Carboxin

Structural formula
General
Surname	Carboxin
other names	2-methyl- N -phenyl-5,6-dihydro-1,4-oxathiine-3-carboxamide Carbathiin Vitavax
Molecular formula	C 12 H 13 NO 2 S
Brief description	colorless, crystalline powder
External identifiers / databases
CAS number 5234-68-4 EC number 226-031-1 ECHA InfoCard 100.023.665 PubChem 21307 ChemSpider 20027 DrugBank DB04657 Wikidata Q2937968
properties
Molar mass	235.30 g mol −1
Physical state	firmly
density	1.45 g cm −3
Melting point	91.5-92.5 ° C
boiling point	decomposes at 210 ° C
solubility	very sparingly soluble in water (0.147 g l −1 at 20 ° C)
safety instructions
GHS labeling of hazardous substances Caution H and P phrases H: 302 P: no P-phrases
Toxicological data	430 mg kg −1 ( LD 50 ,  rat ,  oral ) 8000 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 .

Carboxin is a chemical compound from the group of oxathiines and carboxamides , which was introduced as a fungicide by Uniroyal (now Chemtura ) in the 1960s . Carboxin was the first systemic fungicide to be marketed.

Extraction and presentation

Carboxin can be prepared from diketene and aniline . These react to form acetoacetanilide , which is chlorinated with sulfuryl chloride . The product then reacts with mercaptoethanol and potassium hydroxide . The oxathiine ring closes through reaction with sodium hydroxide at elevated temperature.

use

Carboxin was used exclusively as a seed treatment agent (dressing ) against smut and rust fungi . It is one of the SDH inhibitors that inhibit succinate dehydrogenase in the mitochondria .

Admission

In some EU countries, plant protection products with this active ingredient are approved, but not in Germany, Austria or Switzerland.

Individual evidence

1. ↑ ^{a b} entry on carboxin. In: Römpp Online . Georg Thieme Verlag, accessed on July 6, 2014.
2. ↑ ^{a b c d e} Entry on carboxin in the GESTIS substance database of the IFA , accessed on July 6, 2014 (JavaScript required)
3. ↑ Entry on carboxin in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on April 10, 2019.
4. ↑ ^{a b} Carboxine data sheet at Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
5. ↑ ^{a b} Horst Börner: Plant diseases and plant protection . Springer DE, 2009, ISBN 3-540-49067-1 , pp. 508 .
6. ↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 737 ( preview ).
7. ↑ P. Gunasekaran, P. Tauro: Mechanism of action of carboxin and the development of resistance in yeast . In: Journal of Biosciences . tape 4 , no. 2 , June 1982, pp. 219–225 , doi : 10.1007 / BF02702732 ( PDF ).
8. ↑ General Directorate Health and Food Safety of the European Commission: Entry on carboxin in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on March 25, 2016.