Ciba-geigy Corporation

Janssen Pharmaceutica Nv

Elmar Sturm

Henry Martin

Heinrich Schempp

Robert Nyfeler

Christian Vogel

Hans Jorg Cellarius, Deceased

Jan Heeres

Peter Maienfisch

Georg Pissiotas

Daniel Bellus

Marcus Baumann

Leo J Backx

Niklaus Buhler

Jean J Gallay

Willy Joannes Van Laerhoven

Wolfgang Eckhardt

Odd Kristiansen

Hans Moser

Helmut Zondler

Haukur Kristinsson

Hans Tobler

Robert W Lang

Urs Muller

Bernhard Gloor

Raphael Menasse

Hans Joerg Cellarius

Ernst Fankhauser

Essentially, a process is described for the preparation of the 1-triazolylethyl ether derivatives, defined in claim 1, of the general formula I ##STR1## which consists in (a) reacting an oxirane of the formula II ##STR2## at temperatures of -20.degree. to +100.degree. C., in the presence of an acid catalyst or an acid condensation agent, with an alcohol of the formula III

Process for the preparation of 1-triazolylethyl ether derivatives

The invention relates to novel N-benzoyl-N,-4-(5-phenylpyrimid-2-yloxy)phenylureas of formula ##STR1## wherein X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.3 alkoxy or C.sub.1 -C.sub.3 alkylthio,

Substituted benzoylphenylureas compounds useful as pesticides

The invention relates to ecto- and endoparasitic milbemycins of formula I ##STR1## wherein R is methyl, ethyl, isopropyl or sec-butyl;

5-esters of milbemycins for controlling parasitic pests

The invention relates to novel 5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives of the general formula I ##STR1## wherein X is oxygen or sulfur;

5-(azolyloxyphenylcarbamoyl)barbituric acid derivatives as anthelmintics

The invention relates to novel phenylcarbamoylbarbituric acid derivatives of the general formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, allyl or C.sub.3 -C.sub.6 cycloalkyl,

Barbituric acid derivatives

The present invention relates to milbemycin derivatives of the formula I ##STR1## wherein X is hydrogen or .beta.-halogen, R is methyl, ethyl, isopropyl or sec-butyl and Az is a 5 membered heterocyclic aromatic ring which contains 2-4 nitrogen atoms and is attached in the 1-position and which is unsubstituted or substituted by one or two C.sub.1 -C.sub.6 alkyl groups. These compounds, and the acid addition salts and metal complexes thereof, are effective pesticides for controlling endo-and ectoparasites, especially for controlling neamatodes which are parasites of animals. The may be obtained by appropriate esterification in 5-position of milbemycin derivatives. The selective .beta.-halogenation of 14,15-epoxymilbemycin derivatives can be effected via the intermediate .DELTA..sup.13,14 -15-hydroxymilbemycins with appropriate halogenating agents.

5-azolylacetoxymilbemycins as ecto- and endoparasites

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.

Fluorinated azolyl ethanol growth regulators and microbicides

Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles and 1H-1,2,4-triazoles wherein the 1,3-dioxolane ring is substituted in the 4- and in the 5-positions, said compounds having useful antimicrobial properties.

Fungicidal

The invention describes gametocidal and microbicidal compositions which contain, as active ingredient, a nitroarylalkylsulfone derivative of the formula I ##STR1## wherein R.sub.1 is alkyl, R.sub.2 and R.sub.3 are each hydrogen, alkyl, alkoxy, haloalkyl, halogen, cyano, nitro or amino or together they complete a naphthalene ring; R.sub.4 is hydrogen or --COR.sub.5, wherein R.sub.5 is alkyl, alkoxy, haloalkoxy, alkenyl, haloalkenyl, alkynyl, cycloalkyl, phenyl, benzyl, furyl or tetrahydrofuryl. The invention relates also to the use of these compositions and compounds for stimulating generative plant growth and for obtaining hybrid seeds, as well as to a method of preparing the hydrazinium and ammonium salts within the scope of the formula I, and to a process for preparing agrochemical compositions which contain compounds of the formula I as active ingredient.

Nitroarylalkylsulfone derivatives as plant growth stimulants

Sulfur-containing oxime compounds of the formula I given herein are suitable for protecting cultivated plants against the phytotoxic action of aggressive agricultural chemicals, particularly herbicides. There are described methods for producing sulfur-containing oxime compounds of this type, and examples are given illustrating the application of these compounds.

Sulfur-containing oxime compounds, processes for producing them, and

There are described novel compounds of the formula I defined herein ##STR1## wherein R is a phenyl group which is unsubstituted or mono- to tetra-substituted by C.sub.1 -C.sub.4 -alkyl, halogen, nitro, cyano, trifluoromethyl, phenyl or C.sub.1 -C.sub.3 -alkoxy, or it is 3,4-methylenedioxy-phenyl, including the acid addition salts thereof with organic and inorganic acids as well as metal complexes thereof, all having tolerance to cultivated plants and possessing valuable microbicidal properties. They can be used for combating phytopathogenic microorganisms, particularly phytopathogenic fungi. The compounds of the formula I have for practical purposes a very favorable curative, systemic and preventive action for the protection of cultivated plants, without these being impaired as a result of undesirable side-effects. They can be used in practice on their own or in the form of microbicidal compositions.

Growing community of inventors

Aesch, Switzerland

Elmar Sturm