Flubendiamide

Basic Info

Common NameFlubendiamide(F05973)
2D Structure
FRCD IDF05973
CAS Number272451-65-7
PubChem CID11193251
FormulaC23H22F7IN2O4S
IUPAC Name

1-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2-methylphenyl]-3-iodo-2-N-(2-methyl-1-methylsulfonylpropan-2-yl)benzene-1,2-dicarboxamide

InChI Key

ZGNITFSDLCMLGI-UHFFFAOYSA-N

InChI

InChI=1S/C23H22F7IN2O4S/c1-12-10-13(21(24,22(25,26)27)23(28,29)30)8-9-16(12)32-18(34)14-6-5-7-15(31)17(14)19(35)33-20(2,3)11-38(4,36)37/h5-10H,11H2,1-4H3,(H,32,34)(H,33,35)

Canonical SMILES

CC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)F)NC(=O)C2=C(C(=CC=C2)I)C(=O)NC(C)(C)CS(=O)(=O)C

Isomeric SMILES

CC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)F)NC(=O)C2=C(C(=CC=C2)I)C(=O)NC(C)(C)CS(=O)(=O)C

Synonyms
        
            3-Iodo-N2-(2-methyl-1-(methylsulfonyl)propan-2-yl)-N1-(2-methyl-4-(perfluoropropan-2-yl)phenyl)phthalamide
        
            flubendiamide
        
            272451-65-7
        
            UNII-GEV84ZI4K6
        
            GEV84ZI4K6
        
            CHEBI:38798
        
            N(2)-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N(1)-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}benzene-1,2-dicarboxamide
        
            N(2)-[1,1-dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N(1)-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}phthalamide
        
            Flubendiamide [ISO]
        
            HSDB 7883
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassAnilides
Intermediate Tree NodesAromatic anilides
Direct ParentBenzanilides
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsBenzanilide - Halobenzoic acid or derivatives - 3-halobenzoic acid or derivatives - 2-halobenzoic acid or derivatives - Benzamide - Benzoic acid or derivatives - Benzoyl - Toluene - Halobenzene - Iodobenzene - Aryl halide - Aryl iodide - Vinylogous halide - Sulfonyl - Sulfone - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organoiodide - Organofluoride - Organohalogen compound - Organosulfur compound - Alkyl halide - Alkyl fluoride - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Properties

Property NameProperty Value
Molecular Weight682.392
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count11
Rotatable Bond Count7
Complexity968
Monoisotopic Mass682.023
Exact Mass682.023
XLogP5.3
Formal Charge0
Heavy Atom Count38
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+0.9146
Human Intestinal AbsorptionHIA+0.9621
Caco-2 PermeabilityCaco2-0.5821
P-glycoprotein SubstrateNon-substrate0.5767
P-glycoprotein InhibitorInhibitor0.5123
Non-inhibitor0.9744
Renal Organic Cation TransporterNon-inhibitor0.9210
Distribution
Subcellular localizationMitochondria0.7314
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7155
CYP450 2D6 SubstrateNon-substrate0.8076
CYP450 3A4 SubstrateSubstrate0.6136
CYP450 1A2 InhibitorNon-inhibitor0.7774
CYP450 2C9 InhibitorNon-inhibitor0.5146
CYP450 2D6 InhibitorNon-inhibitor0.8552
CYP450 2C19 InhibitorNon-inhibitor0.5553
CYP450 3A4 InhibitorInhibitor0.6169
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.7836
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9618
Non-inhibitor0.6965
AMES ToxicityNon AMES toxic0.6824
CarcinogensCarcinogens 0.5094
Fish ToxicityHigh FHMT0.9515
Tetrahymena Pyriformis ToxicityHigh TPT0.9716
Honey Bee ToxicityLow HBT0.8108
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityIII0.6068
Carcinogenicity (Three-class)Non-required0.6322
Model Value Unit
Absorption
Aqueous solubility-4.0864LogS
Caco-2 Permeability1.0157LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.5073LD50, mol/kg
Fish Toxicity1.1727pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.5401pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
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*26/06/2018
(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 Union0.02*26/06/2018
SUGAR PLANTS0900000European Union0.01*26/06/2018
Red mustards0251070European Union0.01*26/06/2018
Citrus fruits0110000European Union0.01*26/06/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.01*26/06/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.01*26/06/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.01*26/06/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.01*26/06/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.01*26/06/2018
Others (2)0110990European Union0.01*26/06/2018
Tree nuts0120000European Union0.126/06/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.126/06/2018
Brazil nuts0120020European Union0.126/06/2018
Cashew nuts0120030European Union0.126/06/2018
Chestnuts0120040European Union0.126/06/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.126/06/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.126/06/2018
Macadamias0120070European Union0.126/06/2018
Pecans (Hickory nuts,)0120080European Union0.126/06/2018

References

TitleJournalDatePubmed ID
Persistence, dissipation and consumer risk assessment of a combinationformulation of flubendiamide and deltamethrin on cucumber.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2018Mar29279005
Dissipation kinetics, pre-harvest residue limits, and hazard quotient assessmentsof pesticides flubendiamide and fluopicolide in Korean melon (Cucumis melo L.var. makuwa) grown under regulated conditions in plastic greenhouses.Environ Sci Pollut Res Int2017 Oct28799066
Toxicity and residual effects of insecticides on Ascia monuste and predatorSolenopsis saevissima.Pest Manag Sci2017 Nov28466580
Impact of Feeding on Contaminated Prey on the Life Parameters of NesidiocorisTenuis (Hemiptera: Miridae) Adults.J Insect Sci2016 Sep 3027694345
Estimation and risk assessment of flubendiamide on fodder berseem clover(Trifolium alexandrinum L.) by QuEChERS methodology and LC-MS/MS.Environ Sci Pollut Res Int2016 May26850100
Dissipation pattern of flubendiamide residues on capsicum fruit (Capsicum annuum L.) under field and controlled environmental conditions.J Environ Sci Health B201626549520
Dissipation pattern and risk assessment of flubendiamide on chili at differentagro-climatic conditions in India.Environ Monit Assess2015 May25864080
Insecticidal activities of chiral N-trifluoroacetyl sulfilimines as potentialryanodine receptor modulators.J Agric Food Chem2014 Nov 1925380240
Residual behavior and risk assessment of flubendiamide on tomato at differentagro-climatic conditions in India.Environ Monit Assess2014 Nov25108662
Safety evaluation of flubendiamide and its metabolites on cabbage and persistencein soil in different agroclimatic zones of India.Environ Monit Assess2014 Jun24497081
Chiral dicarboxamide scaffolds containing a sulfiliminyl moiety as potentialryanodine receptor activators.J Agric Food Chem2014 Jul 924949911
Laboratory tests on sorption and transformation of the insecticide flubendiamide in Japanese tea field soil.Sci Total Environ2013 Jan 1523247192
[Residue dynamics of flubendiamide in paddy field].Huan Jing Ke Xue2013 Feb23668149
Determination of residual flubendiamide in the cabbage by QuEChERS-liquidchromatography-tandem mass spectrometry.Bull Environ Contam Toxicol2012 Nov22983724
Laboratory-based toxicological assessments of new insecticides on mortality and fecundity of Neoseiulus fallacis (Acari: Phytoseiidae).J Econ Entomol2012 Jun22812123
Assessment of flubendiamide residues in pigeon pea in different agro-climaticzones of India.Environ Monit Assess2012 Jul21811770
A laboratory assessment of the toxic attributes of six 'reduced risk insecticides' on Galendromus occidentalis (Acari: Phytoseiidae).Chemosphere2011 Jun21458842
Dissipation of flubendiamide in/on Brinjal (Solanum melongena) fruits.Environ Monit Assess2011 Dec21360001
Design, synthesis, and insecticidal activities of phthalamides containing ahydrazone substructure.J Agric Food Chem2010 Jun 920450195
Simple and efficient method for the estimation of residues of flubendiamide andits metabolite desiodo flubendiamide.J Agric Food Chem2008 Apr 918321053