Basic Info

Common NameFenoxaprop-P(F06273)
2D Structure
FRCD IDF06273
CAS Number113158-40-0
PubChem CID11949285
FormulaC16H12ClNO5
IUPAC Name

(2R)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid

InChI Key

MPPOHAUSNPTFAJ-SECBINFHSA-N

InChI

InChI=1S/C16H12ClNO5/c1-9(15(19)20)21-11-3-5-12(6-4-11)22-16-18-13-7-2-10(17)8-14(13)23-16/h2-9H,1H3,(H,19,20)/t9-/m1/s1

Canonical SMILES

CC(C(=O)O)OC1=CC=C(C=C1)OC2=NC3=C(O2)C=C(C=C3)Cl

Isomeric SMILES

C[C@H](C(=O)O)OC1=CC=C(C=C1)OC2=NC3=C(O2)C=C(C=C3)Cl

Synonyms
        
            UNII-9U4W2QEC5Q
        
            (R)-2-[4-(6-CHLORO-1,3-BENZOXAZOL-2-YLOXY)PHENOXY]PROPIONIC ACID
        
            Fenoxaprop-P
        
            113158-40-0
        
            9U4W2QEC5Q
        
            Fenoxaprop-P [ISO]
        
            Fenoxaprop-P (R-enantiomer)
        
            (R)-2-(4-((6-Chloro-2-benzoxazolyl)oxy)phenoxy)propanoic acid
        
            Fenoxaprop P
        
            Propanoic acid, 2-(4-((6-chloro-2-benzoxazolyl)oxy)phenoxy)-, (R)-
        
Classifies
                

                  
                    Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
Subclass2-phenoxypropionic acids
Intermediate Tree NodesNot available
Direct ParentAryloxyphenoxypropionic acids
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
SubstituentsAryloxyphenoxypropionic acid - Diaryl ether - Phenoxyacetate - Benzoxazole - Phenoxy compound - Phenol ether - Alkyl aryl ether - Aryl chloride - Aryl halide - Azole - Heteroaromatic compound - Oxazole - Carboxylic acid derivative - Carboxylic acid - Oxacycle - Ether - Monocarboxylic acid or derivatives - Azacycle - Organoheterocyclic compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Organohalogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as aryloxyphenoxypropionic acids. These are aromatic compounds containing a phenoxypropionic acid that is para-substituted with an aryl group.

Properties

Property NameProperty Value
Molecular Weight333.724
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity415
Monoisotopic Mass333.04
Exact Mass333.04
XLogP3.4
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count1
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+0.9655
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5582
P-glycoprotein SubstrateNon-substrate0.7274
P-glycoprotein InhibitorNon-inhibitor0.9532
Non-inhibitor0.7140
Renal Organic Cation TransporterNon-inhibitor0.9123
Distribution
Subcellular localizationMitochondria0.4560
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6943
CYP450 2D6 SubstrateNon-substrate0.5225
CYP450 3A4 SubstrateSubstrate0.5468
CYP450 1A2 InhibitorInhibitor0.7477
CYP450 2C9 InhibitorNon-inhibitor0.8787
CYP450 2D6 InhibitorNon-inhibitor0.8978
CYP450 2C19 InhibitorNon-inhibitor0.7370
CYP450 3A4 InhibitorNon-inhibitor0.8540
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.5366
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9734
Non-inhibitor0.9153
AMES ToxicityNon AMES toxic0.5873
CarcinogensNon-carcinogens0.9319
Fish ToxicityHigh FHMT0.9794
Tetrahymena Pyriformis ToxicityHigh TPT0.9864
Honey Bee ToxicityHigh HBT0.6771
BiodegradationNot ready biodegradable0.9962
Acute Oral ToxicityIII0.8031
Carcinogenicity (Three-class)Danger0.4292

Model Value Unit
Absorption
Aqueous solubility-3.8896LogS
Caco-2 Permeability0.6956LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2082LD50, mol/kg
Fish Toxicity0.2594pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6288pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Others (2)0161990European Union0.101/09/2008
Kiwi fruits (green, red, yellow)0162010European Union0.101/09/2008
Cherimoyas (Elephant apples, Ilamas, Mammey sapotes, Marmeladedos, Pulasans, Rambutans/hairy litchis, Sapodillas, Sweetsops/sugar apples, Wild sweetsops/custard apples,)0163060European Union0.101/09/2008
Aubergines/eggplants (Antroewas/African eggplants/gboma, Ethiopian eggplants/gilo', Pepinos, Thorn apples, Turkey berries/devil's figs/pea eggplants/pea aubergines, Kangaroo apples/poroporo,)0231030European Union0.101/09/2008
Chives (Chinese chives/oriental garlic/garlic chives, Ramson/wild garlic/bear's garlic,)0256020European Union0.101/09/2008
Peas (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Pigeon peas,)0300030European Union0.101/09/2008
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 Union0.101/09/2008
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 Union0.101/09/2008
Rooibos (Honeybush, Honeybush, Honeybush, Honeybush,)0632020European Union0.101/09/2008
Valerian (Blue flag, Calamus, Couch grass, Cowslip/primrose, Echinacea, Echinacea, Echinacea, Elecampane, Fragrant sumac, Golden root, Herb bennet, Marshmallow, Mexican valerian, Pimpernel, Rhatany...0633010European Union0.101/09/2008
(d) any other parts of the plant (Blond psyllium (seeds, husks), Chamomile (seeds), Cherries (sweet) (stems), China/Jesuit's bark (bark), China/Jesuit's bark (bark), Cocoa (husks), Condurango (bark...0639000European Union0.101/09/2008
Liver1012030European Union0.101/09/2008
(f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo...1016000European Union0.0501/09/2008
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 Union0.101/09/2008
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 Union0.101/09/2008
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 Union0.101/09/2008
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 Union0.101/09/2008
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.101/09/2008
Citrus fruits0110000European Union0.101/09/2008
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.101/09/2008

References

TitleJournalDatePubmed ID
Evolution of toxicity upon hydrolysis of fenoxaprop-p-ethyl.J Agric Food Chem2007 Sep 517685541