Carbofuran

Structural formula
General
Surname	Carbofuran
other names	2,3-dihydro-2,2-dimethyl-benzofuran-7-yl-methylcarbamate ( IUPAC ); Furadan; Curaterr;
Molecular formula	C 12 H 15 NO 3
Brief description	colorless to light brown solid, odorless or with a faint odor of phenol
External identifiers / databases
EC number	216-353-0
ECHA InfoCard	100,014,867
PubChem	2566
Wikidata	Q423136
properties
Molar mass	221.23 g mol −1
Physical state	firmly
density	1.18 g cm −3
Melting point	153-154 ° C
boiling point	Decomposition from 295 ° C
solubility	very bad in water (320 mg l −1 at 25 ° C)
safety instructions
H and P phrases	H: 300 + 330-410
	P: 260-264-273-284-301 + 310-310
MAK	Switzerland: 0.1 mg m −3
Toxicological data	5 mg kg −1 ( LD 50 , rat , oral ) ; 885 mg kg −1 ( LD 50 , rabbit , transdermal ) ; 0.033–10.2 mg l −1 ( LC 50 , fish , 96 hours ) ; 0.00159–68 mg l −1 ( LC 50 , crustaceans , 48 hours ) ; 0.002–0.09 mg l −1 ( EC 50 , crustaceans , 48 hours ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbofuran is a broad spectrum insecticide , acaricide and nematicide . It belongs to the group of substances called carbamates .

synthesis

Carbofuran is produced in a multi-stage reaction from catechol , 3-chloro-2-methylpropene and methyl isocyanate .

effect

Carbofuran is a systemic insecticide that acts as a food and contact poison . Its effect is based on the inhibition of the cholinesterases acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE).

Admission

Due to a decision in June 2007, carbofuran is no longer approved as an active ingredient in plant protection products for the European Union .

In Austria it was in commercial horticulture and for pickling of beet seeds are used. Since December 2008, the sale, use and possession in Austria are prohibited. Carbofuran was not an approved active ingredient in the Federal Republic of Germany, but exemptions were granted if necessary. Carbofuran was approved in Switzerland against a large number of harmful insects in commercial horticulture and in the cultivation of maize, beets, mushrooms and onions. The approval in Switzerland was withdrawn in 2011, the sales period ran until May 2012, the use-by period until May 2013.

toxicity

The LD _{50 determined} for the rat was 8.2–14.1 mg · kg ⁻¹ body weight, and for the dog 19 mg · kg ⁻¹ body weight. In long-term studies (rat, 2 years), the NOEL was 10 mg kg ⁻¹ food, and from 100 mg kg ⁻¹ food growth depression occurred.

Environmental behavior

The half-life for degradation in the soil is 8 to 13 days. Mobility in the soil is high. Carbofuran is toxic to bees .

In Africa, carbofuran has been used, among other things, to poach birds. In Vorarlberg (2012 and 2016) illegal carbofuran was used as bait against birds of prey via pigeons.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on carbofuran in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Entry on carbofuran 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 .
↑ Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 1563-66-2 or Carbofuran ), accessed on November 2, 2015.
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 70 ( limited preview in Google Book search).
↑ Decision of the Commission of June 13, 2007 on the non-inclusion of carbofuran in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF)
↑ Lethal bird of prey poison finally banned! WWF Austria.
↑ Exemption according to § 11 Plant Protection Act for Carbosip in head cabbage species ( Memento of September 27, 2007 in the Internet Archive ), accessed on July 31, 2006.
↑ www.garten.ch: Marshal / Carbosulfan no longer available in stores , accessed on February 20, 2016.
^ Directorate-General for Health and Food Safety of the European Commission: Entry on carbofuran in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.
↑ Werner Perkow (1992): Active substances in plant protection and pesticides , 2nd edition, Erg. Lfg .; Paul Parey Publishing House; ISBN 3-8304-4047-2 .
↑ Fabio Bergamin: Bird hunting with agrochemicals ( memento from February 20, 2016 in the Internet Archive ), Tages-Anzeiger from January 29, 2010.
↑ Pigeon fanciers poison birds of prey orf.at, September 29, 2016, accessed September 29, 2016.

Web links

Information from the US Environmental Protection Agency (Engl.)

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l Entry on carbofuran in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[CLP_100.014.867-2] Entry on carbofuran 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 .

[3] Swiss Accident Insurance Fund (Suva): Limits - Current MAK and BAT values (search for 1563-66-2 or Carbofuran ), accessed on November 2, 2015.

[unger-4] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 70 ( limited preview in Google Book search).

[5] Decision of the Commission of June 13, 2007 on the non-inclusion of carbofuran in Annex I of Council Directive 91/414 / EEC and the revocation of the authorizations for plant protection products with this active substance (PDF)

[WWF_Österreich-6] Lethal bird of prey poison finally banned! WWF Austria.

[Landwirtschaftskammer-7] Exemption according to § 11 Plant Protection Act for Carbosip in head cabbage species ( Memento of September 27, 2007 in the Internet Archive ), accessed on July 31, 2006.

[8] www.garten.ch: Marshal / Carbosulfan no longer available in stores , accessed on February 20, 2016.

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on carbofuran in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; Retrieved February 20, 2016.

[Perkow-10] Werner Perkow (1992): Active substances in plant protection and pesticides , 2nd edition, Erg. Lfg .; Paul Parey Publishing House; ISBN 3-8304-4047-2 .

[11] Fabio Bergamin: Bird hunting with agrochemicals ( memento from February 20, 2016 in the Internet Archive ), Tages-Anzeiger from January 29, 2010.

[12] Pigeon fanciers poison birds of prey orf.at, September 29, 2016, accessed September 29, 2016.