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101200-48-0

101200-48-0 Structure

101200-48-0 Structure
IdentificationMore
[Name]

Tribenuron methyl
[CAS]

101200-48-0
[Synonyms]

EXPRESS
EXPRESS(R)
GRANSTAR
METHYL-2-[[[[(4-METHOXY-6-METHYL-1,3,5-TRIAZIN-2-YL)METHYLAMINO]CARBONYL]-AMINO]SULFONYL]BENZOATE
Methyl 2-[[[[N-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]amino]sulfonyl] benzoate
POINTER
TRIBENURON-METHYL
TRIBENURON METHYL 6
benzoicacid,2-(((((4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino)carbonyl
dpx-l5300
express75df
l5300
matrix
methyl2-[[[[n-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)methylamino]carbonyl]ami
no]sulfonyl]benzoate
sulfmethmeton-methyl
Tribenuronmethylester
DXP-L5300
Express TM
TRIBENURON-METHYL PESTANAL, 100 MG
[EINECS(EC#)]

401-190-1
[Molecular Formula]

C15H17N5O6S
[MDL Number]

MFCD01311816
[Molecular Weight]

395.39
[MOL File]

101200-48-0.mol
Chemical PropertiesBack Directory
[Melting point ]

141°C
[density ]

1.4143 (rough estimate)
[vapor pressure ]

1.24 at pH 7 (25 °C)
[refractive index ]

1.6460 (estimate)
[storage temp. ]

0-6°C
[solubility ]

Chloroform (Slightly), DMSO (Slightly)
[form ]

neat
[pka]

4.34±0.10(Predicted)
[Water Solubility ]

55 g l-1(25 °C)
[color ]

White to off-white
[Henry's Law Constant]

9.7×107 mol/(m3Pa) at 25℃, MacBean (2012)
[Stability:]

Hygroscopic, Unstable in Solution
[InChI]

1S/C15H17N5O6S/c1-9-16-13(18-14(17-9)26-4)20(2)15(22)19-27(23,24)11-8-6-5-7-10(11)12(21)25-3/h5-8H,1-4H3,(H,19,22)
[InChIKey]

VLCQZHSMCYCDJL-UHFFFAOYSA-N
[SMILES]

COC(=O)c1ccccc1S(=O)(=O)NC(=O)N(C)c2nc(C)nc(OC)n2
[CAS DataBase Reference]

101200-48-0(CAS DataBase Reference)
[EPA Substance Registry System]

101200-48-0(EPA Substance)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R43:May cause sensitization by skin contact.
[Safety Statements ]

S22:Do not breathe dust .
S24:Avoid contact with skin .
S37:Wear suitable gloves .
[RIDADR ]

UN 3077 9 / PGIII
[WGK Germany ]

1
[RTECS ]

DH3565000
[REACH Registrations]

Inactive
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
Skin Sens. 1
STOT RE 2
[Hazardous Substances Data]

101200-48-0(Hazardous Substances Data)
[Toxicity]

quail,LD50,oral,> 2250mg/kg (2250mg/kg),Pesticide Manual. Vol. 9, Pg. 840, 1991.
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Xylene-->Methyl formate-->Metsulfuron methyl-->Dicyandiamide-->Triethylenediamine-->Butyl isocyanate-->2-Amino-4-methoxy-6-methyl-1,3,5-triazine-->o-Toluic acid-->cyanic acid-->N-2,4-Dimethylphenyl-N'-methylformamidine-->1,3,5-Triazine-->Diphosgene-->Benzenesulfonyl isocyanate-->2-Carbomethoxybenzenesulfonamide
[Preparation Products]

4-Methoxy-N,6-dimethyl-1,3,5-triazin-2-amine
Hazard InformationBack Directory
[General Description]

Colorless crystals. Non corrosive. Used as an herbicide.
[Reactivity Profile]

A sulfonylurea derivative.
[Air & Water Reactions]

Hydrolysis occurs rapidly at pH <7 or >12.
[Chemical Properties]

Tribenuron-methyl (TBM) is a member of the sulfonylurea herbicide family. It is a relatively polar, weak, acidic compound that is soluble in water. It can be extracted with polar organic solvent, buffer solution, or a mixture of organic solvent and water.
Tribenuron-methyl is a selective herbicide that inhibits the biosynthesis of branched amino acids in sensitive plants by competitively binding to the enzyme system which catalyzes the formation of these amino acids, the acetolactate synthase (ALS). It is used in cereals for the control of broadleaved weeds.
[Uses]

Tribenuron-methyl is a sulfonyl urea herbicide derivative employed for protection of crops such as corn, citrus, potatoes, tomatoes, rice and vines via inhibiting the growth of many grasses and broad-leaf weed species.Tribenuron-methyl is applied as a foliar spray and directly to the soil as it is rapidly absorbed by the foliage and the roots, and is translocated throughout the plant to the growing points.
Tribeneuron-methyl acts by inhibiting the synthesis of amino acids, specifically valine and isoleucine, which prevents cell division and cell growth. Selectivity occurs due to the differences in the metabolism of sulfonylureas between crops and weeds.
Methomyl is a broad spectrum carbamate insecticide with both contact and oral toxicity to control chewing and sucking Lepidotera, Homoptera, Coleoptera and Hemiptera pests in vegetable, orchard, vine and field crops.
[Definition]

ChEBI: The methyl ester of tribenuron.
[Production Methods]

The production of tribenuron-methyl typically involves a two-step chemical synthesis using a one-pot method. First, methyl o-sulphamoylbenzoate reacts with solid phosgene in a solvent with a catalyst to form an intermediate compound. This intermediate then undergoes a second reaction with methyl triazine to yield tribenuron-methyl.
[Agricultural Uses]

Herbicide: Used to control annual grasses and broadleaf weeds on barley, blueberries, oats, wheat, flax and rape seed (canola). Registered for use in EU countries . Registered for use in the U.S. U.S. Maximum Allowable Residue Levels for the residues of the herbicide tribenuron methyl [40 CFR 180.451(a)]: in or on the following raw agricultural commodities: barley, grain 0.05 ppm; barley, straw 0.10ppm; canola, seed 0.02 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 0.10ppm; wheat, grain 0.05ppm; and wheat, straw 0.10 ppm. Tolerances with regional registration, as defined in 180.1(n), are established. [40 CFR 180.451(c)]: in or on the following raw agricultural commodities: grass, forage, fodder and hay, group (except Bermudagrass); forage 0.10ppm; and grass, forage, fodder and hay, group (except Bermudagrass); hay 0.10 ppm.
[Trade name]

ALLY®; CANVAS®; DPX-L-5300®; EXPRESS®; EXPRESS®-75 DF; HARMONY EXTRA®; INL-5300®; L 5300®; MATRIX®
[Mechanism of action]

Selective, absorbed through foliage. Inhibits plant amino acid synthesis - acetohydroxyacid synthase AHAS
[Metabolic pathway]

The chemical structure of tribenuron methyl possesses a mono-N-methyl group in the sulfonylurea linkage which is a unique sulfonylurea herbicide and undergoes complex degradation reactions in the environment. Tribenuron methyl degrades into many degradation products, as indicated in the pathways by photolytic and hydrolytic chemical reactions and by biological degradations by mammal, plant, and soil. It is interesting to note that photolysis in different solvents yields diverse products depending on the individual solvents.
[Degradation]

Methomyl (1) was hydrolysed under alkaline conditions at 25 °C (DT50 ca. 14 days) and was stable under neutral to acidic conditions [DT50 > 30 days at pH 5 and 7 (Friedman, 1983)l. Cleavage of the carbamate ester bond is the primary degradation pathway, yielding S-methyl N-hydroxy-thioacetimidate (2).
Irradiation of methomyl in dilute aqueous solution at 254 nrn yielded acetonitrile (3), dimethyl disulfide, acetone, N-ethylidenethylamine and carbon dioxide (Freeman and Ndip, 1984). Methomyl does not absorb sunlight but underwent degradation to acetonitrile by indirect photolytic reactions in/on soil surfaces (Swanson, 1986).
[Pesticide Type]

Herbicide
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

101200-48-0(sigmaaldrich)
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