Hoechst Aktiengesellschaft

Stephen Lachhein

Lothar Willms

Hilmar Mildenberger

Gunter Schlegel

Hans-Joachim Ressel

Heinz Kehne

Siegbert Rittner

Harald Berger

Heribert Tetzlaff

Gunter Scheffel

Herbicidal sulfonylureas of the formula I, ##STR1## in which X is --O--, --O--NR.sup.2 -- or --SO.sub.2 --NR.sup.2 --, Y is --N-- or CH,

Process for the preparation of sulfonylureas

The invention relates to an improved process for the preparation of a compound of the formula R.sup.1 -X-SO.sub.2 -NCO in which

Continuous process for the preparation of sulfonylisocyanates

2-Aminopyrimidines of the formula I ##STR1## in which X and Y are O or S and R.sup.1 and R.sup.2 independently of one another are lower alkyl, alkoxyalkyl or haloalkyl, are obtained by reacting propanediimidates of the formula II

Process for the preparation of aminopyrimidines

Process for the preparation of phosphino compounds Phosphorus-containing compounds of the formula (I)

Process for the preparation of phosphino compounds

Process for the preparation of pyrazolecarboxylic acid derivatives of the formula I ##STR1## in which R.sup.1 independently of one another is haloalkyl or halogen,

Process for the preparation of pyrazolecarboxylic acid derivatives

Known herbicides of the formula (I) ##STR1## in which R.sup.1 is alkyl, alkenyl or alkynyl, which are optionally substituted by halogen, alkoxy or alkoxycarbonyl,

Process for the preparation of N-alkylsulfonylaminosulfonylureas

The present invention relates to a process for the preparation of arylalkylmethylsilanes of the formula I ##STR1## where X is CH.dbd.CH, N.dbd.CH, CH.dbd.N or S, R.sup.1 and R.sup.2 independently of one another are H, halogen, (C.sub.1 to C.sub.4)alkyl, (C.sub.1 to C.sub.4)alkoxy, (C.sub.1 to C.sub.4)alkylthio, (C.sub.1 to C.sub.4)haloalkyl, (C.sub.1 to C.sub.4)haloalkoxy or (C.sub.1 to C.sub.4)haloalkylthio, R.sup.3 is (C.sub.1 to C.sub.6)alkyl and m and n are 0, 1 or 2, which comprises reacting dichloromethylsilane II ##STR2## first with an arylmagnesium halide of the formula III ##STR3## where R.sup.1, R.sup.2, m, n and X are as defined in Formula I and Hal is halogen, at temperatures of from -78.degree. to 0.degree. C., and subsequently with an alkylmagnesium halide of the formula IV

Process for the preparation of arylalkylmethylsilanes

Aminopyrimidines of the formula (I) ##STR1## in which X and Y are in each case oxygen or sulfur and

The invention relates to a gentle process for the separation of enol ethers from mixtures containing water-soluble alcohols by extraction, wherein an aqueous solution of a base is used as the extraction agent in a phase ratio of the amounts of the aqueous phase: enol ether/alcohol mixture of at least 0.5:1 and the extraction is carried out in several stages or continuously with a theoretical number of stages of at least two. The process is particularly suitable for separating off enol ethers which readily decompose during distillation.

Process for separating off enol ethers from reaction mixtures containing

The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which X and Y denote O or S; R.sup.1 and R.sup.2 denote (substituted) alkyl, R.sup.3 denotes H or a --COR.sup.4 radical in which R.sup.4 is alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, (substituted) phenyl or (substituted) phenoxy, wherein a propanediimidate of the formula II ##STR2## or a salt thereof is reacted, in an inert solvent and in the presence of a base, with a carbonic acid imine derivative of the formula III ##STR3## in which R.sup.5 denotes halogen, alkoxy, alkylthio, phenoxy or phenylthio.

Process for the preparation of pyrimidines

Process for the preparation of aminopyrimidines Pyrimidines of the formula I ##STR1## in which X and Y denote oxygen or sulfur and R.sup.1 and R.sup.2 denote C.sub.1 -C.sub.4 -alkyl, (C.sub.1 -C.sub.4 -alkoxy)-C.sub.1 -C.sub.2 -alkyl or halo-C.sub.1 -C.sub.4 -alkyl, are obtained through reaction of propanediimidates of the formula II ##STR2## or salts thereof with cyanurates of the formula R.sup.3 --O--CN in which R.sup.3 denotes C.sub.1 -C.sub.4 -alkyl, phenyl, phenyl which is substituted by 1, 2 or 3 radicals from the series comprising halogen, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -alkyl radicals, .alpha.- or .beta.-naphthyl or halo-C.sub.1 -C.sub.4 -alkyl, in an organic solvent which is inert under the reaction conditions. The one-step process permits efficient preparation of the compounds of the formula I, which can be used as intermediates for the preparation of herbicidal sulfonylureas.

Process for the preparation of pyrimidines Pyrimidines of the formula I ##STR1## in which X and Y, independently of one another, denote oxygen or sulfur, R.sup.1 and R.sup.2, independently of one another, denote (C.sub.1 --C.sub.4) alkyl, (C.sub.1 --C.sub.4 -alkoxy)-C.sub.1 --C.sub.2 -alkyl or halo-C.sub.1 --C.sub.4 -alkyl, and R.sup.3 denotes C.sub.1 --C.sub.4 -alkyl, phenyl or phenoxy which may both be substituted by one, two or three radicals from the series comprising halogen, C.sub.1 --C.sub.4 -alkoxy and C.sub.1 --C.sub.4 -alkyl radicals, halo-C.sub.1 --C.sub.4 -alkyl or C.sub.1 --C.sub.4 -alkoxy, are obtained in a process in which propanediimidates of the formula II ##STR2## or salt thereof, are reacted with N-cyanoamides of the formula NC--NR.sup.4 --CO--R.sup.3 in which R.sup.4 denotes hydrogen or a cation, in an inert solvent. The compounds of the formula I are suitable as intermediates for the preparation of herbicidal sulfonylureas.

A highly selective, inexpensive and quantitative process is described for the preparation of 5-phenylsulfinyl-1H-2-(methoxycarbonylamino)-benzimidazole (oxfendazole) through reaction of 5-phenylmercapto-1H-2-(methoxycarbonylamino)-benzimidazole with hydrogen peroxide in the presence of one or more aliphatic C.sub.1 -C.sub.6 -alcohols with addition of a strong, nonoxidizing mineral acid.

Process for the preparation of

The invention relates to a new process for the preparation of compounds of the formula (I) ##STR1## in which R.sub.1 denotes alkyl and R.sub.2 denotes H, acetyl or propionyl, by addition of compounds of the formula II ##STR2## onto compounds of the formula III, using radical-formers, the radical-formers being used being compounds of the general formula IV ##STR3## in which R.sub.3 denotes alkyl or phenyl and R.sub.4 denotes alkyl, the reaction being carried out at temperatures in the range from 50.degree. to 100.degree. C., and, for the preparation of compounds of the formula I where R.sub.2 is H, then splitting off the radical R.sub.2.sup.'. Using this process, the compounds of the formula I are obtained in high yield and particular purity.

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Hofheim am Taunus, Germany

Stephen Lachhein