Mesosulfuron-methyl Chemical Properties

Melting point:

195.4°

Density 

1.498±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Solubility in organic solvents (g/l at 20 °C) Acetone 13.66 Ethyl acetate 2.0 Dichloromethane 3.8 n‐Hexane <0.0002 Toluene 0.013.

pka

Dissociation constant (pKa at 20 °C):4.35.

form 

Powder

color 

White to off-white

Water Solubility 

Solubility in water (g/l at 20 °C) 0.007 (pH 5) 0.483 (pH 7) 15.39 (pH 9).

Major Application

agriculture
environmental

InChI

InChI=1S/C17H21N5O9S2/c1-29-13-8-14(30-2)20-16(19-13)21-17(24)22-33(27,28)12-7-10(9-18-32(4,25)26)5-6-11(12)15(23)31-3/h5-8,18H,9H2,1-4H3,(H2,19,20,21,22,24)

InChIKey

NIFKBBMCXCMCAO-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(NC(NC1=NC(OC)=CC(OC)=N1)=O)(=O)=O

EPA Substance Registry System

Mesosulfuron-methyl (208465-21-8)

Safety Information

Hazard Codes 

N

Risk Statements 

50

Safety Statements 

60-61

RIDADR 

UN 3077

WGK Germany 

2

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Acute 1
Aquatic Chronic 1

Hazardous Substances Data

208465-21-8(Hazardous Substances Data)

Toxicity

LD50 in rats (mg/kg): >5000 orally; >5000 dermally; LC50 in rats: >1.33 mg/l air (Hacker)

Mesosulfuron-methyl Usage And Synthesis

Uses

Herbicide.

Agricultural Uses

Mesosulfuron methyl (AE F130060) was the second safened sulfonylurea herbicide for cereal crops to be commercialized, having been introduced by Bayer CropScience in 2001. Its strength is broad spectrum post emergence grass weed control. Mesosulfuron methyl, at a dose rate of 4.5– 15 g a.i. ha−1, reliably controls 24 different grass weed species from 12 different families. Among the commercially important grass weed species, it provides good control of Agrostis spp., A. myosuroides, A. spica‐venti, Avena spp., Lolium spp., P. brachystachys, P. minor, P. paradoxa, P. annua, P. trivialis, Pucciniella spp., and Sclerochloa kengiana. Additionally, mesosulfuron‐methyl controls, or has a strong suppressive effect on, some very persistent grass weed species, such as Bromus catharticus, B. diandrus, B. erectus, B. japonicus, B. mollis, B. tectorum, B. secalinus, B. sterilis, and Vulpia spp. The compound is applied on soft and durum wheat, triticale, and rye, together with mefenpyr‐diethyl as safener as the straight products “Atlantis OF,” “Silverado®,” and “Osprey®” or in combination with iodosulfuron methylsodium (“Atlantis WG,” “Cossack,” “Pacifica®”), diflufenican, and propoxycarbazone sodium.
“Atlantis WG” is positioned in market segments where grass weeds are the main target, whereas “Cossack” is a cross spectrum product that is active against both grasses and a large number of important broadleaf weeds. Mesosulfuronmethyl belongs to the group of modern OnePass® products. It acts predominantly via the leaves of treated weeds; however, highly susceptible grasses, such as Apera and Alopecurus, can also be successfully controlled by uptake of mesosulfuron methyl via the soil and the roots.
The safener mefenpyr diethyl, as with iodosulfuron methyl sodium, selectively accelerates the degradation of the active ingredient to nonphytotoxic compounds in cereals, but not in weeds.

Synthesis

Dissolve 5.0g 5-methylsulfonylaminomethyl saccharin in 30mL methanol, add 2mL concentrated hydrochloric acid, slowly raise the temperature to reflux, continue the reaction for 5h. The system was concentrated by adding dichloromethane, saturated aqueous sodium bicarbonate washed to weak alkaline, saturated brine washed, anhydrous magnesium sulfate drying, filtration, filtrate concentrated under reduced pressure to obtain a white solid 4.4g, the purity of the HPLC analysis of 98.7%. Yield 80.1%, melting point 186-188 ?? (literature: 185-187 ??). 3.0g 2-methoxycarbonyl-5-methanesulfonylaminomethylbenzenesulfonamide, 5.0g 4,6-dimethoxy-2-(phenoxycarbonyl)aminopyrimidine was dissolved in 30mL of acetonitrile, cooled down to 0-5?? in an ice bath, added 2mL 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and reacted at 25?? for 1.5h. The bulk of the solvent was removed in vacuum, and the residue was Add 30mL2mol/LHCl, 20mL isopropyl ether, a large number of solid precipitation, filtration, washing, vacuum drying to obtain the product 4.1g, HPLC purity of 99.3%, yield 87.7%, melting point of 193-195 ?? (literature: 191-193 ??).

Mesosulfuron-methyl(208465-21-8)Related Product Information

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