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111991-09-4

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111991-09-4 Usage

Description

Nicosulfuron is a kind of herbicides belonging to the sulfonylurea family. It is a broad-spectrum herbicide that can controls many kinds of maize weeds including both annual weeds and perennial weed including Johnsongrass, quackgrass, foxtails, shattercane, panicums, barnyardgrass, sandbur, pigweed and morningglory. It is a systemic selective herbicide, being effective in killing plants near the maize. This selectivity is achieved through maize’s capability of metabolizing Nicosulfuron into harmless compound. Its mechanism of action is through inhibiting the enzyme acetolactate synthase (ALS) of the weeds, blocking the synthesis of amino acids such as valine and isoleucine, and finally inhibiting the protein synthesis and causing death of weeds.

References

http://www.agchemaccess.com/Nicosulfuron http://pmep.cce.cornell.edu/profiles/extoxnet/metiram-propoxur/nicosulfuron-ext.html

Chemical Properties

Different sources of media describe the Chemical Properties of 111991-09-4 differently. You can refer to the following data:
1. White Solid
2. White crystalline solid or powder. Phenolic odor.

Uses

Different sources of media describe the Uses of 111991-09-4 differently. You can refer to the following data:
1. Herbicide.
2. Post-emergence sulfonylurea herbicide

Definition

ChEBI: A N-sulfonylurea that is 2-(carbamoylsulfamoyl)-N,N-dimethylpyridine-3-carboxamide substituted by a 4,6-dimethoxypyrimidin-2-yl group at the amino nitrogen.

Agricultural Uses

Herbicide: Used as a post-emergence herbicide to control a variety of weeds on field corn and popcorn crops. Some formulations may be U.S. EPA restricted Use Pesticides (RUP). Approved for use in EU countries.

Trade name

ACCENT?; BASIS?; CELEBRITY?; CHALLENGER?; DASUL?; DPX 79406? Herbicide (with Rimsulfuron); DPX-V9636?; GHIBLI?; LAMA?; MATRIX? Herbicide (with Rimsulfuron); MILAGRO?; MISTRAL?; MOTIVEL?; NISSHIN?; SAMSON?; STEADFAST? (nicosulfuron + rimsulfuron)

Potential Exposure

Nicosulfuron is a sulfonylurea postemergence herbicide used to control a variety of weeds on field corn and popcorn crops. Some formulations may be registered as United States Restricted Use Pesticides (RUP)

Metabolic pathway

In the four systems investigated, the primary degradation pathway is to yield pyridine sulfonamide and 4,6-dimethoxy-2-aminopyrimidine. The plant and its microsomal system include the hydroxylation pathway at the 4-position of the pyrimidine ring, resulting in hydrolysis products by the cleavage of the sulfonylurea linkage. In mammals, contraction or rearrangement of the sulfonylurea linkage for nicosulfuron and N- demethylated nicosulfuron yields two unique products which have the N-pyridyl-N-pyrimidyl urea moiety and result in the uracil metabolite.

Shipping

UN3077 or UN3082 Environmentally hazardous substances, liquid or solid, n.o.s., Hazard Class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.

Incompatibilities

Slowly hydrolyzes in water, releasing ammonia and forming acetate salts. Decomposed >165℃.

Waste Disposal

It is the responsibility of chemical waste generators to determine the toxicity and physical properties and of a discarded chemical and to properly identify its classification and certification as a hazardous waste and to determine the disposal method. United States Environmental Protection Agency guidelines for the classification determination are listed in 40 CFR Parts 261.3. Additionally, waste generators must consult and follow all regional, national, state and local hazardous waste laws to ensure complete and accurate classification and disposal methods.

Check Digit Verification of cas no

The CAS Registry Mumber 111991-09-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,1,9,9 and 1 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 111991-09:
(8*1)+(7*1)+(6*1)+(5*9)+(4*9)+(3*1)+(2*0)+(1*9)=114
114 % 10 = 4
So 111991-09-4 is a valid CAS Registry Number.
InChI:InChI:1S/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)

111991-09-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name nicosulfuron

1.2 Other means of identification

Product number -
Other names 2-[[[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]amino]sulfonyl]-N,N-dimethyl-3-pyridinecarboxamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111991-09-4 SDS

111991-09-4Synthetic route

4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

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

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

nicosulfuron
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%
4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

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

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

nicosulfuron
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

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

N,N-dimethyl-1-oxo-1λ5-pyridine-3-carboxamide
59932-19-3

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
at 50 - 55℃; for 3h; Temperature;94%
4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

sodium isocyanate
917-61-3

sodium isocyanate

2-sulfonyl chloride-N,N-dimethylnicotinamide
112006-58-3

2-sulfonyl chloride-N,N-dimethylnicotinamide

nicosulfuron
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%
phosgene
75-44-5

phosgene

4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
With triethylamine In water; ethyl acetate; acetonitrile
With triethylamine In water; ethyl acetate; acetonitrile
O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
89392-03-0

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

1,8-diazabicyclo[5.4.0]undec-7-ene
6674-22-2

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

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
In water; acetonitrile
In water; acetonitrile
O-phenyl N-(4,6-dimethoxypyrimidin-2-yl)carbamate
89392-03-0

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

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
With potassium carbonate In dichloromethane for 1h; Product distribution / selectivity; Reflux;
4,6-dimethoxypyrimidin-2-ylcarbamoyl chloride
111923-83-2

4,6-dimethoxypyrimidin-2-ylcarbamoyl chloride

2-isocyanato-4,6-dimethoxypyrimidine
111284-03-8

2-isocyanato-4,6-dimethoxypyrimidine

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity;
4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

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

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

nicosulfuron
111991-09-4

nicosulfuron

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

2-chloronicotinic acid

nicosulfuron
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
View Scheme
2-chloropyridine-3-carboxylic acid N,N-dimethylamide
52943-21-2

2-chloropyridine-3-carboxylic acid N,N-dimethylamide

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodiumsulfide nonahydrate; sulfur / water / 22 h / Reflux
1.2: 0.58 h / 75 °C / pH 2.8
2.1: hydrogenchloride / water / 0.5 h
2.2: 0 °C / pH 9
3.1: potassium carbonate / water; acetone / 0 °C
3.2: 0.5 h / 5 °C
4.1: toluene / 8.2 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1: sodium hydroxide; hydrogen sulfide; sodium; sulfur / water / 3 h / 80 °C
2: acetic acid; chlorine / water / 2 h / 40 °C
3: triethylamine / dichloromethane / 3 h / 25 °C
4: 3 h / 40 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydrogensulfide; sulfur; sodium hydroxide; water / 2 h
2: potassium carbonate / acetonitrile / 2 h / 40 - 50 °C / Reflux
3: toluene / 0.5 h / Reflux
View Scheme
2-mercapto-N,N-dimethylnicotinamide
121050-19-9

2-mercapto-N,N-dimethylnicotinamide

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride / water / 0.5 h
1.2: 0 °C / pH 9
2.1: potassium carbonate / water; acetone / 0 °C
2.2: 0.5 h / 5 °C
3.1: toluene / 8.2 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1: acetic acid; chlorine / water / 2 h / 40 °C
2: triethylamine / dichloromethane / 3 h / 25 °C
3: 3 h / 40 °C
View Scheme
N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / water; acetone / 0 °C
1.2: 0.5 h / 5 °C
2.1: toluene / 8.2 h / Reflux
View Scheme
nicotinic acid
59-67-6

nicotinic acid

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene-4-sulfonic acid / methanol / 4 h / 20 °C
2: dihydrogen peroxide; formic acid / water / 2.5 h / 78 - 84 °C
3: 3 h / 50 - 55 °C
View Scheme
N,N-dimethylnicotinamide
6972-69-6

N,N-dimethylnicotinamide

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dihydrogen peroxide; formic acid / water / 2.5 h / 78 - 84 °C
2: 3 h / 50 - 55 °C
View Scheme
4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

2-isocyanatosulfonyl-N,N-dimethylnicotinamide

2-isocyanatosulfonyl-N,N-dimethylnicotinamide

nicosulfuron
111991-09-4

nicosulfuron

Conditions
ConditionsYield
at 40℃; for 3h; Temperature;15.28 g
nicosulfuron
111991-09-4

nicosulfuron

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

Conditions
ConditionsYield
With water at 70℃; for 5h;80%
ethanol
64-17-5

ethanol

nicosulfuron
111991-09-4

nicosulfuron

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

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

Conditions
ConditionsYield
at 50℃; for 20h;75%
methanol
67-56-1

methanol

nicosulfuron
111991-09-4

nicosulfuron

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

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

Conditions
ConditionsYield
at 50℃; for 20h;70%
methanol
67-56-1

methanol

nicosulfuron
111991-09-4

nicosulfuron

A

4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

B

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

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

Conditions
ConditionsYield
at 30℃; Kinetics;
ethanol
64-17-5

ethanol

nicosulfuron
111991-09-4

nicosulfuron

A

4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

B

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

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

Conditions
ConditionsYield
at 30℃; Kinetics;
nicosulfuron
111991-09-4

nicosulfuron

A

4,6-dimethoxy-2-aminopyrimidine
36315-01-2

4,6-dimethoxy-2-aminopyrimidine

B

N,N-dimethyl-2-(aminosulfonyl)-3-pyridinecarboxamide
112006-75-4

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

Conditions
ConditionsYield
With disodium hydrogenphosphate; citric acid at 30℃; pH=4; Kinetics; Further Variations:; pH-values;
nicosulfuron
111991-09-4

nicosulfuron

2-sulfo-nicotinic acid imide

2-sulfo-nicotinic acid imide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80 percent / H2O / 5 h / 70 °C
2: aq. NaHCO3 / 16 h / 70 °C
View Scheme

111991-09-4Relevant articles and documents

Method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide

-

, (2021/10/05)

The invention belongs to the technical field of nicosulfuron original medicine production, and particularly relates to a method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide, wherein the method comprises the following steps: reacting tetramethoxypropane with ethyl cyanoacetate to generate 1-cyano-4-methoxy-1-ethoxycarbonyl-1,3-butadiene (cyanoene for short, the same below); reacting cyano alkene with hydrogen sulfide to generate ethyl 2-mercaptonicotinate (sulfydryl substance for short) in a closed-loop manner; reacting the sulfydryl substance with dimethylamine, and then carrying out oxychlorination reaction to obtain sulfonyl chloride; carrying out ammonolysis reaction on the sulfonyl chloride and ammonia gas to obtain sulfonamide; and reacting sulfonamide with solid light and pyrilamine to obtain the nicosulfuron. According to the method for closed-loop synthesis of nicosulfuron by using hydrogen sulfide, each reaction step is mild and controllable, process equipment is simple, the production cost is low, the product quality is good, three wastes are reduced, energy is saved, the production environment is improved, and the goal of carbon neutralization is favorably realized.

Preparation method of nicosulfuron crude drug

-

Paragraph 0020; 0024; 0026; 0030; 0031; 0035, (2020/03/23)

The preparation method, of the nicosulfuron crude drug comprises the following steps: synthesizing, isocyanate group sulfonyl - NNNN, N-dimethyl nicotinamide: triphosgene 2 - triethylamine and 2 - amino - 4444, 6-dimethoxypyrimidine as main raw materials in, reaction to synthesize nicosulfuron-N, N-dimethylnicotinamide 0-80 °C and 2 - amino - 4444, 6-dimethoxypyrimidine as main raw materials to synthesize nicosulfuron-N, N-dimethylaminopyridine as a main, raw material, and high yield; of nicosulfuron. 2 - The method provided by the invention comprises the following steps, synthesizing 2 - 2 -isocyanuric acid group, sulfonyl - NNNNor N-dimethylaminopyrimidinil in 0-100 °C reaction to form a nicosulfuron prodrug. by reacting. 2 - The preparation method comprises the following. steps, synthesizing nicosulfuron-N, N-dimethyl nicotinamide.

Nicosulfuron crystalline hydrate as well as preparation method and application thereof

-

Paragraph 0050; 0051; 0064-0069, (2019/10/23)

The invention provides nicosulfuron crystalline hydrate as well as a preparation method and the application thereof and belongs to the field of organic synthesis. The invention provides the nicosulfuron crystalline hydrate which has a good crystal form, does not absorb moisture or damp in the air, is good in stability and easy in drying and later processing, in addition, the product is high in chemical purity, uniform in granularity distribution and good in dispersibility, a preparation processed later is good in stability, rapid in disintegration speed, high in bioactivity, remarkable in quality advantage, free of phenomena of material moisture absorption and sticking in the process of drying, crushing, packaging and downstream preparation processing in production workshops, beneficial toclean production and preparation material blending uniformity, and in addition has the advantages of being simple and easy in production process, high in yield, low in cost, and the like.

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