Dodemorph

Structural formula
	Mixture of three stereoisomers
General
Surname	Dodemorph
other names	4-cyclododecyl-2,6-dimethylmorpholine; Meltatox; Milban;
Molecular formula	C 18 H 35 NO
Brief description	crystalline powder
External identifiers / databases
EC number	216-474-9
ECHA InfoCard	100.014.978
PubChem	61899
Wikidata	Q2642073
properties
Molar mass	281.48 g mol −1
Physical state	firmly
density	0.93 g cm −3
Melting point	71 ° C
boiling point	315 ° C
solubility	practically insoluble in water (0.0011 g l −1 )
safety instructions
H and P phrases	H: 314-317-361d-373-410
	EUH: 071
	P: 261-273-305 + 351 + 338
Toxicological data	2650 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dodemorph is a plant protection product from the morpholine group .

History and use

Dodemorph was discovered at BASF in 1965 and launched as a fungicide in 1971 . Dodemorph is the first morpholine fungicide to be commercialized and thus also the first sterol biosynthesis inhibitor. It is used in particular against powdery mildew . Dodemorph acts as an inhibitor of sterol-Δ8 / 7-isomerase and sterol-Δ14-reductase in ergosterol biosynthesis .

Extraction and presentation

Dodemorph can be obtained by reacting cyclododecylamine with propylene oxide and sulfuric acid.

Stereochemistry

Chemically, dodemorph is a mixture of three stereoisomers :

meso connection,
( R , R ) -isomer and
( S , S ) -isomer,

where the ( R , R ) -isomer and the ( S , S ) -isomer form a racemate , ie represent a 1: 1 mixture. This mixture is also called the trans isomer.

Admission

In 2008, the EU Commission included Dodemorph in the list of active ingredients in pesticides, restricting it to “use as a fungicide on ornamental plants in greenhouses” .

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

Individual evidence

↑ ^a ^b ^c Günter Hommel (Ed.): Handbook of dangerous goods: Merkblätter 2072–2502 . Springer, 2004, ISBN 3-540-20370-2 , pp. 2374 ( limited preview in Google Book Search).
↑ ^a ^b ^c ^d ^e Entry on Dodemorph in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Entry on Dodemorph 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 .
↑ Dodemorph data sheet , PESTANAL at Sigma-Aldrich , accessed on June 29, 2016 ( PDF ).
^ Clemens Lamberth, Jürgen Dinges: Bioactive Heterocyclic Compound Classes: Agrochemicals. John Wiley & Sons, 2012, ISBN 978-3-527-33396-7 , p. 119 ( limited preview in Google book search).
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 475 ( limited preview in Google Book search).
↑ Commission Directive 2008/125 / EC of December 19, 2008 (PDF) amending Council Directive 91/414 / EEC to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoic acid methyl ester, metamitron, sulcotrione , Tebuconazole and triadimenol as active ingredients.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on Dodemorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.

[handbuch-1] Günter Hommel (Ed.): Handbook of dangerous goods: Merkblätter 2072–2502 . Springer, 2004, ISBN 3-540-20370-2 , pp. 2374 ( limited preview in Google Book Search).

[GESTIS-2] Entry on Dodemorph in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .

[CLP_100.014.978-3] Entry on Dodemorph 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 .

[Sigma-4] Dodemorph data sheet , PESTANAL at Sigma-Aldrich , accessed on June 29, 2016 ( PDF ).

[5] Clemens Lamberth, Jürgen Dinges: Bioactive Heterocyclic Compound Classes: Agrochemicals. John Wiley & Sons, 2012, ISBN 978-3-527-33396-7 , p. 119 ( limited preview in Google book search).

[Unger-6] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 475 ( limited preview in Google Book search).

[7] Commission Directive 2008/125 / EC of December 19, 2008 (PDF) amending Council Directive 91/414 / EEC to include aluminum phosphide, calcium phosphide, magnesium phosphide, cymoxanil, dodemorph, 2,5-dichlorobenzoic acid methyl ester, metamitron, sulcotrione , Tebuconazole and triadimenol as active ingredients.

[PSM-8] Directorate-General for Health and Food Safety of the European Commission: Entry on Dodemorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on December 6, 2019.