Procymidone

• 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)

Colorless solid

Fixed

Insoluble in water

7,000 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Procymidone is a chemical compound selected from the group of the dicarboximides.

Production and representation

Procymidone can be obtained by reaction of 1,3- Dimethylcyclopropandicarbonsäureanhydrid with 3,5-dichloroaniline, followed by reaction with acetic anhydride. In the first step is produced by ring opening of the cyclic anhydride of an open-chain amide with a free carboxylic acid group. Although this compound is chiral, but is formed as a racemate or of enantiomers as the starting materials are achiral. Since the chirality is canceled in the subsequent step would be a selective synthesis superfluous. The open-chain carboxylic acid is cyclized again in the subsequent reaction with acetic anhydride and obtained procymidone as a cyclic imide. Both the anhydride used as the starting compound and the procymidone is achiral since they have a mirror surface and thus both be a meso compound.

Properties

Procymidone is a colorless solid which is insoluble in water.

Use

Procymidone is used as a fungicide. He was particularly against the fungus gray mold (Botrytis cinerea ) are used. Due to the high genetic variability, however, the slope resistance of this fungus is very high.

Regulation

EU

Plant protection products containing this active ingredient are no longer permitted in Germany since 1997. In the EU in 2006 was re-registration for cucumbers in greenhouses (closed hydroponic systems) and plums ( for processing ) In 2007 came the compound is in the headlines because Greenpeace exceeded the so-called acute reference dose (ARfD ) for table grapes in German and Austrian supermarkets criticized. However, according to the department store chains, the load is well below the permissible limits in the EU, since there the ARfD is not considered. The effect is based on inhibition of triglyceride synthesis in fungi.

The use of procymidone in the EU has been banned since July 2008. The Permitted daily dose is 0.0028, Acute Reference Dose 0.012 and the Acceptable Operator Exposure 0.12 milligrams per kilogram of body weight per day.

In Switzerland, no plant protection products containing this active ingredient are allowed.

Safety

For procymidone in animal experiments an anti-androgenic effect has been demonstrated.