Captan

Structural formula
General
Surname	Captan
other names	N -Trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide; 1,2,3,6-tetrahydro- N - (trichloromethylthio) phthalimide; N - (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide; meso - N -Trichloromethylmercapto-4-cyclohexene-1,2-dicarboximide; meso -1,2,3,6-tetrahydro- N - (trichloromethylthio) phthalimide; meso - N - (trichloromethylthio) cyclohex-4-ene-1,2-dicarboximide; 3a, 4,7,7a-Tetrahydro-2- (trichloromethylthio) isoindole-1,3-dione; 3a, 4,7,7a-Tetrahydro-2- (trichloromethanesulfenyl) -1,3-iso-indoldione;
Molecular formula	C 9 H 8 Cl 3 NO 2 S
Brief description	white to yellow solid with a faint mercaptan odor
External identifiers / databases
EC number	205-087-0
ECHA InfoCard	100.004.626
PubChem	8606
Wikidata	Q2194382
properties
Molar mass	300.59 g mol −1
Physical state	firmly
density	1.74 g cm −3
Melting point	178 ° C ; 158–164 ° C (technical product);
solubility	practically insoluble in water (<0.5 mg l −1 at 25 ° C)
safety instructions
H and P phrases	H: 317-318-331-351-400
	P: 261-273-280-304 + 340 + 311-305 + 351 + 338 + 310-403 + 233
MAK	Switzerland: 5 mg m −3 (measured as inhalable dust )
Toxicological data	9000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rat , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Captan is a chemical compound from the phthalimide group .

Extraction and presentation

Captan can be obtained by reacting 1,2,3,6-tetrahydrophthalimide with trichloromethanesulfenyl chloride (perchloromethyl mercaptan) in the presence of sodium hydroxide .

properties

Captan is a flammable white to yellow (technical product) solid with a weak mercaptan- like odor, which is practically insoluble in water. It decomposes when heated and hydrolyzes slowly under neutral and rapidly under basic conditions.

use

Estimated US application rate in 2011

Captan is used as an active ingredient in crop protection products. It is used as a fungicide against a number of diseases. Captan was first approved in the United States in March 1949. Over 1400 t of Captan are used there annually - mostly in viticulture and fruit growing.

In fruit growing, captan is used as a contact fungicide against fungal storage rot and apple scab .

Admission

The active ingredient Captan was approved for use as a fungicide in the European Union with effect from October 1, 2007.

In many EU countries, including Germany and Austria, as well as Switzerland, plant protection products (e.g. Malvin, Merpan) with this active ingredient are approved.

history

Captan is believed to be a carcinogen . For reasons of user safety (inhalation of captan dust when filling), the approval that had existed since 1971 was not extended in 1986. It was not until 2001 that Captan was approved again in Germany as a non- dusting, water - dispersible granulate (WG).

Web links

Poisons Information Monograph (PIM) for Captan
EFSA: Peer review of the pesticide risk assessment of the active substance captan , June 4, 2009, doi : 10.2903 / j.efsa.2009.296r

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l entry to captan in the GESTIS database of IFA , accessed on January 9, 2019(JavaScript required) .

↑ Entry on Captan in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 133-06-2 or Captan ), accessed on November 2, 2015.

^ Entry on Captan in the Hazardous Substances Data Bank , accessed April 2, 2013.

↑ Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 0-8155-1401-8 , pp. 454 (English, limited preview in Google Book search).

^ ^A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 0-85404-499-X (English, limited preview in Google book search).

^ Robert Irving Krieger, Handbook of Pesticide Toxicology: Principles . 2001, ISBN 0-12-426261-9 , pp. 1712 (English, limited preview in Google Book Search).

↑ Directive 2007/5 / EC of the Commission of February 7, 2007 amending Council Directive 91/414 / EEC to include the active substances captan, folpet, formetanate and methiocarb

^ Directorate-General for Health and Food Safety of the European Commission: Entry on Captan in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.

↑ Answer of the Federal Government to the minor question from Ms. Hönes, Werner (Dierstorf) and the DIE GRÜNEN parliamentary group - printed matter 10/5953 - non- renewal of the approval of 36 plant protection products with the active ingredients Captan, Captafol and Folpet (September 22, 1986)

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l entry to captan in the GESTIS database of IFA , accessed on January 9, 2019(JavaScript required) .

[CLP_100.004.626-2] Entry on Captan in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[3] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 133-06-2 or Captan ), accessed on November 2, 2015.

[HSDB-4] Entry on Captan in the Hazardous Substances Data Bank , accessed April 2, 2013.

[Unger-5] Thomas A. Unger: Pesticide synthesis handbook . 1996, ISBN 0-8155-1401-8 , pp. 454 (English, limited preview in Google Book search).

[Roberts-6] A ^b Terence Robert Roberts, DH Hutson: Metabolic pathways of agrochemicals . Royal Soc of Chemistry, 1999, ISBN 0-85404-499-X (English, limited preview in Google book search).

[Krieger-7] Robert Irving Krieger, Handbook of Pesticide Toxicology: Principles . 2001, ISBN 0-12-426261-9 , pp. 1712 (English, limited preview in Google Book Search).

[8] Directive 2007/5 / EC of the Commission of February 7, 2007 amending Council Directive 91/414 / EEC to include the active substances captan, folpet, formetanate and methiocarb

[PSM-9] Directorate-General for Health and Food Safety of the European Commission: Entry on Captan in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 23, 2016.