Ciba-geigy Corporation

Janssen Pharmaceutica Nv

Novartis Corporation

Adolf Hubele

Wolfgang Eckhardt

Walter Kunz

Peter Riebli

Ronald Zeun

Helmut Zondler

Jan Heeres

Hans Moser

Robert Nyfeler

Leo J Backx

Hanspeter Fischer

Rudolph C Thummel

Rudolf Aebi

Andreas Nyffeler

Jurg Speich

Dieter Reinehr

Marius Sutter

Manfred Kuhne

Urs Muller

Willy Frick

Bernard Hostettler

Wolfgang Eckhart

Sergio Bellucci

Mixtures of certain triazole fungicides (component I) and 4,6-dimethyl-N-phenyl-2-pyrimidinamine (component II) achieve synergistically enhanced activity against fungus infestation. Components I and II can also be applied to plant crops individually, one immediately after the other.

Fungicidal compositions and method of controlling plant fungi

Microbicides

Compounds of formula ##STR1## wherein R.sub.1 is hydrogen, 3-fluorine or 4-fluorine, and R.sub.2 is C.sub.1 -C.sub.4 alkyl, halo- or hydroxy-substituted C.sub.1 -C.sub.2 alkyl, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by identical or different substituents selected from methyl and halogen, have valuable microbicidal properties. The novel compounds can be used in crop protection for preventing an attack on cultivated plants by phytopathogenic microorganisms and for controlling those pests.

2-phenylamino-4-cyano-pyrimidines

Thiazolyl-5-carbonamide derivatives of formula I ##STR1## wherein R.sub.3 is furanyl or thienyl and R.sub.1 and R.sub.2 are as defined herein, have valuable microbicidal activity. They can be used in the form of compositions for controlling or preventing plant diseases.

Pesticidal compositions

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.

Mixtures of certain triazole fungicities (component I) and 4,6-dimethyl-N-phenyl-2-pyrimidinamine (component II) achieve synergistically enhanced activity against fungus infestation. Components I and II can also be applied to plant crops individually, one immediately after the other.

The 2R,4S-isomer of formula I and the 2RS,4S-diastereoisomeric mixture of formula Ia of 1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl)-1H-1,2,4-tri azole ##STR1## and the preparation thereof are described. The compounds of formulae I and Ia have pronounced microbicidal activity without having phytotoxic side-effects. They are used as active ingredients in microbicidal compositions, especially as seed dressings.

Method of controlling or preventing phytopathogenic microorganism

Arylphenyl ether derivatives of the formula ##STR1## wherein Az is 1H-(1,2,4-triazolyl) or is 1-imidazolyl optionally substituted by alkyl,

Arylphenyl ether derivatives, compositions containing these compounds

Compounds of formula V ##STR1## and C.sub.1 -C.sub.6 carboxylic acid esters thereof, wherein R.sub.1 is selected from the group consisting of CH.sub.3, C.sub.2 H.sub.5, n-C.sub.3 H.sub.7, isoC.sub.3 H.sub.7, CH.sub.2 --O--CH.sub.3, CH.sub.2 --O--C.sub.2 H.sub.5, CH.sub.2 --O--CHF.sub.2 and cyclopropyl and R.sub.2 is cyclopropyl or C.sub.1 -C.sub.3 alkyl.

Compounds of the formula ##STR1## wherein: R.sub.1 is phenyl or phenyl mono- to tri-substituted by R.sub.4 ; R.sub.2 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkyl substituted by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or the formyl radical; R.sub.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted by halogen, cyano or by the radical OR.sub.5 or by the radical SR.sub.5, C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by C.sub.1 -C.sub.4 alkyl or by halogen; R.sub.4 is halogen; C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; R.sub.5 is hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.3 -C.sub.5 alkenyl, C.sub.3 -C.sub.5 alkynyl or the radical (CH.sub.2).sub.n -X-C.sub.1 -C.sub.3 -alkyl;

Pesticides

Compounds of the formula ##STR1## in which: R.sub.1 and R.sub.2 independently of one anther are hydrogen, halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 haloalkyl, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 haloalkoxy; R.sub.3 is hydrogen; C.sub.1 -C.sub.4 alkyl; or C.sub.1 -C.sub.4 alkyl substituted by halogen, hydroxy or by cyano; cyclopropyl; or cyclopropyl mono- to tri-substituted by methyl and/or by halogen; and R.sub.4 is C.sub.3 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.6 cycloalkyl mono- to tri-substituted by methyl and/or by halogen, have valuable microbicidal and insecticidal properties. The novel active ingredients can be used in plant protection for preventing an attack on cultivated plants by phytopathogenic microorganisms or by harmful insects, and for controlling these pests.

There are described novel acylated naphthylamines of the formula I defined herein ##STR1## which have valuable fungicidal properties. They can be used in practice on their own or in the form of compositions for the protection of cultivated plants against fungus infection.

Acylated naphthlamines as plant fungicides

In the method of protecting cultivated plants from the harmful effects of agrochemicals, quinoline derivatives of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3 independently of one another are hydrogen, halogen, nitro, cyano, alkyl or alkoxy, R.sub.4, R.sub.5 and R.sub.6 independently of one another are hydrogen, halogen or alkyl, X is an aliphatic, acyclic, saturated hydrocarbon radical having 1 to 3 carbon atoms and Y is a carboxyl group, or a salt thereof, a mercaptocarbonyl group or a salt thereof, a carboxylic acid ester group, a carboxylic acid thiolester group, an unsubstituted or substituted carboxylic acid amide group, a cyclised, unsubstituted or substituted derivative of a carboxylic acid amide group or a carboxylic acid hydrazide group, or X and Y together are an unsbustituted or substituted tetrahydrofuran-2-one ring, including acid addition salts and metal complexes thereof, or compositions containing such derivatives, are used. Novel quinoline derivatives and their preparation are also descirbed.

Growing community of inventors

Magden, Switzerland

Adolf Hubele