Procymidone

Structural formula
General
Surname	Procymidone
other names	N - (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide meso - N - (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide 3- (3,5-dichlorophenyl) -1,5-dimethyl-3-azabicyclo [3.1.0] hexane-2,4-dione ( IUPAC )
Molecular formula	C 13 H 11 Cl 2 NO 2
Brief description	colorless solid
External identifiers / databases
CAS number 32809-16-8 EC number 251-233-1 ECHA InfoCard 100,046,561 PubChem 36242 Wikidata Q416120
properties
Molar mass	284.14 g mol −1
Physical state	firmly
solubility	almost insoluble in water
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 332-413 P: ?
Toxicological data	7000 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 .

Procymidone is a chemical compound from the group of dicarboximides .

Extraction and presentation

Procymidone can be obtained by reacting 1,3-dimethylcyclopropanedicarboxylic acid anhydride with 3,5-dichloroaniline and subsequent reaction with acetic acid anhydride . In the first step, ring opening of the cyclic anhydride forms an open-chain amide with a free carboxylic acid group . Although this compound is chiral, it arises as a racemate or pair of enantiomers because the starting compounds are achiral. Since the chirality is canceled again in the following step, a selective synthesis would be superfluous here. The open-chain carboxamide is cyclized again in the subsequent reaction with acetic anhydride and procymidone is obtained as a cyclic imide . Both the anhydride used as the starting compound and the procymidone are achiral because they have a mirror plane and thus both represent a meso compound .

properties

Procymidone is a colorless solid that is insoluble in water.

use

Procymidone is used as a fungicide . It was used in particular against the harmful fungus gray mold ( Botrytis cinerea ). Due to the high genetic variability, this fungus has a very high tendency to resist.

regulation

EU

Plant protection products with this active ingredient have not been approved in Germany since 1997. In the EU, cucumbers in greenhouses (closed hydroponic systems) and plums (for processing) and plums (for processing) were approved again in 2006. In 2007, the connection hit the headlines because Greenpeace exceeded the so-called acute reference dose (ARfD) for table grapes in German and Austrian supermarkets criticized. According to the department store chains, however, the load is well below the maximum permitted in the EU, since the ARfD is not taken into account there. The effect is based on the inhibition of triglyceride synthesis in fungi.

Admission

The use of procymidone has been banned in the EU since July 2008. The permissible daily dose is 0.0028, the acute reference dose 0.012 and the acceptable user exposure 0.12 milligrams per kilogram of body weight and day. In Switzerland, too, no pesticides containing this active ingredient are permitted.

safety instructions

Animal experiments have shown that procymidone has an anti-androgenic effect.

Individual evidence

1. ↑ ^{a b c d e} data sheet Procymidone at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
2. ↑ There is not yet a harmonized classification for this substance . A labeling of 3- (3,5-dichlorophenyl) -1,5-dimethyl-3-azabicyclo [3.1.0] hexane-2,4-dione in the Classification and Labeling Inventory of the European Chemicals Agency is reproduced from a self-classification by the distributor (ECHA), accessed on July 27, 2020.
3. ↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 978-0-8155-1401-5 , pp. 581 ( limited preview in Google Book search).
4. ↑ Umweltdaten.de: ENVIRONMENTAL RESEARCH PLAN OF THE FEDERAL MINISTRY FOR THE ENVIRONMENT, NATURE CONSERVATION AND NUCLEAR SAFETY, research report 200 67 407, UBA-FB 000458/1 and 2 (PDF; 3.1 MB).
5. ↑ EU: DIRECTIVE 2006/132 / EG OF THE COMMISSION of December 11, 2006 amending Council Directive 91/414 / EEC to include the active ingredient procymidone (PDF) .
6. ↑ Greenpeace: Acute Toxic: Grapes and Lettuce - Chemistry News , January 12, 2007.
7. ↑ NTV: limit values ​​unclear: table grapes with procymidone - n-tv.de , November 21, 2008.
8. ^ Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 978-0-85404-499-3 , pp. 1165 ( limited preview in Google Book search).
9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Procymidone in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 8, 2016.
10. ↑ Hans-Werner Vohr: Toxicology . John Wiley & Sons, 2012, ISBN 3-527-66003-8 , pp. 158 ( limited preview in Google Book search).