Rumianca S.p.a.

Anic S.p.a.

Renato Francese

Luciano Baldi

Vittorio Messori

Roberto Esposito

Corrado Ferrari

Roberta Fruttero

Franco Collecchia

Giuliano Giorcelli

Anna Peluffo

The description relates to heterocyclic compounds having weed-killing activity and defined by the following general formula: ##STR1## where R is a straight-chain or branched alkyl group with 1 to 6 carbon atoms or the phenyl group, R.sub.1 is a straight-chain or branched alkyl group with 1 to 10 carbon atoms (substituted if required by halide, or phenyl group), an alkenyl group, an alkynyl group, a cycloalkyl group, or the phenyl group.

Weed-killing furazan compounds

Chloro-bis(alkylamino)-s-triazines are prepared by step-wise replacement of two chlorine atoms of cyanuric chloride by reaction with amines and alkali metal hydroxide in a medium comprising water and a liquid organic compound which is a solvent for cyanuric chloride and is substantially immiscible with water, the first step being carried out by contacting a first amine with a reaction medium containing the cyanuric chloride and the whole of the alkali metal hydroxide used for the step-wise replacement.

Preparation of chloro-bis(alkylamino)-s-triazines

Chloro-bis(alkylamino)-s-triazines are prepared by step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups. Cyanuric chloride, an inorganic base and an alkylamine are continuously fed to a first tubular zone in stoichiometric proportions and reacted therein under turbulent conditions, at an elevated temperature not exceeding 90.degree. C., and for a short reaction time, and the reaction product is continuously fed to a second tubular reaction zone together with stoichiometric quantities of inorganic base and of a second alkylamine, and reacted therein with the latter at an elevated temperature not exceeding 100.degree. C., under turbulent conditions and for a short reaction time.

Process for the production of chloro-di (alkylamino)-s-triazines

In the commercial process for preparing chloro-bis(alkylamino)-s-triazines by step-wise replacement of two chlorine atoms of cyanuric chloride by means of alkylamino groups in which a molar excess of alkylamine is used in the second replacement step, the formation of tris(alkylamino)-s-triazines is suppressed by adding to the reaction mixture, after the second chlorine atom has been replaced with an alkylamino group, an oxidizing agent selected from the group consisting of hydrogen peroxide and alkali metal hypochlorites, persulphates and permanganates, in an amount of at least 1 equivalent for every mole of unreacted alkylamine present in the said reaction mixture.

Process for preparing chloro-bis(alkylamino)-s-triazines

Chloro-bis(alkylamino)-s-triazine is prepared by means of the step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups in an alkaline medium comprising water and a liquid organic compound which is a solvent for cyanuric chloride and forms a two-phase system with water, in which a molar excess of alkylamine is used in the second replacement step. Upon completion of the second replacement step the reaction mixture is freed from its aqueous phase and the residual suspension or solution of triazine in the organic compound is admixed with water added in a volumetric quantity of from 30 to 150% with respect to that of said aqueous phase. The chloro-bis(alkylamino)-s-triazine thus produced has high characteristics of handling and formulability.

Process for the preparation of chloro-bis(alkylamino)-s-triazines

The commercial method of preparing chloro-bis(alkylamino)-s-triazine by step-wise replacement of two chlorine atoms of cyanuric chloride by means of alkylamino groups in an alkaline medium comprising water and a liquid organic compound is improved by adding to the reaction product, upon completion of the second replacement step, or during or after the distillation of the organic compound, at least 0.5% by weight with respect to the weight of the chloro-bis(alkylamino)-s-triazine, of minerals chosen from the groups of montmorillonite, paligorskite, vermiculite and chlorite and having a base-exchange capacity of at least 10 milli-equivalents for each 100 grams of said solid, thus deactivating the unreacted alkylamine and the tris(alkylamino)-s-triazines present in the reaction product.

Process for the production of chloro-bis(alkylamino)-s-triazines

In the commercial process for preparing chloro-bis(aklylamino)-s-triazines by step-wise replacement of two chlorine atoms of cyanuric chloride with alkylamino groups in which a molar excess of alkylamine is used in the second replacement step, the formation of tris-(alkylamino)-s-triazines is suppressed by submitting the reaction mixture, after the second replacement step is completed, to a pressure not exceeding 400 mm Hg, at a temperature not exceeding about 55.degree. C. and for a period not exceeding about 15 minutes, thereby removing the excess alkylamine from said reaction mixture by volatilization without substantially removing the other components of the reaction mixture.

Production of chloro-bis(alkylamino)-s-triazines

2-CHLORO-S-TRIAZINE SUBSTITUTED IN AT LEAST ONE OF THE POSITIONS 4,6 OF THE TRIAZINE RING WITH AN AMINO GROUP IS OBTAINED BY FEEDING SEPARATELY AN AQUEOUS AMINE SOLUTION AND AN AQUEOUS NaOH solution into a water-organic liquid reaction medium containing cyanuric chloride, delivering to said medium per unit of time from 1.05 to 1.30 moles of amine for each mole of sodium hydroxide, feeding the amine solution until an amount of from 1 to 2 moles of amine per mole of cyanuric chloride is reached in the medium and the NaOH solution until an amount in moles equal to or slightly higher than the amount of amine moles fed in is reached in the medium. The temperature of the reaction medium is maintained at a value of from 5.degree.-15.degree. C to 60.degree.-70.degree. C during the feeding period.

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Turin, Italy

Renato Francese