Ciba-geigy Corporation

Ciba-geiby Corporation

Ernst Beriger

Jozef Drabek

Manfred Boger

Odd Kristiansen

Wolfgang Eckhardt

Haukur Kristinsson

Beat Bohner

Robert Nyfeler

Kurt Rufenacht

Dieter Durr

Dieter Reinehr

Georg Pissiotas

Urs Burckhardt

Manfred Kuhne

Jean J Gallay

Bernardo De Sousa

Jorg Bader, Deceased

A process for the preparation of a compound of the formula ##STR1## where Z and R are defined herein. A compound of formula II ##STR2## where R.sub.1 defined herein, is reacted with hydrazine hydrate and then subjected to hydrolysis to form the compound of formula I ##STR3## and the compound of the formula I is reacted with the aldehyde of the formula ##STR4## into the resulting compound of the formula IV.

Process for the preparation of aminotriazine derivatives

The invention relates to a process for the preparation of a compound of formula ##STR1## useful as intermediate for the preparation of pesticides, wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 10 halogen atoms or by from 1 to 3 radicals selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio and phenyl, phenyl or phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, which comprises reacting with hydrazine hydrate a compound of formula ##STR2## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 9 chlorine atoms, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, phenyl, phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, or pyridyl, and subjecting to hydrolysis the resulting compound of formula ##STR3##

The invention relates to a process for the preparation of a compound of formula ##STR1## useful as intermediate for the preparation of pesticides, wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 10 halogen atoms or by from 1 to 3 radicals selected from the group consisting of C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio and phenyl, phenyl or phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, which comprises reacting with hydrazine hydrate a compound of formula ##STR2## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 alkyl substituted by from 1 to 9 chlorine atoms, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfonyl, C.sub.1 -C.sub.3 alkylsulfonyl, phenyl, phenyl substituted by from 1 to 3 radicals selected from the group consisting of halogen, methyl, ethyl, methoxy, methylthio and nitro, or pyridyl, and subjecting to hydrolysis the resulting compound of formula ##STR3##

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

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 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;

The invention relates to a composition for protecting keratinous material, in particular woollen textiles, from attack by pests that feed on keratin, in particular moth and beetle larvae, which composition contains, as active ingredient combination, a specifically substituted 5-(pyridyloxyphenylcarbamoyl)barbituric acid or a salt thereof and a synthetic pyrethroid, as well as to a process comprising the use of this active ingredient combination for providing said material with a protective finish against attack by pests that feed on keratin.

Mothproofing and beetleproofing composition: 5-(pyridyloxy- or

Oxime phosphates of the formula ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.6 -alkyl,

Oxime phosphates and their use for combating pests

The invention relates to O,S-dialkyl-O-phenyl-thiophosphates and dithiophosphates of the formula ##STR1## wherein R.sub.1 represents methyl or ethyl,

O-Methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and

Compounds of the formula ##STR1## wherein R.sub.1 is Methyl or ethyl, R.sub.2 is C.sub.1 -C.sub.4 -alkyl or allyl, R.sub.4 is halogen, methyl or trifluoromethyl and R.sub.5 is hydrogen, halogen, methyl or trifluoromethyl and their tautomers exhibit valuable insecticidal properties.

Insecticidal 5-phenylcarbamoyl-barbituric acid

Carbimidocarbonylphenylformamidines of the formula ##STR1## wherein each of R.sub.1 to R.sub.6 represents hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl or cyano, a process for their production and their use in pest control.

Growing community of inventors

Allschwil, Switzerland

Ernst Beriger