Hoffmann-la Roche Inc.

Ciba-geigy Corporation

Rene Zurfluh

Albert Pfiffner

Milos Suchy

Peter Loeliger

Ulrich Schwieter

Madhukar Subraya Chodnekar

Synese Jolidon

Philippe Guerry

Christoph Luthy

Silvia Dorn

Jean Wenger

Ronald Zeun

Georg Frater

Hans Bruderer

Microbicidal composition for use in plants, having a synergistic action and comprising at least two active ingredient components, in which component I is a compound selected from the group of the compounds ##STR1## in which: X is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, cyano, thiocarbamoyl or nitro, and Y is hydrogen or fluorine; ##STR2## in which: Z radicals are identical or different and are halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, phenyl, phenoxy or benzyl, these aromatic groups being unsubstituted or not more than trisubstituted by identical or different substituents from the series comprising halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl, and n is 0 to 3; and ##STR3## in which: U is oxygen or the group --CH.sub.2 O--, A radicals are identical or different and are halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl, and n is0to 3; and in which component II is the 2-anilinopyrimidine of the formula II ##STR4## 4-cyclopropyl-6-methyl-N-phenyl-2-pyrimidineamine or a salt or a metal complex thereof.

Microbicides

The compound of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 individually is hydrogen, lower alkyl or lower alkenyl or together signify straight-chain alkylene with 2 to 4 carbon atoms, R.sup.3 is hydrogen, halogen or lower alkyl, Q is alkylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies or alkenylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies and each of Y and Y' individually is a direct bond or the group --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, the group R.sup.1 R.sup.2 N--Q--O-- is attached to the 3- or 4 -position of ring A and the symbol R designates that the ring to which it is attached is unsubstituted or is substituted with at least one substitutent selected from the group consisting of halogen, trifluoromethyl, cyano, nitro, lower alkyl and lower alkoxy, and their pharmaceutically acceptable acid addition salts can be used for the control or prevention of fungal infections, especially of topical or systemic infections which are caused by pathogenic fungi, and for the manufacture of antifungally-active medicaments. The compounds of formula I have not only a pronounced antifungal activity, but they also exhibit synergistic effects in combination with other known antifungally-active substances which inhibit sterol biosynthesis such as ketoconazole and terbinafine.

Substituted aminoalkoxybenzene anti-fungicidal compositions and use

Compunds having the formula ##STR1## wherein each of R.sup.1 and R.sup.2 individually is hydrogen, lower alkyl, or lower alkenyl, R.sup.3 is hydrogen, halogen or lower alkyl, Q is alkylene with 2 to 11 carbon atoms and at least 2 carbon atoms between the two free valencies or alkenylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies and each of Y and Y' individually is a direct bond, the group R.sup.1 R.sup.2 --N--Q--CH.sub.2 -- is attached to the 3- or 4-position of ring A and the symbol R represents that the ring to which it is attached is unsubstituted or is substituted with at least one of halogen, trifluoromethyl, cyano, nitro, lower alkyl or lower alkoxy, and their pharmaceutically acceptable acid addition salts have valuable pharmacological properties. In particular, they have a pronounced antifungal activity and can be used as medicaments, especially for the control or prevention of topical or systemic infections which are caused by pathogenic fungi.

Method of treating fungal infections

The compound of the formula ##STR1## wherein each of R.sup.1 and R.sup.2 individually is hydrogen, lower alkyl or lower alkenyl or together signify straight-chain alkylene with 2 or 4 carbon atoms, R.sup.3 is hydrogen, halogen or lower alkyl, Q is alkylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies or alkenylene with 4 to 11 carbon atoms and at least 4 carbon atoms between the two free valencies and each of Y and Y' individually is a direct bond or the group --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH-- or --C.tbd.C--, the group R.sup.1 R.sup.2 N--Q--O-- is attached to the 3- or 4-position of ring A and the symbol R designates that the ring to which it is attached is unsubstituted or is substituted with at least one substituent selected from the group consisting of halogen, trifluoromethyl, cyano, nitro, lower alkyl and lower alkoxy, and their pharmaceutically acceptable acid addition salts can be used for the control or prevention of fungal infections, especially of topical or systemic infections which are caused by pathogenic fungi, and for the manufacture of antifungally-active medicaments. The compounds of formula I have not only a pronounced antifungal activity, but they also exhibit synergistic effects in combination with other known antifungally-active substances which inhibit sterol biosynthesis such as ketoconazole and terbinafine.

Use of substituted aminoalkoxybenzene derivatives in the control or

The invention relates to compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and X have the significances given herein, their acid addition salts and the preparation of these substances, pest control compositions which contain these substances as active ingredients and the use of the active substances or compositions for the control of pests.

5,7-dihydro-6H dibenz[c,e]azepine-6-(thio)carboximidic acid esters and

The invention is concerned with novel triazole derivatives of the formula ##STR1## wherein R.sup.1 is optionally substituted phenyl and R.sup.2 signifies substituted phenyl, as more precisely defined in the description, and R.sup.3 is halogen, methyl or halomethyl, and their acid addition salts, processes for their preparation, pest control compositions which contain these compounds as the active substance, as well as methods of use of such compounds or compositions for the control of pests.

Heterocyclic compounds

The invention is concerned with novel heterocyclic compounds of the formula ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are as hereinafter set forth, and their acid addition salts, processes for the preparation of these compounds, pest control compositions which contain these compounds as the active substance, as well as the methods of use of such compounds or compositions for the control of pests.

1,2,4-Triazole compounds

The invention is concerned with novel heterocyclic compounds of the formula ##STR1## wherein R is C.sub.1-12 -alkyl, C.sub.3-12 -alkenyl, C.sub.3-12 -alkynyl or C.sub.3-8 -cycloalkyl and X signifies oxygen or sulfur, and none of the possible multiple bonds of R is present in the .alpha.-position to X, and their acid addition salts, processes for their manufacture, insect control compositions which contain these compounds as the active substance as well as the use of such compounds or compositions for the control of insects. Moreover, the invention is concerned with starting materials used for the preparation of such compounds.

5,6-dihydro-6H-dibenz[c,e]azepine-6-(thio)carboximidic acid esters and

Carbamic acid esters of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, X, and Y are as defined hereinafter, process for their preparation, as well as pesticidal compositions containing these compounds as the active ingredient and methods for using the pesticidal compositions for the control of pests are described.

Carbamic acid esters

Carbamic acid compounds of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, X and Y are as hereinafter set forth, processes for their preparation, pesticidal compositions containing one or more of the carbamic acid compounds as the active ingredient and methods for using the pesticidal compositions for the control of pests, particularly insects, mites and nematodes, are described.

Carbamic acid compound and use as a pesticide

Carbamic acid ester compounds of the formula ##STR1## wherein A represents the group (a) or (b) ##STR2## wherein R.sup.1 -R.sup.8, X and Y are as defined hereinafter, processes for their preparation, herbicidal compositions containing these compounds and methods for the use of the compounds and the herbicidal compositions are disclosed.

Carbamic acid ester herbicides

Carbamic acid esters and use as pesticides

1,4-Bis-[(2-propynyloxy)-methyl] cyclohexane

Pesticidal 1,4-bis-[(-propynyloxy)-methyl]-benzene and

Cyclopropane carboxylic acid esters useful as pesticides and methods for their manufacture are disclosed.

Growing community of inventors

Bulach, Switzerland

Rene Zurfluh