Nicosulfuron

• CAS: 111991-09-4
• Catalog Number: ACM111991094
• Category: Main Products
• Molecular Weight: 410.41
• Molecular Formula: C₁₅H₁₈N₆O₆S
• Synonyms: 2-[[(4,6-DIMETHOXYPYRIMIDIN-2-YL) AMINO-CARBONYL]AMINO SULFONYL]-N,N-DIMETHYL-3-PYRIDINE CARBOXAMIDE;2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-n,n-dimethylnicotinamide;1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-dimethylcarbamoyl-2-pyridylsulfonyl)urea;ACCENT;ACCENT (TM);DASUL;NICOSULFURON;NICOSULFURONOXAMIDE
• IUPAC Name: 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-N,N-dimethylpyridine-3-carboxamide
• SMILES: CN(C)C(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC
• InChI Key: RTCOGUMHFFWOJV-UHFFFAOYSA-N
• Melting Point: 141-144°C
• Density: 1.445g/cm³
• Appearance: White solid
• EC Number: 601-148-4
• Exact Mass: 410.10100
• Hazard Statements: Xi,N
• Safety Description: 24/25-26-61
• Stability: Stable at normal temperatures and pressures.
• Supplemental Hazard Statements: H315-H319-H410
• Symbol: GHS07,GHS09

Case Study

Synthesis of Herbicide Ionic Liquids Based on Nicosulfuron

Wang, Weichen, et al. New Journal of Chemistry, 2019, 43(2), 827-833.

In order to maximize the herbicidal effect of nicosulfuron, adjuvants need to be added to stabilize nicosulfuron. Five new herbicide ionic liquids (HIL1-5) based on nicosulfuron were synthesized through acid-base reactions, each with different types of cations.
· Through acid-base reaction, paired with tetrabutylammonium, benzyltriethylammonium, 2-hydroxyethyltrimethylammonium, cetyltrimethylammonium and cetylpyridine, five nicosulfuron-based herbicidal ionic liquids were synthesized.
· HIL1-5 each have different types of cations, including short-chain cations, branched hydrocarbon cations, long-chain branched hydrocarbon cations, fused heterocyclic cations, and aromatic hydrocarbon cations.
· HILs have low solubility and surface tension, as well as moderate octanol-water partition coefficient, which can reduce the risk of leaching and contaminating the water environment to a certain extent.
· Nicosulfuron-based herbicidal ionic liquids are more stable than nicosulfuron under high temperature and ultraviolet irradiation. The order of stability of herbicidal ionic liquids is HIL5>HIL1>HIL3>HIL2>HIL4.

Study on the Photocatalytic Degradation of Nicosulfuron

Dugandžić, Ana M., et al. Journal of Photochemistry and Photobiology A: Chemistry, 2017, 336, 146-155.

Nicosulfuron (C15H18N6O6S) is a sulfonylurea herbicide that can be absorbed by leaves and roots and rapidly translocated to the meristem in the xylem and phloem. In order to understand the photodegradation mechanism of nicosulfuron, the effects of TiO2 catalyst, inorganic ions, isopropyl alcohol, acetone and hydrogen peroxide on the photocatalytic degradation of nicosulfuron were studied.
Photocatalytic degradation properties of nicosulfuron
· Research on the photocatalytic degradation of nicosulfuron in the presence of TiO2 under ultraviolet polychromatic light shows that when the concentration of nicosulfuron is 20 mg/L, the optimal concentration of the catalyst is 1 g/L.
· Reactions in acidic media were found to be faster than reactions in alkaline media. The presence of salts (cations and anions) inhibits the reaction. The influence of anions on the reaction is Cl->(SO4)2->F->NO3-, and the influence of cations on the reaction is Na+>Ca2+>Al3+.
· The addition of isopropanol strongly inhibited the reaction, indicating that ·OH radicals in the solution played an important role in the photodegradation of nicosulfuron.
· The addition of acetone and hydrogen peroxide also inhibited the reaction. The addition of sodium fluoride and isopropyl alcohol completely inhibited the photocatalytic reaction.
Five intermediates originating from the opening of the pyrimidine ring were identified using HPLC-MS.

Effects of Nicosulfuron on Plant Growth and Sugar Metabolism in Nicosulfuron-Tolerant and -Sensitive Sweet Maize

Xu, N.; Wu, Z.; Li, X.; Yang, M.; Han, J.; Lu, B.; Lu, B.; Wang, J. PLoS ONE, 2022, 17, e0276606.

Nicosulfuron applied at 80 mg kg-1 to the sister lines HK301 (tolerant, NT) and HK320 (sensitive, NS) at the four-leaf stage provided a controlled herbicidal stress for dissecting sugar metabolism.
Dose screening over 0, 20, 40, 80, 120, 160, 200, 240, 280 and 320 mg kg-1 established that NT plants grew normally at 80 mg kg-1 whereas NS growth was strongly suppressed, fixing 80 mg kg-1 as the working concentration.
In NT-CK controls plant height rose by about 5.4, 12.2, 18.0 and 22.3% at 1, 3, 5 and 7 days after treatment, while the treated NT line managed only 1.8, 6.7, 10.6 and 15.2%; adventitious root number followed the same trend, increasing 9.1, 27.3, 45.5 and 54.5% in controls versus 0.0 and 8.3% in treated plants.
By 7 days the sensitive line showed sucrose accumulation with sucrose phosphate synthase activity elevated by 175.0%, indicating that carbon was diverted into storage rather than catabolism.
Glycolytic and TCA flux diverged sharply: PFK activity in NT rose 16.3 and 32.1% at 5 and 7 days but fell in NS by 45.2, 25.2, 19.2 and 20.0% at 1, 3, 5 and 7 days, and NS pyruvate and citric acid, although transiently up 25.1 and 38.8% early on, declined significantly thereafter.
The interpretation is that nicosulfuron disrupts glycolysis and the tricarboxylic acid cycle in the sensitive genotype, depriving it of energy, whereas the tolerant line sustains both pathways under the same 80 mg kg-1 nicosulfuron load.

Increasing and Decreasing Spray pH with Buffers to Enhance the Biological Activity of Nicosulfuron on Weeds

Green, J. M.; Hale, T. Weed Technology, 2005, 19, 468-475.

Nicosulfuron, a weak acid sulfonylurea with a pKa of 4.3, was used to test whether raising then lowering spray-solution pH could boost postemergence herbicide activity.
Its pH-dependent water solubility provided the basis for the work: 360 ppm at pH 5, 12,200 ppm at pH 6.9 and 29,200 ppm at pH 8.8, and the selected buffers gave measured values of 1.8 and 2.2 for 0.1% and 1% wt/wt H3PO4, 8.9 and 9.0 for K2HPO4, and 11.6 and 12.2 for K3PO4.
Against large crabgrass at a rate of 15 g/ha, 1% wt/wt K3PO4 fully solubilised nicosulfuron and shifted the optimum nonionic surfactant HLB from a low baseline up into the 13-17 range, whereas adding 1% wt/wt H3PO4 to return the herbicide to its neutral form pulled the optimum HLB back down to roughly 10-14.
Rates were titrated over 1-500 g/ha to build dose-response curves, comparisons used nonylphenol ethoxylates spanning HLB 8.7 to 19.0 at 0.1% wt/wt, and further runs applied 10-40 g/ha with NPE-5 and NPE-20, plus 20 g/ha combination treatments and a 35 g/ha low-HLB comparison.
Under acidic conditions nicosulfuron became about four times more active with low-HLB surfactants than under basic conditions, and NPE-20 at 0.1% wt/wt enhanced activity roughly 40-fold under basic conditions and more than 100-fold under acidic conditions.
Order-of-addition also mattered: acidifying the solubilised herbicide before introducing surfactant gave greater activity than premixing adjuvant and acid, supporting a formulation strategy in which the physicochemical state of the herbicide, the adjuvant HLB and the weed species are matched.

Custom Q&A

What is the molecular formula of nicosulfuron?

The molecular formula of nicosulfuron is C15H18N6O6S.

What is the molecular weight of nicosulfuron?

The molecular weight of nicosulfuron is 410.4 g/mol.

What is the IUPAC name of nicosulfuron?

The IUPAC name of nicosulfuron is 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-N,N-dimethylpyridine-3-carboxamide.

What is the canonical SMILES notation for nicosulfuron?

The canonical SMILES notation for nicosulfuron is CN(C)C(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC.

What is the molecular structure of nicosulfuron?

Nicosulfuron is 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.

What is the CAS number of nicosulfuron?

The CAS number of nicosulfuron is 111991-09-4.

How many hydrogen bond acceptors are present in nicosulfuron?

Nicosulfuron has 9 hydrogen bond acceptor counts.

What is the XLogP3-AA value of nicosulfuron?

The XLogP3-AA value of nicosulfuron is 0.6.

What is the topological polar surface area of nicosulfuron?

The topological polar surface area of nicosulfuron is 161 Ų.

What is the formal charge of nicosulfuron?

The formal charge of nicosulfuron is 0.