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Tribenuron methyl

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Tribenuron methyl Basic information

Product Name:
Tribenuron methyl
CAS:
101200-48-0
MF:
C15H17N5O6S
MW:
395.39
EINECS:
401-190-1
Mol File:
101200-48-0.mol
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Tribenuron methyl Chemical Properties

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
pka
4.34±0.10(Predicted)
form 
neat
Water Solubility 
55 g l-1(25 °C)
CAS DataBase Reference
101200-48-0(CAS DataBase Reference)
EPA Substance Registry System
Tribenuron-methyl (101200-48-0)
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Safety Information

Hazard Codes 
Xi,N
Risk Statements 
43-50/53
Safety Statements 
22-24-37-61-60-46
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
1
RTECS 
DH3565000
Hazardous Substances Data
101200-48-0(Hazardous Substances Data)
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Tribenuron methyl Usage And Synthesis

Uses

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.

General Description

Colorless crystals. Non corrosive. Used as an herbicide.

Air & Water Reactions

Hydrolysis occurs rapidly at pH <7 or >12.

Reactivity Profile

A sulfonylurea derivative.

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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