Patent GB-593320-A (GB)
Title: Insecticidal and fungicidal alkyl amine salts of dinitro-phenols
IPC: C07C205/23
Filed: 1945-06-13
Abstract: Insecticidal and fungicidal amine salts of dinitro-phenols are obtained by treating an alkylamine with a hydrocarbon-substituted 2.4-dinitro phenol to obtain a compound having the formula <FORM:0593320/IV/1> wherein Y represents an alkyl, cycloalkyl, aralkyl, or aryl radical, each X represents an alkyl radical, or a hydrogen atom and the total number of carbon atoms in the alkyl groups attached to the ammonium nitrogen is at least 3.  In examples (1) to (6) and (8) such salts are obtained by filtering off the product from the cooled reaction mixture of 2.4-dinitro-6-cyclohexyl-phenol and: (1) n-octylamine, in hot ethyl alcohol solution; (2) dodecylamine, in hot methyl alcohol solution; (3) di-normal-butyl amine, in hot benzene solution; (4) monoamylamine solvent as in (3); (5) a mixture of di-amylbenzenes solvent as in (3); (6) normal-decylamine, in a solvent mixture of ethanol and benzene; (8) tri-normal-butylamine solvent as in (3); (7) relates to the reaction between 2.4-dinitro-6-methyl-phenol and p normal-octylamine in hot ethyl alcohol solution.  Other specified amines are: diethylamine di-normal propyl amine, N-methyl-N-hexylamine, isopropylamine, N-actyl-dimethylamine, mono-butylamine, tri-secondary-butylamine, tertiary-butylamine, di-octylamine, normal-hexylamine and tri-amylamine.  Other specified phenols are those having formula wherein Y represents (6-position) normal-actyl, normal-hexyl, (41-tertiary-butyl-cyclohexyl), phenyl (41-tertiary-butyl - phenyl), (alpha - phenylethyl), benzyl; (5-position): cyclohexyl, secondary-butyl and benzyl.  Other specified solvents are: chlorobenzene and toluene.ALSO:An insecticidal and fungicidal composition comprises an active toxicant, viz., an alkylamine salt of a hydrocarbon substituted 2.4-dinitrophenol having the formula: <FORM:0593320/VI/1> wherein Y represents an alkyl, cycloalkyl, aralkyl or aryl radical, each X represents an alkyl radical or a hydrogen atom, and the total number of carbon atoms in the alkyl groups attached to the ammonium nitrogen is at least 3, together with a known insecticide or an inert diluent. In Examples: (9), to (15) there are ground together to obtain a concentrate suitable for dispersing in water to act as a spray: (9) the normal-octylamine salt of 2.4-dinitro-6-cyclohexyl-phenol, diatomaceous earth and sodium lauryl sulphate; (10) the normal-octylamine salt of 2.4-dinitro-6-cyclohexyl-phenol; diatomaceous earth, linseed oil, and sodium lauryl sulphate; (11) as in (9) using the dodecylamine salt of 2.4-dinitro-6-cyclohexyl-phenol; (12) the dodecylamine salt of 2.4-dinitro-6-benzyl phenol powdered gypsum, and aluminium naphthenate; (13) the tri-secondary butylamine salt of 2.4 dinitro-6-phenyl-phenol and sodium lauryl sulphate; (14) as in (9) using the di-normal-butylamine salt of 2.4-dinitro-6-cyclohenyl-phenol; (15) the normal decylamine salt of 2.4-dinitro-6-cyclohexyl phenol, diatomaceous earth and sodium lauryl sulphate.  In (16) and (17) there are used as the basis of sprays (16) the product of (15); and (17) an aqueous dispersion of the normal-octylamine salt of 2.4-dinitro-6-methyl-phenol; (18) the normal-octylamine salt of 2.4-dinitro-6-methyl-phenol is ground with pyrophyllite to obtain a fungicidal dust.  Other specified inert carriers are: bentonite, talc, sulphur, wood flours, inorganic phosphates.  The toxicants may be used with inert liquid carriers other than water; with wetting, dispersing and sticking agents in general, and with other standard type insecticidal and fungicidal compositions either as the sole p  toxicant, or in combination with inorganic pigments, organic dyes, pyrethrum, rotenone, cryolite, organic thiocyanates, oils, sulphur, arsenates, copper salts and related toxicants.