Bayer Aktiengesellschaft

Bayer Corporation

Mobay Corporation

Thomas Schmidt

Robert R Schmidt

Ludwig Eue

Gerhard Bonse

Hans-Joachim Santel

Markus Dollinger

Wolfgang Behrenz

Reinhard Lantzsch

Bernd Gallenkamp

Heinz Forster

Wilfried Draber

Vidyanatha A Prasad

Peter E Newallis

Volker Mues

Dennis E Jackman

Klaus Ditgens

Karl Steinbeck

Dietmar B Westphal

Andreas Gunther

Karl-Heinrich Mohrmann

Wolfgang Kramer

Jorg Stetter

Heinz U Blank

Hans-Joachim Diehr

Rudiger Schubart

Klaus Naumann

Wolf Reiser

Eckart Kranz

Helmut Timmler

Rudolf Thomas

Gerhard Marzolph

Hans Kratzer

Rolf-Jurgen Singer

Andreas Wittig

Hans-Peter Sehnem

The present invention provides a process for making 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole. The process includes the steps of reacting methyidithiocarbazinate with trifluoroacetic acid, in the absence of phosphorus trichloride, to form a mixture of 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole and 2,5-bis-(methylthio)-1,3,4-thiadiazole. Further, the process of the present invention includes selectively removing the 2,5-bis-(methylthio)-1,3,4-thiadiazole by acidifying the reaction mixture, and then separating the aqueous and organic phases.

Process for making 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole

The present invention provides a process for making 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole. The process includes the steps of reacting methyldithiocarbazinate with trifluoroacetic acid to form a mixture of 2-(methylthio)-5-(trifluoromethyl)-1,3,4-thiadiazole and 2,5-bis-(methylthio)-1,3,4-thiadiazole and selectively removing the 2,5-bis-(methylthio)-1,3,4-thiadiazole by acidifying the mixture.

Process for making 2-(methylthio)-5(trifluoromethyl)-1,3,4,-thiadiazole

The invention relates to the use of the compound N-(4-fluoro-phenyl)-N-isopropyl-chloroacetamide of the formula (I) ##STR1## which is known, as active compound in selective herbicidal compositions, for example for combating weeds in maize cultures, and to a new process for the preparation of this active compound. The compound (I) is obtained in very high yields by reacting N-isopropyl-4-fluoro-aniline with approximately equimolar amounts of chloroacetyl chloride at temperatures between 20.degree. and 150.degree. C. in the presence of an inert diluent, such as, for example, toluene, without addition of an acid binder.

Herbicidal compositions based on

The invention relates to the use of the compound N-(4-fluoro-phenyl)-N-isopropylchloroacetamide of the formula (I) ##STR1## which is known, as active compound in selective herbicidal compositions, for example for combating weeds in maize cultures, and to a new process for the preparation of this active compound. The compound (I) is obtained in very high yields by reacting N-isopropyl-4-fluoro-aniline with approximately equimolar amounts of chloroacetyl chloride at temperatures between 20.degree. and 150.degree. C. in the presence of an inert diluent, such as, for example, toluene, without addition of an acid binder.

A process for the preparation of a heteroaryloxyacetamide of the formula ##STR1## in which R is a 5 membered heterocycle which may be benzo-fused, and

Preparation of heteroaryloxyacetamides

The novel process ##STR1## gives the end products, known as animal growth-promoters and coccidiostatics. Intermediates II are new.

Process for preparing 1,3,5-triazinetriones

The novel process ##STR1## gives the end products, known as animal growth-promoters and cooccidiostatics. Intermediates II are new.

In the production of an S-substituted isothiourea including the functional group ##STR1## in which R.sup.1 is an alkyl, alkenyl, aryl or aralkyl radical, wherein a thiourea including the functional group ##STR2## is reacted with an etherifying agent to replace H by R.sup.1, the improvement which comprises effecting the reaction in two steps, in the first step reacting the thiourea material with an etherifying agent including the radical R in which

Production of S-substituted isothioureas

In the production of an S-substituted isothiourea including the function group ##STR1## in which R.sup.1 is an alkyl, alkenyl, aryl or aralkyl radical, wherein a thiourea including the functional group ##STR2## is reacted with an etherifying agent to replace H by R.sup.1, the improvement which comprises effecting the reaction in two steps, in the first step reacting the thiourea material with an etherifying agent including the radical R in which

In the preparation of amino-3-ethylthio-6-tert.-butyl-1,2,4-triazin-5-one (I) by reacting 4-amino-3-mercapto-6-tert.-butyl-1,2,4-triazin-5-one (II) with an ethylating agent in aqueous alkali solution, the improvement which comprises contacting the reaction mixture with at least 50 g of petroleum ether per mole of starting compound (II) at a temperature of about 40.degree.-60.degree. C. thereby forming two liquid phases, and cooling the mixture down to about room temperature, whereby substantially pure isomer-free end product of the formula (I) crystallizes out.

Process for preparing virtually isomer-free

A process for preparing a 3,4,6-trisubstituted 3-alkylthio-1,2,4-triazin-5-one of the formula ##STR1## in which R.sup.1 is alkyl, alkenyl, alkynyl, optionally substituted cycloalkyl or optionally substituted aralkyl,

Process for preparing 3,4,6-trisubstituted

A new one-step process for the preparation of hydrazidines of the general formula ##STR1## in which R represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, or their acid addition salts, in high yield comprises reacting iminoalkyl ethers of the general formula ##STR2## in which R has the abovementioned meaning and

Preparation of hydrazidines

A one-step process for the preparation of hydrazidines of the general formula ##STR1## in which R represents an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted aralkyl group, or their acid addition salts, in high yield, comprises reacting appropriate amidines or their acid addition salts with hydrazine in solvents at reduced pressure and at temperatures between -80.degree. C. and +100.degree. C., the reaction being effected in the presence of water present in the solvent and/or in the hydrazine by employing it as hydrazine hydrate. The hydrazidines of formula (I) and their salts are valuable intermediates in heterocyclic chemistry, for example for the synthesis of herbicidally active as-triazinones.

The herbicidal 3,6-substituted 4-amino-1,2,4-triazin-5-one of the general formula ##STR1## wherein R.sup.1 and R.sup.2 have the meaning given in the description, is obtained in good yields by a new two-stage cyclization reaction if an .alpha.-ketocarboxylic acid amide of the general formula

Preparation of 3,6-disubstituted 4-amino-1,2,4-triazin-5-ones

Herbicidal substituted N-pyrazolylmethyl-haloacetanilide compounds of the formula ##STR1## wherein Hal is halogen;

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Haan, Germany

Thomas Schmidt