Chemistry:Esfenvalerate

Esfenvalerate
Names
	Preferred IUPAC name (S)-Cyano(3-phenoxyphenyl)methyl (2S)-2-(4-chlorophenyl)-3-methylbutanoate
	Other names Asana; (S)-Fenvalerate; (S)-cyano-(3-phenoxy phenyl)-methyl-(S)-4-chloro-α-(1-methyl ethyl) benzene acetate; Chloro-α-(1-methylethyl)benzeneacetic acid; cyano(3-phenoxyphenyl)methyl ester (CAS); (S-(R,R))-4-chloro-α-(1-methylethyl) benzeneacetic acid; cyano-(3-phenoxyphenyl)methylester; (S)-α-cyano-3-phenoxy benzyl (S)-2-(4-chloro-phenyl) isovalerate; Fenvalerate A-Alpha; (S-(R,R))-Benzeneacetic acid, 4-chloro-α-(1-methylethyl)-cyano(3-phenoxyphenyl)methylester; Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate; Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate
Identifiers
CAS Number	66230-04-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	4275674
ChEBI	CHEBI:39346;
ChEMBL	ChEMBL1891190;
ChemSpider	8517510;
EC Number	613-911-9;
KEGG	C18147;
PubChem CID	10342051;
UNII	7F07OXM0PP;
UN number	3349
	InChI InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m0/s1 Key: NYPJDWWKZLNGGM-BJKOFHAPSA-N;
	SMILES CC(C)[C@@H](C(=O)O[C@@H](C#N)c1cccc(Oc2ccccc2)c1)c1ccc(Cl)cc1;
Properties
Chemical formula	C25H22ClNO3
Molar mass	419.91 g·mol−1
Density	1.211 g/cm3
Melting point	60 °C (140 °F; 333 K)
log P	6.22
Vapor pressure	0 mmHg at 25 °C
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H313, H316, H317, H320, H330, H335, H370, H373, H410
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+310, P302+352, P304+340, P305+351+338, P307+311, P310, P312, P314, P320, P321, P330, P332+313, P333+313, P337+313, P363, P391
Flash point	256 °C (493 °F; 529 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Esfenvalerate is a synthetic pyrethroid insecticide marketed under the brand Asana.^[2] It is the (S)-enantiomer of fenvalerate.^[3]

In the United States, a limit of .05 ppm of the chemical's residue is permissible in food.^[4]

References

↑ Kelly, Kevin. "Environmental Fate of Esfenvalerate". California Environmental Protection Agency. https://docs.google.com/viewer?a=v&q=cache:Dj4zTYgWkVwJ:www.cdpr.ca.gov/docs/emon/pubs/fatememo/esfen.pdf+&hl=en&gl=us&pid=bl&srcid=ADGEESioBjkb-ZFR_RL4b81PgVXQtE1uuVNiP1oizd-B5RHIElqfOsbh11O7x5n5U7QO5X_Ds0xSwaqa_hO3sr8ipOGsoy7zWrd3ZHnpjvZvb9hV4Ot9XQeZEzZZKUmLOeC13D3sii_j&sig=AHIEtbT0y5uiRpRhAiBnZ4nP9zihtQ56GA.
↑ Fishel, Frederick M. (2012). "Pesticide Toxicity Profile: Synthetic Pyrethroid Pesticides". University of Florida. http://edis.ifas.ufl.edu/pi091.
↑ "Esfenvalerate". EXTONET (Extension Toxicology Network). Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. May 1994. http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/esfenvalerate-ext.html.
↑ The Code of Federal Regulations of the United States of America. U.S. Government Printing Office. 2006. pp. 445–446. https://books.google.com/books?id=ifk6AAAAIAAJ&q=%22%28S%29-cyano+%283-phenoxyphenyl%29+methyl-%28S%29-4-chloro-alpha-%281-methylethyl%29+benzeneacetate%22&pg=PA446.

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[1] Kelly, Kevin. "Environmental Fate of Esfenvalerate". California Environmental Protection Agency. https://docs.google.com/viewer?a=v&q=cache:Dj4zTYgWkVwJ:www.cdpr.ca.gov/docs/emon/pubs/fatememo/esfen.pdf+&hl=en&gl=us&pid=bl&srcid=ADGEESioBjkb-ZFR_RL4b81PgVXQtE1uuVNiP1oizd-B5RHIElqfOsbh11O7x5n5U7QO5X_Ds0xSwaqa_hO3sr8ipOGsoy7zWrd3ZHnpjvZvb9hV4Ot9XQeZEzZZKUmLOeC13D3sii_j&sig=AHIEtbT0y5uiRpRhAiBnZ4nP9zihtQ56GA.

[uf-2] Fishel, Frederick M. (2012). "Pesticide Toxicity Profile: Synthetic Pyrethroid Pesticides". University of Florida. http://edis.ifas.ufl.edu/pi091.

[extonet-3] "Esfenvalerate". EXTONET (Extension Toxicology Network). Cooperative Extension Offices of Cornell University, Michigan State University, Oregon State University, and University of California at Davis. May 1994. http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/esfenvalerate-ext.html.

[4] The Code of Federal Regulations of the United States of America. U.S. Government Printing Office. 2006. pp. 445–446. https://books.google.com/books?id=ifk6AAAAIAAJ&q=%22%28S%29-cyano+%283-phenoxyphenyl%29+methyl-%28S%29-4-chloro-alpha-%281-methylethyl%29+benzeneacetate%22&pg=PA446.

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v t e Pest control: Insecticides
Carbamates	Aldicarb Bendiocarb Carbaryl Carbofuran Ethienocarb Fenobucarb Oxamyl Methomyl Propoxur
Inorganic compounds	Aluminium phosphide Boric acid Chromated copper arsenate Copper(II) arsenate Copper(I) cyanide Cryolite Diatomaceous earth Lead hydrogen arsenate Paris Green Scheele's Green
Insect growth regulators	Benzoylureas Diflubenzuron Flufenoxuron Hydroprene Lufenuron Methoprene Pyriproxyfen
Neonicotinoids	Acetamiprid Clothianidin Dinotefuran Imidacloprid Nitenpyram Nithiazine Thiacloprid Thiamethoxam
Organochlorides	Aldrin Beta-HCH Carbon tetrachloride Chlordane Cyclodiene 1,2-DCB 1,4-DCB 1,1-DCE 1,2-DCE DDD DDE DDT Dicofol Dieldrin Endosulfan Endrin Heptachlor Kepone Lindane Methoxychlor Mirex Tetradifon Toxaphene
Organophosphorus	Acephate Azamethiphos Azinphos-methyl Bensulide Chlorethoxyfos Chlorfenvinphos Chlorpyrifos Chlorpyrifos-methyl Coumaphos Demeton-S-methyl Diazinon Dichlorvos Dicrotophos Diisopropyl fluorophosphate Dimefox Dimethoate Dioxathion Disulfoton Ethion Ethoprop Fenamiphos Fenitrothion Fenthion Fosthiazate Isoxathion Malathion Methamidophos Methidathion Mevinphos Mipafox Monocrotophos Naled Omethoate Oxydemeton-methyl Parathion Parathion-methyl Phenthoate Phorate Phosalone Phosmet Phoxim Pirimiphos-methyl Quinalphos Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon
Pyrethroids	Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin
Ryanoids	Chlorantraniliprole Cyantraniliprole Flubendiamide Ryanodine Ryanodol
Other chemicals	Afoxolaner Amitraz Azadirachtin Buprofezin Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Ryanodine Sarolaner Sesamex Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone
Metabolites	Oxon Malaoxon Paraoxon TCPy
Biopesticides	Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paecilomyces fumosoroseus Paenibacillus popilliae Purpureocillium lilacinum

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Names

Preferred IUPAC name (S)-Cyano(3-phenoxyphenyl)methyl (2S)-2-(4-chlorophenyl)-3-methylbutanoate
Other names Asana (S)-Fenvalerate (S)-cyano-(3-phenoxy phenyl)-methyl-(S)-4-chloro-α-(1-methyl ethyl) benzene acetate Chloro-α-(1-methylethyl)benzeneacetic acid cyano(3-phenoxyphenyl)methyl ester (CAS) (S-(R,R))-4-chloro-α-(1-methylethyl) benzeneacetic acid cyano-(3-phenoxyphenyl)methylester (S)-α-cyano-3-phenoxy benzyl (S)-2-(4-chloro-phenyl) isovalerate Fenvalerate A-Alpha (S-(R,R))-Benzeneacetic acid, 4-chloro-α-(1-methylethyl)-cyano(3-phenoxyphenyl)methylester Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)isovalerate Cyano-3-phenoxybenzyl (S)-2-(4-chlorophenyl)-3-methylbutyrate^[1]
Identifiers
CAS Number	66230-04-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	4275674
ChEBI	CHEBI:39346
ChEMBL	ChEMBL1891190
ChemSpider	8517510
EC Number	613-911-9
KEGG	C18147
PubChem CID	10342051
UNII	7F07OXM0PP
UN number	3349
InChI InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3/t23-,24+/m0/s1 Key: NYPJDWWKZLNGGM-BJKOFHAPSA-N
SMILES CC(C)[C@@H](C(=O)O[C@@H](C#N)c1cccc(Oc2ccccc2)c1)c1ccc(Cl)cc1
Properties
Chemical formula	C₂₅H₂₂ClNO₃
Molar mass	419.91 g·mol⁻¹
Density	1.211 g/cm³
Melting point	60 °C (140 °F; 333 K)
log P	6.22
Vapor pressure	0 mmHg at 25 °C
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H313, H316, H317, H320, H330, H335, H370, H373, H410
GHS precautionary statements	P260, P261, P264, P270, P271, P272, P273, P280, P284, P301+310, P302+352, P304+340, P305+351+338, P307+311, P310, P312, P314, P320, P321, P330, P332+313, P333+313, P337+313, P363, P391
Flash point	256 °C (493 °F; 529 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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