Process of preparing 3-carboxymethyl-2-carboxy-chromones

US4307020A · kind A · utility

Assignee

• BAYER HEALTHCARE LLC · DE

Inventors

• Hans-Joachim Kabbe
• Paul-Ernst Frohberger · Leverkusen, DE
• Peter Roessler · Bensberg, DE

Key dates

• Filing date: Jul 14, 1980
• Grant date: Dec 22, 1981
• Expiry date: Jul 14, 2000

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/24
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

2-Carboxymethyl-3-carboxy-chromones and esters of the formula ##STR1## in which R, R.sup.1 and R.sup.2 each independently is hydrogen, an optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl or aryl group, halogen, hydroxyl, cyano or an optionally substituted alkoxy aryloxy, aralkoxy, alkoxy-carbonyl or dialkylamino group, or PA1 R and R.sup.1, together with two carbon atoms of the benzene ring system, form a carbocyclic or heterocyclic 5-membered or 6-membered ring, and PA1 R.sup.3 is hydrogen, optionally substituted alkyl, alkenyl, cycloalkyl, cycloalkenyl or aralkyl, are characterized by fungicidal and arthropodicidal activities. The novel compounds are produced by reacting an o-hydroxyacetophenone of the formula ##STR2## with a glyoxylic acid derivative of the formula EQU OCH-COOZ in which Z is a cation, in the presence of a basic compound, followed by acidification to form the dicarboxylic acid and, optionally, the ester.