Tolylfluanid

Basic Info

Common NameTolylfluanid(F11103)
2D Structure
FRCD IDF11103
CAS Number731-27-1
PubChem CID12898
FormulaC10H13Cl2FN2O2S2
IUPAC Name

N-[dichloro(fluoro)methyl]sulfanyl-N-(dimethylsulfamoyl)-4-methylaniline

InChI Key

HYVWIQDYBVKITD-UHFFFAOYSA-N

InChI

InChI=1S/C10H13Cl2FN2O2S2/c1-8-4-6-9(7-5-8)15(18-10(11,12)13)19(16,17)14(2)3/h4-7H,1-3H3

Canonical SMILES

CC1=CC=C(C=C1)N(SC(F)(Cl)Cl)S(=O)(=O)N(C)C

Isomeric SMILES

CC1=CC=C(C=C1)N(SC(F)(Cl)Cl)S(=O)(=O)N(C)C

Synonyms
        
            TOLYLFLUANID
        
            Tolylfluanide
        
            Tolyfluanide
        
            731-27-1
        
            Euparen M
        
            Tolyfluanid
        
            Dichlofluanid-methyl
        
            Bayer 5712a
        
            Bayer 49854
        
            BAY 5712a
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassSulfanilides
Intermediate Tree NodesNot available
Direct ParentSulfanilides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsSulfanilide - Toluene - Organic sulfuric acid or derivatives - Trihalomethane - Sulfenyl compound - Organopnictogen compound - Halomethane - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Organonitrogen compound - Organofluoride - Organochloride - Alkyl chloride - Organohalogen compound - Alkyl halide - Alkyl fluoride - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.

Properties

Property NameProperty Value
Molecular Weight347.244
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Complexity393
Monoisotopic Mass345.978
Exact Mass345.978
XLogP3.9
Formal Charge0
Heavy Atom Count19
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+0.9541
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2-0.5145
P-glycoprotein SubstrateNon-substrate0.8600
P-glycoprotein InhibitorNon-inhibitor0.8031
Non-inhibitor0.9735
Renal Organic Cation TransporterNon-inhibitor0.9309
Distribution
Subcellular localizationMitochondria0.7033
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6022
CYP450 2D6 SubstrateNon-substrate0.8007
CYP450 3A4 SubstrateNon-substrate0.5335
CYP450 1A2 InhibitorNon-inhibitor0.6526
CYP450 2C9 InhibitorNon-inhibitor0.6825
CYP450 2D6 InhibitorNon-inhibitor0.9347
CYP450 2C19 InhibitorNon-inhibitor0.5630
CYP450 3A4 InhibitorNon-inhibitor0.9167
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6059
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.8599
Non-inhibitor0.7868
AMES ToxicityNon AMES toxic0.9022
CarcinogensNon-carcinogens0.6051
Fish ToxicityHigh FHMT0.8306
Tetrahymena Pyriformis ToxicityHigh TPT0.9479
Honey Bee ToxicityLow HBT0.6424
BiodegradationNot ready biodegradable0.9843
Acute Oral ToxicityIII0.8052
Carcinogenicity (Three-class)Non-required0.5316
Model Value Unit
Absorption
Aqueous solubility-3.6721LogS
Caco-2 Permeability1.4511LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5723LD50, mol/kg
Fish Toxicity1.3293pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.1996pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
HopJapan50ppm
PeelNetherland5mg/kg
TomatoCAC3mg/kg
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.02*26/04/2017
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 Union0.02*26/04/2017
Table grapes (Kiwiberries/dwarf kiwi (2), Schisandra berries,)0151010European Union0.02*26/04/2017
Dewberries (Boysenberries, Loganberries, Olallieberries, Salmonberries, Tayberries, Thimbleberries, Youngberries, Other species and hybrids of genus Rubus, not elsewhere mentioned,)0153020European Union0.02*26/04/2017
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 Union0.02*26/04/2017
Durians0163100European Union0.02*26/04/2017
Cassava roots/manioc (Blue taros/blue tannias, Canna, Chayotes/christophines roots, Dasheen taros, Eddoe taros, Konjac roots, Tannias/arrowleaf elephant ears/tajer,)0212010European Union0.02*26/04/2017
(b) head brassica0242000European Union0.02*26/04/2017
Head cabbages (Pointed head cabbages, Red cabbages, Savoy cabbages, White cabbage,)0242020European Union0.02*26/04/2017
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 Union0.02*26/04/2017
Beans (with pods) (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, ...0260010European Union0.02*26/04/2017
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 Union0.02*26/04/2017
Olives for oil production0402010European Union0.02*26/04/2017
Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,)0500040European Union0.05*26/04/2017
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 Union0.1*26/04/2017
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 Union0.1*26/04/2017
Celery (Angelica, Lovage,)0810030European Union0.1*26/04/2017

References

TitleJournalDatePubmed ID
Volatilisation of pesticides under field conditions: inverse modelling andpesticide fate models.Pest Manag Sci2016 Jul26374459
A sensitive and selective method for the determination of selected pesticides in fruit by gas chromatography/mass spectrometry with negative chemical ionization.J Chromatogr A2012 Nov 1623058941
Pesticide residues in Portuguese strawberries grown in 2009-2010 using integratedpest management and organic farming.Environ Sci Pollut Res Int2012 Nov22562348
Comparison of QuEChERS sample preparation methods for the analysis of pesticideresidues in fruits and vegetables.J Chromatogr A2010 Apr 1620144460
Development of an LC-MS/MS method for the determination of pesticides and patulin in apples.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2009 Jul19680976
Probabilistic acute dietary exposure assessments to captan and tolylfluanid usingseveral European food consumption and pesticide concentration databases.Food Chem Toxicol2009 Dec19709586
Development of a multi-residue method for the determination of pesticides incereals and dry animal feed using gas chromatography-tandem quadrupole massspectrometry II. Improvement and extension to new analytes.J Chromatogr A2008 Oct 2418778832
Determination of pesticide residues in foods by acetonitrile extraction andpartitioning with magnesium sulfate: collaborative study.J AOAC Int2007 Mar-Apr17474521
Safe apples for baby-food production: survey of pesticide treatment regimesleaving minimum residues.Food Addit Contam2007 Jun17487602
Measurement uncertainty associated with sample processing of oranges and tomatoesfor pesticide residue analysis.J Agric Food Chem2007 Feb 2117256954
[Occurrence of pesticide residues in raspberries in 2000-2005].Rocz Panstw Zakl Hig200718246655
Determination of fungicide residues in field-grown strawberries followingdifferent fungicide strategies against gray mold (Botrytis cinerea).J Agric Food Chem2006 Feb 816448201
Monitoring of pesticide residues in apples, lettuce and potato of the Sloveneorigin, 2001-04.Food Addit Contam2006 Feb16449059
Phytotoxicity of tolylfluanid in tomatoes.Commun Agric Appl Biol Sci200617390776
Baby food production chain: pesticide residues in fresh apples and products.Food Addit Contam2005 Dec16356887
Distribution of multiple pesticide residues in apple segments after homeprocessing.Food Addit Contam2003 Nov14668155
Processing factors and variability of pyrimethanil, fenhexamid and tolylfluanidin strawberries.Food Addit Contam2003 Aug13129790
Assessment of the stability of pesticides during cryogenic sample processing. 1. Apples.J Agric Food Chem2002 Jan 3011804510
Investigation on fungicide residues in greenhouse-grown strawberries.J Agric Food Chem2000 Mar10725174