Bayer Aktiengesellschaft

Peter Siegle

Ingeborg Hammann

Engelbert Kuhle

Wolfgang Behrenz

Bernhard Homeyer

Eckart Kranz

Klaus Sasse

Rudiger Schubart

Alfons Hartmann

Herbert Schwarz

Friedrich Schmidt

Heinrich Steude

Karl-Julius Schmidt

Otto Berendes

Peter Rossler

Gerhard Zumach

Gert Hansen

This invention relates to a new process for the preparation of pinacolone (2.2-dimethyl-3-oxobutane) of the formula

Process for the preparation of pinacolone

3,3-Dimethyl-1-phenoxy-butan-2-ols of the formula ##STR1## in which Y is a halogen atom, an optionally substituted phenyl radical, an optionally substituted phenoxy radical or a nitro, cyano, alkyl, alkoxy, alkoxycarbonyl or cycloalkyl radical, and n is 0, 1, 2 or 3, exhibit plant growth stimulating properties and are also useful in the synthesis of known fungicides. They are produced from tert-butyloxirane and the corresponding phenols.

Preparation of 3,3-dimethyl-1-phenoxy-butan-2-ols as fungicide

In the preparation of a phosphoric acid alkyl ester dichloride by reacting phosphorus oxychloride with an aliphatic alcohol according to the equation ##STR1## in which R represents C.sub.1 -C.sub.5 -alkyl, the improvement which comprises carrying out the reaction continuously at a temperature of about 10.degree. to 50.degree. C. using an excess of phosphorus oxychloride of about 5 to 40%. The excess phosphorus oxychloride is reacted with the alcohol by continuous mixing, the reaction mixture is cooled, substantially all the hydrogen chloride formed is then separated off in a preliminary degassing stage, the reaction mixture is worked up in a distillation column, the unreacted phosphorus oxychloride and any diluent is separated off over the top and condensed, the condensate is recycled to the reaction and the corresponding alkyl ester dichloride is removed continuously as the bottom product.

Continuous preparation of phosphoric acid alkyl ester dichlorides

N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid esters of the formula ##STR1## in which X is halogen, C.sub.1 -C.sub.6 alkyl or hydrogen, and

Insecticidal N-methyl-N-(benzene sulfonic acid

A process for preparing monochloropinacoline (1-chloro-3,3-dimethyl-butan-2-one) by contacting a stoichiometric excess of pinacoline with chlorine at a temperature of -20.degree. to +70.degree. C.

1-Chloro-3,3-dimethyl-butan-2-one

Sulfonic acid-N'-methylamido-N'-sulfenyl-N-methyl-carbamic acid esters of the formula ##STR1## in which R.sup.1 is dialkylamino with 1-4 carbon atoms in each alkyl group, phenyl substituted in the o- or m-position by halogen or by alkyl with 1-4 carbon atoms, or phenyl substituted in the o-, m- or p-position by NO.sub.2, CF.sub.3 or CN, and

Sulfonic acid-N-methylamido-N-sulfenyl-N-methyl-carbamic acid esters

Nematicidally and arthropodicidally active N-methyl-N-(2-toluenesulphonic acid methylamide-N'-sulphenyl)-2,2-dimethyl-2,3-dihydrobenzofuranyl-(7)-carbama te of the formula ##STR1## which possesses nematicidal and arthropodicidal properties.

Nematicidally and arthropodically active N-methyl-N-(2-toluenesulphonic

N-substituted .beta.-aminocrotonic acid esters of the formula ##STR1## in which R.sup.1 is hydrogen, or alkyl or alkenyl with up to 4 carbon atoms;

N-substituted .beta.-aminocrotonic acid esters

N-carboxylated N-methylcarbamic acid aryl esters of the general formula ##EQU1## in which Ar is phenyl, naphthyl, dihydrobenzofuranyl or indanyl optionally substituted by alkyl, alkenyl, alkynyl, alkoxy, alkenoxy, alkynoxy, alkylmercapto, alkenylmercapto, alkynylmercapto, dialkylamino, trihalomethyl, halogen, nitro, cyano, cycloalkyl, formamidino, dioxolanyl, dioxanyl or dialkoxymethyl, and

N-carboxylated N-methylcarbamic acid aryl esters

N-methyl-N-(3-trifluoromethylphenylsulfenyl)-carbonyloxime-carbamates of the formula ##STR1## in which R.sup.1 and R.sup.2 each independently is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkoxycarbonyl, aminocarbonyl or alkylthioalkyl, or together are ##STR2## R.sub.3 is hydrogen or halogen, R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl, and

N-methyl-N-(3-trifluoromethylphenylsulfenyl)-carbonyloxime-carbamates

Benzo-1,3-dioxolan-4-yl N-methyl-N-phenylmercapto-carbamates of the formula ##STR1## in which Ar is benzo-1,3-dioxolan-4-yl and

Benzo-1,3-dioxolan-4-yl N-methyl-N-phenylmercapto-carbamates

N-sulfenylated 2,3-dihydrobenzofuranyl-7-N-methylcarbamates of the formula ##EQU1## in which R.sup.1 is hydrogen or C.sub.1 -C.sub.6 alkyl,

Certain 2,3-dihydrobenzofuranyl esters of certain N-sulfenylated

N-methyl-N-alkoxycarbonylsulphenyl-carbamates of the formula ##EQU1## in which R.sup.1 is C.sub.1.sub.-6 alkyl, and

N-methyl-N-alkoxycarbonylsulphenyl-carbamates

N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid esters of the formula ##SPC1## In which

N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid

N-sulfenylated-N-methyl-carbamic acid esters of 2-oximino-alkanecarboxylic acid nitriles of the formula ##EQU1## in which R.sub.1 is alkyl, cycloalkyl, or alkyl-substituted cycloalkyl, and

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Cologne, Germany

Peter Siegle