Basic Info

Common NameTopramezone(F05835)
2D Structure
FRCD IDF05835
CAS Number210631-68-8
PubChem CID11302979
FormulaC16H17N3O5S
IUPAC Name

4-[3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylbenzoyl]-2-methyl-1H-pyrazol-3-one

InChI Key

BPPVUXSMLBXYGG-UHFFFAOYSA-N

InChI

InChI=1S/C16H17N3O5S/c1-9-10(15(20)11-8-17-19(2)16(11)21)4-5-13(25(3,22)23)14(9)12-6-7-24-18-12/h4-5,8,17H,6-7H2,1-3H3

Canonical SMILES

CC1=C(C=CC(=C1C2=NOCC2)S(=O)(=O)C)C(=O)C3=CNN(C3=O)C

Isomeric SMILES

CC1=C(C=CC(=C1C2=NOCC2)S(=O)(=O)C)C(=O)C3=CNN(C3=O)C

Synonyms
        
            [3-(4,5-Dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl](5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
        
            Topramezone
        
            210631-68-8
        
            UNII-W4934JAQ65
        
            W4934JAQ65
        
            benzuocaotong
        
            Armezon
        
            Clio
        
            (3-(4,5-dihydro-3-isoxazolyl)-2-methyl-4-(methylsulfonyl)phenyl)(5-hydroxy-1-methyl-1H-pyrazol-4-yl)methanone
        
            [3-(4,5-dihydro-1,2-oxazol-3-yl)-2-methyl-4-methylsulfonylphenyl]-(5-hydroxy-1-methylpyrazol-4-yl)methanone
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzoyl derivatives
Intermediate Tree NodesNot available
Direct ParentBenzoylpyrazoles
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsBenzoylpyrazole - Aryl-phenylketone - Benzenesulfonyl group - Aryl ketone - Toluene - Pyrazolinone - Azole - Isoxazoline - Heteroaromatic compound - Pyrazole - Sulfone - Vinylogous amide - Sulfonyl - Ketone - Lactam - Oxacycle - Azacycle - Organoheterocyclic compound - Organopnictogen compound - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Aldehyde - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzoylpyrazoles. These are aromatic compounds containing a benzoyl group substituted with a pyrazole ring.

Properties

Property NameProperty Value
Molecular Weight363.388
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Complexity752
Monoisotopic Mass363.089
Exact Mass363.089
XLogP0.9
Formal Charge0
Heavy Atom Count25
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+0.6831
Human Intestinal AbsorptionHIA+0.9861
Caco-2 PermeabilityCaco2-0.5965
P-glycoprotein SubstrateNon-substrate0.8772
P-glycoprotein InhibitorNon-inhibitor0.9036
Non-inhibitor0.7224
Renal Organic Cation TransporterNon-inhibitor0.7664
Distribution
Subcellular localizationMitochondria0.4987
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5553
CYP450 2D6 SubstrateNon-substrate0.8102
CYP450 3A4 SubstrateSubstrate0.6092
CYP450 1A2 InhibitorNon-inhibitor0.7178
CYP450 2C9 InhibitorInhibitor0.5376
CYP450 2D6 InhibitorNon-inhibitor0.8594
CYP450 2C19 InhibitorNon-inhibitor0.5351
CYP450 3A4 InhibitorNon-inhibitor0.6228
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6352
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9933
Non-inhibitor0.7990
AMES ToxicityNon AMES toxic0.5578
CarcinogensNon-carcinogens0.5327
Fish ToxicityHigh FHMT0.7043
Tetrahymena Pyriformis ToxicityHigh TPT0.7712
Honey Bee ToxicityLow HBT0.7677
BiodegradationNot ready biodegradable0.8419
Acute Oral ToxicityIII0.5416
Carcinogenicity (Three-class)Non-required0.5653

Model Value Unit
Absorption
Aqueous solubility-2.9421LogS
Caco-2 Permeability0.7155LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5706LD50, mol/kg
Fish Toxicity1.5118pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.4404pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Horseradishes (Dandelion roots, Gentiana roots, East Indian galangal/aromatic ginger/sand galangal, Fingerroot, Galangal roots, Galangal roots, Galangal roots, Galangal roots, Ginger roots, Greater...0213040European Union0.01*01/09/2008
Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou...0251040European Union0.01*01/09/2008
Basil and edible flowers (Apple mint, Asiatic pennywort, Bergamot mint/eau-de-Cologne mint, Corsican mint, Courgette (edible flowers), Gingermint, Greek bush basil, Hoary basil, Holy basil/tulsi, L...0256080European Union0.01*01/09/2008
OILSEEDS AND OIL FRUITS0400000European Union0.0101/09/2008
Rapeseeds/canola seeds (Radish seeds, Turnip rape seeds,)0401060European Union0.0101/09/2008
Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei...0631030European Union0.02*01/09/2008
Apples (Crab apples/wild apples, Tejocotes,)0130010European Union0.01*01/09/2008
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union0.01*01/09/2008
Plums (American plums, Beach plums, Cherry plums /myrabolans, Chickasaw plums, Chinese jujubes/red dates/Chinese dates, Damsons/ bullaces, Gages/greengages/Reine Claudes, Japanese plums, Klamath pl...0140040European Union0.01*01/09/2008
Blueberries (Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Aronia berries/chokeberries (black, purple and red), Bearberries, Bilberries/E...0154010European Union0.01*01/09/2008
Prickly pears/cactus fruits (Pitayas/dragon fruits, Red pitayas, Saguaro fruits, Yellow pitayas,)0162040European Union0.01*01/09/2008
American persimmons/Virginia kaki (Black sapotes, Green sapotes, White sapotes, Yellow sapotes/canistels,)0162060European Union0.01*01/09/2008
Cucumbers (Armenian cucumbers, Dosakayi/Indian curry cucumbers,)0232010European Union0.01*01/09/2008
Courgettes (Angled luffas/teroi, Bottle gourds/calabashes/lauki, Chayotes/christophines, Ivy gourds, Pointed gourds/parwals, Snake gourds, Sopropos/bitter melons/balsam pears, Summer squashes/zucch...0232030European Union0.01*01/09/2008
Celery leaves (Angelica (leaves and stems), Burnet, Caraway leaves, Coriander leaves, Culantro/false coriander leaves, Dill leaves, Fennel leaves, Fenugreek leaves, Herb of grace/rue, Lovage leaves...0256030European Union0.01*01/09/2008
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*01/09/2008
Citrus fruits0110000European Union0.01*01/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*01/09/2008
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*01/09/2008
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*01/09/2008

References

TitleJournalDatePubmed ID
Several Pesticides Influence the Nutritional Content of Sweet Corn.J Agric Food Chem2018 Mar 2829432005