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111991-09-4

Basic Information
CAS No.: 111991-09-4
Name: Nicosulfuron
Article Data: 19
Molecular Structure:
Molecular Structure of 111991-09-4 (Nicosulfuron)
Formula: C15H18N6O6S
Molecular Weight: 410.411
Synonyms: HU 195;SL 950;EMA 1534;EPA Pesticide Chemical Code 129008;Accent (herbicide);Milagro;2-((((4,6-Dimethoxy-(2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-N,N-dimethyl-3-pyridinecarboxamide;3-Pyridinecarboxamide, 2-(((((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)--N,N-dimethyl-;Motivell;DPX-V9636;DPX-V 9360;Nicosulfuron 2%SC;Bensulfuronmethyl;Nicosulfuron 95%TC;Nicosulfuron 75%WDG;
EINECS: 244-666-2
Density: 1.445 g/cm3
Melting Point: 141-144 ºC
Boiling Point: 333.8°C at 760 mmHg
Flash Point: 155.7°C
Solubility: 1.20E+04 mg/L at 25 ℃
Appearance: White solid
Hazard Symbols: IrritantXi
Risk Codes: 36/38
Safety: 24/25-26
PSA: 161.09000
LogP: 1.64570
Synthetic route
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

[3-(N,N-dimethylcarbamoyl)-2-pyridyl]sulfonylcarbamate ethyl ester

111991-09-4

nicosulfuron

Conditions
ConditionsYield
With calcium chloride In toluene Autoclave; Heating; Large scale;98.4%
With tetrabutyl phosphonium bromide In acetonitrile at 60 - 100℃; for 5h; Reagent/catalyst;97.13%
In toluene for 0.5h; Reflux;75.6%
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

phenyl N-{[3-(dimethylcarbamoyl)pyridin-2-yl]sulfonyl}carbamate

111991-09-4

nicosulfuron

Conditions
ConditionsYield
In dichloromethane at 40℃; for 5h; Temperature; Large scale;95.47%

[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]sulfamoyl chloride

59932-19-3

N,N-dimethyl-1-oxo-1λ5-pyridine-3-carboxamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
at 50 - 55℃; for 3h; Temperature;94%
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

917-61-3

sodium isocyanate

112006-58-3

2-sulfonyl chloride-N,N-dimethylnicotinamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
Stage #1: sodium isocyanate; 2-sulfonyl chloride-N,N-dimethylnicotinamide With triethylamine In acetonitrile at 25℃; for 5h;
Stage #2: 4,6-dimethoxy-2-aminopyrimidine In acetonitrile at 0 - 40℃; for 1h; Temperature;
92.1%
75-44-5

phosgene

36315-01-2

4,6-dimethoxy-2-aminopyrimidine

112006-75-4

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate; acetonitrile
With triethylamine In water; ethyl acetate; acetonitrile
89392-03-0

O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate

6674-22-2

1,8-diazabicyclo[5.4.0]undec-7-ene

112006-75-4

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
In water; acetonitrile
In water; acetonitrile
89392-03-0

O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate

112006-75-4

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
With potassium carbonate In dichloromethane for 1h; Product distribution / selectivity; Reflux;
111923-83-2

4,6-dimethoxypyrimidin-2-ylcarbamoyl chloride

111284-03-8

2-isocyanato-4,6-dimethoxypyrimidine

112006-75-4

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide

111991-09-4

nicosulfuron

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity;
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

[[3-[(Dimethylamino)carbonyl]-2-pyridinyl]sulfonyl]carbamic acid methyl ester

111991-09-4

nicosulfuron

Conditions
ConditionsYield
In toluene for 8.2h; Time; Reflux;
2942-59-8

2-chloronicotinic acid

111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: thionyl chloride / 4 h / Reflux
1.2: 5.7 h / 8 °C
2.1: sodiumsulfide nonahydrate; sulfur / water / 22 h / Reflux
2.2: 0.58 h / 75 °C / pH 2.8
3.1: hydrogenchloride / water / 0.5 h
3.2: 0 °C / pH 9
4.1: potassium carbonate / water; acetone / 0 °C
4.2: 0.5 h / 5 °C
5.1: toluene / 8.2 h / Reflux
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    Product Name: Nicosulfuron Synonyms: 2-[[(4,6-DIMETHOXYPYRIMIDIN-2-YL) AMINO-CARBONYL]AMINO SULFONYL]-N,N-DIMETHYL-3-PYRIDINE CARBOXAMIDE;2-[(4,6-dim…Appearance:Solid powder Storage:Sealed,light and oxygen resistant Package:aluminum foil bag,carton

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Specification

The IUPAC name of Nicosulfuron is 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-N,N-dimethylpyridine-3-carboxamide. With the CAS registry number 111991-09-4, it is also named as 2-((((4,6-Dimethoxy-(2-pyrimidinyl)amino)carbonyl)amino)sulfonyl)-N,N-dimethyl-3-pyridinecarboxamide. The product's categories are Herbicide; Agro-Products; Amines; Heterocycles; Sulfur & Selenium Compounds. It is white solid which should be stored at the temperature of 0-6 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.36; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -2.2; (4)ACD/LogD (pH 7.4): -2.36; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 12; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Index of Refraction: 1.593; (13)Molar Refractivity: 96.33 cm3; (14)Molar Volume: 283.9 cm3; (15)Polarizability: 38.19×10-24 cm3; (16)Surface Tension: 67 dyne/cm; (17)Rotatable Bond Count: 6; (18)Tautomer Count: 5; (19)Exact Mass: 410.100853; (20)MonoIsotopic Mass: 410.100853; (21)Topological Polar Surface Area: 161; (22)Heavy Atom Count: 28; (23)Complexity: 642.

Preparation of Nicosulfuron: Using 2-chloro-nicotinic acid as the starting material. Then we can get the intermediate 2-amino-sulfonyl-N, N-dimethyl pyridine amide by amidation, sulfonation and ammoniation. And then 2-amino-sulfonyl-N, N-dimethyl pyridine reacts with chloroformate to obtain the compound 1. At last, we can get Nicosulfuron by the reaction of compound 1 with 2-amino-4,6-dimethoxy pyrimidine.

Uses of Nicosulfuron: It is post-emergence sulfonylurea herbicide which can be used to control single and double leaf weeds in corn field. It is also used used to control broadleaf weeds and sedge weeds in rice seedling bed, Honda and paddy fields. In addition, it can react with methanol to get C10H13N3O5S. This reaction reacts at temperature of 50 °C. The reaction time is 20 hours. The yield is 70%.  

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes and skin, so people shold svoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

People can use the following data to convert to the molecule structure.
1. SMILES:O=C(Nc1nc(OC)cc(OC)n1)NS(=O)(=O)c2ncccc2C(=O)N(C)C
2. InChI:InChI=1/C15H18N6O6S/c1-21(2)13(22)9-6-5-7-16-12(9)28(24,25)20-15(23)19-14-17-10(26-3)8-11(18-14)27-4/h5-8H,1-4H3,(H2,17,18,19,20,23)

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
quail LD50 oral > 2250mg/kg (2250mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C219, 1991.
rabbit LD50 skin > 2gm/kg (2000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C219, 1991.
rat LD50 oral > 5gm/kg (5000mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C219, 1991.

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