- Process for preparing alkoxytriazolinones
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A process for preparing alkoxytriazolinones of general formula (1): in which R1and R2independently represent an alkyl group, an aryl group, an arylalkyl group or cycloalkyl group. The alkoxytriazolinones are prepared by reacting, in a first stage, water-dissolved iminocarboxylic acid diesters in the presence of a mineral acid or by reacting a mixture of water with a water-miscible polar organic solvent and a carboxylic acid ester, yielding hydrazine carboxylic acid ester; and in a second stage, by further reacting the thus obtained reaction product with an amine, a polar organic solvent or mixtures thereof in the presence of water.
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- Process for the preparation of alkoxytriazolinones
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Alkoxytriazolinones of the general formula (I), STR1 in which R1 and R2 independently of one another represent in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, (which can be used as intermediates for the preparation of herbicidal active compounds) are obtained in very good yields and in high purity by reacting iminothiocarbonic diester (II) with carbazinic esters (III) STR2 in which R3 and R4 in each case represent, for example, alkyl or aryl, at -20° C. to +50° C. (1st step) and subjecting the semicarbazide derivatives (IV) formed in this process with elimination of R3 -SH STR3 to a cyclizing condensation reaction and if appropriate in the presence of a base at 20° C. to 100° C. with elimination of R4 --OH, if appropriate after intermediate isolation (2nd step).
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- Process for the preparation of alkoxytriazolinones
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Alkoxytriazolinones of the formula (I), STR1 in which R1 and R2 independently of one another represent in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, (which can be used as intermediates for the preparation of herbicidal active compounds) are obtained in good yields and in high purity by reacting iminocarbonic diesters (II) with carbazinic esters (III) STR2 in which R2 and R3 in each case represent, for example, alkyl or aryl, at -20° C. to +120° C. (1st step) and subjecting the semicarbazide derivatives (IV) formed in this process with elimination of R2 --OH STR3 to a cyclizing condensation reaction in the presence of a base at 20° C. to 150° C. with elimination of R3 --OH, if appropriate (2nd step) and, finally, by reacting the resulting 5-alkoxytriazolinones of the formula (V) with an alkylating agent of the formula R1 --X (VI) at 0° C. to 150° C., if appropriate in the presence of a base (3rd step: highly selective 4-alkylation).
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- Process for the preparation of alkoxytriazolinones
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Alkoxytriazolinones of the general formula (I), STR1 in which R1 and R2 independently of one another represent in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, (which can be used as intermediates for the preparation of herbicidal active compounds) are obtained in very good yields and in high purity by reacting iminocarbonic diesters (II) with carbazinic esters (III) STR2 in which R3 and R4 in each case represent, for example, alkyl or aryl, at -20° C. to +120° C. (1st step) and subjecting the semicarbazide derivatives (IV) formed in this process with elimination of R3 -OH STR3 to a cyclizing condensation reaction in the presence of a base at +20° C. to 100° C. with elimination of R4 -OH, if appropriate after intermediate isolation (2nd step).
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- Sulphonylaminocarbonyltriazolinones
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Herbicidal sulphonylaminocarbonyltriazolinones of the formula STR1 in which R1 represents hydrogen, hydroxyl or amino, or represents an optionally substituted radical from the series comprising alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkylamino and dialkylamino, R2 represents hydrogen, hydroxyl, mercapto or amino, or represents an optionally substituted radical from the series comprising alkyl, cycloalkyl, cycloalkenyl, aralkyl, aryl, alkoxy, alkylamino and dialkylamino, and R3 represents an optionally substituted radical from the series comprising alkyl, aralkyl, aryl and heteroaryl, and salts thereof. Intermediates of the formula STR2 in which A1 represents in each case optionally substituted alkyl, alkenyl, cycloalkyl, alkoxy or dialkylamino and A2 represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aralkyl, aryl or alkoxy, provided that both A1 and A2 do not simultaneously represent alkyl, are also new.
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