Dichlorvos

from Wikipedia, the free encyclopedia
Structural formula
Structure of dichlorvos
General
Non-proprietary name Dichlorvos
other names
  • Dichlorphos
  • Dichlorfos
  • Chlorvinphos
  • Vinylphos
  • 2,2-dichlorovinyl dimethyl phosphate
  • DDVP
Molecular formula C 4 H 7 Cl 2 O 4 P
Brief description

colorless liquid with an aromatic odor

External identifiers / databases
CAS number 62-73-7
EC number 200-547-7
ECHA InfoCard 100,000,498
PubChem 3039
Wikidata Q420622
Drug information
ATC code
properties
Molar mass 220.98 g · mol -1
Physical state

liquid

density

1.43 g cm −3 (20 ° C)

Melting point

<−60 ° C

boiling point

140 ° C (13 hPa)

Vapor pressure

2.1 Pa (25 ° C)

solubility

little in water (10 g l −1 at 20 ° C)

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic 09 - Dangerous for the environment

danger

H and P phrases H: 300 + 310 + 330-317-400
P: 260-280-284-301 + 310 + 330-302 + 352 + 310-304 + 340 + 310
MAK
  • DFG : 0.11 ml m −3 or 1 mg m −3
  • Switzerland: 0.1 ml m −3 or 1 mg m −3
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dichlorvos is an insecticide from the group of phosphoric acid esters introduced in 1951 . Dichlorvos is a viscous, colorless to yellow-brown liquid. It has an aromatic odor and is flammable.

Manufacturing

Dichlorvos can be produced both by the dehydrochlorination of trichlorfon and by the reaction of trimethyl phosphite and chloral . The world annual production in 1984 was about 4220 t. About 300 t of this was produced in Western Europe.

use

As a contact and food poison, dichlorvos is used against pests in the hygiene sector and in agriculture. In Germany, several Dichlorvos preparations were still approved for stored product protection until the end of 2006. In November 2006, the EU Directive 2006/92 / EC was published, according to which dichlorvos residues may only be detectable in food in a very small proportion. In order to implement this guideline, the approvals of all dichloro-containing plant protection products were revoked in Germany and Austria in the course of 2007 (products for protecting stored products are legally considered as plant protection products). In Switzerland, dichlorvos could be used in greenhouse crops against lice, caterpillars, spider mites , whitefly and thrips ; today (2016) no pesticides containing dichlorvos are permitted in Switzerland either. Some of the sprays and cold misters approved for stored product protection contained pyrethrins as additional active ingredients.

According to European legislation (Directive 98/8 / EC on the placing of biocidal products on the market) and with the resolution of May 10, 2012, a decision has been made not to include the active substance dichlorvos in the corresponding list (Annex I / IA of Directive 98/8 / EG) for biocidal products (product type 18). The sale of biocidal products that contain the active ingredient dichlorvos is therefore no longer permitted in the EU (Switzerland has adopted this provision) for insecticides from November 1, 2012.

Biological importance

Dichlorvos is extremely toxic to invertebrates, fish, birds and bees. Dichlorvos showed a mutagenic effect in tests with microorganisms . This did not occur in mammals - presumably because of the rapid breakdown in the organism. Long-term feeding studies with extremely high doses on mice and rats have shown carcinogenic effects. As a result, the IARC's classification was changed from a fundamentally lacking carcinogenic potential to a possible carcinogenic potential .

The tendency to bioaccumulate is very low because of the esters in water more rapidly, in an alkaline medium hydrolyzed . Dichlorvos is also rapidly broken down by microorganisms in water and in the soil. When dichlorvos and other organophosphates are broken down, dimethyl phosphate (DMP) is formed, which can be used to assess the exposure to humans by examining the urine.

safety instructions

Like all phosphoric acid esters , Dichlorvos has an inhibitory effect on the enzyme cholinesterase and thereby disrupts the function of nerve cells . The substance can be absorbed not only through the gastrointestinal tract, but also by inhalation or through the skin. There is a particular danger when handling dichlorvos and, due to the high vapor pressure, in absorption via the respiratory tract. The amounts ingested with food and drinking water are small. The WHO assumes 4 µg / kg / d as the permitted daily dose for the tolerable daily intake.

In various studies with animals such as mice, rats and dogs, Dichlorvos showed symptoms such as drowsiness, diarrhea, vomiting (dog), increased tear flow and muscle tremors (mouse, rat), dyspnoea (rat) and dysfunction of the salivary gland (rat).

Individual evidence

  1. ↑ Entry on Dichlorvos. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2014.
  2. ↑ a b c d e f g h i j k Entry on Dichlorvos in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
  3. ↑ Entry on Dichlorvos in the SRC PhysProp Database , accessed on September 11, 2012.
  4. ↑ Entry on dichlorvos 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. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 62-73-7 or Dichlorvos ), accessed on November 2, 2015.
  6. ↑ Agrochemicals Handbook, with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86, Vol. A141, p. 1984.
  7. ↑ Osaka Shiritsu Daigaku Igaku Zasshi. Journal of the Osaka City Medical Center. Vol. 15, pp. 553, 1966.
  8. ↑ Japan Pesticide Information. Vol. (13), p. 36, 1972.
  9. ↑ Dichlorvos (DDVP, Vapona) - Chemical Profile 3/88 .
  10. ^ A b Rainer Koch: Environmental chemicals , 3rd edition (1995), VCH, Weinheim, ISBN 3-527-30061-9 .
  11. ↑ EU: Directive 2006/92 / EG amending the ... Directives ... with regard to the maximum residue levels for Captan, Dichlorvos, Ethion and Folpet (PDF) Official Journal of the European Communities - L 311/31 - November 10, 2006.
  12. ↑ Federal Office for Food Safety: List of the terminated approvals of the last 12 months, sorted according to the end of approval . Retrieved February 17, 2008.
  13. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on dichlorvos in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved March 3, 2016.
  14. ↑ EU: Directive 98/8 / EC of February 16, 1998 on the placing of biocidal products on the market (PDF) Official Journal of the European Communities - L 123/1 - April 24, 1998.
  15. ↑ EU: Decision of May 10, 2012 on the non-inclusion of dichlorvos in Annex I of Directive 98/8 / EC on the placing of biocidal products on the market (PDF) Official Journal of the European Communities - L 125/53 - May 12, 2012.
  16. ↑ TSS Dikshith, PV Diwan: Industrial Guide to Chemical and Drug Safety. Wiley-IEEE, 2003, ISBN 978-0-471-23698-6 .
  17. ↑ LGL Bavaria: Research project: Investigation of a grocery shopping basket for pesticides and their metabolites in human metabolism , August 22, 2014.
  18. ^ Australian Veterinary Journal. Vol. 49, p. 113, 1973.
  19. ↑ a b Gigiena i Sanitariya. HYSAAV. Vol. 33 (12), p. 35, 1968.
  20. ↑ Acta Pharmacologica et Toxicologica , Supplementun. Vol. 49 (5), p. 67, 1981.