Tolclofos-Methyl

Basic Info

Common NameTolclofos-Methyl(F05852)
2D Structure
FRCD IDF05852
CAS Number57018-04-9
PubChem CID91664
FormulaC9H11Cl2O3PS
IUPAC Name

(2,6-dichloro-4-methylphenoxy)-dimethoxy-sulfanylidene-$l^{5}-phosphane

InChI Key

OBZIQQJJIKNWNO-UHFFFAOYSA-N

InChI

InChI=1S/C9H11Cl2O3PS/c1-6-4-7(10)9(8(11)5-6)14-15(16,12-2)13-3/h4-5H,1-3H3

Canonical SMILES

CC1=CC(=C(C(=C1)Cl)OP(=S)(OC)OC)Cl

Isomeric SMILES

CC1=CC(=C(C(=C1)Cl)OP(=S)(OC)OC)Cl

Synonyms
        
            Toclofos-methyl
        
            Phosphorothioic acid, O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl ester
        
            Tolclofos-methyl
        
            57018-04-9
        
            Risolex
        
            Rizolex
        
            Basilex
        
            UNII-G42OQL6F5B
        
            Tolclofos-methyl [BSI:ISO]
        
            S-3349
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassOrganic thiophosphoric acids and derivatives
SubclassThiophosphoric acid esters
Intermediate Tree NodesAryl thiophosphates
Direct ParentPhenyl thiophosphates
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPhenyl thiophosphate - Phenoxy compound - 1,3-dichlorobenzene - Thiophosphate triester - Chlorobenzene - Halobenzene - Toluene - Aryl chloride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Hydrocarbon derivative - Organic oxygen compound - Organohalogen compound - Organochloride - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as phenyl thiophosphates. These are organothiophosphorus compounds that contain a thiophosphoric acid O-esterified with a phenyl group.

Properties

Property NameProperty Value
Molecular Weight301.118
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Complexity260
Monoisotopic Mass299.954
Exact Mass299.954
XLogP4.7
Formal Charge0
Heavy Atom Count16
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+0.9384
Human Intestinal AbsorptionHIA+0.9973
Caco-2 PermeabilityCaco2+0.5534
P-glycoprotein SubstrateNon-substrate0.8278
P-glycoprotein InhibitorNon-inhibitor0.5822
Non-inhibitor0.9963
Renal Organic Cation TransporterNon-inhibitor0.9179
Distribution
Subcellular localizationMitochondria0.8051
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7311
CYP450 2D6 SubstrateNon-substrate0.7183
CYP450 3A4 SubstrateSubstrate0.5755
CYP450 1A2 InhibitorInhibitor0.6465
CYP450 2C9 InhibitorNon-inhibitor0.6572
CYP450 2D6 InhibitorNon-inhibitor0.9257
CYP450 2C19 InhibitorInhibitor0.6445
CYP450 3A4 InhibitorInhibitor0.6109
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5142
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7402
Non-inhibitor0.8527
AMES ToxicityNon AMES toxic0.8922
CarcinogensNon-carcinogens0.5103
Fish ToxicityHigh FHMT0.9459
Tetrahymena Pyriformis ToxicityHigh TPT0.9557
Honey Bee ToxicityHigh HBT0.9601
BiodegradationNot ready biodegradable0.9830
Acute Oral ToxicityIII0.8338
Carcinogenicity (Three-class)Non-required0.6793
Model Value Unit
Absorption
Aqueous solubility-5.8227LogS
Caco-2 Permeability1.1495LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.4871LD50, mol/kg
Fish Toxicity0.9243pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6982pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*11/07/2017
Pine nut kernels (Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels from other species than Pinus pinea, Pine nut kernels ...0120090European Union0.01*11/07/2017
Celeriacs/turnip rooted celeries0213030European Union0.01*11/07/2017
Escaroles/broad-leaved endives (Curly endives/ frisée endives, Dandelions, Puntarelle, Radicchio/red-leaved chicories, Sugar loaf chicories, Wild chicories/common chicories,)0251030European Union0.911/07/2017
Asparagus (Hop sprouts,)0270010European Union0.01*11/07/2017
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*11/07/2017
Wheat (Durum wheat, Einkorn wheat/small spelt/one-grain wheat, Emmer wheat, Khorasan wheat, Spelt, Triticale, Other species of genus Triticum, not elsewhere mentioned,)0500090European Union0.01*11/07/2017
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 Union0.05*11/07/2017
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*11/07/2017
Bark spices0830000European Union0.05*11/07/2017
Others (2) (Birches (trunk sap), Manna ashes (trunk sap), Maples (trunk sap), Palms (trunk sap), Palms (trunk sap), Other sugar plants,)0900990European Union0.01*11/07/2017
(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 Union0.01*11/07/2017
Kidney1017040European Union0.01*11/07/2017
Edible offals (other than liver and kidney)1017050European Union0.01*11/07/2017
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*11/07/2017
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*11/07/2017
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 Union0.911/07/2017
FRUITS, FRESH or FROZEN; TREE NUTS0100000European Union0.01*11/07/2017
Citrus fruits0110000European Union0.01*11/07/2017
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*11/07/2017

References

TitleJournalDatePubmed ID
Effect of phenylpyrrole-resistance on fitness parameters and ochratoxin production in Aspergillus carbonarius.Int J Food Microbiol2013 Aug 123800740