Fenpropimorph

Structural formula
	Structural formula without complete stereochemistry
General
Surname	Fenpropimorph
other names	cis -4- (3- ( p - tert -Butylphenyl) -2-methylpropyl) -2,6-dimethyl-morpholine; (±) - cis -4- [3- (4- tert -Butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine ( IUPAC );
Molecular formula	C 20 H 33 NO
Brief description	colorless and odorless liquid
External identifiers / databases
EC number	266-719-9
ECHA InfoCard	100.060.636
PubChem	93365
Wikidata	Q2368524
properties
Molar mass	303.49 g mol −1
Physical state	liquid
density	0.931 g cm −3
Melting point	approx. −16 ° C
boiling point	120 ° C (at 0.067 mbar)
Vapor pressure	negligible at room temperature
solubility	practically insoluble in water; soluble in toluene, acetone and ethanol;
safety instructions
H and P phrases	H: 302-315-361d-411
	P: 273-281
Toxicological data	3000 mg kg −1 ( LD 50 , rat , oral ) ; 4200 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 .

Fenpropimorph is a racemic chemical compound belonging to the group of morpholines .

Extraction and presentation

Various ways of representing fenpropimorph have been described in the literature:

It can be obtained by reacting diisopropanolamine with sulfuric acid and the reaction of the 2,6-dimethylmorpholine formed with formic acid and 3- para - tert- butylphenyl-2-methylpropanal.

Fenpropimorph can also be synthesized in ionic liquids such as 1-butyl-1-methyl-pyrrolidinium-bis [(trifluoromethyl) sulfonyl] amide ([bmpyrr] [NTf ₂ ]). The starting point is either 4- tert- butylbenzyl iodide, which is converted into Lilial by means of a Heck reaction and then reductively aminated with 2,6-dimethylmorpholine to form fenpropimorph. Alternatively, it is also possible to start from 4- tert- butylbenzaldehyde, which can be converted into the product by means of aldol condensation, hydrogenation and likewise reductive amination.

A seven-step stereoselective synthesis of the ( S ) -enantiomer is also known from the literature.

properties

Fenpropimorph is a flammable, not very volatile, colorless and odorless liquid that is practically insoluble in water. It is stable to photolysis and hydrolysis at pH values of 5, 7 and 9.

use

Fenpropimorph is used as a fungicide . It is used as a preventive wood preservative against wood-discolouring and wood-destroying fungi. It inhibits the enzymes involved in building up the cell wall and prevents sterol biosynthesis. It also serves to combat powdery mildew in wheat, barley and rye, yellow and brown rust in wheat and Rhynchosporium leaf spot disease in winter barley. The compound was launched in 1983.

Admission

In the states of the European Union, the active ingredient fenpropimorph has been permitted for use as a fungicide in pesticides since May 2009. In the meantime, plant protection products containing this active ingredient are no longer authorized in the EU. In Switzerland, however, there is an approval.

safety instructions

Fenpropimorph is classified as toxic to reproduction and can potentially harm the unborn child.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on fenpropimorph in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ ^a ^b FAO: Fenpropimorph (PDF; 426 kB).
↑ Entry on cis-4- [3- (p-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Distributors can expand the harmonized classification and labeling .
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 476 ( limited preview in Google Book search).
^ ^A ^b Clemens Lamberth: Bioactive Heterocyclic Compound Classes. John Wiley & Sons, 2012, ISBN 978-3-527-66443-6 , p. 59. ( limited preview in Google Book Search).
↑ Stewart A. Forsyth, HQ Nimal Gunaratne et al. a .: One-Pot Multistep Synthetic Strategies for the Production of Fenpropimorph Using an Ionic Liquid Solvent. In: Organic Process Research & Development. 10, 2006, p. 94, doi : 10.1021 / op050172m .
↑ BAUA: Fenpropimorph ( Memento from June 23, 2013 in the Internet Archive )
^ Müfit Bahadir, Harun Parlar, Michael Spiteller: Springer Umweltlexikon. Springer DE, 2000, ISBN 3-642-56998-6 , pp. 427 ( limited preview in Google Book search).
^ Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49068-X , p. 496 ( limited preview in Google Book search).
↑ Commission Directive 2008/107 / EC of November 25, 2008 amending Council Directive 91/414 / EEC to include the active substances abamectin, epoxiconazole, fenpropimorph, fenpyroximate and tralkoxydim (PDF)
↑ General Directorate Health and Food Safety of the European Commission: Entry on fenpropimorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ Entry on fenpropimorph in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[FAO-2] FAO: Fenpropimorph (PDF; 426 kB).

[CLP_100.060.636-3] Entry on cis-4- [3- (p-tert-butylphenyl) -2-methylpropyl] -2,6-dimethylmorpholine Template: Linktext-Check / Escaped in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Distributors can expand the harmonized classification and labeling .

[Unger-4] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 476 ( limited preview in Google Book search).

[Lamberth-5] A ^b Clemens Lamberth: Bioactive Heterocyclic Compound Classes. John Wiley & Sons, 2012, ISBN 978-3-527-66443-6 , p. 59. ( limited preview in Google Book Search).

[6] Stewart A. Forsyth, HQ Nimal Gunaratne et al. a .: One-Pot Multistep Synthetic Strategies for the Production of Fenpropimorph Using an Ionic Liquid Solvent. In: Organic Process Research & Development. 10, 2006, p. 94, doi : 10.1021 / op050172m .

[7] BAUA: Fenpropimorph ( Memento from June 23, 2013 in the Internet Archive )

[Müfit_Bahadir,_Harun_Parlar,_Michael_Spiteller-8] Müfit Bahadir, Harun Parlar, Michael Spiteller: Springer Umweltlexikon. Springer DE, 2000, ISBN 3-642-56998-6 , pp. 427 ( limited preview in Google Book search).

[Horst_Börner,_Klaus_Schlüter-9] Horst Börner, Klaus Schlueter: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49068-X , p. 496 ( limited preview in Google Book search).

[10] Commission Directive 2008/107 / EC of November 25, 2008 amending Council Directive 91/414 / EEC to include the active substances abamectin, epoxiconazole, fenpropimorph, fenpyroximate and tralkoxydim (PDF)

[PSM-11] General Directorate Health and Food Safety of the European Commission: Entry on fenpropimorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.