Spirodiclofen

Basic Info

Common NameSpirodiclofen(F06160)
2D Structure
FRCD IDF06160
CAS Number148477-71-8
PubChem CID177863
FormulaC21H24Cl2O4
IUPAC Name

[3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl] 2,2-dimethylbutanoate

InChI Key

DTDSAWVUFPGDMX-UHFFFAOYSA-N

InChI

InChI=1S/C21H24Cl2O4/c1-4-20(2,3)19(25)26-17-16(14-9-8-13(22)12-15(14)23)18(24)27-21(17)10-6-5-7-11-21/h8-9,12H,4-7,10-11H2,1-3H3

Canonical SMILES

CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl

Isomeric SMILES

CCC(C)(C)C(=O)OC1=C(C(=O)OC12CCCCC2)C3=C(C=C(C=C3)Cl)Cl

Synonyms
        
            UNII-3X7G31F5MX
        
            3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl 2,2-dimethylbutanoate
        
            spirodiclofen
        
            148477-71-8
        
            3X7G31F5MX
        
            CHEBI:38639
        
            Envidor
        
            [3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-yl] 2,2-dimethylbutanoate
        
            Spirodiclofen [ISO]
        
            HSDB 7940
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesChlorobenzenes
Direct ParentDichlorobenzenes
Alternative Parents
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents1,3-dichlorobenzene - Fatty acid ester - Aryl chloride - Aryl halide - 2-furanone - Dicarboxylic acid or derivatives - Fatty acyl - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Dihydrofuran - Enol ester - Carboxylic acid ester - Lactone - Organoheterocyclic compound - Oxacycle - Carboxylic acid derivative - Organochloride - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organohalogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as dichlorobenzenes. These are compounds containing a benzene with exactly two chlorine atoms attached to it.

Properties

Property NameProperty Value
Molecular Weight411.319
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity634
Monoisotopic Mass410.105
Exact Mass410.105
XLogP5.9
Formal Charge0
Heavy Atom Count27
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+0.8703
Human Intestinal AbsorptionHIA+1.0000
Caco-2 PermeabilityCaco2+0.5637
P-glycoprotein SubstrateSubstrate0.7114
P-glycoprotein InhibitorInhibitor0.9084
Inhibitor0.9044
Renal Organic Cation TransporterNon-inhibitor0.8720
Distribution
Subcellular localizationMitochondria0.7842
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8265
CYP450 2D6 SubstrateNon-substrate0.8742
CYP450 3A4 SubstrateSubstrate0.7059
CYP450 1A2 InhibitorNon-inhibitor0.7808
CYP450 2C9 InhibitorInhibitor0.5872
CYP450 2D6 InhibitorNon-inhibitor0.8753
CYP450 2C19 InhibitorInhibitor0.5166
CYP450 3A4 InhibitorNon-inhibitor0.6159
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.6950
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9304
Non-inhibitor0.7165
AMES ToxicityNon AMES toxic0.8053
CarcinogensNon-carcinogens0.8316
Fish ToxicityHigh FHMT0.9997
Tetrahymena Pyriformis ToxicityHigh TPT1.0000
Honey Bee ToxicityHigh HBT0.7622
BiodegradationNot ready biodegradable0.9860
Acute Oral ToxicityIII0.4409
Carcinogenicity (Three-class)Non-required0.4235
Model Value Unit
Absorption
Aqueous solubility-5.0712LogS
Caco-2 Permeability0.9876LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.2591LD50, mol/kg
Fish Toxicity-0.7708pLC50, mg/L
Tetrahymena Pyriformis Toxicity1.4437pIGC50, 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 Union0.524/11/2016
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.524/11/2016
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.524/11/2016
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.424/11/2016
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.424/11/2016
Others (2)0110990European Union0.424/11/2016
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.124/11/2016
Brazil nuts0120020European Union0.0524/11/2016
Cashew nuts0120030European Union0.0524/11/2016
Chestnuts0120040European Union0.0524/11/2016
Coconuts (Areca nuts/betel nuts,)0120050European Union0.0524/11/2016
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.0524/11/2016
Macadamias0120070European Union0.0524/11/2016
Pecans (Hickory nuts,)0120080European Union0.0524/11/2016
Pistachios0120100European Union0.0524/11/2016
Walnuts0120110European Union0.0524/11/2016
Others (2)0120990European Union0.0524/11/2016
Pome fruits0130000European Union0.824/11/2016
Pears (Nashi pears/Oriental pears, Wild pears, Ya pears/Chinese white pears,)0130020European Union0.824/11/2016
Quinces (Chinese quinces, Japanese quinces,)0130030European Union0.824/11/2016

References

TitleJournalDatePubmed ID
Industrial prune processing and its effect on pesticide residue concentrations.Food Chem2018 Dec 130064756
Factors Affecting the Bioaccessibility and Intestinal Transport ofDifenoconazole, Hexaconazole, and Spirodiclofen in Human Caco-2 Cells Followingin Vitro Digestion.J Agric Food Chem2017 Oct 1828915046
Behavior of fluopyram and tebuconazole and some selected pesticides in ripeapples and consumer exposure assessment in the applied crop protection framework.Environ Monit Assess2017 Jul28646436
Residue level, persistence and safety of spirodiclofen-pyridaben mixture incitrus fruits.Food Chem2016 Mar 126471621
[Dissipation dynamics of spirodiclofen in wolfberry fruit].Zhongguo Zhong Yao Za Zhi2016 Jun28901058
Synthesis, Acaricidal Activity, and Structure-Activity Relationships of PyrazolylAcrylonitrile Derivatives.J Agric Food Chem2016 Dec 2827976890
Ionic liquid-based totally organic solvent-free emulsification microextractioncoupled with high performance liquid chromatography for the determination ofthree acaricides in fruit juice.Talanta2013 Oct 1524054632
Dissipation, residues, and risk assessment of spirodiclofen in citrus.Environ Monit Assess2013 Dec23880916
Resistance to acaricides in Italian strains of Tetranychus urticae: toxicologicaland enzymatic assays.Exp Appl Acarol2012 May22447041
Monitoring and risk assessment of pesticide residues in yuza fruits (Citrus junosSieb. ex Tanaka) and yuza tea samples produced in Korea.Food Chem2012 Dec 1522980892
Effect of seven new orchard pesticides on Galendromus occidentalis in laboratory studies.Pest Manag Sci2009 Jun19206104
A modified excised leaf disc method to estimate the toxicity of slow- andfast-acting reduced-risk acaricides to mites.J Econ Entomol2009 Dec20069835
The multiple target use of spirodiclofen (Envidor 240 SC) in IPM pomefruit inBelgium.Commun Agric Appl Biol Sci200920218531
Baseline susceptibility and cross resistances of some new acaricides in theEuropean red mite, Panonychus ulmi.Exp Appl Acarol200516323048
An index for selective toxicity of miticides to phytophagous mites and their predators based on orchard trials.Pest Manag Sci2003 Dec14667054