| Identification | More | [Name]
Azimsulfuron | [CAS]
120162-55-2 | [Synonyms]
3-(4,6-Dimethoxypyrimidin-2-yl)-1-[2-methyl-4-(2-methyltetrazol-5-yl)pyrazol-3-yl]sulfonyl-urea
AZIMSULFURON
GULLIVER
N-(((4,6-Dimethoxy-2-pyrimidinyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
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
1-(4,6-dimethyoxypyrimidin-2-yl)-3-(1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-pyrazol-5-ylssulfonyl)urea
azimsulfuron (bsi,e-iso)
AZIMSULPHURON
AZIMSULFURON STANDARD
1-(4,6-Dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-yl-sulfonyl]urea
N-(((4,6-Dimethoxy-2-pyrimidinyl)amino)carbonyl)-1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazole-5-sulfonamide
azimsulfuron (ISO) 1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-ylsulfonyl]urea
1-（4，6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl) pyrazole-5-ylsulfonyl] urea
Expret
JS 458 | [Molecular Formula]
C13H16N10O5S | [MDL Number]
MFCD02102190 | [Molecular Weight]
424.4 | [MOL File]
120162-55-2.mol |
| Chemical Properties | Back Directory | [Melting point ]
170° | [density ]
1.74±0.1 g/cm3(Predicted) | [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 | [form ]
neat | [pka]
Dissociation constant (pKa at 20 °C) 3.6 | [color ]
White to Off-White | [Water Solubility ]
Solubility in water (g/l at 20 °C): 0.072 (pH 5) 1.050 (pH 7) 6.536 (pH 9). | [BRN ]
8284859 | [Henry's Law Constant]
2.0×109 mol/(m3Pa) at 25℃, Maniere et al. (2011) | [Major Application]
agriculture
environmental | [InChI]
1S/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) | [InChIKey]
MAHPNPYYQAIOJN-UHFFFAOYSA-N | [SMILES]
COc1cc(OC)nc(NC(=O)NS(=O)(=O)c2c(cnn2C)-c3nnn(C)n3)n1 | [LogP]
0.650 | [CAS DataBase Reference]
120162-55-2(CAS DataBase Reference) | [EPA Substance Registry System]
120162-55-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
N | [Risk Statements ]
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
WGK 2 | [HS Code ]
29350090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Acute 1
Aquatic Chronic 1 | [Toxicity]
LD50 in rats, bobwhite quail, mallard duck (mg/kg): >5000, >2250, >2250 orally; in rats (mg/kg): >2000 dermally (Marquez); LC50 (96 hr) in carp, bluegill sunfish, rainbow trout (ppm): >300, >1000, 154 (Marquez) |
| Hazard Information | Back Directory | [Description]
A sulfonylurea herbicide for the control of a range of broadleaved and sedge weeds in paddy fields and other crops. It is highly soluble in water, semi-volatile and, based on its physico-chemical properties, appears to have potential for leaching to groundwater. It is not expected to be persistent in the field but can be persistent in water systems. It has a low mammalian toxicity but has high potential for bioaccumulation. No adverse health effects have been identified. Azimsulfuron is moderately toxic to algae, honeybees and earthworms but less so to birds and fish. | [Uses]
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).
| [Uses]
Herbicide. | [Definition]
ChEBI: Azimsulfuron is an N-sulfonylurea that is urea in which a nitrogen attached to one of the nitrogens has been replaced by a 4,6-dipyrimidin-2-yl group while a hydrogen attached to the other urea nitrogen has been replaced by a [1-methyl-4-(2-methyl-2H-tetrazol-5-yl)-1H-pyrazol-5-yl]sulfonyl group. An acetolactate synthase inhibitor, it is used as a herbicide for the control of a variety of broad-leaved and sedge weeds in paddy fields and other aquatic situations. It has a role as a herbicide and an EC 2.2.1.6 (acetolactate synthase) inhibitor. It is an aromatic ether, a biaryl, a N-sulfonylurea, a member of tetrazoles and a pyrazole pesticide. | [Production Methods]
The production of azimsulfuron involves a multi-step synthesis beginning with the formation of a key sulfonyl chloride intermediate. This is achieved by treating a precursor compound with reagents such as aqueous acetic acid or formic acid and chlorine gas or sodium hypochlorite, in the presence of hydrochloric acid and chlorinated solvents like dichloromethane or tetrahydrofuran. The resulting sulfonyl chloride is then converted into a sulfonamide, which is subsequently reacted with phenyl (4,6-dimethoxypyrimidin-2-yl) carbamate to yield azimsulfuron. | [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.” | [Mechanism of action]
Selective, absorbed by foliage. It inhibits plant amino acid synthesis - acetohydroxyacid synthase (AHAS) | [Safety Profile]
Low toxicity by ingestion,inhalation, skin contact, and intraperitoneal routes. A mildeye irritant. When heated to decomposition it emits toxicvapors of NOx and SOx. | [Safety Profile]
Very unstable, explosivecompound. Very sensitive to heat. Samples have explodedduring analytical combustion. When heated todecomposition it emits toxic fumes of NOx. See AZIDES. | [Pesticide Type]
Herbicide |
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