Carpropamide

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Structural formula
Structural formula of carpropamide
Simplified structural formula without stereoisomerism
General
Surname Carpropamide
other names

2,2-dichloro- N - [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide

Molecular formula C 15 H 18 Cl 3 NO
Brief description

colorless solid

External identifiers / databases
CAS number 104030-54-8
EC number 600-513-5
ECHA InfoCard 100.121.351
PubChem 153847
Wikidata Q27106077
properties
Molar mass 334.67 g mol −1
Physical state

firmly

density

1.17 g cm −3

Melting point

159.7 ° C

Vapor pressure

0.0025 mPa (20 ° C)

solubility

practically insoluble in water (0.0018 g l −1 at 20 ° C)

safety instructions
GHS labeling of hazardous substances
09 - Dangerous for the environment

Caution

H and P phrases H: 411
P: 273
Toxicological data

> 5000 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 .

Carpropamide is a complex mixture of different isomeric chemical compounds from the group of cyclopropanecarboxamides.

Stereochemistry

Carpropamid of technical quality is a mixture of substances

  • (1 R , 3 S ) -2,2-dichloro- N - [( R ) -1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,
  • (1 S , 3 R ) -2,2-dichloro- N - [( R ) -1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide,
  • (1 S , 3 R ) -2,2-dichloro- N - [( S ) -1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide and
  • (1 R , 3 S ) -2,2-dichloro- N - [( S ) -1- (4-chlorophenyl) ethyl] -1-ethyl-3-methylcyclopropanecarboxamide.

The proportion of the first two stereoisomers mentioned is at least 95%.

effect

Point of attack in melanin synthesis

Carpropamide is mainly used as a fungicide against rice blight ( Magnaporthe oryzae ). The effect is based on the inhibition of scytalon dehydratase in melanin biosynthesis .

In addition, carpropamide acts as a resistance inducer, which stimulates the induced lignification and the production of the phytoalexin momilactone A.

Admission

With regard to the active ingredient carpropamide, there has never been a regulation in the EU for its use in plant protection products, so its use is not permitted. In Germany, Austria and Switzerland - also because of the lack of rice cultivation - no pesticides with this active ingredient are permitted.

See also

Individual evidence

  1. ↑ a b c data sheet carpropamide from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
  2. ↑ a b c d e Entry on carpropamide in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on October 9, 2013.
  3. ↑ a b M. Thieron, R. Pontzen, Y. Kurahashi: Carpropamid: a rice fungicide with two modes of action . In: Plant Protection News Bayer . tape 51 , no. 3 , 1998, p. 257-278 .
  4. ↑ General Directorate Health and Food Safety of the European Commission: Entry on carpropamide in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 18, 2016.