Ciba-geigy Corporation

Urs Muller

Hans Tobler

Hermann Rempfler

Helmut Zondler

Marius Sutter

Adolf Hubele

Wolfgang Eckhardt

Odd Kristiansen

Hans-Georg Brunner

Peter Ackermann

Elmar Sturm

Robert W Lang

Alfred Meyer

Bernhard Hostettler

Yasuchika Yamaguchi

Bernard Hostettler

Compounds of formula I ##STR1## where R.sub.1 -R.sub.5, R.sub.8, R.sub.13, m and n are as defined herein. The novel compounds have valuable biocidal properties. They can be used in crop protection for protecting cultivated plants against attack by pests, and for controlling those pests.

Aminopyrimidine derivatives as microbicides, insecticides and acaricides

Benzimidazolesulfonic acid derivatives of the formula I ##STR1## in which R.sub.1 is an unsaturated 5-membered heterocycle having not more than two hetero atoms N and/or S or is an unsaturated 6-membered heterocycle having not more than two N atoms, it being possible for each of the heterocycles to be substituted, and X is oxygen or sulfur, while R.sub.2, R.sub.3, R.sub.4 and n are as defined herein, are valuable microbicides. They can be used in crop protection in the form of suitable compositions, for example for controlling fungal disease.

Microbicides

Benzotriazolesulfonic acid derivatives of formula I ##STR1## wherein R.sub.3 =R.sub.4 X and R.sub.4 is an unsaturated 6-membered heterocycle having a maximum of 2 nitrogen atoms, it being possible for the heterocycle to be substituted, and X is oxygen or sulfur, while R.sub.1 and R.sub.2 are as defined herein, are valuable microbicides. They can be used in plant protection in the form of suitable compositions, for example for controlling fungal diseases.

Benzotriazolesulfonic acid derivatives as microbicides

2-(Pyrimidyl or pyrazinyl)-imino-1,3-dithietanes ##STR1## wherein Ar is one of the radicals ##STR2## R is unsubstituted C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkyl which is substituted by halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio or cyano, independently of one another, or is unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkenyl, unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkynyl, or C.sub.3 -C.sub.5 cycloalkyl, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylamino, nitro or halogen,

Azinyliminodithietanes and their fungicidal and nematocidal methods of

The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives of the formula I below are suitable for protecting crop plants against the phytotoxic action of herbicides and for regulating the plant growth. The 1-(3,5-bis-trifluoromethylphenyl)-2-thioxopyrrolidine-4-carboxylic acid derivatives are those of the formula I ##STR1## wherein A is --COOR.sub.1, --COSR.sub.1, --COO.sup..crclbar. M.sup..sym., --CONR.sub.2 R.sub.3 or --COCl; R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl; R.sub.2 and R.sub.3 independently of one another are hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.7 cycloalkyl; or R.sub.2 and R.sub.3 together with the nitrogen atom to which they are bonded are a saturated 3- to 7-membered heterocycle which can contain an additional hetero atom selected from the group comprising O, N and S and which is unsubstituted or up to trisubstituted by C.sub.1 14 C.sub.4 alkyl; and M.sup..sym. is the equivalent of an alkali metal cation or an alkaline earth metal cation or HN.sup..sym. (R.sub.2).sub.3, and their isomers in optically pure or enriched form.

N-phenylpyrrolidines

The invention relates to azolylpropane derivatives of the general formula I ##STR1## wherein R.sub.1 is an azolyl group,

Microbicidal and growth regulating compositions

The present invention relates to a novel, optimized process for the preparation of cyclohexanedionecarboxylic acid derivatives of formula I which can be carried out in a single vessel affording a very good yield, which process comprises heating a reactive carboxylic acid derivative of formula III ##STR1## wherein X is a halide, an alkylsulfonic or arylsulfonic acid radical or the molecular radical ##STR2## which is necessary to form an anhydride and R.sub.1 is alkyl or cycloalkyl, with an alkali metal cyanide or copper cyanide, in an inert organic solvent, to give a mixture, then adding in succession to said mixture, at a temperature in the range from 0.degree. C. to room temperature, zinc chloride, an equimolar amount, with respect to the carboxylic acid derivative of formula III, of a 3,5-cyclohexanedione-1-carboxylic acid derivative of formula II ##STR3## wherein A is an ester or amide radical, and, dropwise, an amine, and, after acidifying the reaction mixture with an aqueous acid, isolating the resultant 4-acyl-3,5-cyclohexanedione-1-carboxylic acid derivative of formula I ##STR4## by extraction. Said cyclohexanedionecarboxylic acid derivatives have herbicidal and plant growth regulating properties.

Process for the preparation of cyclohexanedionecarboxylic acid

Fluoroazolylpropane derivatives of the formula I ##STR1## are described, in which Az is imidazolyl or triazolyl, R.sup.1 is hydrogen, alkyl or aralkyl which is unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl, nitro, cyano, carboxyl or alkoxycarbonyl, R.sup.2 is C.sub.1 -C.sub.10 -alkyl which is unsubstituted or substituted by alkoxy, aralkoxy or phenyl, it being possible for the aromatic nuclei of aralkoxy and phenyl in turn to be unsubstituted or substituted by halogen, alkyl, alkoxy, halogenoalkyl, cyano, carboxyl or alkoxycarbonyl, R.sup.3 is hydrogen, alkyl, alkylcarbonyl or aralkyl which is unsubstituted or substituted by halogen, alkoxy, alkyl, halogenoalkyl, cyano, carboxyl or alkoxycarbonyl, R.sup.5 is an unsubstituted or monosubstituted or polysubstituted radical selected from the series comprising C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, phenyl, naphthyl, biphenyl, benzylphenyl, benzyloxyphenyl, phenoxyphenyl and aralkyl, and X is oxygen or sulfur; including the acid addition salts, quaternary azolium salts and metal complexes. Methods of preparing these products are also disclosed, as are agrochemical compositions containing one of these compounds as the active substance. A process for controlling phytopathogenic microorganisms and/or for regulating plant growth by means of these substances is also described.

Microbicidal and growth-regulating compositions

The invention relates to novel 5-acylaminopyrimidines of the general formula I ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy, lower alkoxy-lower alkyl, thioalkyl or halogen; phenyl or phenoxy, each unsubstituted or substituted by halogen, halo-lower alkyl, carbalkoxy-lower alkyl, halo-lower alkoxy, lower alkoxy, phenoxy, halophenoxy, halo-lower alkylthio, cyano or nitro; lower alkenyl or lower alkynyl, or unsubstituted or substituted cycloalkyl

5-acylaminopyrimidines

The compounds described are those of the general formula I ##STR1## in which R.sub.1 is an azolyl group; R.sub.2 is C.sub.1 -C.sub.12 -alkyl; R.sub.3 is hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.4 -alkenyl or C.sub.2 -C.sub.4 -alkinyl, or benzyl which is unsubstituted or substituted by C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkyl, halogen and/or cyano; R.sub.4 is hydrogen, fluorine or C.sub.1 -C.sub.6 -alkyl; R.sub.5 is an unsubstituted or substituted radical chosen from the series comprising phenyl, naphthyl, biphenyl, benzylphenyl and benzyloxyphenyl, the substituents being chosen from the series comprising halogen, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy C.sub.1 -C.sub.6 -haloalkyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.3 -haloalkylthio, nitro and/or thiocyano; and X is oxygen or sulfur; including the acid addition salts, quaternary azolium salts and metal complexes. Methods for the preparation of these products are also disclosed, as well as agrochemical compositions containing one of these compounds as the active substance. A method of controlling phytopathogenic microorganisms and/or of regulating plant growth with the aid of these substances is furthermore described.

Growing community of inventors

Munchenstein, Switzerland

Urs Muller