Sulfoxaflor

Structural formula
	Structural formula without stereochemistry (mixture of stereoisomers)
General
Surname	Sulfoxaflor
other names	(Methyl-oxo- {1- [6- (trifluoromethyl) pyridin-3-yl] ethyl} -λ 6 -sulfanylidene) cyanamide ( IUPAC )
Molecular formula	C 10 H 10 F 3 N 3 OS
Brief description	white powder with a sharp odor
External identifiers / databases
EC number	807-366-8
ECHA InfoCard	100.234.961
PubChem	16723172
Wikidata	Q14566721
properties
Molar mass	277.27 g mol −1
Physical state	firmly
density	1.5378 g cm −3
Melting point	112.9 ° C
boiling point	decomposes at 167.7 ° C
solubility	very sparingly soluble in water: 0.568 g l −1 (20 ° C)
safety instructions
H and P phrases	H: 302-410
	P: 273-391-501
Toxicological data	1000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sulfoxaflor is an insecticide from the group of sulfoximines .

Sulfoxaflor is like the neonicotinoids a nAChR - agonist , the nicotinic acetylcholine receptors blocked. Sulfoxaflor is hardly cross-resistant to neonicotinoids .

Stereochemistry

Sulfoxaflor is a mixture of four stereoisomers , one stereocenter is “localized” on the benzylic carbon atom and one on the sulfur atom .

regulation

European Union

Sulfoxaflor has been approved as an active ingredient by the EU since August 18, 2015. In some EU member states are pesticides registered with sulfoxaflor, including in July 2018 Austria against aphids in cereal and in Germany since December 2018 against aphids and whitefly in vegetables and ornamental plants. It was criticized that the approval of the preparations was applied for, although there was already knowledge of a harmful effect on dark bumblebees . No pesticides containing sulfoxafluoride are permitted in Switzerland.

United States

Sulfoxaflor has been approved in the USA since 2013. After a court ruling in 2015, the EPA ( Environmental Protection Agency ) plans to adapt the approval with a more restricted range of applications and additional protective measures for bees.

Ecotoxicity

In 2014, the European Food Safety Authority (EFSA) warned in its risk assessment that a high risk for honey bees could not be ruled out when used in the field .

literature

Harry Siviter, Mark JF Brown, Ellouise Leadbeater: Sulfoxaflor exposure reduces bumblebee reproductive success . In: Nature . 2018, doi : 10.1038 / s41586-018-0430-6 .

Individual evidence

↑ ^a ^b ^c Entry on sulfoxaflor in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ ^a ^b ^c ^d CLH report. Proposal for Harmonized Classification and Labeling. SULFOXAFLOR , 2012.
↑ Entry on Sulfoxaflor (ISO); [Methyl (oxo) {1- [6- (trifluoromethyl) -3-pyridyl] ethyl} -λ6-sulfanyliden] cyanamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 9, 2017. Manufacturer or distributor can expand the harmonized classification and labeling .
↑ ^a ^b Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides, Volume 1 . Wiley-VCH, Weinheim 2011, ISBN 978-3-527-32965-6 , pp. 1231 ( limited preview in Google Book search).
↑ Ulrich Schirmer, Peter Jeschke, Matthias Witschel (Eds.): Modern Crop Protection Compounds: Herbicides, Volume 1 . 2012, ISBN 978-3-527-32965-6 , pp. 1235 ( limited preview in Google Book search).
↑ Thomas C. Sparks, Gerrit J. DeBoer, Nick X. Wang, James M. Hasler, Michael R. Loso, Gerald B. Watson: Differential metabolism of sulfoximine and neonicotinoid insecticides by Drosophila melanogaster monooxygenase CYP6G1. In: Pesticide Biochemistry and Physiology. 103, 2012, pp. 159-165.
↑ ^a ^b Directorate-General for Health and Food Safety of the European Commission: Entry on sulfoxaflor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 8, 2019.
↑ Zeit Online: Ersatz-Pestgiftet harms Hummeln , August 15, 2018, accessed on November 6, 2019.
^ Proposed Decision to Register the Insecticide Sulfoxaflor with Reduced Uses . 22nd August 2016.
↑ Conclusion on the peer review of the pesticide risk assessment of the active substance sulfoxaflor. In: EFSA Journal. 12, 2014, doi: 10.2903 / j.efsa.2014.3692 .

[GESTIS-1] Entry on sulfoxaflor in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[echa-2] CLH report. Proposal for Harmonized Classification and Labeling. SULFOXAFLOR , 2012.

[CLP_100.234.961-3] Entry on Sulfoxaflor (ISO); [Methyl (oxo) {1- [6- (trifluoromethyl) -3-pyridyl] ethyl} -λ6-sulfanyliden] cyanamide in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on January 9, 2017. Manufacturer or distributor can expand the harmonized classification and labeling .

[mcp1-4] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds: Herbicides, Volume 1 . Wiley-VCH, Weinheim 2011, ISBN 978-3-527-32965-6 , pp. 1231 ( limited preview in Google Book search).

[mcp2-5] Ulrich Schirmer, Peter Jeschke, Matthias Witschel (Eds.): Modern Crop Protection Compounds: Herbicides, Volume 1 . 2012, ISBN 978-3-527-32965-6 , pp. 1235 ( limited preview in Google Book search).

[Ariens-6] Thomas C. Sparks, Gerrit J. DeBoer, Nick X. Wang, James M. Hasler, Michael R. Loso, Gerald B. Watson: Differential metabolism of sulfoximine and neonicotinoid insecticides by Drosophila melanogaster monooxygenase CYP6G1. In: Pesticide Biochemistry and Physiology. 103, 2012, pp. 159-165.

[PSM-Verz-7] Directorate-General for Health and Food Safety of the European Commission: Entry on sulfoxaflor in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 8, 2019.

[8] Zeit Online: Ersatz-Pestgiftet harms Hummeln , August 15, 2018, accessed on November 6, 2019.

[9] Proposed Decision to Register the Insecticide Sulfoxaflor with Reduced Uses . 22nd August 2016.

[DOI10.2903/j.efsa.2014.3692-10] Conclusion on the peer review of the pesticide risk assessment of the active substance sulfoxaflor. In: EFSA Journal. 12, 2014, doi: 10.2903 / j.efsa.2014.3692 .