Bayer Aktiengesellschaft

Mobay Chemical Corporation

Karlfried Dickore

Robert R Schmidt

Ludwig Eue

Engelbert Kuhle

Walter Merz

Hans Kratzer

Hans Dieter Engels

Hans-Joachim Santel

Harry Strang

Wilfried Draber

Helmut Timmler

Klaus Lurssen

Kurt Findeisen

Reinhard Lantzsch

Klaus Sasse

Winfried Lunkenheimer

Gerhard Bonse

Markus Lindig

Eckart Kranz

Michael Schwamborn

Gerhard Heywang

Klaus Ditgens

Wolfgang Kreiss

Carl Fedtke

Donovan Norman Smith, Jr

Johann Dahm

Helmut Hack

Henning Dorr

Herbicidal substituted triazolinones of the formula ##STR1## in which R.sup.1 represents hydrogen, alkyl, alkenyl, alkynyl, halogenoalkyl, halogenoalkenyl, halogenoalkynyl, alkoxyalkyl, alkoxy, cycloalkylalkyl, cycloalkyl or in each case optionally substituted aralkyl or aryl,

Herbicidal substituted triazolinones

Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.2 precipitates out and is separated from the substantially pure dissolved salt of 3,3-dimethyl-2-oxo-butyric acid. The produce is a known compound suited for further syntheses.

Production of 3,3-dimethyl-2-oxo-butyric acid salt

Herbicidal 3,4,6-trisubstituted 1,2,4-triazin-5(4H)-ones of the formula ##STR1## in which R.sup.1 represents hydrogen or methyl,

3,4,6-trisubstituted 1,2,4-triazin-5(4H)-one herbicides

A herbicidal composition comprising a herbicidally effective among of

Herbicidal agents containing photosynthesis-inhibiting herbicides in

Dichloropinacolone is produced by introducing into pinacolone twice the molar amount of chlorine, the exothermic reaction mass being cooled initially to maintain the temperature below about 50.degree. C. until about 60 to 80% of the chlorine has been introduced, and then heating the reaction mass to a temperature above 50.degree. C. during introducing of the remainder of the chlorine, thereby to produce dichloropinacolone, and terminating chlorine introduction when the dichloropinacolone content of the reaction mass is at least about 97%. The molten product is added to an aqueous solution of an alkali maintained at a temperature of at least about 50.degree. C., the alkali being present in more than three times the molar amount of the dichloropinacolone. To the resulting solution of a salt of 3,3-dimethyl-2-hydroxy-butyric acid, brought to a pH of about 9 to 12, there is added approximately the stoichiometric amount of potassium permanganate. Solid MnO.sub.2 precipitates out and is separated from the substantially pure dissolved salt of 3,3-dimethyl-2-oxo-butyric acid. The product is a known compound suited for further syntheses.

A process for the preparation of a herbicidally active 1-amino-1,3,5-triazone-2,4 (1H,3H)-dione of the formula ##STR1## comprising in a first stage at a temperature from about 0.degree. to 100.degree. C. reacting an isocyanate of the formula

Process for the preparation of 1-amino-1,3,5-triazine-2,4(1H,3H)-diones

The present invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formula

Process for the preparation of N-substituted imido-dicarboxylic acid

A selectively herbicidal composition of matter comprising a herbicidally effective amount of (i) 4-amino-6-tert.-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one, and (ii) at least one of

Selectively herbicidal

Novel N-substituted imido-dicarboxylic acid diaryl ester compounds of the general formula ##STR1## in which R.sup.1 represents an optionally substituted aliphatic, cycloaliphatic, araliphatic, aromatic, heterocyclic radical and

N-Substituted imido-dicarboxylic acid diaryl ester method of preparation

3-Dimethylamino-4-methyl-1,2,4-triazin-5(4H)-one compounds of the formula ##STR1## in which R.sup.1 is t-butyl, sec.-butyl or cyclohexyl; are effective herbicides.

3-Dimethylamino-4-methyl-1,2,4-triazin-5(4H)-ones and herbicidal

N-Substituted imido-dicarboxylic acid diaryl ester compounds and

Herbicidal 1-amino-1,3,5-triazine-2,4(1H, 3H)-diones of the general formula ##STR1## are obtained in good yields if an N-substituted O-aryl N-chlorocarbonyl carbamate of the general formula ##STR2## is reacted with an isothiosemicarbazone of the general formula ##STR3## or hydrohalide thereof, (R.sup.1 to R.sup.4 in formulae (I) to (III) having the meanings given in the description), at a temperature between 0.degree. and 50.degree. C., in the presence of an acid-binding agent, the open-chain intermediate products formed thereby are then heated (if appropriate without intermediate isolation), in a second stage, to a temperature between 50.degree. and 150.degree. C. and, finally, in a third stage, the 1-alkylideneamino-1,3,5-triazine-2,4(1H, 3H)-dione formed thereby is hydrolyzed (if appropriate again without intermediate isolation) in an acid medium.

Preparation of 1-amino-1,3,5-triazine-2,4(1H, 3H)-diones

This invention relates to a process for the preparation of N-substituted imido-dicarboxylic acid diaryl ester compound of the formula

Novel method for regulating the growth of plants which method comprises applying to the plants or their habitat, effective amounts of heterocyclic compound of the formula ##STR1## in which R.sup.1 is alkyl or optionally substituted aryl,

Method of regulating the growth of plants

The invention provides herbicidal compositions containing as active ingredients (1) a 1,2,4-triazin-5-(4H)-one derivative of the general formula ##STR1## in which R is amino or isobutylideneamino, and (2) a phenoxyalkanecarboxylic acid of the general formula ##STR2## in which X is methylene or methylmethylene,

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Leverkusen, Germany

Karlfried Dickore