Dimethomorph

Structural formula
	Structural formula of the ( E ) isomer
General
Surname	Dimethomorph
other names	( E , Z ) -4- [3- (4-chlorophenyl) -3- (3,4-dimethoxyphenyl) acryloyl] morpholine
Molecular formula	C 21 H 22 ClNO 4
Brief description	white, odorless solid
External identifiers / databases
EC number	404-200-2
ECHA InfoCard	100.100.586
PubChem	86298
ChemSpider	77841
Wikidata	Q27155626
properties
Molar mass	387.86 g mol −1
Physical state	firmly
density	1.318 g cm −3
Melting point	125.2–149.2 ° C (48:52 E / Z mixture)
boiling point	Decomposition from 270 ° C
Vapor pressure	9.7 10 −9 Pa (20 ° C)
solubility	practically insoluble in water (0.06 g l −1 at 20 ° C); soluble in acetone , dichloroethane and ethyl acetate ;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
H and P phrases	H: 411
	P: 273
Toxicological data	3900 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethomorph is a mixture of two cis , trans -isomeric chemical compounds from the group of cinnamic acid amides .

Extraction and presentation

To produce Dimethomorph, pyrocatechol is first methylated with bromomethane to form veratrole . This reacts with 4-chlorobenzoyl chloride . Triethylphosphonoacetate is added to the product . An ethyl group is split off with HCl and morpholine is added to it.

properties

Dimethomorph is a white, odorless solid that is poorly soluble in water. It consists of a mixture of approximately equal proportions of the ( E ) and ( Z ) isomers of the compound.

use

Dimethomorph is one of the CAA fungicides . The effect is based on the inhibition of cellulose synthase.

Admission

In 2007 the EU Commission added Dimethomorph to the list of approved active ingredients for pesticides for use as a fungicide .

Several preparations (e.g. Forum and Acrobat ) with the active ingredient are approved in a number of EU countries, including Germany and Austria, as well as Switzerland .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h FAO: Dimethomorph (PDF; 1.1 MB)
↑ ^a ^b ^c Datasheet Dimethomorph, PESTANAL at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).
↑ Entry on Dimethomorph (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .
↑ Dimethomorph at EXTOXNET
↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 472–473 ( limited preview in Google Book search).
↑ Commission Directive 2007/25 / EC of April 23, 2007 (PDF) amending Council Directive 91/414 / EEC to include the active substances dimethoate, dimethomorph, glufosinate, metribuzin, phosmet and propamocarb.
↑ General Directorate Health and Food Safety of the European Commission: Entry on Dimethomorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.

[fao-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h FAO: Dimethomorph (PDF; 1.1 MB)

[Sigma-2] Datasheet Dimethomorph, PESTANAL at Sigma-Aldrich , accessed on May 18, 2017 ( PDF ).

[CLP_100.100.586-3] Entry on Dimethomorph (ISO) in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on March 12, 2017. Manufacturers or distributors can expand the harmonized classification and labeling .

[cornell-4] Dimethomorph at EXTOXNET

[unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 472–473 ( limited preview in Google Book search).

[6] Commission Directive 2007/25 / EC of April 23, 2007 (PDF) amending Council Directive 91/414 / EEC to include the active substances dimethoate, dimethomorph, glufosinate, metribuzin, phosmet and propamocarb.

[PSM-7] General Directorate Health and Food Safety of the European Commission: Entry on Dimethomorph in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.