Ciba-geigy Corporation

Wolfgang Eckhardt

Walter Kunz

Adolf Hubele

Helmut Zondler

Robert Nyfeler

Ernst Beriger

Peter Riebli

Alfred Meyer

Hans Moser

Willy Meyer

Odd Kristiansen

Hans-Georg Brunner

Werner Topfl

Elmar Sturm

Haukur Kristinsson

Urs Muller

Bernhard Gloor

Philip Huxley

Hans Suess

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

Mercapto-bis-[1,3,4-oxa- and -thiadiazoles] ##STR1## in which X.sub.1 and X.sub.2 independently of one another are oxygen or sulfur, R.sub.1 is hydrogen or C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen, C.sub.1 -C.sub.3 alkoxy or cyano; C.sub.3 -C.sub.7 alkenyl which is unsubstituted or substituted by halogen; or C.sub.3 -C.sub.7 alkynyl which is unsubstituted or substituted by halogen,

Nematocidal and fungicidal compositions

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

Novel substituted isonicotinic acid amides of the general formula ##STR1## in which X in ortho/ortho'-position are equal and represent fluorine, chlorine, bromine or iodine;

Compositions for protecting plants against disease

2-Mercapto-1,3,4-oxadiazoles and 2-mercapto-1,3,4-thiadiazoles of the formula I ##STR1## in which X.sub.1 and X.sub.2 independently of one another are oxygen or sulfur, R.sub.1 is difluoromethyl or 3,4,4-trifluoro-3-butenyl, R.sub.2 is hydrogen or C.sub.1 -C.sub.3 alkyl and R.sub.3 is hydrogen, C.sub.1 -C.sub.5 alkyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkenyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, C.sub.3 -C.sub.7 alkynyl which is unsubstituted or substituted by halogen or C.sub.1 -C.sub.3 alkoxy, or phenyl which is unsubstituted or substituted by halogen, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.3 -alkyl or C.sub.1 -C.sub.3 alkoxy, or wherein, furthermore, R.sub.2 and R.sub.3 together can form the methylene chain (--CH.sub.2 --)n as a constituent of a 5- or 6-membered ring with the heteroatom X.sub.1, in which n is 3 or 4, and processes for the preparation of the compounds of the formula I are described. The compounds of the formula I have nematicidal properties. Nematicidal compositions which contain at least one active substance of the formula I as the active substance and furthermore methods of using the active substances and the compositions for controlling nematodes are described.

Nematicidal compositions

Novel substituted isonicotinic acid amides and isonicotinic acid hydrazides of the general formula ##STR1## in which Hal, each independently of the other, is fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine; Y is CH-R.sub.1 or NH; n is 1 or 0; R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl; X is a 5-membered saturated or unsaturated, unsubstituted or C.sub.1 -C.sub.8 alkyl-, halogen-, trifluoromethyl-, cyano- or nitro-substituted heterocycle having from 1 to 3 hereto atoms, such as N, O or S, wherein the heterocycle may, in addition, contain an oxo or thiono group. The novel active ingredients have plant-protecting properties and are suitable especially for the preventive protection of plants against attack by phytopathogenic microorganisms such as fungi, bacteria and viruses.

Isonicotinic acid amides for protecting plants against disease

Acylated naphthylamines as plant fungicides

Novel compounds of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.12 alkyl that is unsubstituted or substituted by halogen, phenyl, C.sub.1 -C.sub.3 alkoxy or by hydroxy, C.sub.1 -C.sub.3 alkyl that is substituted by carbonyl, O-alkylcarboxy, amino or by a heterocycle, unsubstituted or halo-substituted C.sub.3 -C.sub.7 cycloalkyl or unsubstituted cyclopropylmethyl, unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkenyl, unsubstituted or halo-substituted C.sub.3 -C.sub.7 alkynyl, benzyl that is unsubstituted or mono-, di-or tri-substituted in the nucleus by C.sub.1 -C.sub.4 alkyl, halogen, nitro, cyano or by trifluoromethyl, or is the radical R.sub.2 --(O--CH.sub.2 --CH.sub.2 --)n wherein R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl and n is a number from 1 to 3, as active ingredients for controlling nematodes that parasitise plants and for preventing damage to cultivated plants caused by nematode attack.

The invention relates to 2-mercapto-5-pyridyl-1,3,4-oxadiazoles and 2-mercapto-5-pyridyl-1,3,4-thiadiazoles of the formula I ##STR1## wherein X is oxygen or sulfur,

2-mercapto-5-pyridyl-1,3,4-oxadiazoles and

2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles and 2-mercapto-5-pyrazinyl-1,3,4-thiadiazoles of formula I ##STR1## wherein X is oxygen or sulfur,

2-Mercapto-5-pyrazinyl-1,3,4-oxadiazoles or

Novel compounds of the formula ##STR1## in which R' represents C.sub.1 -C.sub.5 -alkyl, halogen, trifluoromethyl or C.sub.1 -C.sub.3 -alkoxy;

A method of combating undesirable plant growth and of regulating plant growth, which comprises allowing a herbicidal or plant-regulating amount of a compound of the formula I ##STR1## in which R.sub.1 is SR.sub.2 ; OR.sub.2 ; O--CHR.sub.10 R.sub.2 ; N(R.sub.3) (CHR.sub.10 R.sub.4); N(R.sub.11)(CHR.sub.10 R.sub.4) or NR.sub.3 R.sub.4 ; R.sub.2 is optionally substituted C.sub.1 -C.sub.10 -alkyl C.sub.1 -C.sub.4 -haloalkyl; C.sub.3 -C.sub.8 -alkenyl; (3-methyloxetan-3-yl)methyl; C.sub.3 -C.sub.8 -alkynyl; or an optionally substituted radical from the group comprising phenyl, benzyl, C.sub.3 -C.sub.7 -cycloalkyl, furanyl or furfuryl R.sub.3 and R.sub.4 independently of one another are hydrogen; an optionally substituted phenyl or benzyl radical; C.sub.1 -C.sub.8 -alkyl; or C.sub.3 -C.sub.6 -cycloalkyl; or R.sub.3 and R.sub.4, together with the nitrogen atom, form a saturaated 5- or 6-membered heterocyclic ring which contains up to two heteroatoms from the group comprising N, O and S and can be mono- or disubstituted by C.sub.1 -C.sub.4 -alkyl; R.sub.5 is hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl; nitro; cyano; C.sub.1 -C.sub.4 -haloalkoxy; phenylthio; di-C.sub.1 -C.sub.4 - alkylamino; phenyl; or is optionally substituted phenoxy; and R.sub.6 and R.sub.7 independently of one another are hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; nitro; cyano; or di-C.sub.1 -C.sub.4 -alkylamino, and R.sub.10 and R.sub.11 independently of one another are C.sub.1 -C.sub.4 -alkyl; and salts of compounds of the formula I with acids and bases, to act on the plants or on the environment of the plants, and novel compounds of the formula I' ##STR2## process for their preparation and herbicidal or plant growth-regulating compositions containing these novel compounds.

Method of combating undesirable plant growth and of regulating plant

2-Arylmethyliminopyrazines of the formula I ##STR1## in which R.sub.1 is SR.sub.2 ; OR.sub.2 ; O--CHR.sub.10 R.sub.2 ; N(R.sub.3)(CHR.sub.10 R.sub.4); N(R.sub.11)(CHR.sub.10 R.sub.4) or NR.sub.3 R.sub.4 ; R.sub.2 is C.sub.1 -C.sub.10 - alkyl which is unsubstituted or substituted by hydroxyl, mercapto, C.sub.1 -C.sub.4 -alkoxycarbonyl, mercaptoalkoxy, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, mono- or di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -haloalkoxy, tri-(C.sub.1 -C.sub.4 -alkoxy)-silyl, cyano, nitro or phenyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.3 -C.sub.8 -alkenyl; (3-methyl-oxetan-3-yl)methyl; C.sub.3 -C.sub.8 -alkynyl; or a radical from the group comprising phenyl, benzyl, C.sub.3 -C.sub.7 -cycloalkyl, furanyl or furfuryl which is unsubstituted or mono-, di- or trisubstituted by identical or different substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylcarbonyl, nitro, C.sub.1 -C.sub.4 -alkoxy and C.sub.1 -C.sub.4 -haloalkyl; R.sub.3 and R.sub.4 independently of one another are hydrogen; a phenyl or benzyl radical which is unsubstituted or mono-, di-, tri- or tetrasubstituted by identical or different substituents from the group comprising halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylcarbonyl, nitro, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -haloalkylthio; C.sub.1 -C.sub.8 -alkyl; or C.sub.3 -C.sub.6 -cycloalkyl; or R.sub.3 and R.sub.4, together with the nitrogen atom, form a saturated 5- or 6-membered heterocyclic ring which contains up to two heteroatoms from the group comprising N, O and S and can be mono- or disubstituted by C.sub.1 -C.sub.4 -allkyl; R.sub.5 is hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkyl; nitro; cyano; C.sub.1 -C.sub.4 -haloalkoxy; phenylthio; di-C.sub.1 -C.sub.4 -alkylamino; phenyl; or is phenoxy which is unsubstituted or substituted by the radicals R.sub.8 and R.sub.9 ; and R.sub.6, R.sub.7, R.sub.8 and R.sub.9 independently of one another are hydrogen; halogen; C.sub.1 -C.sub.8 -alkyl; C.sub.1 -C.sub.4 -haloalkyl; C.sub.1 -C.sub.4 -alkoxy; C.sub.1 -C.sub.4 -haloalkoxy; nitro; cyano; or di-C.sub.1 -C.sub.4 -alkylamino; and R.sub.10 and R.sub.11 independently of one another are C.sub.1 -C.sub.4 -alkyl; and salts of compounds of the formula I with acids and bases, process for their preparation and herbicidal or plant growth-regulating compositions containing compounds of the formula I.

2-arylmethyliminopyrazines pyrazines, compositions and method of

N-Acylated N-phenyl-aminotetrahydro-2-furanones of the formula ##STR1## wherein R represents C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy or halogen,

Growing community of inventors

Lorrach, Germany

Wolfgang Eckhardt