Mandipropamid

Structural formula
	Structural formula without stereoisomerism
General
Surname	Mandipropamid
other names	( RS ) -2- (4-Chlorophenyl) - N - [3-methoxy-4- (2-propinyloxy) phenethyl] -2- (2-propynyloxy) acetamide; (±) -2- (4-Chlorophenyl) - N - [3-methoxy-4- (2-propinyloxy) phenethyl] -2- (2-propynyloxy) acetamide; DL -2- (4-chlorophenyl) - N - [3-methoxy-4- (2-propinyloxy) phenethyl] -2- (2-propynyloxy) acetamide; MPD;
Molecular formula	C 23 H 22 ClNO 4
Brief description	odorless, light brown solid
External identifiers / databases
EC number	609-434-0
ECHA InfoCard	100.130.842
PubChem	11292824
ChemSpider	9467809
Wikidata	Q2057167
properties
Molar mass	411.9 g mol −1
Physical state	firmly
density	1.24 g cm −3
Melting point	96.4-97.3 ° C
boiling point	Decomposition from 200 ° C
solubility	practically insoluble in water (4.2 mg l −1 at 25 ° C and pH 8.1); Easily soluble in acetone and dichloromethane ;
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 410
	P: ?
Toxicological data	> 2000 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Mandipropamid is a chemical compound from the class of mandelic acid amides and a fungicide from the family of CAA fungicides ( carboxamides ). Mandipropamid is an inhibitor for cellulose - synthase and effective against downy mildew and Phytophthora infestans . Mandipropamid is a very effective active ingredient: the EC ₈₀ against Phythophthora infestans is 0.1 mg · l ⁻¹ , that against Plasmopara viticola is 1.2 mg · l ⁻¹ .

Stereochemistry

The drug molecule contains a stereogenic center, hence there are two stereoisomers:

( R ) -2- (4-Chlorophenyl) - N - [3-methoxy-4- (2-propinyloxy) phenethyl] -2- (2-propinyloxy) acetamide and
( S ) -2- (4-Chlorophenyl) - N - [3-methoxy-4- (2-propinyloxy) phenethyl] -2- (2-propynyloxy) acetamide.

Enantiomers of mandipropamide
CAS number: 527697-63-8	CAS number: 1591271-18-9

Mandipropamid is used as a 1: 1 mixture ( racemate ) of these enantiomers .

Approvals

The EU Commission approved the use of mandipropamid as an active ingredient in plant protection products with effect from August 1, 2013. Mandipropamid is approved under the trade names Revus and Pergado in Germany, Austria and Switzerland.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f FAO data sheet (PDF; 1.0 MB).
↑ Entry on mandipropamid in the GESTIS substance database of the IFA , accessed on July 23, 2016(JavaScript required) .
↑ Entry on 2- (4-chloro-phenyl) -N- [2- (3-methoxy-4-prop-2-ynyloxy-phenyl) -ethyl] -2-prop-2-ynyloxy-acetamide Template: Linktext-Check / Escaped 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 .
↑ ^a ^b data sheet mandipropamid at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
↑ Clemens Lamberth, Andre Jeanguenat, Fredrik Cederbaum, Alain De Mesmaeker, Martin Zeller, Hans-Joachim Kempf, Ronald Zeun: Multicomponent reactions in fungicide research. The discovery of mandipropamid . In: Bioorganic & Medicinal Chemistry . tape 16 , no. 3 , 2008, p. 1531–1545 , doi : 10.1016 / j.bmc.2007.10.019 (English, PDF ).
↑ Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 20.
↑ ^a ^b Implementing Regulation (EU) No. 188/2013 of the Commission of March 5, 2013 for the approval of the active substance mandipropamid 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 the Annex of the Implementing Regulation (EU) No. 540/2011
↑ General Directorate Health and Food Safety of the European Commission: Entry on mandipropamid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.

[fao-1] ↑ ^a ^b ^c ^d ^e ^f FAO data sheet (PDF; 1.0 MB).

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

[CLP_100.130.842-3] Entry on 2- (4-chloro-phenyl) -N- [2- (3-methoxy-4-prop-2-ynyloxy-phenyl) -ethyl] -2-prop-2-ynyloxy-acetamide Template: Linktext-Check / Escaped 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] ta sheet mandipropamid at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[5] Clemens Lamberth, Andre Jeanguenat, Fredrik Cederbaum, Alain De Mesmaeker, Martin Zeller, Hans-Joachim Kempf, Ronald Zeun: Multicomponent reactions in fungicide research. The discovery of mandipropamid . In: Bioorganic & Medicinal Chemistry . tape 16 , no. 3 , 2008, p. 1531–1545 , doi : 10.1016 / j.bmc.2007.10.019 (English, PDF ).

[Ulrich-6] Elim M. Ulrich, Candice M. Morrison, Michael M. Goldsmith, William T. Foremann: Chiral Pesticides: Identification, Description, and Environmental Implications . In: Reviews of Environmental Contaminations and Toxicology. Springer 2012, Boston, Volume 217, pp. 1–74, DOI: 10.1007 / 978-1-4014-2329-4_1 , see p. 20.

[VO-2013-188-7] Implementing Regulation (EU) No. 188/2013 of the Commission of March 5, 2013 for the approval of the active substance mandipropamid 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 the Annex of the Implementing Regulation (EU) No. 540/2011

[PSM-8] General Directorate Health and Food Safety of the European Commission: Entry on mandipropamid in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 19, 2016.