Nicosulfuron

Basic Info

Common NameNicosulfuron(F05747)
2D Structure
FRCD IDF05747
CAS Number111991-09-4
PubChem CID73281
FormulaC15H18N6O6S
IUPAC Name

2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-N,N-dimethylpyridine-3-carboxamide

InChI Key

RTCOGUMHFFWOJV-UHFFFAOYSA-N

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)

Canonical SMILES

CN(C)C(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC

Isomeric SMILES

CN(C)C(=O)C1=C(N=CC=C1)S(=O)(=O)NC(=O)NC2=NC(=CC(=N2)OC)OC

Synonyms
        
            Nicosulfuron
        
            111991-09-4
        
            Milagro
        
            Motivell
        
            Accent (herbicide)
        
            SL 950
        
            Accent (pesticide)
        
            DPX-V 9360
        
            HU 195
        
            UNII-CG297D9264
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganoheterocyclic compounds
ClassPyridines and derivatives
SubclassPyridinesulfonamides
Intermediate Tree NodesNot available
Direct ParentPyridinesulfonamides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsPyridine-2-sulfonamide - Nicotinamide - Pyridinecarboxamide - Pyridine carboxylic acid or derivatives - Alkyl aryl ether - Sulfonylurea - Pyrimidine - Heteroaromatic compound - Organic sulfonic acid or derivatives - Aminosulfonyl compound - Tertiary carboxylic acid amide - Sulfonyl - Organosulfonic acid or derivatives - Carboxamide group - Carboximidic acid derivative - Carboxylic acid derivative - Ether - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organosulfur compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyridinesulfonamides. These are heterocyclic compounds containing a pyridine ring substituted by one or more sulfonamide groups.

Properties

Property NameProperty Value
Molecular Weight410.405
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count9
Rotatable Bond Count6
Complexity642
Monoisotopic Mass410.101
Exact Mass410.101
XLogP0.6
Formal Charge0
Heavy Atom Count28
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.6912
Human Intestinal AbsorptionHIA+0.7124
Caco-2 PermeabilityCaco2-0.5986
P-glycoprotein SubstrateNon-substrate0.6121
P-glycoprotein InhibitorNon-inhibitor0.6474
Non-inhibitor0.9493
Renal Organic Cation TransporterNon-inhibitor0.9017
Distribution
Subcellular localizationMitochondria0.6029
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5598
CYP450 2D6 SubstrateNon-substrate0.8508
CYP450 3A4 SubstrateNon-substrate0.6414
CYP450 1A2 InhibitorNon-inhibitor0.8642
CYP450 2C9 InhibitorNon-inhibitor0.7113
CYP450 2D6 InhibitorNon-inhibitor0.9303
CYP450 2C19 InhibitorNon-inhibitor0.8150
CYP450 3A4 InhibitorNon-inhibitor0.8966
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7615
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9759
Non-inhibitor0.6361
AMES ToxicityNon AMES toxic0.6968
CarcinogensNon-carcinogens0.6882
Fish ToxicityHigh FHMT0.9453
Tetrahymena Pyriformis ToxicityHigh TPT0.7454
Honey Bee ToxicityLow HBT0.8588
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7873
Carcinogenicity (Three-class)Non-required0.6089
Model Value Unit
Absorption
Aqueous solubility-3.5478LogS
Caco-2 Permeability0.6117LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.9455LD50, mol/kg
Fish Toxicity1.6348pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4546pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*02/01/2015
(c) grape leaves and similar species (Climbing wattle/acacia shoots, Malabar nightshades,)0253000European Union0.01*02/01/2015
(a) Solanaceae and Malvaceae0231000European Union0.01*02/01/2015
Tomatoes (Alkekengi/Chinese lanterns/ground cherries, Cape gooseberries, Cherry tomatoes, Dwarf Cape gooseberries/strawberry tomatoes, Gojiberries/wolfberries, Gojiberries/wolfberries, Litchi tomat...0231010European Union0.01*02/01/2015
Brazil nuts0120020European Union0.02*02/01/2015
Cashew nuts0120030European Union0.02*02/01/2015
Chestnuts0120040European Union0.02*02/01/2015
Citrus fruits0110000European Union0.01*02/01/2015
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*02/01/2015
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*02/01/2015
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*02/01/2015
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*02/01/2015
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*02/01/2015
Others (2)0110990European Union0.01*02/01/2015
Tree nuts0120000European Union0.02*02/01/2015
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*02/01/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*02/01/2015
Macadamias0120070European Union0.02*02/01/2015
Pecans (Hickory nuts,)0120080European Union0.02*02/01/2015
Pistachios0120100European Union0.02*02/01/2015

References

TitleJournalDatePubmed ID
Several Pesticides Influence the Nutritional Content of Sweet Corn.J Agric Food Chem2018 Mar 2829432005
Nicosulfuron Plus Atrazine Herbicides and Trichogrammatidae (Hymenoptera) inNo-Choice Test: Selectivity and Hormesis.Bull Environ Contam Toxicol2017 Nov28975358
Influence of soil biochar aging on sorption of the herbicides MCPA, nicosulfuron,terbuthylazine, indaziflam, and fluoroethyldiaminotriazine.J Agric Food Chem2014 Nov 1225338136
Soil surface colonization by phototrophic indigenous organisms, in two contrastedsoils treated by formulated maize herbicide mixtures.Ecotoxicology2014 Nov25129149
Sulfonylurea herbicides in an agricultural catchment basin and its adjacent wetland in the St. Lawrence River basin.Sci Total Environ2014 May 124534695
On-line preconcentration and determination of six sulfonylurea herbicides incereals by MEKC with large-volume sample stacking and polarity switching.Electrophoresis2013 May23436573
Characterization of nicosulfuron availability in aged soils.J Agric Food Chem2008 Jul 2318570433
[Determination of six pesticides in milk using cloud point extraction-highperformance liquid chromatography].Se Pu2007 Nov18257303
Dissipation of nicosulfuron and rimsulfuron in surface soil.J Agric Food Chem2002 Jul 3112137479
Nicosulfuron: alcoholysis, chemical hydrolysis, and degradation on variousminerals.J Agric Food Chem2002 Jan 3011804524