122931-48-0

Basic information

• Product Name: Rimsulfuron
• Synonyms: RIMSULFURO;1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-ethylsulfonyl-2-pryidylsulfonyl)urea;RIMSULFURON PESTANAL, 100 MG;RIMSULPHURON;Totis;3-(4,6-Dimethoxypyrimidin-2-yl)-1-(3-ethylsulfonylpyridin-2-yl)sulfonylurea;Rimsulfuron,1-(4,6-Dimethoxy-2-pyrimidinyl)-3-[3-(ethylsulfonyl)-2-pyridylsulfonyl]urea;Rimsulfuron 100mg [122931-48-0]
• CAS NO: 122931-48-0
• Molecular Formula: C₁₄H₁₇N₅O₇S₂
• Molecular Weight: 431.44
• EINECS: 248-697-83
• Mol File: 122931-48-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 172-177°C
• Flash Point: >200 °C
• Appearance: White crystal or light yellow powder
• Density: 1.4918 (rough estimate)
• Refractive Index: 1.6460 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Very Slightly, Heated)
• PKA: 4.1(at 25℃)
• BRN: 7501778
• CAS DataBase Reference: Rimsulfuron(CAS DataBase Reference)
• NIST Chemistry Reference: Rimsulfuron(122931-48-0)
• EPA Substance Registry System: Rimsulfuron(122931-48-0)

Safety Data

• RIDADR: UN3077(solid)
• WGK Germany: 1
• RTECS: UT7900000
• Hazardous Substances Data: 122931-48-0(Hazardous Substances Data)

Usage

Description

Rimsulfuron is an herbicide for the treatment of annual broadleaf weeds, certain grasses and perennial broadleaf weeds. It is quite effective in the treatment of glyphosate-resistant weed species such as marestail/horseweed. Its mechanism of action is through inhibiting the acetolactate synthase (ALS), which is involved in the synthesis of isoleucine, leucine and valine of plant, further blocking protein synthesis and the growth of weeds.

Reference

Rathinasabapathi, Bala. "Physiological Basis for Differential Tolerance of Tomato and Pepper to Rimsulfuron and Halosulfuron: Site of Action Study." Weed Science 52.2(2004):201-205. Schneiders, G. E., et al. "Fate of rimsulfuron in the environment. " Journal of Agricultural & Food Chemistry 41.12(1993): 2404-2410. Ackley, John A., and T. E. Hines. "Efficacy of Rimsulfuron and Metribuzin in Potato (Solanum tuberosum)." Weed Technology 10.3(1996):475-480. Koeppe, M. K., et al. "Basis of Selectivity of the Herbicide Rimsulfuron in Maize ☆." Pesticide Biochemistry & Physiology 66.3(2000):170-181.

Uses

Rimsulfuron is used as a pesticide.

Definition

ChEBI: A N-sulfonylurea that is N-carbamoyl-3-(ethylsulfonyl)pyridine-2-sulfonamide substituted by a 4,6-dimethoxypyrimidin-2-yl group at the amino nitrogen atom.

Agricultural Uses

Herbicide: For controlling broadleaf weeds. Registered for use in the U.S. and Canada. A U.S. EPA restricted Use Pesticide (RUP) for some formulations. Registered for use in some EU countries.

Trade name

ACCENT?; BASIS? (rimsulfuron+thifensulfuron methyl); DPX-E9636?; DPX 79406? (nicosulfuron+rimsulfuron); Matrix? (nicosulfuron+rimsulfuron); SHADEOUT?; STEADFAST?, (nicosulfuron+rimsulfuron); TRANXIT?

Metabolic pathway

The primary degradation pathway in most of the systems examined is the contraction or rearrangement and hydrolysis of the sulfonylurea linkage to yield two products that have N-pyridyl-N- pyrimidyl urea and N-pyridyl-N-pyrimidylamine moieties, and fragments of pyridine sulfonamide, 4,6- dimethoxy-2-pyrimidylurea, and 4,6-dimethoxy-2- amino-pyrimidine, respectively. In plants, demethylation and hydroxylation reactions follow the contraction or rearrangement to give N-3,4-dihydroxy- 5-methoxy-2-pyrimidyl-N(3-ethylsulfonyl-2- pyridyl)amine.

InChI:InChI=1/C14H17N5O7S2/c1-4-27(21,22)9-6-5-7-15-12(9)28(23,24)19-14(20)18-13-16-10(25-2)8-11(17-13)26-3/h5-8H,4H2,1-3H3,(H2,16,17,18,19,20)

Upstream product

• 89392-03-0 O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate 

Downstream Products

• 151331-80-5 N-((3-(ethylsulfonyl)-2-pyridinyl)-4,6-dimethoxy-2-pyrimidineamine) 
• 138724-53-5 N-(2,4-dimethoxy-2-pyrimidinyl)-N-[(3-(ethylsulfonyl)-2-pyridinyl)]urea 
• 87695-79-2 2-chloro-3-(ethylsulfonyl)pyridine 

Relevant articles and documents

Synthesis method of rimsulfuron

The invention relates to the technical field of herbicide synthesis, and discloses a rimsulfuron synthesis method, which comprises the following steps of: S1, preparation of raw materials; S2, condensation; and S3, purification: A, adding a rimsulfuron crude product obtained in S2 into a first solvent, heating to 40-100 DEG C, and keeping the temperature for 2-5 hours, wherein the mass ratio of the rimsulfuron crude product to the first solvent is 1: 2; B, adding a second solvent into the liquid treated in the step A, then cooling a liquid system to -10 to 20 DEG C, then filtering precipitates, and taking a filter cake for later use, wherein the mass ratio of the second solvent to the first solvent in the step A is 1: 2; C, adding the filter cake obtained in the step B into a third solvent, stirring and pulping, and keeping the pulping temperature at 0-50 DEG C for 2-6 hours, wherein the mass ratio of the third solvent to the first solvent in the step A is 1: 2.5; and D, filtering anddrying the substance treated in the step C to obtain the rimsulfuron active compound. The purity of the finally prepared rimsulfuron can be improved.

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.

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.