# Pyrethrin II

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Pyrethrin II Names Preferred IUPAC name (1S)-2-Methyl-4-oxo-3-[(2Z)-penta-2,4-dien-1-yl]cyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate Identifiers CAS Number 121-29-9 Y 3D model (JSmol) Interactive image ChemSpider 4478783 ECHA InfoCard 100.004.057 EC Number 204-462-6 PubChem CID 5320807 UNII 5N9245585U Y CompTox Dashboard (EPA) DTXSID2042353 InChI InChI=1S/C22H28O5/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6/h7-9,11,16,18-19H,1,10,12H2,2-6H3/b9-8+,13-11-/t16-,18?,19?/m0/s1 Key: VJFUPGQZSXIULQ-CDPVRPLUSA-N SMILES CC1=C(C(=O)CC1OC(=O)C2[C@@H](C2(C)C)/C=C(/C)\C(=O)OC)C/C=C/C=C Properties Chemical formula C22H28O5 Molar mass 372.45472 Hazards GHS labelling: Pictograms Signal word Warning Hazard statements H302, H312, H332, H410 Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

**Pyrethrin II** is an [organic compound](/source/Organic_compound) that is a potent [insecticide](/source/Insecticide). It is one of the two [pyrethrins](/source/Pyrethrin), the other being [pyrethrin I](/source/Pyrethrin_I). Thousands of tons this mixture are produced annually from chrysanthemum plants, which are cultivated in warm climates.[1]

## Structure and related compounds

Whereas pyrethrin I is a derivative of (+)-*trans*-[chrysanthemic acid](/source/Chrysanthemic_acid), in pyrethrin II one methyl group is oxidized to a carboxymethyl group, the resulting core being called pyrethric acid. Knowledge of their chemical structures opened the way for the production of synthetic analogues, which are called [pyrethroids](/source/Pyrethroid). In terms of their [biosynthesis](/source/Biosynthesis), pyrethrins are classified as [terpenoids](/source/Terpenoid), being derived from [dimethylallyl pyrophosphate](/source/Dimethylallyl_pyrophosphate).[2]

## References

1. **[^](#cite_ref-Ullmann_1-0)** Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Weinheim, 2002. [doi](/source/Doi_(identifier)):[10.1002/14356007.a14_263](https://doi.org/10.1002%2F14356007.a14_263)

1. **[^](#cite_ref-2)** Susan B. Rivera, Bradley D. Swedlund, Gretchen J. King, Russell N. Bell, Charles E. Hussey, Jr., Donna M. Shattuck-Eidens, Wislawa M. Wrobel, Galen D. Peiser, and C. Dale Poulter "Chrysanthemyl diphosphate synthase: Isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from *Chrysanthemum cinerariaefolium*" Proceedings of the National Academy of Sciences **2001**, volume 98, p 4373-4378. [doi](/source/Doi_(identifier)):[10.1073/pnas.071543598](https://doi.org/10.1073%2Fpnas.071543598)

v t e Pest control: Insecticides Carbamates Aldicarb Aminocarb Bendiocarb Butocarboxim Carbaryl Carbofuran Carbosulfan m-Cumenyl methylcarbamate Ethienocarb Fenobucarb Isoprocarb Methomyl Metolcarb Oxamyl Promecarb 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 (Bistrifluron, Diflubenzuron, Flufenoxuron, Lufenuron, Novaluron, Noviflumuron) Hydroprene Methoprene Pyriproxyfen Neonicotinoids Acetamiprid Clothianidin Dinotefuran Imidacloprid Imidaclothiz Nitenpyram Nithiazine Paichongding 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 DFDT 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 R-16661 Schradan Temefos Tebupirimfos Terbufos Tetrachlorvinphos Tribufos Trichlorfon Pyrethroids Acrinathrin Allethrins Bifenthrin Bioallethrin Cyfluthrin Cyhalothrin Cypermethrin Cyphenothrin Deltamethrin Empenthrin Esfenvalerate Etofenprox Fenpropathrin Fenvalerate Flumethrin Fluvalinate Imiprothrin Metofluthrin Permethrin Phenothrin Prallethrin Pyrethrin (I, II; chrysanthemic acid) Pyrethrum Resmethrin Silafluofen Tefluthrin Tetramethrin Tralomethrin Transfluthrin Diamides Chlorantraniliprole Cyantraniliprole Flubendiamide Other chemicals Afoxolaner Amitraz Azadirachtin Bensultap Buprofezin Cartap Chlordimeform Chlorfenapyr Cyromazine Fenazaquin Fenoxycarb Fipronil Fluralaner Hydramethylnon Indoxacarb Limonene Lotilaner Pyridaben Pyriprole Sarolaner Adjuvants (Piperonyl butoxide, Sesamex) Spinosad Sulfluramid Tebufenozide Tebufenpyrad Veracevine Xanthone Metaflumizone Ryanodine Ryanodol Metabolites Oxon Malaoxon Paraoxon TCPy Schradan N-oxide Biopesticides Bacillus thuringiensis Baculovirus Beauveria bassiana Beauveria brongniartii Isaria fumosorosea Metarhizium acridum Metarhizium anisopliae Nomuraea rileyi Lecanicillium lecanii Paenibacillus popilliae Purpureocillium lilacinum Spinosad

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Adapted from the Wikipedia article [Pyrethrin II](https://en.wikipedia.org/wiki/Pyrethrin_II) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Pyrethrin_II?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.