Ciba-geigy Corporation

Ciba-geigy Ag

Syngenta Crop Protection, Inc.

Syngenta Investment Corporation

Helmut Zondler

Wolfgang Eckhardt

Robert Nyfeler

Roland Moser

Adolf Hubele

Walter Kunz

Friedrich Lohse

Hans Lehmann

Rudolf Kirchmayr

Rolf Schmid

Peter Riebli

Alfred Meyer

Werner Stauffer

Urs Muller

Andr&eacute; Stoller

Michael Fischer

Emil Saladin

Odd Kristiansen

Hans-Georg Brunner

Friedrich Stockinger

Elmar Sturm

Jean Wenger

Hans Tobler

Thaddeus Audykowski

Wolfgang Schneider

Christoph L&uuml;thy

Srinivasachari Rajappa

Wolfgang Pfleiderer

Herbicidal 1,2,4,6-thiatriazines

Compounds of formula (I) in which Q,is an unsaturated five-membered optionally substituted or condensed heterocyclic ring and X is O, S, SO or SO2, and agronomically tolerated salts/N-oxides/isomers/enantiomers of these compounds are suitable as herbicides

Herbicidal S-substituted 1,2,4,6-thiatriazines

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

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 is hydrogen, halogen, methyl, methoxy or trifluoromethyl; n is 1 or 2; R.sub.2 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl which is substituted by halogen, cyano or methoxy, or is C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl, benzyl, COR.sub.5, CON(R.sub.5)R.sub.6, CSN(R.sub.5)R.sub.6, CO(OR.sub.6), CO(SR.sub.6), CS(SR.sub.5), SO.sub.2 R.sub.7, PO(OR.sub.6).sub.2 or Si(R.sub.6).sub.3 ; R.sub.3 and R.sub.4 independently of one another are hydrogen, C.sub.1 -C.sub.5 alkyl, CH.sub.2 OR.sub.6, cyclopropyl, methylcyclopropyl, C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkynyl or C.sub.1 -C.sub.2 haloalkyl; R.sub.5 is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.3 alkyl which is substituted by 1 to 3 halogens, C.sub.1 -C.sub.3 alkyl which is substituted or OR.sub.6 or SR.sub.6, or is C.sub.2 -C.sub.5 alkenyl, C.sub.2 -C.sub.5 alkenyl which is substituted by 1 to 3 halogens, C.sub.2 -C.sub.5 alkynyl, C.sub.3 -C.sub.6 cycloalkyl, phenyl or phenyl which is monosubstituted to trisubstituted by halogen, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, C.sub.1 -C.sub.3 alkoxy, nitro or cyano; R.sub.6 is C.sub.1 -C.sub.6 alkyl; R.sub.7 is C.sub.1 -C.sub.3 alkyl, phenyl, phenyl which is monosubstituted or disubstituted by halogen, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, methoxy or nitro; including the acid addition salts, have valuable microbicidal properties. The novel active substances can be employed in crop protection for preventing crop plants being attacked by phytopathogenic microorganisms, and for controlling these pests.

Microbicides

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

Novel substituted isonicotinic acid esters of the general formula ##STR1## in which Y is halogen;

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

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

The invention discloses novel N-(2-nitrophenyl)-5-aminopyrimidine derivatives of the general formula ##STR1## wherein R.sub.1 and R.sub.2 are each independently NO.sub.2 or CF.sub.3, or one of R.sub.1 and R.sub.2 is hydrogen,

N-(2-nitrophenyl)-5-aminopyrimidine derivatives and useful for

There are described novel, microbicidally active 5-(arylmethylimino)-pyrimidines of the formula I ##STR1## wherein R.sub.n --A-- is an unsubstituted or substituted phenyl, naphthyl, biphenyl, phenoxyphenyl or phenylthiophenyl, and R.sub.1 is an ether, thioether or amino function, these substances being produced according to the invention by substitution of the halogen atom in the claimed intermediates of the formula II ##STR2## The use of these substances in plant protection, and also further important intermediates, are likewise described.

Antifungal and antibacterial diazine derivatives 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 invention discloses novel N-(2-nitrophenyl)-2-aminopyrimidine derivatives of the general formula I ##STR1## wherein R.sub.1 and R.sub.2 are hydrogen, NO.sub.2 or CF.sub.3, with the proviso that only R.sub.1 or R.sub.2 can be NO.sub.2 ;

Growing community of inventors

Bottmingen, Switzerland

Helmut Zondler