Patent IE-41836-B1 (IE)
Title: Pyrazoline compounds
IPC: C07C45/75
Filed: 1975-07-09
Abstract: 1514285 Pyrazoline derivatives PHILIPS GLOEILAMPENFABRIEKEN NV 9 July 1975 [12 July 1974] 28895/75 Heading C2C Novel pyrazoline derivatives of general formula wherein R 1 has the following meaning: an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, a phenyl alkyl group of which the phenyl nucleus may be substituted with halogen, alkyl or nitro, a heterocyclic ring which comprises 1-2 nitrogen atoms and may be substituted with halogen, alkyl or nitro, a phenyl group, or a substituted phenyl group, in which the phenyl nucleus has 1 or 2 substituents in the 2, 3 or 4 positions which are chosen from the group consisting of a halogen atom, an alkyl group having 1 to 4 carbon atoms which may be substituted with halogen, a cycloalkyl group having 3-6 carbon atoms, an alkylthio group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a dialkylamino group of which each alkyl radical contains 1-4 carbon atoms, an alkylsulphonyl group having 1-4 carbon atoms, an acyl group, an acylamino group, a cyano group, a nitro group and a phenyl group which, if desired, is substituted with halogen, R 2 and R 3 are equal or different and have the meanings of an alkyl group having 1-4 carbon atoms, a cycloalkyl group having 3-6 carbon atoms, a pyridyl group or thienyl group which may be substituted with halogen, nitro or alkyl, a phenyl group, or a substituted phenyl group in which the phenyl group contains 1-2 substituents which are chosen from a halogen atom, an alkyl group having 1-4 carbon atoms which may be substituted with halogen, a cycloalkyl group having 3-6 carbon atoms, an alkylthio group having 1-4 carbon atoms, an alkoxy group having 1-4 carbon atoms, an alkylenedioxy group, a mono or dialkylamino group in which each alkyl radical has 1-4 carbon atoms, a nitro group, a phenyl group which, if desired, is substituted with halogen and a cyano group, R 4 is a hydrogen atom or an alkyl group having 1-15 carbon atoms, and wherein X is an oxygen atom or a sulphur atom, are prepared by reacting a compound of formula with a compound R 1 -N = C = X in the presence of a solvent and the resulting compounds where R 4 is H are converted, if desired, by alkylation, for example, with an alkyl halogenide in a polar solvent in the presence of an acid binding reagent, into derivatives in which R 4 is an alkyl group. Amongst the examples the compounds 1 - (4 - chlorophenylcarbamoyl) - 3 - (4 - chlorophenyl) - 4 - phenyl - #2 - pyrazoline and 1 - (4 - chlorophenyl - carbamoyl) - 3 - (4 - chlorophenyl) - 4 - methyl - #2 - pyrazoline are prepared. 2 - Phenyl - 41 - chloroacrylylphenone is obtained by reacting (4-chlorophenyl)-benzylketone with H . CHO. 3 - (4 - Chlorophenyl) - 4 - phenyl - #2 - pyrazoline is prepared by reacting 2-phenyl-41- chloroacrylylphenone with hydrazine hydrate. 3 - Dimethylamino - 2 - methyl - 41 - chloropropiophenone is produced from p-chloropropiophenone and dimethylamine in the presence of H . CHO. 3 - (4. Chlorophenyl) - 4 - methyl - #2 - pyrazoline is obtained from the reaction of 3-dimethylamino - 2 - methyl - 41 - chloropropiophenone and hydrazine hydrate. Insecticidal compositions comprise as active ingredient a compound of Formula I together with solid or liquid inert carrier material.