Pyriproxyfen

Structural formula
	Structural formula without stereochemistry
General
Surname	Pyriproxyfen
other names	Pyriproxifene; ( RS ) -4-phenoxyphenyl 2- (2-pyridyloxy) propyl ether; ( RS ) -2- [1- (4-phenoxyphenoxy) propan-2-yloxy] pyridine; (±) -4-Phenoxyphenyl 2- (2-pyridyloxy) propyl ether; (±) -2- [1- (4-Phenoxyphenoxy) propan-2-yloxy] pyridine;
Molecular formula	C 20 H 19 NO 3
External identifiers / databases
EC number	429-800-1
ECHA InfoCard	100.102.814
PubChem	91753
ChemSpider	82851
Wikidata	Q413089
Drug information
ATC code	Q P53AX23
properties
Molar mass	321.37 g mol −1
Physical state	firmly
density	1.23 g cm −3 (20 ° C)
Melting point	45-47 ° C
Vapor pressure	0.29 m Pa (at 20 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: 273-501
Toxicological data	> 5 g kg −1 ( LD 50 , rat , oral ) ; > 2 g 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 .

Pyriproxyfen is a chemical compound that is one of the derivatives of pyridine and is effective as an insecticide . Pyriproxyfen has a similar structure to the related fenoxycarb , which is also an artificial juvenile hormone . It prevents the larva from developing into an adult animal and thus preventing reproduction.

use

It was introduced in the US in 1996 against whiteflies on cotton plants , but it also protects other crops. It works against cat fleas and is used together with permethrin against the tropical rat mite .

Stereochemistry

Pyriproxyfen has a stereocenter and accordingly forms two enantiomers . The racemate is used , i.e. a 1: 1 mixture of the ( S ) and the ( R ) enantiomer:

Enantiomers of pyriproxyfen
CAS number: 95737-56-7	CAS number: 95737-55-6

Approvals

Pesticides

Pyriproxyfen has been approved as an active ingredient in plant protection products in the European Union since 2010 . In Germany and Switzerland, pyriproxyfen is not part of an approved pesticide product. Pyriproxyfen is on the market in Austria.

Biocides

According to Directive 98/8 / EC of February 16, 1998, biocidal products should only be permitted if their active ingredients have been included in the appendix of the above-mentioned directive for a defined product type. Due to a transitional regulation (Art. 16 Para. 1 of Directive 98/8 / EC), the placing on the market of biocidal products with other "old active substances" should be permitted for a further ten years, provided that they were already on the market on May 14, 2000.

According to Regulation (EC) 1896/2000 of September 7, 2000, manufacturers who wanted to apply for the inclusion of an “old active substance” in Annexes I, IA and IB had to notify the relevant active substance for the corresponding substance by March 28, 2002 Reported product type. This period was extended by Regulation (EC) 1687/2000 from September 25, 2002 to January 31, 2003. The "notified active substances" were allowed to remain on the market until the decision on inclusion or non-inclusion in the annex of EU Directive 98/8 / EC.

With Regulation (EC) 2032/2003 of November 4, 2003, the active substance pyriproxyfen was included in the list (Annex II) of notified active substances for product types 3 (hygiene in the veterinary sector) and 18 (insecticides). Regulation (EC) 1451/2007 of December 4, 2007 included the active substance pyriproxyfen in the final list (Appendix II) of the active substances to be examined within the scope of the test program, but only for product type 18 (insecticides).

On the basis of Directive 2013/5 / EU of February 14, 2013, the active ingredient pyriproxyfen was added to the corresponding list (Annex I of Directive 98/8 / EC) for product type 18 (insecticides) from February 1, 2015. The sale of biocidal products that contain the active ingredient pyriproxyfen is therefore still permitted in the EU (Switzerland has adopted this provision) for product type 18 (insecticides), initially limited to January 31, 2025.

Trade names

Veterinary medicine:

Monopreparations : Cyclio Spot on ad us. vet. (D, CH)
Combination preparations : Duowin ad us. vet. (with permethrin ), Bolfo (with cyfluthrin )

Individual evidence

↑ ^a ^b ^c data sheet pyriproxifene from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
↑ Entry on pyriproxyfen in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ Entry on 2- (1-methyl-2- (4-phenoxyphenoxy) ethoxy) pyridine in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)
↑ Entry on 2- (1-methyl-2- (4-phenoxyphenoxy) ethoxy) pyridine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ ^a ^b Pesticide Manual. Vol. 9, p. 745, 1991.
^ Robert L. Metcalf, Abraham Rami Horowitz: Ullmann's Encyclopedia of Industrial Chemistry . 2000, ISBN 978-3-527-30673-2 , Insect Control, 2. Individual Insecticides, p. 64 , doi : 10.1002 / 14356007.s14_s01 (English).
↑ ^a ^b Directorate-General for Health and Food Safety of the European Commission: Entry on pyriproxyfen in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 8, 2019.
↑ Directive 2010/39 / EU of the Commission of June 22, 2010 amending Annex I of Directive 91/414 / EEC of the Council with regard to special provisions for the active substances clofentezine, diflubenzuron, lenacil, oxadiazon, picloram and pyriproxyfen
↑ Directive 98/8 / EC of February 16, 1998 on the placing of biocidal products on the market . In: Official Journal of the European Communities . L, No. 123, April 24, 1998, pp. 1-63.
↑ Regulation (EC) No. 1896/2000 of September 7, 2000 on the first phase of the program in accordance with Article 16 Paragraph 2 of Directive 98/8 / EC on biocidal products . In: Official Journal of the European Communities . L, No. 228, September 8, 2000, pp. 6-17.
↑ Regulation (EC) No. 1687/2002 of September 25, 2002 on an additional deadline for the notification of certain active substances . In: Official Journal of the European Communities . L, No. 258, September 26, 2002, pp. 15-16.
↑ EU: Regulation (EC) No. 2032/2003 of November 4, 2003 on the second phase of the ten-year work program on placing biocidal products on the market . In: Official Journal of the European Communities. L, No. 307, November 24, 2003, p. 1.
↑ Regulation (EC) No. 1451/2007 of December 4, 2007 on the second phase of the ten-year work program on placing biocidal products on the market . In: Official Journal of the European Communities . L, No. 325, December 11, 2007, pp. 3-65.
↑ Directive 2013/5 / EU of 14 February 2013 amending Directive 98/8 / EC to include the active substance in Annex I pyriproxyfen . In: Official Journal of the European Union . L, No. 44, February 15, 2013, pp. 14-17.

Web links

Entry on pyriproxyfen at Vetpharm, accessed on August 11, 2012.

[Sigma-1] ta sheet pyriproxifene from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).

[2] Entry on pyriproxyfen in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[GESTIS-3] Entry on 2- (1-methyl-2- (4-phenoxyphenoxy) ethoxy) pyridine in the GESTIS substance database of the IFA , accessed on February 1, 2016 (JavaScript required)

[CLP_100.102.814-4] Entry on 2- (1-methyl-2- (4-phenoxyphenoxy) ethoxy) pyridine in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[pestman-5] Pesticide Manual. Vol. 9, p. 745, 1991.

[6] Robert L. Metcalf, Abraham Rami Horowitz: Ullmann's Encyclopedia of Industrial Chemistry . 2000, ISBN 978-3-527-30673-2 , Insect Control, 2. Individual Insecticides, p. 64 , doi : 10.1002 / 14356007.s14_s01 (English).

[PSM-7] Directorate-General for Health and Food Safety of the European Commission: Entry on pyriproxyfen 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] Directive 2010/39 / EU of the Commission of June 22, 2010 amending Annex I of Directive 91/414 / EEC of the Council with regard to special provisions for the active substances clofentezine, diflubenzuron, lenacil, oxadiazon, picloram and pyriproxyfen

[9] Directive 98/8 / EC of February 16, 1998 on the placing of biocidal products on the market . In: Official Journal of the European Communities . L, No. 123, April 24, 1998, pp. 1-63.

[10] Regulation (EC) No. 1896/2000 of September 7, 2000 on the first phase of the program in accordance with Article 16 Paragraph 2 of Directive 98/8 / EC on biocidal products . In: Official Journal of the European Communities . L, No. 228, September 8, 2000, pp. 6-17.

[11] Regulation (EC) No. 1687/2002 of September 25, 2002 on an additional deadline for the notification of certain active substances . In: Official Journal of the European Communities . L, No. 258, September 26, 2002, pp. 15-16.

[12] EU: Regulation (EC) No. 2032/2003 of November 4, 2003 on the second phase of the ten-year work program on placing biocidal products on the market . In: Official Journal of the European Communities. L, No. 307, November 24, 2003, p. 1.

[13] Regulation (EC) No. 1451/2007 of December 4, 2007 on the second phase of the ten-year work program on placing biocidal products on the market . In: Official Journal of the European Communities . L, No. 325, December 11, 2007, pp. 3-65.

[14] Directive 2013/5 / EU of 14 February 2013 amending Directive 98/8 / EC to include the active substance in Annex I pyriproxyfen . In: Official Journal of the European Union . L, No. 44, February 15, 2013, pp. 14-17.