Chlorsulfuron

Base Information

• Chemical Name: Chlorsulfuron
• CAS No.: 64902-72-3
• Deprecated CAS: 112143-77-8
• Molecular Formula: C12H12ClN5O4S
• Molecular Weight: 357.777
• Hs Code.: 2935009011
• European Community (EC) Number: 279-271-4,265-268-5
• UN Number: 3077,2588
• UNII: O6S620ML45
• DSSTox Substance ID: DTXSID7023980
• Nikkaji Number: J20.653I
• Wikipedia: Chlorsulfuron
• Wikidata: Q424796
• Metabolomics Workbench ID: 67755
• ChEMBL ID: CHEMBL1229721
• Mol file: 64902-72-3.mol

Synonyms:chlorsulfuron;chlorsulfuron, monoammonium salt

Chemical Property of Chlorsulfuron

Chemical Property:

• Appearance/Colour: Colorless crystal
• Melting Point: 174-178 °C
• Refractive Index: 1.617
• Boiling Point: 563oC
• PKA: 4.21±0.10(Predicted)
• PSA: 131.55000
• Density: 1.536 g/cm³
• LogP: 2.89710
• Storage Temp.: 0-6°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 357.0298527
• Heavy Atom Count: 23
• Complexity: 514
• Transport DOT Label: Class 9

Purity/Quality:

98% ^*data from raw suppliers

Chlorosulfuron ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N, Xi
• Hazard Codes: N,Xi
• Statements: 50/53
• Safety Statements: 60-61-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Pesticides -> Herbicides, Sulfonylurea
• Canonical SMILES: CC1=NC(=NC(=N1)OC)NC(=O)NS(=O)(=O)C2=CC=CC=C2Cl
• Uses: Intrinsic and super-efficient sulfonylurea herbicide. When absorbed by surfaces or roots of weeds, the agent is conducted to the whole plant. It inhibits the synthesis of branched chain amino acids, valine and leucine by inhibiting the activity of acetyl lactase, thereby stopping cell division, producing chlorosis and withering away to death. It is used to control broadleaf weeds and grass weeds in cereal crop fields, such as goosefoot, polygonum, amaranth, cleaver, piemarker, field bindweed, cirsium arvense, black bindweed, german camomile, setaria viridis, ryegrass, bluegrass, allium macrostemon bunge and so on. Not effective for avena fatua and solanum nigrum. It is used early before or after germination and usually administered after autumn crops are sowed but before germination or after germination of spring weeds. It is more suitable to provide leaf surface treatments after germination. Mix 0.15~0.6 grams of active ingredient per 100m2 with water to spray. It has good effects when mixed with chlortoluron and isoproteron. The crops such as corn, rape and so on are sensitive to the second stubble. It has little effect on the following rice when the dosage exceeds 0.6g. Chlorsulfuron is a new type of sulfonylurea herbicide developed by DuPont Company of America in 1978. DuPont has turned it into a commercial product from 1981. The product is a super-efficient herbicide with low toxicity characterized by high activity, broad spectrum, selective safety of wheat seedlings. Triazine urea herbicide used to control broad-leaved weeds and some annual grass weeds. Chlorsulfuron is used as a postemergence herbicide for the control of dicotyledonous weeds, with excellent safety for wheat and other cereals crops. While chlorsulfuron is primarily used to control weeds in cereals, it can also be used in range and pasture applications. It is currently only used to a minor extent for nonfood industrial applications and right-of-way purposes.
• Description: Chlorsulfuron is one of the first sulfonylurea herbicides developed and commercialized by DuPont. Dr George Levitt and his team at DuPont first synthesized chlorsulfuron in 1976, and it was commercialized for use as a herbicide in 1981. It is currently registered by DuPont in the United States, Canada, the European Union, Russia, the Ukraine, Australia, New Zealand, South Africa, Saudi Arabia, and in several countries of South America. Compared with many other herbicides that are applied at levels of pounds per acre (or kilograms per acre), sulfonylureas are highly effective at use rates of less than an ounce per acre (approximately 6 g per acre for chlorsulfuron).

Technology Process of Chlorsulfuron

There total 4 articles about Chlorsulfuron which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-chlorobenzenesulfonamide (6961-82-6) → 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (64902-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,4-diaza-bicyclo[2.2.2]octane / toluene / 20 h / 20 - 100 °C

2: toluene / 8 h / 70 °C

With 1,4-diaza-bicyclo[2.2.2]octane; In toluene;

DOI:10.1039/c5ra25765d

Reference yield:

2-chlorophenylsulfonyl isocyanate (64900-65-8) + 4-methoxy-6-methyl-1,3,5-triazin-2-amine (1668-54-8) → 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (64902-72-3)

Guidance literature:

In toluene; at 70 ℃; for 8h;

DOI:10.1039/c5ra25765d

Reference yield:

Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester (99502-89-3) + 2-Chlorbenzensulfonamid-Natriumsalz (97135-93-8) + 4-methoxy-6-methyl-1,3,5-triazin-2-amine (1668-54-8) → 1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea (64902-72-3)

Guidance literature:

Yield given. Multistep reaction; 1) THF, -5 deg C, 30 min and 2 h, r.t., 2) DMF, 3 h, r.t.;

upstream raw materials:

Chlorameisensaeure-N-hydroxy-norborn-5-en-2,3-dicarboximidester

2-Chlorbenzensulfonamid-Natriumsalz

4-methoxy-6-methyl-1,3,5-triazin-2-amine

2-chlorophenylsulfonyl isocyanate

Downstream raw materials:

4-methoxy-6-methyl-1,3,5-triazin-2-amine

2-chlorobenzenesulfonamide

methanol

Refernces

• 1、 -. "Herbicidal compositions with increased crop safety". . . Retrieved 2008/06/13.
• 2、 -. "Soybean plants with dominant selectable trait for herbicide resistance". . . Retrieved 2008/06/13.