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101200-48-0

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Identification

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 Properties

Melting point 
141°C
mp 
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
pka
4.34±0.10(Predicted)
Water Solubility 
55 g l-1(25 °C)
form 
neat
CAS DataBase Reference
101200-48-0(CAS DataBase Reference)
EPA Substance Registry System
101200-48-0(EPA Substance)

Safety Data

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
Hazardous Substances Data
101200-48-0(Hazardous Substances Data)

Raw materials And Preparation Products

Hazard Information

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.
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®
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).

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