Basf Aktiengesellschaft

Basf Aktiengsellschaft

Hermann Koehler

Toni Dockner

Bruno Wuerzer

Gerhard Hamprecht

Ulrich Wriede

Jochem Henkelmann

Thomas Wettling

Irene Troetsch-Schaller

Uwe Kempe

Helmut Karn

Karl-Otto Westphalen

Klaus Ebel

Michael Hesse

Wolfgang Hoelderich

Thomas Kuekenhoehner

Leopold Hupfer

Christof Taubitz

Wolfgang Franzischka

Thomas-Michael Kahl

A process for the preparation of aromatic aryl chloroformates of the general formula I ##STR1## in which Ar denotes an aryl radical optionally mono- to penta-substituted by C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.3 -C.sub.8 -alkyl-cycloalkyl, C.sub.1 -C.sub.20 -haloalkyl, C.sub.1 -C.sub.20 -alkoxy, C.sub.1 -C.sub.20 -alkylthio, halo, cyano, C.sub.2 -C.sub.20 -alkylcarbonyloxy, C.sub.3 -C.sub.20 -carboalkoxy, formyl, C.sub.2 -C.sub.20 -dialkylamino, aryl, aryloxy, arylthio, aroyl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -aralkoxy, arylsulfonyl and/or C.sub.7 -C.sub.20 -aralkylthio and/or optionally mono- or di-substituted by chloroformyl and/or nitro, from phosgene and phenols of the general formula II

Preparation of aryl chloroformates

4-Aryl-2-haloimidazole-5-carboxylic esters of the general formula Ia and Ib ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl,

4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use

1-Aryl- and 1-hetarylimidazolecarboxylic esters of the general formulae Ia and Ib ##STR1## where R.sup.1 is halogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl;

Crop protection agents based on 1-aryl- or 1-hetarylimidazose carboxylic

The preparation of an alkyl, alkenyl, or alkynyl chloride by the reaction of a corresponding alcohol with phosgene or thionyl chloride in the presence of a phosphine oxide acting as catalyst, wherein the catalyst used is an aliphatic, cycloaliphatic, or cyclic/aliphatic phosphine oxide.

Preparation of alkyl, alkenyl, and alkynyl chlorides

4,5-Disubstituted imidazole-2-carboxylic acids are prepared by reacting 4,5-disubstituted imidazoles with carbon dioxide under superatmospheric pressure at from 150.degree. to 300.degree. C. in the presence of a base.

Preparation of imidazole-2-carboxylic acids

Crop protection agents based on 1-aryl- or 1-hetarylimidazolecarboxylic

A process for the preparation of imidazoles which are substituted with p-nitrophenyl in the 2- and/or 4- and/or 5-position and may carry additional substituents, by reacting imidazoles which are substituted by phenyl in the 2- and/or 4- and/or 5-position and may carry additional substituents with mixtures of sulfuric acid and nitric acid, wherein the reaction is carried out in the presence of urea.

Preparation of p-nitrophenyl-imidazoles

Acylated imidazoles of the formula ##STR1## where R.sup.1 and R.sup.3 are each H, alkyl of from 1 to 12 carbon atoms, alkenyl of from 1 to 12 carbon atoms, aryl, aralkyl or alkylaryl, R.sup.4 is H, alkyl of from 1 to 12 carbon atoms, alkenyl of from 1 to 12 carbon atoms, aryl, aralkyl or alkylaryl, and R.sup.5 is alkyl of from 1 to 12 carbon atoms, alkenyl of from 1 to 12 carbon atoms, aryl, aralkyl, alkylaryl or carboxyl, are prepared by reacting imidazoles of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 are each alkyl of from 1 to 12 carbon atoms, alkenyl of from 1 to 12 carbon atoms, aryl, aralkyl or alkylaryl, at least one of the radicals R.sup.1, R.sup.2 and R.sup.3 being hydrogen, and R.sup.4 is H, alkyl of from 1 to 12 carbon atoms, alkenyl of from 1 to 12 carbon atoms, aryl, aralkyl or alkylaryl, with widely used acylating agents of the formula ##STR3## where R.sup.5 is as defined above and Y is halide, alkoxy, acyloxy or hydroxyl, in the presence of acidic metal oxides and/or phosphates, preferably in the gas phase.

Preparation of acylated imidazoles

4-Nitro-5-imidazolyl ethers and thioethers of the formula I ##STR1## where R.sup.1 is alkyl, alkoxyalkyl, cycloalkyl, aryl, aralkyl or alkylaryl, R.sup.2 is hydrogen, alkyl, cycloalkyl, aryl, aralkyl or alkylaryl, R.sup.3 is alkyl, cycloalkyl, aryl, aralkyl, alkylaryl or a heterocyclic or heteroaromatic radical or a counter-ion of the corresponding alcoholate or thiolate or, where X is sulfur, R.sup.3 is hydrogen, and X is oxygen or sulfur, and the stated organic radicals may furthermore carry substituents which are inert under the reaction conditions, are prepared by reacting a dinitroimidazole of the formula II ##STR2## with an alcohol or thiol of the formula III

Preparation of 4-nitro-5-imidazolyl ethers and thioethers

Process for the preparation of 1-alkylimidazoles of the general formula (I) ##STR1## where R.sup.1 is alkyl, R.sup.2 and R.sup.3 are hydrogen, alkyl, aryl, arylalkyl, or alkylaryl, R.sup.4 is carboxy, alkoxycarbonyl R.sup.5 OCC--, carbamoyl, or cyano, and R.sup.5 is an alkyl of from 1 to 8 carbon atoms--by the reaction of imidazoles of the general formula (II) ##STR2## with dialkyl sulfates of the general formula (III)

Preparation of 1-alkylimidazoles

4(5)-nitroimidazole-5(4)-carboxylic acids are prepared by reacting an imidazole-4(5)-carboxylic acid with a mixture of sulfuric acid and nitric acid at not less than 80.degree. C., the water content of the reaction mixture at the beginning of the reaction being no higher than 5% by weight, based on the reaction mixture.

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Bobenheim, Germany

Hermann Koehler