Ciba-Geigy Corporation

Dag Dawes

Beat Bohner

Willy Meyer

Haukur Kristinsson

Kurt Rufenacht

Beat Boehner

Jean Perchais

Hanspeter Fischer

Rudolph C Thummel

Hermann Kny

New 1,2,4-triazoles, their manufacture and use as active ingredient on pest control is disclosed. The triazoles correspond to the formula ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or C.sub.1 -C.sub.6 -alkylthio,

Phosphorus esters of 1-cyanoethyl-1,2,4-triazol-3-ols

1,2,4-TRIAZOLE DERIVATIVES WHICH HAVE PARTICULAR IMPORTANCE AS INTERMEDIATES FOR, E.G., THE PREPARATION OF ACTIVE SUBSTANCES FOR PEST CONTROL, CORRESPONDING TO THE FORMULA ##STR1## wherein R.sup.1 represents an unsubstituted or substituted alkyl, alkenyl, or alkynyl, naphthyl, benzyl, phenylethyl, ##STR2## or phenylpropyl radical, or a mono or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member, or a substituted phenyl radical, And new processes for the preparation of compounds of the formula ##STR3## wherein R represents hydrogen, an optionally substituted alkyl, alkenyl or alkynyl radical, an optionally substituted phenyl, naphthyl, benzyl, phenylethyl or phenylpropyl radical, a mono- or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member and/or be substituted by alkyl, or a partially hydrogenated naphthyl radical, which processes are performed by addition to a hydrazine of the formula

Process for preparing 1,2,4-triazole derivatives

Process for the production of 3-hydroxy-1,2,4-triazole derivatives of the formula I ##STR1## wherein R.sub.1 represents an alkyl or cycloalkyl group, R.sub.2 denotes an alkyl, cycloalkyl, alkenyl, alkynyl or an optionally substituted benzyl group and X stands for oxygen, sulphur or a group &lt;N--R.sub.3, wherein R.sub.3 denotes an alkyl, alkenyl or alkynyl group, or together with radical R.sub.2 and the adjacent nitrogen atom it denotes a pyrrolidino or morpholino group, wherein a 2-R.sub.1 -hydrazinecarboxylic acid ester is reacted with cyanogen chloride to form the corresponding 2-R.sub.1 -2-cyanohydrazinecarboxylic acid ester which is subsequently cyclized under alkaline conditions in the presence of a compound R.sub.2 XH.

Process for the production of 3-hydroxy-1,2,4-triazole derivatives

A process for the production of 3-hydroxy-1,2,4-triazole derivatives of formula I ##STR1## wherein R.sub.1 and R.sub.2 each represent a straight-chain or branched-chain alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms, and

1,2,4-triazolylphosphoric and 1,2,4-triazolylphosphonic acid esters of the formula ##STR1## wherein R.sub.1 represents hydrogen, alkyl, cycloalkyl, phenyl, benzyl, or phenethyl, R.sub.2 represents alkenyl or alkinyl, R.sub.3 represents alkyl, alkoxy, alkylthio, amino, monoalkylamino or dialkylamino, R.sub.4 represents alkyl, and X represents oxygen or sulphur, a process for their manufacture and their use in pest control.

1,2,4-Triazolyl-phosphoric acid and phosphonic acid esters

Triazolylphosphorus compounds of the formula ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.5 -alkyl, cyclopentyl, cyclohexyl or unsubstituted phenyl,

Triazolylphosphorus compounds

1,2,3-Triazolyl phosphorus compounds, their manufacture and use as active ingredients for controlling insects, representatives of the order acarina and phytopathogenic nematodes. The compounds correspond to the formula ##STR1## wherein R.sub.1 represents alkyl, alkoxy, alkylthio, alkoxyalkylthio, amino, monoalkylamino or dialkylamino,

Pesticidal 2-phenyl-1,2,3-triazolyl-(4) and-triazox-(1)-yl-(4) phosphate

1,2,4-Oxadiazoles, their manufacture and use as active ingredients in pesticides especially insecticides and acaricides. The compounds correspond to the formula ##STR1## wherein R.sub.1 represents hydrogen, unsubstituted alkyl, benzyl or phenyl, R.sub.2 represents methyl or ethyl, and R.sub.3 represents unsubstituted C.sub.1 -C.sub.7 alkyl optionally interrupted by oxygen or represents C.sub.3 -C.sub.4 alkenyl.

O,S-dialkyl- and O-alkyl-S-alkoxyalkyl-S-1,2,4-oxa-diazolyl-3-methylene

1,1-Diphenyl-2-nitro-pentane, 1,1-diphenyl-2-nitro-hexane and 1,1-diphenyl-2-nitro-heptane derivatives of the formula ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.3 -alkyl,

1-P-Alkylphenyl-1-p-(alkoxyphenyl)-2-nitroalkanes

Preparation of 1-isopropyl-3-hydroxy-5-chloro-1,2,4-triazole by reacting isopropylhydrazine hydrochloride with N-chlorocarbonylisocyanidedichloride.

Process for the preparation of 1,2,4-triazole derivatives

1,2,4-Triazolylphosphoric and 1,2,4-triazolylphosphonic acid esters of the formula ##SPC1## Wherein R.sub.1 represents hydrogen, alkyl, cycloalkyl, phenyl, benzyl, or phenethyl, R.sub.2 represents substituted phenyl, benzyl, phenethyl, or unsubstituted diphenylmethyl, .beta.-naphthyl, or ##SPC2## R.sub.3 represents alkyl, alkoxy, alkylthio, amino, monoalkylamino or dialkylamino, R.sub.4 represents alkyl, and X represents oxygen or sulphur, a process for their manufacture and their use in pest control.

1,2,4-Triazolyl-phosphoric and -phosphonic acid esters

Process for the production of 1-alkyl-3-hydroxy-5-chloro-1,2,4-triazoles wherein an alkylhydrazine is reacted in an inert solvent in the presence of an acid binding agent with cyanogen chloride to 1-alkyl-1-cyanohydrazine which is subsequently cyclized with phosgene.

Process for the production of 1,2,4-triazole derivatives

Insecticidal and acaricidal composition and method utilizing triazolyl phosphoric acid esters of the formula ##EQU1## wherein R.sub.1 represents a phenyl group susbstituted by one or more fluorine atoms or lower haloalkyl groups or by at least one chlorine atom and at least one fluorine atom or lower haloalkyl groups, R.sub.2 and R.sub.3 are each lower alkyl and X and Y are each oxygen or sulphur.

Insecticidal and acaricidal composition and method with triazolyl

Certain sulfonic acid esters

New urea phosphonates, their manufacture and use as active ingredients in pesticides especially insecticides and acaricides is disclosed. The compounds correspond to the formula ##EQU1## wherein R.sub.1 represents C.sub.3 -C.sub.5 -alkyl, R.sub.2 represents methyl or ethyl, R.sub.3 represents C.sub.1 -C.sub.4 -alkyl or C.sub.3 -C.sub.4 -alkenyl, and R.sub.4 represents optionally substituted phenyl.

Growing community of inventors

Pratteln, Switzerland

Dag Dawes