Acrinathrin

Basic Info

Common NameAcrinathrin(F04045)
2D Structure
Description

A pyrethroid is a synthetic chemical compound similar to the natural chemical pyrethrins produced by the flowers of pyrethrums (Chrysanthemum cinerariaefolium and C. coccineum). Pyrethroids are common in commercial products such as household insecticides and insect repellents. In the concentrations used in such products, they are generally harmless to human beings but can harm sensitive individuals. They are usually broken apart by sunlight and the atmosphere in one or two days, and do not significantly affect groundwater quality except for being toxic to fish. (L811)

FRCD IDF04045
CAS Number101007-06-1
PubChem CID6436606
FormulaC26H21F6NO5
IUPAC Name

[(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3S)-3-[(Z)-3-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate

InChI Key

YLFSVIMMRPNPFK-WEQBUNFVSA-N

InChI

InChI=1S/C26H21F6NO5/c1-24(2)18(11-12-20(34)38-23(25(27,28)29)26(30,31)32)21(24)22(35)37-19(14-33)15-7-6-10-17(13-15)36-16-8-4-3-5-9-16/h3-13,18-19,21,23H,1-2H3/b12-11-/t18-,19+,21-/m0/s1

Canonical SMILES

CC1(C(C1C(=O)OC(C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)C=CC(=O)OC(C(F)(F)F)C(F)(F)F)C

Isomeric SMILES

CC1([C@H]([C@H]1C(=O)O[C@H](C#N)C2=CC(=CC=C2)OC3=CC=CC=C3)/C=C\C(=O)OC(C(F)(F)F)C(F)(F)F)C

Synonyms
        
            Acrinathrin
        
            (S)-cyano(3-phenoxyphenyl)methyl (1R,3S)-2,2-dimethyl-3-{(1Z)-3-oxo-3-[2,2,2-trifluoro-1-(trifluoromethyl)ethoxy]prop-1-en-1-yl}cyclopropanecarboxylate
        
            101007-06-1
        
            Acrinathrin [ISO]
        
            UNII-QUI1AZ37K6
        
            QUI1AZ37K6
        
            CHEBI:39091
        
            [(S)-cyano-(3-phenoxyphenyl)methyl] (1R,3S)-3-[(Z)-3-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
        
            Cy6clopropanecarboxylic acid, 2,2-dimethyl-3-(3-oxo-3-(2,2,2-trifluoro-1-(trifluoromethyl)ethoxy)-1-propenyl)-, cyano(3-phenoxyphenyl)methyl ester, (1R-(1alpha(S*),3alpha(Z)))-
        
            AC1O5M0W
Classifies
                

                  
                    Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassLipids and lipid-like molecules
ClassFatty Acyls
SubclassFatty acid esters
Intermediate Tree NodesNot available
Direct ParentPyrethroids
Alternative Parents
Molecular FrameworkAromatic homomonocyclic compounds
SubstituentsPyrethroid skeleton - Diphenylether - Diaryl ether - Benzyloxycarbonyl - Carbocyclic fatty acid - Phenoxy compound - Phenol ether - Monocyclic benzene moiety - Cyclopropanecarboxylic acid or derivatives - Benzenoid - Dicarboxylic acid or derivatives - Alpha,beta-unsaturated carboxylic ester - Enoate ester - Carboxylic acid ester - Carboxylic acid derivative - Ether - Carbonitrile - Nitrile - Alkyl halide - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Alkyl fluoride - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organohalogen compound - Organofluoride - Aromatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.

Properties

Property NameProperty Value
Molecular Weight541.446
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Complexity917
Monoisotopic Mass541.132
Exact Mass541.132
XLogP6.8
Formal Charge0
Heavy Atom Count38
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Citrus fruits0110000European Union0.02*21/01/2018
Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,)0110010European Union0.02*21/01/2018
Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,)0110020European Union0.02*21/01/2018
Lemons (Buddha's hands/Buddha's fingers, Citrons,)0110030European Union0.02*21/01/2018
Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,)0110040European Union0.02*21/01/2018
Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,)0110050European Union0.02*21/01/2018
Others (2)0110990European Union0.02*21/01/2018
Tree nuts0120000European Union0.02*21/01/2018
Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,)0120010European Union0.02*21/01/2018
Brazil nuts0120020European Union0.02*21/01/2018
Cashew nuts0120030European Union0.02*21/01/2018
Chestnuts0120040European Union0.02*21/01/2018
Coconuts (Areca nuts/betel nuts,)0120050European Union0.02*21/01/2018
Hazelnuts/cobnuts (Acorns, Filberts,)0120060European Union0.02*21/01/2018
Macadamias0120070European Union0.02*21/01/2018
Pecans (Hickory nuts,)0120080European Union0.02*21/01/2018
Prickly pears/cactus fruits (Pitayas/dragon fruits, Red pitayas, Saguaro fruits, Yellow pitayas,)0162040European Union0.02*21/01/2018
Star apples/cainitos0162050European Union0.02*21/01/2018
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*21/01/2018
Pistachios0120100European Union0.02*21/01/2018