5, 7.2% organic matter), 12 in a sandy loam (pH 7.7, 5.2% organic matter), 29 in a loam soil (pH 5.4, 3.9% organic matter), 7 in a loam soil (pH 7.6, 3.6% organic matter), 9 in a sandy clay loam (pH 7.5, 5.8% organic matter), 12 in a clay loam (pH 5.3, 4.4% organic matter), 4 in a sandy loam (pH 7.1, 2.3% organic matter), 44 in a sandy loam (pH 5.4, 19.0% organic matter), 60 in a silt loam (pH 6.5, 4.02% organic matter), 53 in a silt loam (pH 6.4, 2.75% organic matter), 50 in a sandy loam (pH 5.6, 1.40 % organic matter), and 206 in a sandy soil (pH 6.1, 0.3% organic matter)(1). Koc values measured for metsulfuron methyl in tropical soils (pH ranging from 3.63-4.23) were 194.79 (33.8% organic matter), 137.76 (21.89% organic matter), 169.90 (16.16% organic matter), 196.34 (6.15% organic matter), and 345.34 (2.77% organic matter)(2). Adsorption of metsulfuran methyl has been shown to increase with increasing soil organic matter and decreasing soil pH(2,3).
The Henry's Law constant for metsulfuron methyl is estimated as 1.32X10-16 atm-cu m/mole(SRC) derived from its vapor pressure, 2.50X10-12 mm Hg(1), and water solubility, 9.50X10+3 mg/L(1). This Henry's Law constant indicates that metsulfuron methyl is expected to be essentially nonvolatile from moist soil and water surfaces(2). Metsulfuron methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
SURFACE WATER: Metsulfuron methyl was not detected above 0.01 ug/L in 130 samples collected from Midwestern streams and rivers during 1998(1). The concentrations of metsulfuron methyl measured in water collected from the Iowa River near Rowan, IA, from the Mississippi River near Clinton, IA, and from a site on the Illinois River were 0.04, 0.05, and 0.04 ug/L, respectively during the summer of 1997(2).
Occupational exposure to metsulfuron methyl may occur through dermal contact with this compound at workplaces where metsulfuron methyl is produced or used. (SRC)
Drug Information
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 <0.1% to 1%) regardless of exposure protocol; the gastrointestinal tract, carcass, and skin had the highest concentrations of radioactivity. For the single or repeated low dose groups, the tissue content was 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.
Four metabolites and parent were recovered in both urine and feces /of rats/ in all treatment groups. Parent compound accounted for most of the urinary and fecal radioactivity (77-90% and 1.8-6.2% of the administered dose, respectively). Metabolite I was consistent with (methyl 2-((amino)sulfonyl)benzoate); Metabolite II - (2-((amino)sulfonyl)benzoic acid); and Metabolite III was consistent with (methyl 2-((((amino)carbonyl)amino)sulfonyl)benzoate). Metab. I and II appeared to result from sequential hydrolysis reactions terminating in the formation of saccharin while metab. III was formed by cleavage of the two ring structures. Total metabolites (in urine + feces of each group) accounted for approximately 5.4-8.2% of the administered dose. The metabolite profiles were qualitatively similar for urine and feces in that parent compound and the four metabolites (saccharin, metabolites I, II, and III) were found in both matrices.|(Phenyl-(U)-(14)C)sulfometuron-methyl was metabolized in excised wheat seedlings (sensitive to sulfometuron-methyl) to (14)C methyl 2-(((((4-hydroxymethyl)-6-methylpyrimindin-2-yl)amino)carbonyl)amino sulfonyl)benzoate and its carbohydrate conjugate. This metabolic pathway is consistent with sulfometuron-methyl metabolism in tolerant species such as Bermuda grass. Sulfometuron-methyl was metabolized at a slower rate than metsulfuron-methyl in wheat. When plants were exposed to (14)C methyl-4-hydroxy-2(((((4-methoxy-6-methyl-1,3,5-triazin-2- yl-) amino)carbonyl)amino)-sulfonyl)benzoate and (14)C methyl 2-(((((4-hydroxymethyl)-6-methylpyrimindin-2-yl) amino)carbonyl)amino)sulfonyl)benzoate (the primary hydroxylated wheat metabolites of metsulfuron-methyl and sulfometuron-methyl, respectively), the rate of glucose conjugation of methyl-4-hydroxy-2(((((4-methoxy-6-methyl- 1,3,5-triazin-2-yl-)amino)carbonyl)amino)-sulfonyl)benzoate was much faster than the rate of glucose conjugation of methyl 2-(((((4-hydroxymethyl)-6- methylpyrimindin-2- yl)amino)carbonyl)amino)sulfonyl)benzoate. Along with their parent cmpd, both methyl 2-(((((4-hydroxymethyl)-6- methylpyrimindin-2- yl)amino)carbonyl)amino)sulfonyl)benzoate and methyl-4-hydroxy-2(((((4-methoxy-6-methyl-1,3,5-triazin-2- yl- )amino)carbonyl)amino)-sulfonyl)benzoate are potent inhibitors of wild mustard acetolactate synthase. These results indicate that wheat intolerance to sulfometuron-methyl (but tolerance to the structurally closed related metsulfon-methyl) reflects not only a reduced ability to hydroxylate the parent molecule but also a reduced ability to conjugate the primary toxic metabolite to a nontoxic moiety.|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.
Based on time course urinary and fecal excretion data /in rats/, 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) ...
benzoic acid, 2-(((((4-methoxy-6-methyl-1,3,5-triazin-2- yl)methylamino)carbonyl)amino)sulfonyl)-, methyl ester
Metsulfuron-methyl Use and Manufacturing
Preparation ... G. Levitt, EP 7687 (1980 to DuPont); idem, US 4383113 (1983 to DuPont).
Metsulfuron methyl is a systemic selective selective wheat field high-efficiency sulfonylurea herbicide. It is another high-efficiency variety developed by DuPont in the United States in 1980 after chlorsulfuron. Its activity is three times higher than that of chlorsulfuron. The mechanism of action of metsulfuron methyl is similar to that of chlorsulfuron, which is absorbed through the roots, leaves and stems of the plant, and is rapidly conducted in the body, inhibiting the activity of acetolactate synthase (ALS), causing the biosynthesis of valine and isoleucine to be blocked, resulting in growth Suppressed and died. After absorption, the resistant crop wheat undergoes benzene ring hydroxylation in the body, and this hydroxylation product quickly forms a conjugate with glucose Chemicalbook, thereby losing activity. Metsulfuron methyl is the most active species among the existing sulfonylurea herbicides. It is suitable for all kinds of soil, pre-emergence soil treatment or post-emergence stem and leaf spraying, mainly to control most broad-leaved weeds in wheat fields, and has a significant inhibitory effect on grass weeds. When soil treatment is carried out under drought conditions, shallow soil after spraying can improve the effect of controlling grass weeds. Because of the poor activity of metsulfuron-methyl on pigs, maidenhair, and bluegrass, the mixed formulation Finesse with chlorsulfuron was prepared. Its influence on the subsequent works and application technology are still under study.
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).|For more Formulations/Preparations (Complete) data for METSULFURON-METHYL (7 total), please visit the HSDB record page.
Sulfonyl urea used as pre- and postemergence herbicide.|Affects sensitive weeds through inhibition of the enzyme acetolactate synthase (ALS). Inhibition of ALS leads to the rapid cessation of cell division and subsequent growth processes in plants. Mode of action: Selective systemic herbicide absorbed through the roots and foliage and translocated to the apex of the plants. Symptoms appear within days, with death within 2-4 weeks.
Product and residue analysis by hplc/ms/ms.|Determination of the sulfonylurea herbicide metsulfuron-methyl in soil, water and plant material was performed by GC of its pentafluorobenzyl derivatives. Amt of herbicide derivative as low as 0.1 pg per injection can be detected.|Method: USGS O-2060-01; Determination of Pesticides in Water by Graphitized Carbon-Based Solid-Phase Extraction and HPLC-MS; Analyte: metsulfuron-methyl; Matrix: water; Detection Limit: 0.0123 ug/L.
Agrochemicals -> Herbicides|Herbicides|Pesticides -> Herbicides -> Urea herbicides -> Sulfonylurea herbicides|Environmental transformation -> Pesticides (parent, predecessor)
Metsulfuron-methyl has known environmental transformation products that include 2-Amino-4-methoxy-6-methyl-1,3,5 triazine and Methyl 2-(aminosulfonyl)benzoate.|Metsulfuron-methyl has known environmental transformation products that include Acid sulphonamide (IN-D5119), Carbamoyl guanidine (IN-NC148), Ester sulfonamide (IN-D5803), Metsulfuron acid (IN F5438), O-desmethyl metsulfuron-methyl (IN-B5067), Phenylurea (IN-B5685), Saccharin (IN-00581), and Triazine amine (IN-A4098).
Computed Properties
Molecular Weight:381.37
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:381.07430439
Monoisotopic Mass:381.07430439
Topological Polar Surface Area:158
Heavy Atom Count:26
Complexity:609
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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- 2024 Central Plains (Handan) Modern Agriculture Expo and agricultural materials trading Conference will be held in August
Learn More Other Chemicals
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2,4-D Butotyl
1929-73-3
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Diquat dichloride
4032-26-2
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2,4-DB dimethylammonium
2758-42-1
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4-(2,4,5-Trichlorophenoxy)butanoic acid Formula
93-80-1
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2,4-D Isobutyl ester Formula
1713-15-1
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Fenchlorazole-ethyl Formula
103112-35-2
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(3,4-Dichlorophenoxy)acetic acid Structure
588-22-7
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(2,6-Dichlorophenoxy)acetic acid Structure
575-90-6
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What is Mesotrione
104206-82-8
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What is Fenclorim
3740-92-9
- Hot Searches
- cubr
- ivorit
- sodium tetraborate
- magnesium iodide
- butanal
- epichlorohydrin