120162-55-2

Basic information

• Product Name: Azimsulfuron
• Synonyms: 1h-pyrazole-5-sulfonamide,n-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-1-m;a8947;dpx47;dpx-a8947;ethyl-4-(2-methyl-2h-tetrazol-5-yl)-;in-a8947;3-(4,6-Dimethoxypyrimidin-2-yl)-1-[2-methyl-4-(2-methyltetrazol-5-yl)pyrazol-3-yl]sulfonyl-urea;AZIMSULFURON
• CAS NO: 120162-55-2
• Molecular Formula: C13H16N10O5S
• Molecular Weight: 424.4
• Product Categories: Herbicide
• Mol File: 120162-55-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 170°
• Appearance: /
• Density: 1.75 g/cm³
• Refractive Index: 1.759
• Storage Temp.: 0-6°C
• Solubility: Solubility in organic solvents (g/l at 25 °C) Acetone 26.4 Acetonitrile 13.9 Ethyl acetate 13.0 Dichloromethane 65.9 n‐Hexane <0.2 Methanol 2.1 Toluene 1.8
• PKA: 3.6(at 25℃)
• Water Solubility: Solubility in water (g/l at 20 °C): 0.072 (pH 5) 1.050 (pH 7) 6.536 (pH 9).
• BRN: 8284859
• CAS DataBase Reference: Azimsulfuron(CAS DataBase Reference)
• NIST Chemistry Reference: Azimsulfuron(120162-55-2)
• EPA Substance Registry System: Azimsulfuron(120162-55-2)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 120162-55-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 120162-55-2 differently. You can refer to the following data:
1. Herbicide.
2. Azimsulfuron may be used as an analytical reference standard for the determination of the pesticide in:Paddy field water by direct injection using liquid chromatography-hybrid triple quadrupole-linear ion trap-mass spectrometry (LC-QqLIT-MS).Tap and leaching water samples by solid-phase extraction (SPE), followed by LC coupled to tandem mass spectrometry (LC-MS/MS).

General Description

Azimsulfuron is a sulfonylurea based pesticide.

Agricultural Uses

Azimsulfuron (DPX‐A8947) is a new rice herbicide introduced in 1996 by DuPont for the control of broadleaf weeds (including hard‐to‐control perennials). At application rates of 8–20 g a.i. ha?1, it provides superior weed control, including E. crus-galli, when compared with the first‐generation sulfonylurea bensulfuron at 50–75 g a.i. ha?1. Azimsulfuron is targeted to replace or supplement bensulfuron in some applications. In Japan, in planted rice, azimsulfuron is used as a premixture with bensulfuron (6 + 30 g a.i. ha?1) to boost the activity against perennial weeds. Good control has also been reported of other members of the Echinochloa family, such as E. hispidula, E. oryzicola, and E. oryzoides. Other weeds controlled include Alisma lanceolatum, A. plantago‐aquatica, Butomus umbellatus, Cyperus difformis, Scirpus maritimus, S. mucronatus, S. supinus, Heteranthera limosa, Potamogeton nodosus, Ammannia coccinea, A. robusta, Bergia capensis, and Lindernia dubia. Azimsulfuron is sold under the trade names “Gulliver” and “Azin.”

Safety Profile

Different sources of media describe the Safety Profile of 120162-55-2 differently. You can refer to the following data:
1. Low toxicity by ingestion,inhalation, skin contact, and intraperitoneal routes. A mildeye irritant. When heated to decomposition it emits toxicvapors of NOx and SOx.
2. Very unstable, explosivecompound. Very sensitive to heat. Samples have explodedduring analytical combustion. When heated todecomposition it emits toxic fumes of NOx. See AZIDES.

InChI:InChI=1/C13H16N10O5S/c1-22-11(7(6-14-22)10-18-21-23(2)19-10)29(25,26)20-13(24)17-12-15-8(27-3)5-9(16-12)28-4/h5-6H,1-4H3,(H2,15,16,17,20,24)

Upstream product

• 173448-04-9 2-methyl-5-(1-methyl-5-amino-1H-pyrazol-4-yl)-2H-tetrazole 
• 1269293-80-2 5-bromo-1-methyl-1H-pyrazole-4-carbonitrile 
• 111493-52-8 5-chloro-1-methyl-1H-pyrazole-4-carbonitrile 
• 5334-41-8 5-amino-4-cyano-1-methylpyrazole 
• 89392-03-0 O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate 

Relevant articles and documents

Preparation method and applications of azimsulfuron key intermediate

The present invention provides a preparation method of 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)1H-pyrazole-5-sulfamide. The preparation method comprises that trimethyl orthoformate and malononitrile are adopted as starting raw materials, a three-step reaction is performed to obtain 1-methyl-5-amino-4-(tetrazole-5-yl)pyrazole, the 1-methyl-5-amino-4-(tetrazole-5-yl)pyrazole reacts with dimethylsulfate in the presence of an acid-binding agent to obtain 2-methyl-5-(1-methyl-5-amino-1H-pyrazole-4-yl)-2H-tetrazole, the 2-methyl-5-(1-methyl-5-amino-1H-pyrazole-4-yl)-2H-tetrazole is subjected to a sodium nitrite diazo-reaction under an acid condition, the obtained material reacts with a sodium sulfite-copper chloride-acetic acid mixture, and finally hydrolysis with ammonia is performed to obtain the target product. The present invention further provides a preparation method of azimsulfuron prepared from the 1-methyl-4-(2-methyl-2H-tetrazole-5-yl)1H-pyrazole-5-sulfamide. The preparation method of the present invention has characteristics of short reaction route, environmental protection raw materials, and high yield.

PROCESS OF PREPARATION OF AZIMSULFURON

The present disclosure provides process for preparation of azimsulfuron or its salts, isomers, and other derivatives thereof. The process involves treating a compound of formula I, (Formula I should be inserted here.) with aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite in presence of hydrochloric acid in chlorinated solvents such as dichloromethane, 1,2-dichloroethane or with aqueous acetic acid and N-chlorosuccinimide or hydrogen peroxide in presence of hydrochloric acid in aqueous cyclic ether such as tetrahydrofuran, 1,4-dioxane to obtain 1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonyl chloride; converting the sulfonyl chloride to a sulfonamide and treating the sulfonamide with a phenyl(4,6-dimethoxypyrimidin-2-yl) carbamate to obtain azimsulfuron or its salts, isomers, and other derivatives thereof.