Sulfosulfuron

Basic Info

Common NameSulfosulfuron(F06018)
2D Structure
FRCD IDF06018
CAS Number141776-32-1
PubChem CID86426
FormulaC16H18N6O7S2
IUPAC Name

1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea

InChI Key

RBSXHDIPCIWOMG-UHFFFAOYSA-N

InChI

InChI=1S/C16H18N6O7S2/c1-4-30(24,25)13-14(22-8-6-5-7-10(22)17-13)31(26,27)21-16(23)20-15-18-11(28-2)9-12(19-15)29-3/h5-9H,4H2,1-3H3,(H2,18,19,20,21,23)

Canonical SMILES

CCS(=O)(=O)C1=C(N2C=CC=CC2=N1)S(=O)(=O)NC(=O)NC3=NC(=CC(=N3)OC)OC

Isomeric SMILES

CCS(=O)(=O)C1=C(N2C=CC=CC2=N1)S(=O)(=O)NC(=O)NC3=NC(=CC(=N3)OC)OC

Synonyms
        
            Sulfosulfuron [ISO]
        
            Imidazo[1,2-a]pyridine-3-sulfonamide, N-[[(4,6-dimethoxy-2-pyrimidinyl)amino]carbonyl]-2-(ethylsulfonyl)-
        
            Sulfosulfuron
        
            141776-32-1
        
            UNII-Y0XC20DL6D
        
            Y0XC20DL6D
        
            1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea
        
            HSDB 7942
        
            Imidazo(1,2-a)pyridine-3-sulfonamide, N-(((4,6-dimethoxy-2-pyrimidinyl)amino)carbonyl)-2-(ethylsulfonyl)-
        
            AC1L3BIN
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassSulfonylureas
Intermediate Tree NodesNot available
Direct ParentPyrimidinyl-2-sulfonylureas
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsPyrimidinyl-2-sulfonylurea - Imidazopyridine - Imidazo[1,2-a]pyridine - Alkyl aryl ether - N-substituted imidazole - Pyridine - Pyrimidine - Azole - Imidazole - Heteroaromatic compound - Sulfone - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Carbonic acid derivative - Ether - Organoheterocyclic compound - Azacycle - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organopnictogen compound - Organic oxide - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrimidinyl-2-sulfonylureas. These are aromatic heterocyclic compounds containing a pyrimidine ring which is substituted with a sulfonylurea at the ring 2-position.

Properties

Property NameProperty Value
Molecular Weight470.475
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count7
Complexity832
Monoisotopic Mass470.068
Exact Mass470.068
XLogP1.9
Formal Charge0
Heavy Atom Count31
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-0.6783
Human Intestinal AbsorptionHIA+0.9574
Caco-2 PermeabilityCaco2-0.6096
P-glycoprotein SubstrateNon-substrate0.6523
P-glycoprotein InhibitorNon-inhibitor0.7129
Non-inhibitor0.8649
Renal Organic Cation TransporterNon-inhibitor0.8869
Distribution
Subcellular localizationMitochondria0.4610
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6180
CYP450 2D6 SubstrateNon-substrate0.8281
CYP450 3A4 SubstrateNon-substrate0.5808
CYP450 1A2 InhibitorNon-inhibitor0.7338
CYP450 2C9 InhibitorNon-inhibitor0.5513
CYP450 2D6 InhibitorNon-inhibitor0.9056
CYP450 2C19 InhibitorNon-inhibitor0.7576
CYP450 3A4 InhibitorNon-inhibitor0.7058
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6914
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9633
Non-inhibitor0.6531
AMES ToxicityNon AMES toxic0.6536
CarcinogensNon-carcinogens0.6233
Fish ToxicityHigh FHMT0.9306
Tetrahymena Pyriformis ToxicityHigh TPT0.8777
Honey Bee ToxicityLow HBT0.8038
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.7136
Carcinogenicity (Three-class)Non-required0.6096
Model Value Unit
Absorption
Aqueous solubility-3.7252LogS
Caco-2 Permeability0.4081LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1869LD50, mol/kg
Fish Toxicity1.6048pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4965pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Others (2)0260990European Union0.01*02/01/2015
Cultivated fungi (Common mushrooms/button mushrooms/champignons mushrooms, Corn smuts/ Mexican truffles, Enokitake/winter mushrooms, Fusarium venenatum, Horse mushrooms, Jew's ears/hirneola, Nameko...0280010European Union0.01*02/01/2015
Algae and prokaryotes organisms (Carrageen mosses/Irish mosses, Kombu, Spirulina, Spirulina, Other algae, Other procaryotes organisms, Rockweed /knotted kelp,)0290000European Union0.01*02/01/2015
Beans (Azuki beans, Black eyed peas/cowpeas, Broad beans/fava beans/horse beans/tic beans, Borlotti beans/cannelini beans/common beans/flageolets/French beans/slicing beans/snap beans, Ervils/lenti...0300010European Union0.02*02/01/2015
Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe...0632010European Union0.05*02/01/2015
Others (2) (Birches (trunk sap), Manna ashes (trunk sap), Maples (trunk sap), Palms (trunk sap), Palms (trunk sap), Other sugar plants,)0900990European Union0.01*02/01/2015
Others (2) (Bactrian camel, Dromedary, Elk/moose, Reindeer, Other milk producer animals,)1020990European 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
Brazil nuts0120020European Union0.02*02/01/2015
Cashew nuts0120030European Union0.02*02/01/2015
Chestnuts0120040European Union0.02*02/01/2015
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*02/01/2015

References

TitleJournalDatePubmed ID
Sulfonylurea herbicides in an agricultural catchment basin and its adjacent wetland in the St. Lawrence River basin.Sci Total Environ2014 May 124534695
Non-target-site-based resistance to ALS-inhibiting herbicides in six Bromusrigidus populations from Western Australian cropping fields.Pest Manag Sci2012 Jul22383419
Trace level determination of selected sulfonylurea herbicides in wetland sedimentby liquid chromatography electrospray tandem mass spectrometry.J Environ Sci Health B2010 Jan20390926
Influence of long-term used herbicides on resistance development in Aperaspica-venti L. to sulfonylureas.Commun Agric Appl Biol Sci200920222609
Water purification from organic pollutants by optimized micelle-clay systems.Environ Sci Technol2005 Apr 115871274
Mammalian toxicology overview and human risk assessment for sulfosulfuron.Regul Toxicol Pharmacol2004 Jun15135210
Sulfosulfuron incorporated in micelles adsorbed on montmorillonite for slowrelease formulations.J Agric Food Chem2003 Apr 912670166
Degradation of sulfosulfuron, a sulfonylurea herbicide, as influenced by abiotic factors.J Agric Food Chem2002 Jul 3112137477