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{{chembox
{{chembox
| verifiedrevid = 415337142
| verifiedrevid = 443757269
| Name = Fenoxycarb
| Name = Fenoxycarb
| ImageFile = Fenoxycarb.PNG
| ImageFile = Fenoxycarb.PNG
<!-- | ImageSize = 300px -->
| ImageSize = 260
| ImageAlt = Skeletal formula of fenoxycarb
| ImageName = Fenoxycarb
| ImageFile1 = Fenoxycarb-3D-spacefill.png
⚫
| IUPACName =<small>ethyl N-[2-(4-phenoxyphenoxy)ethyl]carbamate</small>
| ImageSize1 = 240
| ImageAlt1 = Space-filling model of the fenoxycarb molecule
⚫
| PIN = Ethyl [2-(4-phenoxyphenoxy)ethyl]carbamate
| OtherNames = Varikill, Insegar, Logic
| OtherNames = Varikill, Insegar, Logic
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
Line 21: Line 24:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HJUFTIJOISQSKQ-UHFFFAOYSA-N
| StdInChIKey = HJUFTIJOISQSKQ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 72490-01-8
| CASNo = 72490-01-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| SMILES = O=C(OCC)NCCOc2ccc(Oc1ccccc1)cc2
| UNII = JEN0LSV1G9
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5009
⚫
| SMILES = O=C(OCC)NCCOc2ccc(Oc1ccccc1)cc2
}}
}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
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}}
}}


'''Fenoxycarb''' is a [[carbamate]] [[insecticide]]. It has a low toxicity for [[bees]], [[birds]], and [[humans]], but is toxic to [[fish]].
'''Fenoxycarb''' is a carbamate [[insect growth regulator]].<ref>[http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenoxycarb-ext.html Cornell University site on Fenoxycarb]</ref> It has a low toxicity for [[bees]], [[birds]], and [[humans]], but is toxic to [[fish]].{{cn|date=May 2018}} The oral [[LD50|LD<sub>50</sub>]] for rats is greater than {{convert|16,800|mg/kg}}.<ref>U.S. Environmental Protection Agency (1983-85). Chemical Information Fact Sheet. Office of Pesticides and Toxic Substances, Office of Pesticide Programs (TS-766C)</ref>

Fenoxycarb is non-neurotoxic and does not have the same mode of action as other [[carbamate]] insecticides. Instead, it prevents immature insects from reaching maturity by mimicking [[juvenile hormone]].<ref>[http://www.cdpr.ca.gov/docs/emon/pubs/fatememo/fenxycrb.pdf John Sullivan, Dept. of Pesticide Regulation, Sacramento CA 2000]</ref><ref name="Dhadialla-et-al-1998">{{cite journal | last1=Dhadialla | first1=Tarlochan S. | last2=Carlson | first2=Glenn R. | last3=Le | first3=Dat P. | title=New insecticides with ecdysteroidal and juvenile hormone activity | journal=[[Annual Review of Entomology]] | publisher=[[Annual Reviews (publisher)|Annual Reviews]] | volume=43 | issue=1 | year=1998 | issn=0066-4170 | doi=10.1146/annurev.ento.43.1.545 | pages=545–569 | pmid=9444757}}</ref>


==References==
==References==
{{Unreferenced|date =September 2007}}
<references/>
<references/>


==External links==
==External links==
* {{PPDB|304}}
* [http://pmep.cce.cornell.edu/profiles/extoxnet/dienochlor-glyphosate/fenoxycarb-ext.html Cornell University site on Fenoxycarb]


{{insecticides}}
{{insecticides}}
{{Cholinergics}}



⚫
[[Category:Anticholinesterases]]
[[Category:Carbamate insecticides]]
[[Category:Carbamate insecticides]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
⚫
[[Category:Ethyl esters]]



{{organic-compound-stub}}
{{organic-compound-stub}}

[[de:Fenoxycarb]]
[[fr:Fénoxycarbe]]
[[fi:Fenoksikarbi]]

Latest revision as of 14:33, 29 February 2024

Fenoxycarb
Skeletal formula of fenoxycarb
Space-filling model of the fenoxycarb molecule
Names
Preferred IUPAC name
Ethyl [2-(4-phenoxyphenoxy)ethyl]carbamate
Other names
Varikill, Insegar, Logic
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.069.702 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C17H19NO4/c1-2-20-17(19)18-12-13-21-14-8-10-16(11-9-14)22-15-6-4-3-5-7-15/h3-11H,2,12-13H2,1H3,(H,18,19) checkY
    Key: HJUFTIJOISQSKQ-UHFFFAOYSA-N checkY
  • InChI=1/C17H19NO4/c1-2-20-17(19)18-12-13-21-14-8-10-16(11-9-14)22-15-6-4-3-5-7-15/h3-11H,2,12-13H2,1H3,(H,18,19)
    Key: HJUFTIJOISQSKQ-UHFFFAOYAM"
  • O=C(OCC)NCCOc2ccc(Oc1ccccc1)cc2
Properties
C17H19NO4
Molar mass 301.34 g/mol
Melting point 53.5 °C (128.3 °F; 326.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Fenoxycarb is a carbamate insect growth regulator.[1] It has a low toxicity for bees, birds, and humans, but is toxic to fish.[citation needed] The oral LD50 for rats is greater than 16,800 milligrams per kilogram (0.269 oz/lb).[2]

Fenoxycarb is non-neurotoxic and does not have the same mode of action as other carbamate insecticides. Instead, it prevents immature insects from reaching maturity by mimicking juvenile hormone.[3][4]

References

[edit]
  1. ^ Cornell University site on Fenoxycarb
  2. ^ U.S. Environmental Protection Agency (1983-85). Chemical Information Fact Sheet. Office of Pesticides and Toxic Substances, Office of Pesticide Programs (TS-766C)
  3. ^ John Sullivan, Dept. of Pesticide Regulation, Sacramento CA 2000
  4. ^ Dhadialla, Tarlochan S.; Carlson, Glenn R.; Le, Dat P. (1998). "New insecticides with ecdysteroidal and juvenile hormone activity". Annual Review of Entomology. 43 (1). Annual Reviews: 545–569. doi:10.1146/annurev.ento.43.1.545. ISSN 0066-4170. PMID 9444757.
[edit]
  • Fenoxycarb in the Pesticide Properties DataBase (PPDB)
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