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CAS No.: | 111991-09-4 |
---|---|
Name: | Nicosulfuron |
Article Data: | 19 |
Molecular Structure: | |
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: | Xi |
Risk Codes: | 36/38 |
Safety: | 24/25-26 |
PSA: | 161.09000 |
LogP: | 1.64570 |
4,6-dimethoxy-2-aminopyrimidine
nicosulfuron
Conditions | Yield |
---|---|
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% |
4,6-dimethoxy-2-aminopyrimidine
nicosulfuron
Conditions | Yield |
---|---|
In dichloromethane at 40℃; for 5h; Temperature; Large scale; | 95.47% |
N,N-dimethyl-1-oxo-1λ5-pyridine-3-carboxamide
nicosulfuron
Conditions | Yield |
---|---|
at 50 - 55℃; for 3h; Temperature; | 94% |
4,6-dimethoxy-2-aminopyrimidine
sodium isocyanate
2-sulfonyl chloride-N,N-dimethylnicotinamide
nicosulfuron
Conditions | Yield |
---|---|
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% |
phosgene
4,6-dimethoxy-2-aminopyrimidine
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
nicosulfuron
Conditions | Yield |
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With triethylamine In water; ethyl acetate; acetonitrile | |
With triethylamine In water; ethyl acetate; acetonitrile |
O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
1,8-diazabicyclo[5.4.0]undec-7-ene
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
nicosulfuron
Conditions | Yield |
---|---|
In water; acetonitrile | |
In water; acetonitrile |
O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
nicosulfuron
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane for 1h; Product distribution / selectivity; Reflux; |
4,6-dimethoxypyrimidin-2-ylcarbamoyl chloride
2-isocyanato-4,6-dimethoxypyrimidine
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
nicosulfuron
Conditions | Yield |
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In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity; |
4,6-dimethoxy-2-aminopyrimidine
nicosulfuron
Conditions | Yield |
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In toluene for 8.2h; Time; Reflux; |
2-chloronicotinic acid
nicosulfuron
Conditions | Yield |
---|---|
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 View Scheme |
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. |