Philagro

Rhone-Poulenc S.a.

Michel Sauli

Jean Metivier

Novel 1,3,4-oxadiazoline-5-one derivatives, their preparation and the insecticidal compositions in which they are present are disclosed. The novel 1,3,4-oxadiazoline-5-one derivatives correspond to the formula: ##STR1## in which: X represents a halogen atom,

Oxadiazoline-1,3,4 one-5s

Dextrorotatory 2-phenoxypropionic acids are made by heating an alkali metal salt of dextrorotatory 2-chloropropionic acid with an alkali metal phenate in an inert organic solvent of high boiling point under reflux.

Process for the preparation of dextrorotatory 2-phenoxypropionic acid

A process for the manufacture of 3-(3,5-dichlorophenyl)-hydantoin comprises cyclizing 3-(3,5-dichloro-phenyl)-ureidoacetic acid in the presence of a catalytic amount relative to the ureidoacetic acid of an acid dehydrating agent and in the presence of an organic solvent which forms an azeotrope with water; the water formed during the reaction is eliminated by azeotropic distillation.

Process for the preparation of 3-(3,5-dichlorophenyl)-hydantoin

Derivatives of 3-(3,5-dichlorophenyl)-ureidoacetic acid, of the general formula: ##STR1## wherein R is a linear or branched alkyl radical containing 1 to 4 carbons, or an alkenyl of 2 to 4 carbons, is obtained by the action of an inorganic base such as sodium hydroxide, potassium hydroxide or ammonia, in an aqueous-organic solution such as a mixture of ethanol and water, on a hydantoin derivative of the general formula: ##STR2## IN WHICH R is defined as above. The compounds (I) have fungicidal activity.

Derivatives of 3-(3,5-dichlorophenyl)-ureidoacetic acid

Fungicidal 1-carbamoyl-3-(3,5-dichlorophenyl)-hydantoins are prepared by reacting 3 mols an isocyanate of the general formula R -- N .dbd. C .dbd. 0 (wherein R is alkyl of 1-4 carbons or alkenyl of 2-4 carbons) with one mol of 3-(3,5-dichlorophenyl)-ureidoacetic acid in an anhydrous medium in the presence of an organic base.

Process for the preparation of

Pyrazoline compounds of the formula:- ##SPC1## Wherein Ar represents phenyl optionally substituted by at most three atoms or radicals selected from halogen, alkyl and alkoxy of 1 through 4 carbon atoms, trifluoromethyl and nitro, and R.sub.1 and R.sub.2 represent hydrogen or methyl, are new compounds possessing insecticidal, acaricidal and nematicidal properties.

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Paris, France

Michel Sauli