Hexythiazox

Basic Info

Common NameHexythiazox(F05423)
2D Structure
Description

Hexythiazox is an acaricide used for the control of eggs and larvae of many phytophagous mites and functions as a mite growth regulator. It is also considered as a thiazolidine based acaricide that has long-lasting effects against many kinds of mites and is applied at any stage of the plant growth from budding to fruiting. Its mode of action is non-systemic with contact and stomach action.

FRCD IDF05423
CAS Number78587-05-0
PubChem CID13218777
FormulaC17H21ClN2O2S
IUPAC Name

(4S,5S)-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide

InChI Key

XGWIJUOSCAQSSV-XHDPSFHLSA-N

InChI

InChI=1S/C17H21ClN2O2S/c1-11-15(12-7-9-13(18)10-8-12)23-17(22)20(11)16(21)19-14-5-3-2-4-6-14/h7-11,14-15H,2-6H2,1H3,(H,19,21)/t11-,15+/m0/s1

Canonical SMILES

CC1C(SC(=O)N1C(=O)NC2CCCCC2)C3=CC=C(C=C3)Cl

Isomeric SMILES

C[C@H]1[C@@H](SC(=O)N1C(=O)NC2CCCCC2)C3=CC=C(C=C3)Cl

Synonyms
        
            Cesar
        
            Hexythiazox
        
            Savey
        
            Acarflor
        
            Acariflor
        
            Calibre
        
            Matacar
        
            Nissorun
        
            Ordoval
        
            Trevi
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassHalobenzenes
Intermediate Tree NodesNot available
Direct ParentChlorobenzenes
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsChlorobenzene - Aryl chloride - Aryl halide - Thiazolidine - Isourea - Carbonic acid derivative - Thiocarbamic acid derivative - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Azacycle - Organoheterocyclic compound - Carboximidic acid derivative - Hydrocarbon derivative - Organonitrogen compound - Organochloride - Organohalogen compound - Organic nitrogen compound - Organopnictogen compound - Organooxygen compound - Carbonyl group - Organic oxide - Organic oxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.

Properties

Property NameProperty Value
Molecular Weight352.877
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count2
Complexity448
Monoisotopic Mass352.101
Exact Mass352.101
XLogP4.5
Formal Charge0
Heavy Atom Count23
Defined Atom Stereocenter Count2
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+0.9639
Human Intestinal AbsorptionHIA+0.9930
Caco-2 PermeabilityCaco2-0.5297
P-glycoprotein SubstrateNon-substrate0.6175
P-glycoprotein InhibitorNon-inhibitor0.5172
Non-inhibitor0.9408
Renal Organic Cation TransporterNon-inhibitor0.7413
Distribution
Subcellular localizationMitochondria0.5082
Metabolism
CYP450 2C9 SubstrateNon-substrate0.5745
CYP450 2D6 SubstrateNon-substrate0.8118
CYP450 3A4 SubstrateNon-substrate0.5351
CYP450 1A2 InhibitorNon-inhibitor0.5517
CYP450 2C9 InhibitorInhibitor0.7402
CYP450 2D6 InhibitorNon-inhibitor0.8274
CYP450 2C19 InhibitorInhibitor0.8154
CYP450 3A4 InhibitorInhibitor0.5165
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.8630
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7869
Non-inhibitor0.5535
AMES ToxicityNon AMES toxic0.7013
CarcinogensNon-carcinogens0.8534
Fish ToxicityHigh FHMT0.9986
Tetrahymena Pyriformis ToxicityHigh TPT0.9944
Honey Bee ToxicityLow HBT0.8837
BiodegradationNot ready biodegradable0.9765
Acute Oral ToxicityIII0.7760
Carcinogenicity (Three-class)Non-required0.5471
Model Value Unit
Absorption
Aqueous solubility-4.7849LogS
Caco-2 Permeability1.3112LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.8801LD50, mol/kg
Fish Toxicity1.4740pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.7191pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Mandarins (Inc Clementines & Similar Hybrids)New Zealand0. 2mg/kg
Peaches (Incl Nectarines & Similar HybridsNew Zealand0. 5mg/kg
Seed spices0810000European Union0.05*26/07/2012
Citrus fruits0110000European Union126/07/2012
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union126/07/2012
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union126/07/2012
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union126/07/2012
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union126/07/2012
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union126/07/2012
Others (2)0110990European Union126/07/2012
Tree nuts0120000European Union0.526/07/2012
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.526/07/2012
Brazil nuts0120020European Union0.526/07/2012
Cashew nuts0120030European Union0.526/07/2012
Chestnuts0120040European Union0.526/07/2012
Coconuts (Areca nuts/betel nuts,)0120050European Union0.526/07/2012
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.526/07/2012
Macadamias0120070European Union0.526/07/2012
Pecans (Hickory nuts,)0120080European Union0.526/07/2012
Pistachios0120100European Union0.526/07/2012

References

TitleJournalDatePubmed ID
Occurrence of pesticide residues in Spanish beeswax.Sci Total Environ2017 Dec 1528679118
Lethal and sublethal effects of pesticides on Chrysoperla carnea larvae (Neuroptera: Chrysopidae) and the influence of rainfastness in their degradation pattern over time.Ecotoxicology2016 Jul26975320
Dissipation dynamic, residue distribution and processing factor of hexythiazox instrawberry fruits under open field condition.Food Chem2016 Apr 126593595
QuEChERS Adaptability for the Analysis of Pesticide Residues in Beehive Products Seeking the Development of an Agroecosystem Sustainability Monitor.J Agric Food Chem2015 May 1325880394
The economic importance of acaricides in the control of phytophagous mites and anupdate on recent acaricide mode of action research.Pestic Biochem Physiol2015 Jun26047107
Determination and surveillance of nine acaricides and one metabolite in honey by liquid chromatography-tandem mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201525967980
Patterns of presence and concentration of pesticides in fish and waters of theJúcar River (Eastern Spain).J Hazard Mater2014 Jan 3024315814
Evaluation of etoxazole against insects and acari in vegetables in China.J Insect Sci201425199415
Investigation of pesticide residues in vegetables and fruits grown in variousregions of Hatay, Turkey.Food Addit Contam Part B Surveill201224786407
Photodegradation of hexythiazox in different solvent systems under the influence of ultraviolet light and sunlight in the presence of TiO2, H2O2, and KNO3 andidentification of the photometabolites.J Agric Food Chem2011 Nov 921967247
Glove accumulation of pesticide residues for strawberry harvester exposureassessment.Bull Environ Contam Toxicol2011 Jun21503692
Ionic liquid based dispersive liquid-liquid microextraction for the extraction ofpesticides from bananas.J Chromatogr A2009 Oct 2319700165
Pesticide extraction from table grapes and plums using ionic liquid baseddispersive liquid-liquid microextraction.Anal Bioanal Chem2009 Dec19779926
Analysis of pesticides in dried hops by liquid chromatography-tandem massspectrometry.J Agric Food Chem2008 Aug 2718593182
[Compatibility of two fungal biocontrol agents conidia with commercial chemicalacaricides].Ying Yong Sheng Tai Xue Bao2006 Jul17044504
Screening and evaluation of fruit samples for four pesticide residues.J AOAC Int2005 May-Jun16001861
Baseline susceptibility and cross resistances of some new acaricides in theEuropean red mite, Panonychus ulmi.Exp Appl Acarol200516323048
Application of liquid chromatography with electrospray tandem mass spectrometryto the determination of a new generation of pesticides in processed fruits andvegetables.J Chromatogr A2004 May 2115146917
Passion fruit green spot virus vectored by Brevipalpus phoenicis (Acari:Tenuipalpidae) on passion fruit in Brazil.Exp Appl Acarol200314756419
Characterization of resistance to clofentezine in populations of European redmite from orchards in Ontario.Exp Appl Acarol200212593584