Captafol

Structural formula
General
Surname	Captafol
other names	1,2,3,6-tetrahydro- N - (1,1,2,2-tetrachloroethylthio) phthalimide N - (1,1,2,2-tetrachloroethylthio) -3,6,7,8-tetrahydrophthalimide Difolatan
Molecular formula	C 10 H 9 Cl 4 NO 2 S
Brief description	colorless solid
External identifiers / databases
CAS number 2425-06-1 EC number 219-363-3 ECHA InfoCard 100.017.604 PubChem 16760159 Wikidata Q1864653
properties
Molar mass	349.06 g mol −1
Physical state	firmly
Melting point	160-161 ° C
solubility	practically insoluble in water
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 317-350-410 P: 201-273-280-308 + 313-501
MAK	Switzerland: 0.1 mg m −3 (measured as inhalable dust )
Toxicological data	2,500 mg kg −1 ( LD 50 ,  rat ,  oral ) 15,400 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Captafol is a chemical compound from the phthalimide group and is structurally related to Difolpet and Captan .

Extraction and presentation

Captafol can be obtained by reacting the sodium salt of 1,2,3,6-tetrahydrophthalimide in benzene with 1,1,2,2-tetrachloroethylsulfenyl chloride.

properties

Captafol is a flammable colorless solid that is practically insoluble in water. It decomposes when heated. It hydrolyzes slowly in aqueous solutions, but quickly under basic conditions.

use

Captafol has been used as a fungicide in fruit growing, vegetables, ornamental plants and viticulture since 1961 and is also used for seed dressing . The effect is based on the inhibition of enzymes in the carbohydrate, amino acid and phosphate metabolism.

Admission

Because of the carcinogenic effects of phthalimide compounds found in animal experiments, the approval was not extended in the FRG in 1986.

The use as an active ingredient in plant protection products is prohibited in the EU. In Germany, Austria and Switzerland, no pesticides with this active ingredient are permitted.

safety instructions

Captafol can cause contact allergies and is classified as carcinogenic.

The Rotterdam Convention must be observed for international trade in the substance .

Individual evidence

1. ↑ ^{a b c d e f g h} Entry on Captafol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
2. ↑ Entry on Captafol 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. ↑ Captafol data sheet , PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 2425-06-1 or Captafol ), accessed on November 2, 2015.
5. ^ Entry on Captafol in the Hazardous Substances Data Bank , accessed April 3, 2013.
6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 453 ( limited preview in Google Book search).
7. ^ ^{A b} G. Matolcsy, M. Nádasy, V. Andriska: Pesticide Chemistry . Elsevier, 1989, ISBN 0-08-087491-6 , pp. 250 ( limited preview in Google Book Search).
8. ^ M. Bahadir, H. Parlar, Michael Spiteller: Springer Umweltlexikon . Springer, 2000, ISBN 978-3-540-63561-1 , pp. 250 ( limited preview in Google Book Search).
9. ^ Directorate-General for Health and Food Safety of the European Commission: Entry on Captafol in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.
10. ↑ Robert Irving Krieger: Handbook of pesticide toxicology, Volume 1 . Academic Press, 2001, ISBN 978-0-12-426260-7 , pp. 319 f .
11. ↑ WHO: The WHO Recommended Classification of Pesticides by Hazard and Guidelines to Classification 2009 (PDF; 2.2 MB).