Dichloroprop

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Structural formula
Structure of (±) -dichloroprop
Simplified structural formula without stereochemistry
General
Surname Dichloroprop
other names
  • (±) -2- (2,4-dichlorophenoxy) propionic acid
  • rac -2- (2,4-dichlorophenoxy) propionic acid
  • ( RS ) -2- (2,4-dichlorophenoxy) propionic acid
  • 2,4-DP
Molecular formula C 9 H 8 Cl 2 O 3
Brief description

colorless and odorless solid

External identifiers / databases
CAS number 120-36-5 ( racemate )
EC number 204-390-5
ECHA InfoCard 100.003.991
PubChem 8427
ChemSpider 8120
Wikidata Q148946
properties
Molar mass 235.07 g mol −1
Physical state

firmly

density

1.42 g cm −3 (dichlorprop)

Melting point

116-120 ° C [( R ) - (+) - Dichlorprop, Dichlorprop-P]

pK s value

3.1 (dichloroprop)

solubility

very bad in water (350 mg l −1 at 20 ° C) (dichloroprop)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
05 - Corrosive 07 - Warning

danger

H and P phrases H: 302-312-315-318
P: 280-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dichlorprop is a chemical compound used as a herbicide and plant growth regulator.

Stereochemistry

Dichlorprop contains a stereocenter, hence there are two enantiomers, the ( R ) -form and the ( S ) -form. Dichlorprop is a 1: 1 mixture ( racemate ) of the ( R ) form and the ( S ) form. The pure ( R ) - enantiomer of diclorprop is called dichlorprop-P and is used in some countries as a pesticide.

The pure ( S ) - enantiomer of diclorprop has no practical significance.

Enantiomers of dichloroprop
Surname ( R ) -Dichloroprop ( S ) -dichloroprop
other names Dichloroprop-P
Structural formula (R) -Dichlorprop Structural Formula V.1a.svg (S) -Dichlorprop Structural Formula V.1a.svg
CAS number 15165-67-0 15165-69-2
120-36-5 ( racemate )
EC number 403-980-1
204-390-5 ( racemate )
ECHA info card 100.100.566
100.003.991 ( racemate )
PubChem 119435 84811
8427 ( racemate )
Wikidata Q27145258 Q27145259
Q148946 ( racemate )

Admission

In the EU states including Germany and Austria as well as in Switzerland no plant protection products with dichlorprop as an active ingredient are permitted.

Dichlorprop-P is approved in Austria and Germany as a post-emergence herbicide against dicotyledonous weeds in grain cultivation. Dichlorprop-P is not listed in the list of approved plant protection products in Switzerland.

safety instructions

Dichlorprop is classified as harmful and, in toxic concentrations, mainly affects the central and peripheral nervous system, although long-term effects from storage in fat and the brain cannot be ruled out. The racemic dichloropropane has a significantly higher toxicity (oral LD 50 value for rats 344 mg / kg body weight) than the pure ( R ) form (825 mg / kg).

Derived connections

A number of other compounds, especially various salts and esters, are known of dichloroprop:

  • Dichloroprop-butotyl
  • Dichloroprop-dimethylammonium
  • Dichloroprop-ethylammonium
  • Dichloroprop-2-ethylhexyl
  • Dichloroprop-isoctyl
  • Dichloroprop-methyl
  • Dichloroprop potassium
  • Dichloroprop sodium

Individual evidence

  1. ↑ a b c d e Entry on dichlorprop in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ Reregistration Eligibility Decision (RED) for Dichlorprop-p (2,4-DP-p) of the Environmental Protection Agency (EPA) of the United States of America from August 29, 2007.
  3. ↑ a b c Entry on dichlorprop in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ↑ Entry on dichlorprop in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ a b Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, p. 177, 1992.
  6. ↑ a b Entry on dichlorprop-P in the ChemIDplus database of the United States National Library of Medicine (NLM)
  7. ↑ a b Pesticide Manual. Vol. 9, p. 258, 1991.
  8. ↑ a b Directorate-General for Health and Food Safety of the European Commission: Entry on dichlorprop in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 11, 2016.
  9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on dichlorprop-P in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 11, 2016.
  10. ↑ External identifiers or database links for dichloroprop-butotyl : CAS number: 53404-31-2, EC number: 258-528-4, ECHA InfoCard: 100.053.191 , PubChem : 62037 , ChemSpider : 55881 , Wikidata : Q27271869 .
  11. ↑ External identifiers or database links for dichlorprop-dimethylammonium : CAS number: 53404-32-3, EC number: 258-530-5, ECHA InfoCard: 100.053.192 , PubChem : 62038 , ChemSpider : 55882 , Wikidata : Q27258236 .
  12. ↑ External identifiers of or database links for dichlorprop-ethylammonium : CAS number: 84731-66-8, EC number: 283-826-6, ECHA InfoCard: 100.076.177 , PubChem : 6452360 , ChemSpider : 4954794 , Wikidata : Q27281047 .
  13. ↑ External identifiers or database links for dichlorprop-2-ethylhexyl : CAS number: 79270-78-3, EC number: 279-123-9, ECHA InfoCard: 100.071.908 , PubChem : 3086106 , ChemSpider : 2342807 , Wikidata : Q27275906 .
  14. ↑ External identifiers of or database links to dichloroprop-isoctyl : CAS number: 28631-35-8, EC number: 249-110-2, ECHA InfoCard: 100.044.631 , PubChem : 15754796 , ChemSpider : 15538491 , Wikidata : Q27274883 .
  15. ↑ External identifiers or database links for dichlorprop-methyl : CAS number: 57153-17-0, EC number: 621-372-6, ECHA InfoCard: 100.150.230 , PubChem : 90988 , ChemSpider : 82169 , Wikidata : Q89912956 .
  16. ↑ External identifiers of or database links for dichlorprop potassium : CAS number: 5746-17-8, EC number: 227-269-9, ECHA InfoCard: 100.024.791 , PubChem : 23673648 , ChemSpider : 144945 , Wikidata : Q27286765 .
  17. ↑ External identifiers of or database links for dichlorprop sodium : CAS number: 39104-30-8, EC number: 254-293-7, ECHA InfoCard: 100.049.340 , PubChem : 118984406 , ChemSpider : 32697542 , Wikidata : Q27236975 .