Patent GB-792035-A (GB)
Title: Pesticidal compositions
Inventor: FITCH HOWARD MONTGOMERY
Filed: 1956-07-03
Abstract: Compounds of the formula: (CH3)2NOCO-A-CH2Y wherein A is phenyl, alkyl substituted phenyl (the alkyl portion containing not over 4 C atoms), nitrophenyl, or chlorophenyl and Y is lower dialkylamino having not over two carbon atoms per alkyl group, N-piperidino, N-morpholino or N-pyrrolidino are prepared by reacting a dimethyl carbamyl halide with a tertiary-aminomethylphenol, or an alkali metal salt of a tertiary-aminomethylphenol.  In an example, 4 - dimethylaminomethyl - 2 - methyl-5-isopropylphenol and dimethylcarbamyl chloride in anhydrous pyridine are heated under reflux to produce the dimethylcarbamate of 4-dimethylaminomethyl - 2 - methyl - 5 - isopropylphenol.  The acid oxalate may be prepared by adding excess oxalic acid to the base in absolute alcohol and the pure base may be obtained by treating a solution of the purified oxalate with sodium carbonate.  Other dialkyl-carbamates of dialkylaminomethylphenols and their salts may be prepared in a similar manner or by reacting a dialkyl-carbamylchloride with an aqueous solution of an alkali metal salt of a dialkylaminomethylphenol.  Specified compounds are the dimethylcarbamates of (1) 2-dimethylaminomethylphenol; (2) 4-dimethylaminomethylphenol; (3) 4-dimethylaminomethyl - 2 - methyl - 5 - isopropylphenol; (4) 4 - piperidinomethyl - 2 - methyl - 5 - isopropylphenol; (5) 4-piperidinomethyl-3,6-dimethylphenol; (6) 4-piperidinomethyl-3-methyl-6-isopropylphenol; (7) 4-piperidinomethyl-3-methyl-6 - tert. - butylphenol; (8) 2 - dimethylaminomethyl - 4 - tert. - butylphenol; (9) 2 - dimethylaminomethyl - 4 - (a ,a ,g ,g  - tetra - methylbutyl) - phenol; (10) 2 - dimethylaminomethyl - 4 - chlorophenol; (10) 2 - dimethylaminomethyl - 4 - methylphenol; (12) 2 - dimethylaminomethyl - 4 - nitrophenol; (13) 4 - pyrrolidinomethyl - 2 - methyl - 5 - isopropylphenol, neutral oxalate salt of 1, hydrochloride salt of 2, acid oxalate salt of 3, acid oxalate salt of 4, acid oxalate salt of 5, acid oxalate salt of 6, acid oxalate salt of 7, acid oxalate salt of 8, acid oxalate salt of 9, acid oxalate salt of 10, acid oxalate salt of 11, hydrochloride salt of 12, acid oxalate salt of 13.ALSO:A pesticidal composition comprises a toxicant of the formula (CH3)2NOCO-A-CH2Y, wherein A is phenyl, alkyl substituted phenyl, the alkyl portion containing not over 4 carbon atoms, nitro-phenyl, or chlorophenyl and Y is lower dialkylamino having not over two carbon atoms per alkyl group, N-piperidino, N-morpholino or N-pyrrolidino, preferably in an amount of at least 0.003 per cent of the total composition and either in the form of free base, an acid salt or partially in the form of an acid salt, together with a non-phytotoxic carrier substance.  The composition may be applied in dust form or with usual inert diluents sprayed as a liquid, e.g. solutions, emulsions, dispersions with usual wetting, emulsifying and surface-active agents or as an aerosol dissolved in acetone and heavy petroleum oil with a propellant, e.g. methyl chloride or dichloro difluoromethane.  Other pesticides and fungicides and casein and blood may also be incorporated.  The toxicant may be a dimethyl carbamate of a dialkylaminomethylphenol having not over 2 carbon atoms in each alkyl group therefore or a dimethylcarbamate of a lower dialkylaminomethyllower alkylphenol, the N-alkyl groups each containing not over two carbon atoms.  Examples of many specified toxicants are the oxalates of dimethylcarbamates of 2-methyl-4-piperidinomethyl-5-isopropylphenol, 2 - methyl - 4 - pyrrolidinomethyl - 5 - isopropylphenol, 2 - methyl - 4 - morpholino - methyl - 5 - isopropylphenol, 3-methyl - 4 - piperidino - 6 - isopropylphenol, as well as of 2-methyl-4-dimethylaminomethyl-5-isopropylphenol.