Ciba-geigy Corporation

Alfred Grieder

Hansjakob Fah

Klaus-Jurgen Coers

Saleem Farooq

Peter Labuhn

Karl Scheuzger

Production of 2-chloropyridines of the formula I ##STR1## wherein R independently of one another is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenalkyl, halogen or carboxyl and

Process for producing 2-chloropyridines

Production of 2,3,5-trichloropyridine by reacting 3,5-dichloro-2-pyridone at 30.degree. to 150.degree. with phosgene in the presence of an N,N-disubstituted formamide of the formula ##STR1## in which R.sub.1 and R.sub.2 can be identical or different and are each an alkyl group having 1 to 4 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom form the pyrrolidino, piperidino or morpholino, and in the presence of an inert solvent. 2,3,5-Trichloropyridine is a valuable intermediate for producing herbicidally active .alpha.-[4-(3',5'-dichloropyrid-2-yloxy)-phenoxy]-alkanecarboxylic acids and derivatives thereof.

Process for producing 2,3,5-trichloropyridine

Novel substituted 1,3-benzodithiol-2-N,N-dialkyliminium salts of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another are each hydrogen, C.sub.1 -C.sub.5 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.3 -alkenyl, C.sub.3 -C.sub.5 -alkynyl or the radical --(CH.sub.2).sub.n --OR, in which R is C.sub.1 -C.sub.4 -alkyl, and n is the number 2 or 3; R.sub.3 and R.sub.4 independently of one another are each C.sub.1 -C.sub.4 -alkyl, or together they are the radical --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 --; and X.sup..crclbar. is a molar equivalent of an anion of an inorganic or organic acid; processes for producing these compounds, as well as compositions containing them, and their use for combating pests, particularly for combating members of the order Acarina which infest plants and animals. The novel compounds are distinguished by their special effectiveness against mites which damage plants.

1,3-Benzodithiol-2-N,N-dialkyliminium salts and pesticidal use

Production of 2,3,5-trichloropyridine by reacting 3,5-dichloro-2-pyridone at 30.degree. to 150.degree. with phosgene in the presence of an N,N-disubstituted formamide of the formula ##STR1## in which R.sub.1 and R.sub.2 can be identical or different and are each an alkyl group having 1 to 4 carbon atoms, or R.sub.1 and R.sub.2 together with the nitrogen atom form the pyrrolidino, piperidino or morpholino, and in the presence of an inert solvent. 2,3,5-trichloropyridine is a valuable intermediate for producing herbicidally active .alpha.-[4-(3',5'-dichloropyrid-2-yloxy)-phenoxy]-alkanecarboxylic acids and derivatives thereof.

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-chloropropionate or alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the 2-halogenopropionic acid ester at 110.degree.-130.degree. C. in the presence of an alkali metal iodide as the catalyst, and of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, in excess 2,6-dialkylaniline as the solvent, removing, by distillation, the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

Process for the preparation of

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the alkyl 2-bromopropionate at 110.degree. to 125.degree. C. in excess 2,6-dialkylaniline as the solvent, in the presence of a quaternary compound of nitrogen or of phosphorus, and in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, distilling off the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1-4 carbon atoms. According to this process, a 2-chloropropionic acid ester having 1-4 carbon atoms in the alkyl group is reacted in the presence of water and of a quaternary ammonium or phosphonium salt with an alkali metal iodide to give a mixture of the 2-chloropropionic acid ester and the 2-iodopropionic acid ester, and this mixture is subsequently reacted, after separating off the aqueous phase, at 110-130.degree. C., in the presence of an alkali metal carbonate or alkali metal bicarbonate as an acid-binding agent, with excess 2,6-dialkylaniline, the reaction mixture is extracted with water and the mixture of the 2,6-dialkylaniline of the formula IV and the N-(1'-alkoxycarbonylethyl)-2,6-dialkylaniline of the formula I, which is obtained after separating off the aqueous extract, is separated by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

An improved process for the production of 2-amino-chlorotoluene hydrochloride comprising chlorination of 2-formyl-amino-toluene, splitting off the formyl group of the 2-formyl-amino-chlorotoluenes and isolation of crystalline 2-amino-5-chlorotoluene hydrochloride is disclosed, in which process the 2-formylamino-5-chlorotoluene formed by chlorination of 2-formylamino-toluene in an inert solvent is reacted with methanol to form 2-amino-5-chlorotoluene and methyl formate, and the 2-amino-5-chlorotoluene is isolated as hydrochloride.

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Bockten, Switzerland

Alfred Grieder