2,6-dimethyl-4-tridecylmorpholine

Structural formula
Representative structural formula without stereochemistry - the chain length of the side chain is variable
General
Surname	2,6-dimethyl-4-tridecylmorpholine
other names	Tridemorph
Molecular formula	C 19 H 39 NO (main component in the mixture of substances)
External identifiers / databases
CAS number 24602-86-6 56048-48-7 ( meso shape) 56048-49-8 [( S , S ) -form] 81412-43-3 as a mixture with other isomers EC number 246-347-3 ECHA InfoCard 100.042.119 PubChem 32518 ChemSpider 30142 Wikidata Q209280
properties
Molar mass	297.52 g mol −1
Physical state	liquid
density	0.87 g cm −3 (20 ° C)
Melting point	<−20 ° C
boiling point	134 ° C (at 0.7 mbar )
Vapor pressure	0.006 mbar (50 ° C)
solubility	almost insoluble in water (12 mg l −1 )
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 302-332-315-360D-410 P: 201-273-308 + 313-501
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Dimethyl-4-tridecylmorpholine belongs to the group of alkylated morpholines . It acts as an inhibitor of sterol biosynthesis by interfering with ergosterol synthesis. 2,6-Dimethyl-4-tridecylmorpholine was used as the main component in a mixture with its isomers as a fungicidal active ingredient under the name Tridemorph .

Tridemorph

General structural formula of the ingredients of Tridemorph:
n = 10, 11, 12 (60–70%), 13

Tridemorph is a fungicidal active ingredient that was developed by BASF in the 1960s and approved for the first time in 1969. It was sold under the trade name Calixin and used to control the fungus species Erysiphe graminis ( powdery mildew ) in cereals , Mycosphaerella species in bananas and Caticum solmonicolor in tea . It is also used as a wood preservative (in conjunction with alkylammonium compounds ).

Chemically, tridemorph is a mixture of isomers of different morpholine derivatives with different lengths and branches of the alkyl chains and undefined stereochemical configuration on the morpholine structure. The main component with 60 to 70% is 2,6-dimethyl-4-tridecylmorpholine. The chain length and the absolute configuration play only a subordinate role with regard to the effectiveness as a fungicide.

In Germany, Austria and Switzerland it is no longer approved as a plant protection product.

It is believed that tridemorph can cause damage to human embryos if the child's mother comes into contact with tridemorph.

Derived connections

• Tridemorphfluoroborate

Individual evidence

1. ↑ ^{a b c d e f g} Entry on Tridemorph in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
2. ↑ Entry on Tridemorph in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
3. ↑ ^{a b} Entry on Tridemorph. In: Römpp Online . Georg Thieme Verlag, accessed on March 27, 2011.
4. ↑ Pommer, E.-H. (1984) Chemical structure-fungicidal activity relationships in substituted morpholines. Pesticide Science, 15: 285-295, doi : 10.1002 / ps.2780150311
5. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Tridemorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.