Ciba-geigy Corporation

Gunter Mattern

Walter Traber

Manfred Boger

Jozef Drabek

Haukur Kristinsson

Urs Burckhardt

Hans U Brechbuhler

Josef Drabek

Niels Clauson-Kaas

Erik Frandsen

Gottfried Bohtz

Water Traber

Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each a chlorine atom or the methyl group, Y is the group ##STR2## or --CH.dbd.N--R.sub.5, in which R.sub.3 is methyl or ethyl, R.sub.4 is alkyl having 1 to 4 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthio having 1 to 4 carbon atoms, or phenyl, X is an oxygen atom or a sulfur atom, and R.sub.5 is an unsubstituted or substituted pyridinyl group which is linked by way of one of its carbon atoms, to the main part of the molecule, and which has substituents selected from the group comprising halogen and alkyl having 1 to 4 carbon atoms, including the acid addition salts thereof, processes for producing the novel compounds by reaction of 2-(anilinomethyl)-2-imidazoline derivatives either with (thio)phosphoric acid dialkyl ester halides or alkyl(thio) phosphonic acid alkyl ester halides, or with N-pyridinylformiminoalkoxy derivatives. The resulting compounds and compositions containing them are effective against members of the order Acarina, and against animal and plant lice, as well as against members of the Calliphoridae family.

Substituted 2-(anilinomethyl)-2-imidazoline derivatives, compositions

Novel 2-(phenoxy-.alpha.-alkyl)-imidazolines of the formula ##STR1## wherein R.sub.1 and R.sub.2, each independently of the other, are methyl or chlorine, or together they are --(CH.sub.2).sub.3 or --(CH.sub.2).sub.4 group and R.sub.3 is ethyl, n-propyl or isopropyl, processes for obtaining these compounds and compositions containing them for the control of plant-damaging mites and mites which are parasites of animals.

Miticidal 2-(phenoxy-alpha-alkyl)-imidazolines

Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each chlorine or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sub.4 is C.sub.1 -C.sub.6 -alkyl optionally substituted by cyano or phenyl optionally substituted by halogen and/or methyl are novel and are pesticidally in particular acaricidally active.

Acaricidal 1-alkylthio-substituted and 1-phenylthio substituted

Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each chlorine or methyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl and R.sub.4 is cyano or a group of the formula A or B. ##STR2## and their acid addition salts possess useful pesticidal in particular acaricidal properties.

1-Iminomethylene-substituted 2-(phenoxy-alkyl)-2-imidoazoline derivatives

Compounds of the formula I ##STR1## wherein R.sub.1 and R.sub.2 are each methyl or chlorine, R.sub.3 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sub.4 is methyl or ethyl, R.sub.5 is methoxy, ethoxy, C.sub.1 -C.sub.4 -alkylthio or phenyl and X is oxygen or sulphur have valuable pesticidal in particular acaricidal properties.

1-Phosphorylated 2-(phenoxyalkyl)-2-imidazoline derivatives and their

Compound of the formula I ##STR1## wherein R.sub.1, R.sub.1 ', R.sub.2 and R.sub.2 ' are each chlorine or methyl and R.sub.3 and R.sub.3 ' are each hydrogen or C.sub.1 --C.sub.4 -alkyl possess valuable pesticidal in particular acaricidal properties.

Bis-(phenoxyalkyl-2-imidazolin)-1,1-sulfides, process for their

A process for the production of 3-hydroxy-5-chloropyridine and 3-hydroxy-5-bromopyridine is disclosed which process comprises reacting 2-furfurylamine in aqueous mineral-acid solution at -20.degree. to +5.degree. C. with chlorine or bromine, neutralizing the hydrohalic acid formed, heating the reaction mixture at reflux temperature, and isolating the formed 3-hydroxy-5-halopyridine. The 3-hydroxy-5-halopyridines obtained are intermediates for the production of insecticides.

Process for producing 3-hydroxy-5-halopyridines

Novel 3-phenyl-2-thioxo-2H,5H-pyrano[3,2-c][I]benzopyran-5-one derivatives, a process for their manufacture, compositions which contain these compounds as active substances for controlling harmful rodents, and the use of the active substances, or of compositions which contain them, as rodenticides. The novel 3-phenyl-2-thioxo-2H,5H-pyrano[3,2-c][I]benzopyran-5-one derivatives have the general formula I ##STR1## wherein each of R and R' independently represents hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, or halogen.

3-Phenyl-2-thioxo-2H,5H-pyrano[3,2-c][I]benzopyran-5-one derivatives, a

A process for the production of 3-hydroxy-2-imino-1(2H)-pyridinesulphonic acid comprising oxidation of furfurol and reaction of the oxidation product with sulphamic acid is disclosed which is carried out in the presence of an oxyacid of tri- or pentavalent phosphorus.

Process for the production of 3-hydroxy-2-imino-(2H)-pyridinesulphonic

2-Amino-3-hydroxy-5-chloropyridine and 2-amino-3-hydroxy-5-bromopyridine are produced by selective hydrolysis of corresponding 2-amino-3,5-dihalopyridines.

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Liestal, Switzerland

Gunter Mattern