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{{Short description|Chemical compound used as an insecticide.}}
{{Chembox
{{Chembox
| ImageFile = Cyantraniliprole.svg
| ImageFile = Cyantraniliprole.svg
| ImageSize = 200px
| ImageSize = 200px
| IUPACName = 3-Bromo-1-(3-chloro-2-pyridinyl)-''N''-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-1''H''-pyrazole-5-carboxamide
| PIN = 4-Bromo-1-(3-chloropyridin-2-yl)-''N''-[4-cyano-2-methyl-6-(''N''-methylcarbamoyl)phenyl]-1''H''-pyrazole-5-carboxamide
| OtherNames = Cyazypyr; Exirel
| OtherNames = Cyazypyr; Exirel
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo = 736994-63-1
| CASNo = 736994-63-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII = LO6K6H48FD
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 11578610
| PubChem = 11578610
| ChemSpiderID = 9753377
| ChemSpiderID = 9753377
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| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt = 217-219 °C
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
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}}
}}


'''Cyantraniliprole''' is an insecticide of the [[Diamide insecticides|diamide]] class ([[Insecticide Resistance Action Committee|IRAC]] [[mode of action|MoA]] group 28).<ref name="IRAC-MoAs">{{cite web|url=http://irac-online.org/documents/moa-classification/|date=March 2020|publisher=[[Insecticide Resistance Action Committee]]|title=IRAC Mode of Action Classification Scheme Version 9.4|author=IRAC International MoA Working Group}}</ref> It shows strong activity and [[lepidoptera]] ([[Caterpillar|caterpillars]]), and since it shows systemic activity it is also active against sucking pests such as [[Aphid|aphids]] and [[whitefly]].<ref name=":1">{{Cite journal |last=Du |first=Shaoqing |last2=Hu |first2=Xueping |date=February 15, 2023 |year=2023 |title=Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators |url=https://pubs.acs.org/doi/abs/10.1021/acs.jafc.2c08414 |journal=Journal of Agricultural and Food Chemistry |volume=71 |issue=8 |pages=3620-3638}}</ref>
'''Cyantraniliprole''' is an insecticide of the [[ryanoid]] class. It is approved for use in the [[United States]], [[Canada]], [[China]], and [[India]].<ref>{{cite news | url = http://news.agropages.com/News/NewsDetail---10696.htm | date = Oct 10, 2013 | title = Australia to approve DuPont's Exirel insecticide cyantraniliprole | publisher = AgroNews}}</ref> Because of its uncommon [[mechanism of action]] as a ryanoid, it has activity against pests such as ''[[Diaphorina citri]]'' that have developed resistance to other classes insecticides.<ref>{{cite journal | journal = Pest Manag Sci | date = Sep 2013 | volume = 69 | issue = 9 | pages = 1066–1072 | doi = 10.1002/ps.3468 | title = Effects of cyantraniliprole, a novel anthranilic diamide insecticide, against Asian citrus psyllid under laboratory and field conditions | author = Tiwari S, Stelinski LL}}</ref> Cyantraniliprole is highly toxic to bees, which resulted in registration of its use as a pesticide being delayed in the USA.<ref>{{cite web|url=http://chemlinked.com/news/agrochemical-news/statistics-expert-review-icama-registration-h2-2012|title=ICAMA Registration Expert Review Statistics Released - H2 of 2012|date=12 December 2012|publisher=}}</ref>

As part of an ongoing court dispute by the [[Center for Biological Diversity]], in November 2022, the [[U.S. Court of Appeals for the D.C. Circuit]] ordered the [[United States Environmental Protection Agency]] to consider harms to plants and animals under the [[Endangered Species Act]], and to put in place appropriate protections.<ref>[https://biologicaldiversity.org/w/news/press-releases/legal-victory-court-orders-epa-to-protect-endangered-wildlife-from-toxic-pesticide-2022-11-22/ Legal Victory: Court Orders EPA to Protect Endangered Wildlife From Toxic Pesticide]</ref> The draft report by the EPA showed that cyantraniliprole is likely to adversely affect about 41% of endangered or threatened species.<ref>{{Cite journal |last=Erickson |first=Britt E. |date=February 3, 2023 |title=Cyantraniliprole likely harms endangered species, EPA finds. |url=https://cen.acs.org/environment/pesticides/Cyantraniliprole-likely-harms-endangered-species/101/i5 |journal=Chemical and Engineering News |volume=101 |issue=5}}</ref>


==References==
==References==
{{reflist}}
{{reflist}}

==External links==


{{insecticides}}
{{insecticides}}

Latest revision as of 12:12, 12 November 2024

Cyantraniliprole
Names
Preferred IUPAC name
4-Bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(N-methylcarbamoyl)phenyl]-1H-pyrazole-5-carboxamide
Other names
Cyazypyr; Exirel
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.205.162 Edit this at Wikidata
UNII
  • InChI=1S/C19H14BrClN6O2/c1-10-6-11(9-22)7-12(18(28)23-2)16(10)25-19(29)14-8-15(20)26-27(14)17-13(21)4-3-5-24-17/h3-8H,1-2H3,(H,23,28)(H,25,29)
    Key: DVBUIBGJRQBEDP-UHFFFAOYSA-N
  • InChI=1/C19H14BrClN6O2/c1-10-6-11(9-22)7-12(18(28)23-2)16(10)25-19(29)14-8-15(20)26-27(14)17-13(21)4-3-5-24-17/h3-8H,1-2H3,(H,23,28)(H,25,29)
    Key: DVBUIBGJRQBEDP-UHFFFAOYAE
  • CC1=CC(=CC(=C1NC(=O)C2=CC(=NN2C3=C(C=CC=N3)Cl)Br)C(=O)NC)C#N
Properties
C19H14BrClN6O2
Molar mass 473.72 g·mol−1
Melting point 217-219 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cyantraniliprole is an insecticide of the diamide class (IRAC MoA group 28).[1] It shows strong activity and lepidoptera (caterpillars), and since it shows systemic activity it is also active against sucking pests such as aphids and whitefly.[2]

As part of an ongoing court dispute by the Center for Biological Diversity, in November 2022, the U.S. Court of Appeals for the D.C. Circuit ordered the United States Environmental Protection Agency to consider harms to plants and animals under the Endangered Species Act, and to put in place appropriate protections.[3] The draft report by the EPA showed that cyantraniliprole is likely to adversely affect about 41% of endangered or threatened species.[4]

References

[edit]
  1. ^ IRAC International MoA Working Group (March 2020). "IRAC Mode of Action Classification Scheme Version 9.4". Insecticide Resistance Action Committee.
  2. ^ Du, Shaoqing; Hu, Xueping (February 15, 2023). "Comprehensive Overview of Diamide Derivatives Acting as Ryanodine Receptor Activators". Journal of Agricultural and Food Chemistry. 71 (8): 3620–3638.{{cite journal}}: CS1 maint: date and year (link)
  3. ^ Legal Victory: Court Orders EPA to Protect Endangered Wildlife From Toxic Pesticide
  4. ^ Erickson, Britt E. (February 3, 2023). "Cyantraniliprole likely harms endangered species, EPA finds". Chemical and Engineering News. 101 (5).
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