83055-99-6

Basic information

• Product Name: Bensulfuron methyl
• Synonyms: bensulfuron-methyl(patented-no-supply);benzoicacid,2-((((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl;Benzoicacid,2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methy]-,methylester;f5384;methylalpha-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-o-toluate;methylbensulfuron;2-[[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]methyl]benzoic acid methyl ester;METHYL-2-[[[[[(4,6-DIMETHOXY-2-PYRIMIDINYL)AMINO]CARBONYL]-AMINO]SULFONYL] METHYL]BENZOATE
• CAS NO: 83055-99-6
• Molecular Formula: C₁₆H₁₈N₄O₇S
• Molecular Weight: 410.4
• EINECS: 401-340-6
• Product Categories: HERBICIDE;MetabolitesAnalytical Standards;PAHsPesticides&Metabolites;Urea structureMore...Close...;A-BAnalytical Standards;Alpha sort;AromaticsAlphabetic;Chemical Class;BA - BHEnvironmental Standards;Alphabetic;B;Herbicides;MetabolitesPesticides&Metabolites;Pesticides&Metabolites;Urea structure
• Mol File: 83055-99-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 185-188°C
• Appearance: /
• Density: 1.4087 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 0-6°C
• PKA: 12.34±0.70(Predicted)
• BRN: 7447488
• CAS DataBase Reference: Bensulfuron methyl(CAS DataBase Reference)
• NIST Chemistry Reference: Bensulfuron methyl(83055-99-6)
• EPA Substance Registry System: Bensulfuron methyl(83055-99-6)

Safety Data

• Hazard Codes: Xi;N,N,Xi
• Statements: 43-51/53
• Safety Statements: 2-24-37-61
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: DG8733000
• Hazardous Substances Data: 83055-99-6(Hazardous Substances Data)

Usage

Description

Bensulfuron-methyl (BSM) is a new kind of sulfonylurea herbicide widely used to control various weeds and sedges. It is moderately soluble in water, non-volatile and moderately mobile. It would not be expected to persistent in soil but could be persistent in water systems under certain conditions. It is not highly toxic to mammals. It also shows a low toxicity to birds and earthworms but is more of a concern to aquatic plants, algae and honeybees.

Uses

Bensulfuron methyl (BSM) was the first sulfonylurea herbicide commercialized for use in rice, and it remains the dominant sulfonylurea for broadleaf and sedge weed control in this crop.

Definition

ChEBI: Bensulfuron-methyl is the methyl ester of bensulfuron. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of both annual and perennial weeds in crops, particularly wheat and rice. It is not licensed for use within the UK. It has a role as a herbicide, an agrochemical and an EC 2.2.1.6 (acetolactate synthase) inhibitor. It is a N-sulfonylurea, a member of pyrimidines, a methyl ester and an aromatic ether. It derives from a bensulfuron.

Metabolic pathway

Bensulfuron methyl is metabolized by mammals and birds and the major metabolites identified include mono-O-demethylated and 5-hydroxylated bensulfuron methyl and 5-hydroxy-2-amino-3,5- dimethoxypyrimidine. As bird metabolites, cleavage of the pyrimidine ring of bensulfuron methyl is observed which results in two pyrimidine ring-opening metabolites. In rice plants, bensulfuron methyl undergoes rapid O-demethylation at one of the methoxy groups on the pyrimidine ring which will proceed through hydroxylation at the methyl group. Alcoholysis and hydrolysis of bensulfuron methyl (H1) involve mainly the breakdown of the urea moiety which leads to several degradation products, some of which are also identified as metabolites in mammals and plants.

InChI:InChI=1/C16H18N4O7S/c1-25-12-8-13(26-2)18-15(17-12)19-16(22)20-28(23,24)9-10-6-4-5-7-11(10)14(21)27-3/h4-8H,9H2,1-3H3,(H2,17,18,19,20,22)

Downstream Products

• 99283-01-9 2-{[({[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl}amino)sulfonyl]methyl}benzoic acid 

Relevant articles and documents

Herbicidal mixtures having a synergistic effect

PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.

Agrochemical formulations for water surface application

New agrochemical formulations for application to the water of paddy fields, which formulations comprise A) at least one solid core material having an apparent specific density of less than 1 and a particle diameter within the range from about 300 μm to about 1,400 μm, and B) a coating layer comprising at least one biologically active compound, at least one substance having the ability to reduce the interfacial tension between water and air, at least one oily substance and, if appropriate, one or more additives, and the use of such agrochemical formulations for applying biologically active compounds to the water of paddy fields.

Soybean plants with dominant selectable trait for herbicide resistance

The utilization of a positive selection seed screening process to isolate rate variants with resistance to a herbicide is described. The ability to screen large numbers of mutagenized seed has made it feasible to pursue and isolate plants with low frequency dominant herbicide-resistance mutations. The dominant herbicide resistance mutations are useful for many applications including expanding the utility of sulfonylurea herbicides for soybean weed control, production of F1 and F2 seeds, and as selectable markers for efficient seed purification.