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{{chembox
{{chembox
| Verifiedfields = changed
| verifiedrevid = 431792898
| Watchedfields = changed
|ImageFile=Empenthrin.svg
| verifiedrevid = 445808035
|ImageSize=200px
| ImageFile=Empenthrin.svg
|IUPACName=(''E'')-(''RS'')-1-Ethynyl-2-methylpent-2-enyl (1''RS'',3''RS'';1''RS'',3''SR'')-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
| ImageSize=200px
|OtherNames=Vaporthrin
| IUPACName=(''E'')-(''RS'')-1-Ethynyl-2-methylpent-2-enyl (1''RS'',3''RS'';1''RS'',3''SR'')-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
| OtherNames=Vaporthrin
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=54406-48-3
| CASNo=54406-48-3
| PubChem=6434488

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII =K45WEG8WYL
| PubChem=6434488
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C18524
| KEGG = C18524
| SMILES=CCC=C(C)C(C#C)OC(=O)C1C(C1(C)C)C=C(C)C
| SMILES=CCC=C(C)C(C#C)OC(=O)C1C(C1(C)C)C=C(C)C
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4939400
| InChI = 1/C18H26O2/c1-8-10-13(5)15(9-2)20-17(19)16-14(11-12(3)4)18(16,6)7/h2,10-11,14-16H,8H2,1,3-7H3/b13-10+
| InChIKey = YUGWDVYLFSETPE-JLHYYAGUBJ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C18H26O2/c1-8-10-13(5)15(9-2)20-17(19)16-14(11-12(3)4)18(16,6)7/h2,10-11,14-16H,8H2,1,3-7H3/b13-10+
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = YUGWDVYLFSETPE-JLHYYAGUSA-N
}}
}}

|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=18|H=26|O=2
| C=18 | H=26 | O=2
| Appearance=
| Appearance=
| Density=
| Density=
| MeltingPt=
| MeltingPt=
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
}}
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}


'''Empenthrin''' (also called '''vaporthrin''') is a synthetic [[pyrethroid]] used in [[insecticide]]s. It is active against broad spectrum of flying [[insect]]s including [[clothing moth|moths]] and other pests damaging [[textile]].<ref name=ppdb /> It has low acute [[mammalian]] [[toxicity]] (its oral [[lethal dose|LD<sub>50</sub>]] is above 5000 mg/kg in male [[rat]]s, above 3500 mg/kg in female rats and greater than 3500 mg/kg in [[mouse|mice]]).<ref>[http://www.ncbi.nlm.nih.gov/pubmed/1293329 Mammalian toxicity of empenthrin (Vaporthrin, S-2852F)]</ref> It is however very toxic to [[fish]] and other aquatic organisms (96-hour LC<sub>50</sub> in ''[[Oncorhynchus mykiss]]'' is 1.7 μg/L, 48-hour EC<sub>50</sub> in ''[[Daphnia magna]]'' is 20 μg/L).<ref name=ppdb>[http://sitem.herts.ac.uk/aeru/iupac/Reports/1596.htm empenthrin (Ref: S 2852 Forte)]</ref>
'''Empenthrin''' (also called '''vaporthrin''') is a synthetic [[pyrethroid]] used in [[insecticide]]s. It is active against broad spectrum of flying [[insect]]s including [[clothing moth|moths]] and other pests damaging [[textile]].<ref name=ppdb /> It has low acute [[mammalian]] [[toxicity]] (its oral [[lethal dose|LD<sub>50</sub>]] is above 5000&nbsp;mg/kg in male [[rat]]s, above 3500&nbsp;mg/kg in female rats and greater than 3500&nbsp;mg/kg in [[mouse|mice]]).<ref>{{cite journal |author1=Hideo Kaneko |author2=Shinobu Kawaguchi |author3=Yoshinori Misaki |author4=Y Koyama |author5=A Nakayama |author6=H Kawasaki |author7=A Hirohashi |author8=A Yoshitake |author9=H Yamada |title=MAMMALIAN TOXICITY OF EMPENTHRIN (VAPORTHRIN<sup>R</sup>, S-2852F) |journal=The Journal of Toxicological Sciences |date=Nov 1992 |volume=17 |issue=Supplement 3 |pages=313–334 |doi=10.2131/jts.17.supplementiii_313 |pmid=1293329 |url=https://www.jstage.jst.go.jp/article/jts1976/17/SupplementIII/17_SupplementIII_313/_article |publisher=The Japanese Society of Toxicology |location=Japan |language=JA|doi-access=free }}</ref> It is however very toxic to [[fish]] and other aquatic organisms (96-hour LC<sub>50</sub> in ''[[Rainbow trout|Oncorhynchus mykiss]]'' is 1.7 μg/L, 48-hour EC<sub>50</sub> in ''[[Daphnia magna]]'' is 20 μg/L).<ref name=ppdb>{{cite web |title=empenthrin |url=http://sitem.herts.ac.uk/aeru/iupac/Reports/1596.htm |website=PPDB: Pesticide Properties DataBase |publisher=University of Hertfordshire |access-date=2020-07-29 |language=en}}</ref>


[[File:Empenthrin insekticid.jpg|thumb|left|100px|Empenthrin preparation against [[clothing moth]]s]]{{clear-left}}
[[File:Empenthrin insekticid.jpg|thumb|left|128px|Empenthrin preparation against [[clothing moth]]s]]{{clear left}}


==References==
==References==
<references />
<references />



{{insecticides}}
{{insecticides}}


[[Category:Pyrethroids]]
[[Category:Chrysanthemate esters]]
[[Category:Alkynes]]
[[Category:Ethynyl compounds]]

[[cs:Empenthrin]]
[[hu:Empentrin]]

Latest revision as of 04:10, 27 August 2023

Empenthrin
Names
IUPAC name
(E)-(RS)-1-Ethynyl-2-methylpent-2-enyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
Other names
Vaporthrin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.053.759 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C18H26O2/c1-8-10-13(5)15(9-2)20-17(19)16-14(11-12(3)4)18(16,6)7/h2,10-11,14-16H,8H2,1,3-7H3/b13-10+ ☒N
    Key: YUGWDVYLFSETPE-JLHYYAGUSA-N ☒N
  • InChI=1/C18H26O2/c1-8-10-13(5)15(9-2)20-17(19)16-14(11-12(3)4)18(16,6)7/h2,10-11,14-16H,8H2,1,3-7H3/b13-10+
    Key: YUGWDVYLFSETPE-JLHYYAGUBJ
  • CCC=C(C)C(C#C)OC(=O)C1C(C1(C)C)C=C(C)C
Properties
C18H26O2
Molar mass 274.404 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Empenthrin (also called vaporthrin) is a synthetic pyrethroid used in insecticides. It is active against broad spectrum of flying insects including moths and other pests damaging textile.[1] It has low acute mammalian toxicity (its oral LD50 is above 5000 mg/kg in male rats, above 3500 mg/kg in female rats and greater than 3500 mg/kg in mice).[2] It is however very toxic to fish and other aquatic organisms (96-hour LC50 in Oncorhynchus mykiss is 1.7 μg/L, 48-hour EC50 in Daphnia magna is 20 μg/L).[1]

Empenthrin preparation against clothing moths

References[edit]

  1. ^ a b "empenthrin". PPDB: Pesticide Properties DataBase. University of Hertfordshire. Retrieved 2020-07-29.
  2. ^ Hideo Kaneko; Shinobu Kawaguchi; Yoshinori Misaki; Y Koyama; A Nakayama; H Kawasaki; A Hirohashi; A Yoshitake; H Yamada (Nov 1992). "MAMMALIAN TOXICITY OF EMPENTHRIN (VAPORTHRINR, S-2852F)". The Journal of Toxicological Sciences (in Japanese). 17 (Supplement 3). Japan: The Japanese Society of Toxicology: 313–334. doi:10.2131/jts.17.supplementiii_313. PMID 1293329.