136849-15-5

Basic information

• Product Name: CYCLOSULFAMURON
• Synonyms: CYCLOSULFAMURON;JIN-QUI;SAVIOUR;cyclosulfamuron (pa iso, ansi);CYCLOSULFAMURON STANDARD;1-[2-（cyclopropylcarbonyl) phenylsulfamoyl]-3-(4,6-dimethoxypyrimidin-2-yl) urea;AC 322140;Invest
• CAS NO: 136849-15-5
• Molecular Formula: C₁₇H₁₉N₅O₆S
• Molecular Weight: 421.43
• Mol File: 136849-15-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 162.0℃
• Appearance: /
• Density: 1.532 g/cm³
• Refractive Index: 1.654
• Storage Temp.: 0-6°C
• Solubility: Solubility in organic solvents (g/l at 20 °C) Acetone 21.0 Ethyl acetate 5.0 Dichloromethane 50.0 n‐Hexane <0.001 Methanol 1.5 Toluene 1
• PKA: Dissociation constant (pKa at 20 °C) 5.04
• Water Solubility: Solubility in water (g/l at 25 °C): 0.001 (pH 5) 0.003 (pH 6) 0.006 (pH 7) 0.032 (pH 8).
• BRN: 9011949
• CAS DataBase Reference: CYCLOSULFAMURON(CAS DataBase Reference)
• NIST Chemistry Reference: CYCLOSULFAMURON(136849-15-5)
• EPA Substance Registry System: CYCLOSULFAMURON(136849-15-5)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 136849-15-5(Hazardous Substances Data)

Usage

Uses

Cyclosulfamuron can be used in analytical study of importance of optimizing chromatographic conditions and mass spectrometric parameters for supercritical fluid chromatography?/mass spectrometry.

Agricultural Uses

Cyclosulfamuron (AC 322140) herbicide was launched in 1997 by American Cyanamid and is marketed by BASF for control of a wide range of broadleaf weeds and sedge species in rice, wheat, and barley. Rice weeds controlled with greater 90% efficiency at an application rate of 45–60 g a.i. ha?1 include Cyperus serotinus, C. difformis, Elatine triandra, Eleocharis congesta, E. kuroguwai, Lindernia annua, L. procumbens, M. vaginalis, Rotala indica, Sagittaria pygmaea, S. trifolia, and Scirpus juncoides. Selectivity in the rice paddy is achieved due to various factors, including rapid metabolic degradation of the herbicide in rice shoots, placement of rice seedlings during transplanting, and the compound’s soil‐binding properties, which retain cyclosulfamuron in the upper soil layer of the paddy. In rice, cyclosulfamuron is commercialized under the trade name “Ichiyonmaru” and “Saviour.” In combinations with daimuron and cafenstrole, it is sold as “Nebiros” and in combination with pentoxazone as “Utopia.” “Shakariki” is the trade name for the mixture with esprocarb. “Kanetsugu‐Radical” is a combination of cyclosulfamuron and pretilachlor that was recently introduced in Japan in 2015. At application rates of 25–50 g a.i. ha?1, cyclosulfamuron can also be used in cereal crops for pre‐ and post‐emergent control of several important broadleaf weeds, such as Veronica persica, V. hederifolia, G. aparine, Matricaria spp., and P. convolvulus. Cyclosulfamuron cannot be synthesized by any of the general methods depicted in Scheme 2.2.1. From the methods reported in the patent literature, Brady et al. describe a straightforward reaction of 2‐amino‐4,6‐dimethoxypyrimidine with chlorosulfonylisocyanate (CSI) at 0 °C with a mixture of 2‐aminophenyl cyclopropyl ketone and triethylamine to yield 70% of the desired herbicide. The synthesis of cyclosulfamuron and its intermediate products was also reported in 2005 by Tan et al.

InChI:InChI=1/C17H19N5O6S/c1-27-13-9-14(28-2)19-16(18-13)20-17(24)22-29(25,26)21-12-6-4-3-5-11(12)15(23)10-7-8-10/h3-6,9-10,21H,7-8H2,1-2H3,(H2,18,19,20,22,24)

Upstream product

• 36315-01-2 4,6-dimethoxy-2-aminopyrimidine 
• 136832-46-7 (2-aminophenyl)-cyclopropylmethanone 

Relevant articles and documents

Method for producing a solid herbicide formulation

The invention relates to a method for producing a solid herbicide formulation containing a) a herbicide from the group of sulfonylurea, or the salts thereof which are useful in the agricultural domain, b) optionally at least one other herbicide, c) optionally a safener, and d) at least one formulation adjuvant. A suspension is formed in water, consisting of the sulfonylurea a), optionally at least one other herbicide b), optionally a safener c) and at least one formulation adjuvant d). The suspension is adjusted to a pH value between 6.5 and 8 by adding an acid or a base, and is then dried to obtain the solid formulation.

Process for the manufacture of herbicidal 1-{[2-(cyclopropylcarbonyl)phyenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds

There is provided an effective and efficient, three step process for the manufacture of crop-selective, herbicidal 1-{[2-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dialkoxy-2-pyrimidinyl)urea compounds, and an intermediate for use therein.