Chlorpyrifos-methyl

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Structural formula
Structural formula of chlorpyrifos-methyl
General
Surname Chlorpyrifos-methyl
other names
  • O , O -Dimethyl- O- (3,5,6-trichloropyrid-2-yl) thiophosphate
  • Thiophosphoric acid O , O -dimethyl- O - (3,5,6-trichloro-2-pyridyl) ester
  • Chlorpyriphos-methyl
  • Reldan
  • Cert
Molecular formula C 7 H 7 Cl 3 NO 3 PS
Brief description

colorless, crystalline solid

External identifiers / databases
CAS number 5598-13-0
EC number 227-011-5
ECHA InfoCard 100.024.556
PubChem 21803
ChemSpider 20493
Wikidata Q2964145
properties
Molar mass 322.54 g mol −1
Physical state

firmly

density

1.67 g cm −3

Melting point

45.5-46.5 ° C

boiling point

decomposes before boiling at 175 ° C

Vapor pressure

3 · 10 −3  Pa (20 ° C)

solubility

practically insoluble in water (2.74 mg l −1 at 20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
07 - Warning 09 - Dangerous for the environment

Caution

H and P phrases H: 317-410
EUH: 208
P: 261-280-284-304 + 340 + 311-342 + 311-403 + 233
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Chlorpyrifos-methyl is a synthetic pesticides active ingredient with insecticidal and acaricidal effect of the chemical family of organophosphate . These are the methyl - derivative of chlorpyrifos (chlorpyrifos-ethyl).

properties

Chlorpyrifos-methyl is a colorless, crystalline solid with a slight odor of mercaptan . It is almost insoluble in water, but can be dissolved in most organic solvents . In the presence of water , chlorpyrifos-methyl hydrolyzes with a half-life of 9.4 to 22.7 days at 25 ° C. in the pH range from 4.2 to 8.0. Half-lives between 1.4 and 12.5 days were observed in the soil.

effect

The mode of action of chlorpyrifos-methyl corresponds to that of other phosphoric acid esters. It inhibits the enzyme acetylcholine esterase in the nerve cells . This causes a disruption of the transmission of stimuli in the nervous system, which can cause muscle functions to come to a standstill. Paralysis up to respiratory arrest and ultimately death can result.

Chlorpyrifos-methyl is an insecticide and acaricide with a broad spectrum of activity. It acts both as a contact poison and as a food poison and can also be used for fumigating.

use

The active ingredient has been used successfully for a long time in fruit, vegetable and grain cultivation against a number of pests . The organisms it is used against include scale and aphids , caterpillars , flies , termites and cockroaches , among others .

Admission

Chlorpyrifos was approved in the European Union in 2006. Authorization ran until January 31, 2020. Member States had to withdraw their authorizations for plant protection products containing chlorpyrifos-methyl as an active ingredient by February 16, 2020 at the latest. Any use-by dates ended on April 16, 2020 at the latest. In many EU member states, preparations containing the active ingredient were approved until the end, but not in Germany.

In Switzerland, the Federal Office for Agriculture (FOAG) decided in May 2019 to withdraw the license for all pesticides with the active ingredients chlorpyrifos-methyl and chlorpyrifos and to gradually take them off the market; However, the decision is not yet final. The Federal Administrative Court confirmed that eight complaints had been received in this context. According to Greenpeace and WWF Switzerland , Dow AgroSciences , Syngenta and Sintrago , among others , have filed a complaint against the decision. The plant protection products concerned are expected to be banned from July 2020.

Individual evidence

  1. ↑ a b c d e Entry on chlorpyrifos-methyl in the GESTIS substance database of the IFA , accessed on May 14, 2019(JavaScript required) .
  2. ↑ a b c d e f g Entry on Chlorpyrifos-methyl in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on May 14, 2019.
  3. ↑ Entry on Chlorpyrifos-methyl in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on May 14, 2019. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Data sheet Chlorpyrifos-methyl from Sigma-Aldrich , accessed on May 14, 2019 ( PDF ).
  5. ↑ 325. Chlorpyrifos-methyl (WHO Pesticide Residues Series 5). Retrieved May 15, 2019 .
  6. ^ Hill, Dennis S., 1934-: Agricultural insect pests of temperate regions and their control . Cambridge University Press, Cambridge [Cambridgeshire] 1987, ISBN 0-521-24013-1 ( limited preview in Google Book Search).
  7. ↑ Entry on Chlorpyrifos-methyl in the Hazardous Substances Data Bank , accessed on May 14, 2019.
  8. ↑ Implementing Regulation (EU) 2020/17 of the Commission of 10 January 2020 on the non-renewal of the approval of the active substance chlorpyrifos-methyl according to Regulation (EC) No. 1107/2009 of the European Parliament and of the Council on the placing of plant protection products on the market and amending the Annex of the Commission Implementing Regulation (EU) No. 540/2011
  9. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Chlorpyrifos-methyl in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on May 14, 2019.
  10. ↑ Federal government wants to ban harmful pesticides. In: naturschutz.ch. June 12, 2019, accessed June 13, 2019 .
  11. ↑ Ban on pesticides: Agrochemicals resist. In: schweizerbauer.ch . July 19, 2019, accessed August 12, 2019 .
  12. ↑ Insecticide banned from July. In: schweizerbauer.ch. January 28, 2020, accessed January 28, 2020 .