Oxolinic acid

Structural formula
General
Surname	Oxolinic acid
other names	5,8-dihydro-5-ethyl-8-oxo-1,3-dioxolo [4.5 g ] quinoline-7-carboxylic acid
Molecular formula	C 13 H 11 NO 5
External identifiers / databases
EC number	238-750-8
ECHA InfoCard	100.035.213
PubChem	4628
Wikidata	Q287840
properties
Molar mass	261.23 g mol −1
density	1.55 g cm −3
Melting point	315 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302
	P: 301 + 312 + 330
Toxicological data	525 mg kg −1 ( LD 50 , rat , oral ) ; > 2000 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 .

Oxolinic acid is a gyrase inhibitor (topoisomerase II inhibitor) from the family of quinolone antibiotics .

Extraction and presentation

Oxolinic acid can be obtained by a multi-stage reaction starting from catechol . This reacts with formaldehyde to form methylenedioxybenzene , which further reacts with nitric acid , hydrogen and diethyl ethoxymethylene malonate. The end product is now created through thermal decomposition and reaction with sodium hydroxide and iodoethane .

Alternatively, oxolinic acid can be obtained starting from 1,2-methylenedioxybenzene . This is nitrated to 3,4-methylenedioxy-1-nitrobenzene , which is hydrogenated to 3,4-methylenedioxyaniline . This then reacts with ethoxymethylene malonate to form the substitution product, which cyclizes to the ethyl ester of 4-hydroxy-6,7-methylenedioxyquinoline-3-carboxylic acid by heating. Hydrolysis with a base in dimethylformamide and reaction with iodoethane now leads to the end product.

use

Oxolinic acid is an antibiotic and is used as a bactericide ( starner ) in rice cultivation. It is also effective against fire blight. In the European Union and in Switzerland, oxolinic acid is not approved as a crop protection agent.

Individual evidence

↑ ^a ^b Entry on Oxolinic acid in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 4, 2020.
↑ ^a ^b ^c ^d data sheet Oxolinic acid from Sigma-Aldrich , accessed on August 04, 2020 ( PDF ).
↑ Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 589 ( limited preview in Google Book search).
^ Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 0-444-52166-6 , pp. 515 ( limited preview in Google Book search).
↑ J. Adaskaveg, H. Förster, BA Holtz, E. Hoffman, D. Gubler, E. Erickson: Evaluation of Bactericides for Control of Fire Blight of Pears and Apples Caused by Erwinia Amylovora . In: Acta Horticulturae . No. 704 , February 2006, p. 277–282 , doi : 10.17660 / ActaHortic.2006.704.39 .
^ Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.

[PPDB-1] Entry on Oxolinic acid in the Pesticide Properties DataBase (PPDB) of the University of Hertfordshire , accessed on August 4, 2020.

[Sigma-2] ta sheet Oxolinic acid from Sigma-Aldrich , accessed on August 04, 2020 ( PDF ).

[unger-3] Thomas A. Unger: Pesticide Synthesis Handbook . William Andrew, 1996, ISBN 0-8155-1853-6 , pp. 589 ( limited preview in Google Book search).

[hruby-4] Ruben Vardanyan, Victor Hruby: Synthesis of Essential Drugs . Elsevier, 2006, ISBN 0-444-52166-6 , pp. 515 ( limited preview in Google Book search).

[5] J. Adaskaveg, H. Förster, BA Holtz, E. Hoffman, D. Gubler, E. Erickson: Evaluation of Bactericides for Control of Fire Blight of Pears and Apples Caused by Erwinia Amylovora . In: Acta Horticulturae . No. 704 , February 2006, p. 277–282 , doi : 10.17660 / ActaHortic.2006.704.39 .

[6] Directorate-General for Health and Food Safety of the European Commission: EU pesticide database ; Entry in the national directory of plant protection products in Switzerland ; Retrieved June 20, 2016.