Bayer Aktiengesellschaft

Claus Stolzer

Ingeborg Hammann

Wolfgang Kramer

Hans-Ludwig Elbe

Eckart Kranz

Hermann Arold

Gunter Unterstenhofer

Karl H Buchel

Hans-Jochem Riebel

Bernhard Homeyer

Wolfgang Behrenz

Jorg Stetter

Werner Meiser

Rudolf Thomas

A process for the preparation of N,N-dimethyl-N'-(2-bromo-4-methyl-phenyl)-triazene of the formula ##STR1## comprising (a) reacting N-acetyl-p-toluidine of the formula ##STR2## with bromine at a temperature between about 0.degree. and 100.degree. C., to give the intermediate product of the formula ##STR3## (b) reacting the intermediate product with hydrochloric acid by either (i) adding a dilute solution of aqueous hydrochloric acid to the intermediate product in its reaction solution and heating the mixture to a temperature between about 50.degree. and 120.degree. C., or

Process for the preparation of

In the preparation of a phenoxy-azolyl-butanone derivative of the formula ##STR1## in which X is a halogen atom,

Preparation of phenoxy-azolyl-butanone derivatives

In the reaction of 1-chloro-3,3-dimethylbutan-2-one with a phenol to form an ether-ketone, halogenating it to form a halogenoether-ketone and reacting it with imidazole or 1,2,4-triazole to form a 1-azolyl-3,3-dimethyl-1-phenoxybutan-2-one of the formula ##STR1## in which X is N or CH,

Preparation of 1-azolyl-3,3-dimethyl-1-phenoxy-butan-2-ones

In the preparation of O,O-diethyl-O-(1-phenyl-2-cyano-prop-1-enyl)-thionophosphoric acid ester by reacting a benzoic acid ester with propionitrile in the presence of an alkali metal alcoholate and then reacting the reaction mixture with O,O-diethyl-thionophosphoric acid diester chloride, the improvement which comprises employing about 5 to 50 moles of the propionitrile per mole of benzoic acid ester, distilling off the alcohol obtained during the reaction of propionitrile, benzoic acid ester and alcoholate before the addition of the O,O-diethyl-thionophosphoric acid diester chloride, and maintaining the volume of the reaction mixture approximately constant by adding propionitrile during the distillation. Advantageously the alcoholate is sodium methylate, ethylate or tert.-butylate or potassium methylate, ethylate or tert.-butylate, the reaction is effected at about 80.degree. to 120.degree. C., about 5 to 25 moles of propionitrile are employed per mole of benzoic acid ester, about 1 to 1.3 moles of benzoic acid ester and about 1 to 1.15 moles of alkali metal alcoholate are employed per mole of O,O-diethyl-thionophosphoric acid diester chloride, and the benzoic acid ester is the methyl ester or ethyl ester.

Preparation of

O,S,N-tri-aliphatic hydrocarbon-thionothiolphosphoric acid ester amides of the general formula ##STR1## in which R, R.sup.1 and R.sup.2, which may be the same or different, each is an alkyl, alkenyl or alkynyl radical with up to 6 carbon atoms, optionally substituted with at least one halo, phenyl, cyano, alkoxy, alkylmercapto, phenylmercapto or naphthylmercapto radical, the mercapto radicals being optionally chloro- or cyano-substituted, Which possess nematocidal, insecticidal, acaridical, fungicidal and mammalian-repellent properties.

O,S,N-tri-aliphatic hydrocarbon-thionothiolphosphoric acid ester amides

A process for the preparation of a 1,2,4-triazolyl-(1)-phenoxy-acyl-methane of the formula ##STR1## in which R is alkyl or aryl,

Preparation of 1,2,4-triazolyl-(1)-phenoxy-acyl-methanes

S-(alkoxycarbonyl)-alkyl-thiophosphoric acid ester amides of the general formula ##EQU1## in which R, R' and R' each independently is alkyl of 1 to 10 carbon atoms or lower alkenyl,

S-(alkoxycarbonyl)-alkyl-thiophosphoric acid ester amides

S-(amidocarbonyl)-methyl-O-alkyl monothiophosphoric acid ester amides of the formula ##EQU1## in which R and R' each independently is alkyl of 1 to 6 carbon atoms,

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Wuppertal-Vohwinkel, Germany

Claus Stolzer