Basf Aktiengesellschaft

Dietrich Mangold

Karl-Heinz Koenig

Gerhard Hamprecht

Bernd Zeeh

Heinz-Guenter Oeser

Christian Reitel

Norbert Goetz

Ernst-Heinrich Pommer

Gernot Reissenweber

Josef Wahl

Peter Jacobs

Wolfgang Rohr

Volker Schwendemann

Adolf Fischer

Peter Schaefer

Peter Tonne

Winfried Richarz

Bjoern Girgensohn

Wolf-Karlo Aders

Aromatic azomethines are prepared by reacting anilines with formaldehyde and then removing the greater part of the water by distillation, low-boiling alcohols, in certain amounts, being present during the distillation and, if desired, during the reaction or during a part thereof. The aromatic azomethines obtainable by the novel process are valuable starting materials for the preparation of herbicides, especially pre-emergence herbicides and post-emergence herbicides, fungicides, insecticides, bacteriostatic agents, fungistatic agents and vulcanization accelerators.

Preparation of aromatic azomethines

A process for the preparation of pyrazoles by reacting a pyrazoline with sulfur or selenium in a solvent.

Preparation of pyrazoles

Acetals of malonaldehyde are prepared by reacting an orthoester with a vinyl ether in the presence of a catalytic amount of FeCl.sub.3. The malonaldehyde acetals obtainable by the process according to the invention are valuable intermediates in the preparation of dyes, crop protection agents and drugs.

Preparation of acetals of malonaldehyde

.alpha.-Bromoacetophenone-oxime-ethers are prepared by reacting acetophenone-oxime-ethers with a brominating agent at from 20.degree. to 100.degree. C., in the absence of light. The .alpha.-bromoacetophenone-oxime-ethers obtained are valuable starting materials for the preparation of drugs, dyes and pesticides.

Preparation of .alpha.-bromoacetophenone-oxime-ethers

Organic isocyanates are prepared by thermal decomposition of N,N'-disubstituted allophanic acid esters in an organic carbonate at from 150.degree. to 400.degree. C. The isocyanates obtainable by this process are valuable starting materials for the preparation of crop protection agents, pesticides, dyes, synthetic resins, plastics, textile waterproofing agents, detergents, bleaching agents and adhesives.

Preparation of aliphatic isocyanates

Alkyl anthranilates are prepared by reacting an isatin with an alkanol and hydrogen peroxide in the presence of an alkali metal alkanolate. The alkyl anthranilates obtainable by the process of the invention are valuable starting materials for the preparation of pesticides, dyes and drugs.

Preparation of alkyl anthranilates

A mixture of an alkyl 3-chloroanthranilate and an alkyl 6-chloroanthranilate, with a particular molar ratio of the components, is prepared by (a) reacting 3-chlorophthalic anhydride with ammonia, an alkali metal hydroxide and an alkali metal hypochlorite or (b) converting 3-chlorophthalic anhydride to 3-chlorophthalimide followed by reaction of the latter with an alkali metal hydroxide and an alkali metal hypochlorite, and, finally, esterifying the mixture of 5-chloroisatoic anhydride and 8-chloroisatoic anhydride, obtained by method (a) or method (b), with an alkanol. The compounds obtainable by the process of the invention are valuable starting materials for the preparation of dyes, crop protection agents and scents.

Preparation of a mixture of an alkyl 3-chloroanthranilate and an alkyl

A process for the preparation of a 2,3-dioxo-1,4-benzoxazine derivative of the formula I ##STR1## where R.sup.1 and R.sup.2 are identical or different and each is hydrogen, alkyl, halogen, haloalkyl, alkoxy, haloalkoxy or nitro, by oxidizing an isatin of the formula II ##STR2## where R.sup.1 and R.sup.2 have the above meanings, with a peroxydisulfate dissolved or suspended in 30-98% strength sulfuric acid. The 2,3-dioxo-1,4-benzoxazine derivatives obtainable by the novel process have fungicidal or fungistatic properties.

Preparation of 2,3-dioxo-1,4-benzoxazine derivatives

Amidosulfonic acids are prepared by reacting ureas with oleum of a particular composition, first at a low temperature and then at a higher temperature, in the presence of an organic solvent. The products are starting materials for the preparation of dyes and pesticides.

Preparation of amidosulfonic acids

Sulfamyl halides are prepared by reacting sulfamic acids with halogen in the presence of phosphorus or of a phosphorus trihalide; the sulfamic acid can first be prepared from an isocyanate or urea and then be reacted as above in a one-vessel method. The compounds obtainable by the process of the invention are valuable starting materials for the preparation of crop protection agents, dyes and drugs.

Preparation of sulfamyl halides

.alpha.-haloalkylcarbamyl halides are manufactured by reacting N-tert.-alkyl-N-1-alkenyl-carbamyl halides with a hydrogen halide at from -78.degree. C. to +80.degree. C. The .alpha.-haloalkylcarbamyl halides, e.g. .alpha.-chloroalkylcarbamyl chlorides, especially .alpha.-chloroethylcarbamyl chloride, prepared by the process of the invention, are valuable starting materials for the manufacture of surface-coating raw materials, textile coatings, dyes, drugs and crop protection agents.

Manufacture of .alpha.-haloalkylcarbamyl halides

Fluorobenzenes are manufactured by reacting substituted chlorobenzenes with potassium fluoride in the presence of catalytic amounts of cesium fluoride and in the presence of certain solvents; m-nitrofluorobenzenes and m-cyanofluorobenzenes can also be manufactured in the absence of cesium fluoride. The products are starting materials for the manufacture of dyes, pharmaceuticals and pesticides.

Manufacture of substituted fluorobenzenes

A process for the preparation of substituted fluorobenzenes which contain a nitro group or a cyano group and may or may not contain an aliphatic radical or an additional halogen atom, wherein the corresponding substituted chlorobenzene is reacted with potassium fluoride in the presence of a crown ether and a solvent at from 150.degree. to 230.degree. C.

Preparation of substituted fluorobenzenes

2,4-Dioxo-oxazolidines are manufactured by reacting aromatic amines with .alpha.-hydroxycarboxylic acid of the formula ##STR1## where R.sup.1 and R.sup.2 have the above meanings, Hal is halogen, preferably chlorine, and R.sup.4 is alkyl of 1 to 4 carbon atoms in the presence of a base, preferably at 20-120.degree. C.

Manufacture of 2,4-dioxo-oxazolidines

N-Vinyl-N-alkyl-carbamic acid chlorides are manufactured by reacting crude Schiff bases, which have advantageously been manufactured in the presence of pentane, with phosgene and tertiary amines, treating the reaction mixture with water and then isolating the end product, after having separated off the aqueous phase containing the amine salt. The products are starting materials for the manufacture of surface-coating intermediates, plastics, paints and crop protection agents.

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Neckargemuend, Germany

Dietrich Mangold