Sulfoxaflor
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| ImageFile =Sulfoxaflor Structural Formula V2.svg
| IUPACName=[Methyl(oxo){1-[6-(trifluoromethyl)-3-pyridyl]ethyl}-λ6-sulfanylidene]cyanamide
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|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=946578-00-3
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| ChEBI = 133305
| ChEMBL = 2230078
| ChemSpiderID = 17626728
| EC_number = 807-366-8
| PubChem = 16723172
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 671W88OY8K
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C10H10F3N3OS/c1-7(18(2,17)16-6-14)8-3-4-9(15-5-8)10(11,12)13/h3-5,7H,1-2H3
| StdInChIKey = ZVQOOHYFBIDMTQ-UHFFFAOYSA-N
| SMILES = CC(c1ccc(nc1)C(F)(F)F)S(=NC#N)(=O)C
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|Section2={{Chembox Properties
| C=10 | H=10 | F=3 | N=3 | O=1 | S=1
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|Section3={{Chembox Hazards
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Sulfoxaflor, also marketed as Isoclast,[http://msdssearch.dow.com/PublishedLiteratureDAS/dh_08fd/0901b803808fd73f.pdf?filepath=nz/pdfs/noreg/012-10813.pdf&fromPage=GetDoc Isoclast™ active (sulfoxaflor) Dow Technical Bulletin] msdssearch.dow.com (retrieved 10 June 2019) is a systemic insecticide that acts as an insect neurotoxin. A pyridine and a trifluoromethyl compound, it is a member of a class of chemicals called sulfoximines, which act on the central nervous system of insects.
Mechanism of action
Sulfoxaflor is a systemic insecticide, acts as a neurotoxin to affected insects, and kills through contact or ingestion.
Sulfoxaflor is classified for use against sap-feeding insects as a sulfoximine, which is a sub-group of insecticides that act as nicotinic acetylcholine receptor (nAChR) competitive modulators.{{cite journal | doi = 10.1146/annurev-ento-120811-153645 | title=Neuroactive insecticides: targets, selectivity, resistance, and secondary Effects | journal=Annual Review of Entomology | date=2013 | volume=58 | pages=99–117 | first1=J.E. | last1=Casida|first2=K.A.|last2=Durkin | pmid=23317040}}{{cite web|url=https://www.mda.state.mn.us/sites/default/files/inline-files/nair-sulfoxaflor.pdf|title=Sulfoxaflor|website=mda.state.mn.us|access-date=11 June 2019}} Sulfoxaflor binds to nAChRs in place of acetylcholine. Sulfoxaflor binding causes uncontrolled nerve impulses resulting in muscle tremors followed by paralysis and death.
Other nAChR competitive modulator sub-groups that bind differently on the receptor than sulfoximines include neonicotinoids, nicotine, and butenolides.{{cite web|title=IRAC Mode of Action Classification Scheme|url=http://www.irac-online.org/documents/moa-classification|access-date=11 June 2019|website=irac-online.org}}{{cite web|url=http://www.rsc.org/chemistryworld/2015/09/court-rejects-us-approval-sulfoxaflor-pesticide|title=Court rejects US approval of sulfoxaflor pesticide|publisher=Royal Society of Chemistry |date=2015-09-16 |access-date=2015-09-17}}
Because sulfoxaflor binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is selectively more toxic to insects than mammals.{{cite journal | doi = 10.1146/annurev.ento.48.091801.112731 | title=Selective toxicity of neonicotinoids attributable to specificity of insect and mammalian nicotinic receptors | journal=Annual Review of Entomology | date=2003 | volume=48 | pages=339–64 |first1=M.|last1=Tomizawa|first2=J.E.|last2=Casida | pmid=12208819}}
=Off-target effects=
Application is only recommended when pollinators are not likely to be present in an area as sulfoxaflor is highly toxic to bees if they come into contact with spray droplets shortly after application; toxicity is reduced after the spray has dried.
Registration
On May 6, 2013, the United States Environmental Protection Agency (EPA) approved the first two commercial pesticide products that contain sulfoxaflor, marketed under the brand names "Transform" and "Closer", to the Dow Chemical Corporation.
On September 10, 2015 the U.S. 9th Circuit Court of Appeals overturned the EPA's approval of sulfoxaflor, citing insufficient evidence from studies regarding bee health to justify how sulfoxaflor was approved.{{cite news|url=http://www.latimes.com/local/lanow/la-me-ln-bees-insecticide-20150910-story.html |title=Court revokes approval of insecticide, citing 'alarming' decline in bees |newspaper=LA Times |date=2015-09-10 |access-date=2015-09-14}} Beekeepers and environmental groups supported the decision, saying that the EPA must assess the health of entire hives, not just individual bees.{{cite news |last=Philpott |first=Tom |date=11 September 2015 |title=Federal Court to EPA: No, You Can't Approve This Pesticide That Kills Bees |url=https://www.motherjones.com/tom-philpott/2015/09/federal-court-nixes-epa-approval-pesticide-known-be-highly-toxic-honey-bees |newspaper=Mother Jones |access-date=19 September 2015}}
On October 14, 2016, the United States Environmental Protection Agency (EPA) approved new registrations for sulfoxaflor, "Transform" and "Closer", to the Dow Chemical Corporation.
Previously, the Dow Chemical Corporation owned and sold these products. However, as of June, 2019, the agricultural wing of the Dow Chemical Corporation was split into an independent public corporation called Corteva Agriscience, who now sells the sulfoxaflor-based pesticides.{{cite news |last=Knickmeyer |first=Ellen |date=12 July 2019 |title=EPA restores broad use of pesticide opposed by beekeepers |url=https://www.marketbeat.com/articles/epa-restores-broad-use-of-pesticide-opposed-by-beekeepers-2019-07-12/ |newspaper=Market Beat |access-date=12 July 2019}}
On July 12, 2019, the EPA announced it will allow the use of sulfoxaflor, citing new studies that show lower harm levels to bees than other available pesticides. The EPA concluded that sulfoxaflor would lessen the danger to bees since industry-backed studies assessed it dissipated more quickly and required few applications than other pesticides.{{cite news |last=Dennis |first=Brady |date=12 July 2019 |title=EPA to allow use of pesticide considered 'very highly toxic' to bees |url=https://www.washingtonpost.com/climate-environment/2019/07/12/epa-allow-use-pesticide-considered-very-highly-toxic-bees/ |newspaper=Washington Post |access-date=28 June 2020}} On December 21, 2022, the US 9th Circuit Court of Appeals ruled that the EPA broke the law in allowing new uses of sulfoxaflor because it failed to assess its risks to endangered species nor give the public a chance to comment on the decision. The court then ordered the EPA to allow the public 180 days to comment on expanding the uses of sulfoxaflor.{{Cite journal|first=Britt E. |last=Erickson|date=2023-01-02|title=EPA to reconsider sulfoxaflor's risks|url=https://cen.acs.org/environment/pesticides/EPA-reconsider-sulfoxaflor-insecticide-risks/100/web/2022/12 |journal=C&EN|language=en|volume=101|issue=1|pages=13|doi=10.1021/cen-10101-polcon3|s2cid=255681187 |issn=2474-7408}}
The California registration for sulfoxaflor was overturned following a lawsuit filed in 2020 against the state's Department of Pesticide Regulation by beekeepers and environmental groups.{{cite news |last1=Erickson |first1=Britt E. |title=California court orders end to sulfoxaflor use |url=https://cen.acs.org/environment/pesticides/California-court-orders-end-sulfoxaflor/99/web/2021/12 |access-date=3 May 2024 |work=Chemical & Engineering News |date=December 9, 2021}}
Sulfoxaflor is currently registered in 47 countries, including US, Canada, Mexico, Argentina, Chile, India, China and Australia.{{Cite web |url=https://iaspub.epa.gov/apex/pesticides/f?p=105:6:::NO::P6_XCHEMICAL_ID:3967 |title=Chemical Name: Sulfoxaflor | US EPA |access-date=2017-10-26 |archive-date=2017-10-26 |archive-url=https://web.archive.org/web/20171026214530/https://iaspub.epa.gov/apex/pesticides/f?p=105:6:::NO::P6_XCHEMICAL_ID:3967 |url-status=dead }} The registration of Closer and Transform in France was overturned by a court decision in November, 2017.{{Cite news|date=2017-11-24|title=French court suspends two Dow pesticides over potential harm to bees|language=en|work=Reuters|url=https://www.reuters.com/article/us-france-pesticides-idUSKBN1DO1M9|access-date=11 June 2019}}
See also
References
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External links
- [http://www.epa.gov/oppfead1/cb/csb_page/updates/2013/sulfoxaflor-decision.html The EPA’s Final Decision on the New Active Ingredient Sulfoxaflor]
- [http://newsroom.dowagro.com/press-release/dow-agrosciences-receives-us-epa-registration-sulfoxaflor Dow AgroSciences Receives U.S. EPA Registration for Sulfoxaflor Dow AgroSciences Receives U.S. EPA Registration for Sulfoxaflor (Press release)]
- [https://cen.acs.org/environment/pesticides/Sulfoxaflor-put-dozens-species-risk/101/i12?emci=94eecd3c-92d8-ed11-8e8b-00224832eb73&emdi=d56097d4-3eda-ed11-8e8b-00224832eb73&ceid=1693521 Sulfoxaflor may put dozens of species at risk of extinction]
{{Insecticides}}