Spiroxamine

Structural formula
	Structural formula with no clear stereochemistry
General
Surname	Spiroxamine
other names	8- tert -Butyl-1,4-dioxa-spiro [4.5] dec-2-ylmethyl-ethylpropyl-amine
Molecular formula	C 18 H 34 NO 2
Brief description	beige liquid with a slightly amine-like odor, technical product and both diastereomers
External identifiers / databases
EC number	601-505-4
ECHA InfoCard	100.124.360
PubChem	86160
Wikidata	Q1850388
properties
Molar mass	296.47 g mol −1
Physical state	liquid
density	0.938 g cm −3 (technical product) ; 0.93 g cm −3 (both diastereomers) ;
boiling point	128-131 ° C (technical product) ; 120 ° C (decomposition for both diastereomers);
Vapor pressure	<0.001 hPa (25 ° C)
solubility	practically insoluble in water ; at 20 ° C and pH 7: 470 mg l −1 diastereomer A ; 340 mg l −1 diastereomer B ; soluble in organic solvents such as acetone and dichloromethane;
safety instructions
H and P phrases	H: 302-312-332-315-317-361d-373-410
	P: 273-280-501
Toxicological data	> 500 mg kg −1 ( LD 50 , rat , oral ) ; 1043 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 .

Spiroxamine is a mixture of several isomeric chemical compounds from the group of spiroketalamines .

Extraction and presentation

Spiroxamine, by reaction of 4- tert -butylcyclohexanone with racemic 3-chloro-1,2-propanediol and subsequent substitution of the chlorine by ethylpropylamine be obtained.

properties

Spiroxamine is a beige liquid. Its water solubility changes between pH 3 and 9 between very soluble (> 200 g / l) and soluble (≤ 0.5 g / l). It is stable to hydrolysis at pH 5, 7 and 9 and stable to photolysis . The compound consists of two diastereomers , the technical product having a mixing ratio of about 50:50 of the two diastereomers.

use

Point of attack in ergosterol biosynthesis

Spiroxamine is used as an active ingredient in crop protection products. It is a systemic fungicide that inhibits the biosynthesis of sterols in fungi. It was launched by Bayer in 1997 .

In 1999, the EU Commission granted active substance approval for use as a fungicide, which was renewed in 2011. In Germany, Austria and Switzerland, plant protection products with this active ingredient are approved.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet Spiroxamine at Sigma-Aldrich , accessed on January 28, 2018 ( PDF ).
↑ BVL: PSM approval report BAY 18540 F , October 25, 2010, accessed on January 28, 2018.
↑ ^a ^b ^c Entry on spiroxamine in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e BVL: Spiroxamine , January 29, 1997, accessed on January 28, 2018.
↑ ^a ^b ^c ^d ^e Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 795 f . ( limited preview in Google Book search).
↑ Entry on 8-tert-butyl-1,4-dioxaspiro [4.5] decan-2-ylmethyl (ethyl) (propyl) amine Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturer or . marketer can use the harmonized classification and labeling expand .
↑ Directive 1999/73 / EC of the Commission of July 19, 1999 (PDF) for the inclusion of the active substance spiroxamine in Appendix I of the Council Directive 91/414 / EEC on the placing of plant protection products on the market.

↑ Implementing Regulation (EU) No. 797/2011 of the Commission of August 9, 2011 (PDF) approving the active substance spiroxamine according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.

↑ Directorate-General for Health and Food Safety of the European Commission: Entry on Spiroxamine in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Data sheet Spiroxamine at Sigma-Aldrich , accessed on January 28, 2018 ( PDF ).

[BVL_Zulassung-2] BVL: PSM approval report BAY 18540 F , October 25, 2010, accessed on January 28, 2018.

[GESTIS-3] Entry on spiroxamine in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[BVL_Spiroxamin-4] BVL: Spiroxamine , January 29, 1997, accessed on January 28, 2018.

[ModernCPC-5] Wolfgang Krämer, Ulrich Schirmer, Peter Jeschke, Matthias Witschel: Modern Crop Protection Compounds . Wiley-VCH, 2011, ISBN 978-3-527-32965-6 , pp. 795 f . ( limited preview in Google Book search).

[CLP_100.124.360-6] Entry on 8-tert-butyl-1,4-dioxaspiro [4.5] decan-2-ylmethyl (ethyl) (propyl) amine Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturer or . marketer can use the harmonized classification and labeling expand .

[7] Directive 1999/73 / EC of the Commission of July 19, 1999 (PDF) for the inclusion of the active substance spiroxamine in Appendix I of the Council Directive 91/414 / EEC on the placing of plant protection products on the market.

[8] Implementing Regulation (EU) No. 797/2011 of the Commission of August 9, 2011 (PDF) approving the active substance spiroxamine according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending it of the Annex of the Commission Implementing Regulation (EU) No. 540/2011.

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on Spiroxamine in the EU pesticide database ; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.