Hoechst Aktiengesellschaft

Roland Schmierer

Hilmar Mildenberger

Helmut Burstell

Reinhard Handte

Hermann Bieringer

Klaus Bauer

Burkhard Sachse

Helmut Bustell

Erwin Hacker

Thomas Maier

Rudolf Kunstmann

Ernst-Friedrich Schulze

Rainer Liebl

The invention relates to a process for the preparation of compounds of the formula I ##STR1## in which R.sup.1 denotes (substituted) aryl or (substituted) cyclohexyl and R.sup.2 =alkyl, in which a compound of the formula R.sup.1 --NH.sub.2 is reacted with at least twice the molar amount of glyoxylic acid in the presence of water and the resulting acid is then esterified.

Process for the preparation of N-alkoxycarbonylmethyl-N-formyl-amines

The invention relates to imidazole-5-carboxylic acid derivatives in which the imidazole ring is substituted in the 1-position by a 2,6-dialkylphenyl radical and which have the formula ##STR1## in which X=O, S or N. The compounds are obtained from appropriately substituted bisformyl esters, either by reacting the latter with formamide or with ammonium acetate or by subjecting aminomethylene compounds prepared from the bisformyl esters to an intramolecular condensation reaction. The new substances can be used as biocides, in particular herbicides, fungicides and growth regulators.

1-substituted imidazole-5-carboxylic acid derivatives, their preparation

The compounds of the formula I, or salts thereof, ##STR1## in which R.sup.1 and R.sup.2, independently of one another, denote (C.sub.1 -C.sub.4)-alkyl,

2,3,6-substituted phenylimidazole derivatives and the use thereof as

The new compounds of the formula I ##STR1## in which R denotes substituted phenyl,

1-phenylimidazole compounds as growth regulators

The salts of 1-phenylimidazole-5-carboxylic acids substituted in the phenyl ring, of the general formula (I) ##STR1## exhibit a good plant growth-regulating activity. In the general formula the symbols have the following meaning:

Salts of 1-phenylimidazole-5-carboxylic acids, composition containing

The compounds of the formula I ##STR1## wherein R denotes (substituted) phenyl, (substituted) cyclohexyl or (substituted) cyclohexenyl,

1,2,5-Substituted imidazole compounds and their use as growth regulators

The compounds of the formula (I) ##STR1## in which R.sup.1 denotes (C.sub.1 -C.sub.3)alkyl and R.sup.2 denotes H, methyl or halogen, and salts thereof have excellent actions as plant growth regulators, in particular in rice crops.

1-phenylimidazolecarboxylic acid amides and their use as growth

The new compounds of the formula I or salts thereof ##STR1## in which R denotes a (substituted) cyclohexyl radical or a (substituted) cyclohexenyl radical; and Y denotes cyano, a (substituted) (di)(thio)carboxylic acid (ester), carboxamide or acetal radical, a keto or oxime radical or a heterocyclic radical, possess an advantageous action as plant growth-regulators and, in addition, have favorable herbicidal and fungicidal properties.

Growth-regulating, fungicidal, and herbicidal cyclohexylimidazole and

Compounds of the formula ##STR1## in which A denotes C-R.sup.4 or N; X denotes alkyl and Y denotes alkyl, cycloalkyl, alkenyl, alkynyl, phenyl or benzoyl, or, together with X, cycloalkyl; R.sup.1 -R.sup.4 denote H, alkyl, alkoxy, alkoxycarbonyl, halogen, NO.sub.2, CN, phenoxy or (substituted) phenyl; R.sup.5 denotes H or alkyl; and R.sup.6 denotes H, (substituted) alkyl, halogenoalkenyl, cycloalk(en)yl, alkynyl, (substituted) phenyl or carboxylic acid ester, carboxylic acid amide, sulfo-ester or acyl radicals, are effective plant treatment agents, in particular herbicides.

Isoindoles, processes for their preparation and their use as herbicidal

Compounds of the formula ##STR1## wherein A denotes N or CR.sup.4, B denotes a carboxyl, carbo-(thio) ester, (substituted) carboxamide or carboxanilide, carbohydroxy(alkoxy)-amide, (substituted) carbohydrazide or (substituted) oxazoline group, X and Y denote, inter alia, alkyl or, together, spiroalkyl, Z denotes a carbo-(di)(thio) ester, carboxyl, (substituted) (thio)-carboxamide or -carboxanilide group or the radical of a ketone-acid or of a ketone-ester and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 denote H or are identical or different and denote halogen, alkyl, alkoxy, alkoxycarbonyl, halogenoalkyl, NO.sub.2, CN, (substituted) phenyl or phenoxy, or two of these radicals can form a --CH.dbd.CH--CH.dbd.CH-- group, are useful total or selective herbicides for application by the pre-emergence and, in some cases, the post-emergence method.

Herbicidal 1-acylimidazolinones

Imidazolinones of the formula ##STR1## in which A denotes N or C--R.sup.4 ; B denotes halogenoalkyl, alkoxymethyl, cyanomethyl or thiocyanatomethyl; X denotes alkyl; and Y denotes alkyl, cycloalkyl, alkenyl, phenyl or benzyl; or X and Y, together with C, denote a spiro-cycloalkyl group; Z denotes H, (substituted) alkyl, alkenyl, propargyl or an alkyl, carboxylic acid ester or sulfonic acid ester group; and R.sup.1 -R.sup.4 denote H, halogen, alkyl, alkoxy, alkoxycarbonyl, halogenoalkyl, NO.sub.2, CN, (substituted) phenoxy or (substituted) phenyl, or in each case two adjacent radicals together denote the radical --CH.dbd.CH--CH--CH--, are active herbicides and growth regulators.

Growing community of inventors

Todtenweis, Germany

Roland Schmierer