Patent GB-593331-A (GB)
Title: Insecticidal and fungicidal aralkylamine salts of dinitro-phenols
IPC: C07C205/23
Filed: 1945-06-14
Abstract: Insecticidal and fungicidal aralkylamine salts of di-nitrophenols are obtained by reacting an aralkylamine with a hydrocarbon-substituted 2.4-dinitrophenol to obtain a compound having the formula <FORM:0593331/IV/1> wherein R represents an aralkyl radical, n represents an integer not greater than 3 and Y represents an alkyl, cycloalkyl or aryl radical.  In examples, such salts are obtained by reacting together: (1) 2.4-dinitro-6-phenyl-phenol with benzylamine, in benzene-monochlorobenzene solution, and decanting the solvent from the product; (2) 2.4-dinitro-6-cyclohexyl-phenol and alpha-naphthylmethylamine in benzene solution, and recovering the product by filtration; (3) benzylamine and 2.4-dinitro-6-cyclohexyl-phenol substantially as in (2), but in hot solution; (4) benzylamine and 2.4-dinitro-6-methyl-phenol, as in (3); (5) dibenzylamine and 2.4-dinitro-6-cyclohexyl-phenol, as in (4); (6) beta-phenylethylamine and 2.4-dinitro-6-cyclohexyl-phenol, as in (1); (7) alpha-phenylethylamine and 2.4-dinitro-6-cyclohexyl-phenol, as in (2).  Other specified amines are: tri-benzylamine: 4-methyl-benzylamine, 2-cyclohexylbenzylamine, gamma - phenylpropylamine, omega-phenyloctylamine and di-(alpha-naphthyl-methyl)-amine.  Other specified phenols are: 2.4 - dinitro - 5 - cyclohexyl - phenol, 2.4 - dinitro - 6 - benzyl - phenol, 2.4 - dinitro - 6 - (beta - phenylethyl) - phenol, 2.4 - dinitro - 6 - normal - octyl - phenol, 2.4 - dinitro - 5 - phenyl - phenol, 2.4-dinitro-5-secondary-butyl-phenol and 2.4-dinitro - 5 - methyl - phenol.  Another specified solvent is toluene.ALSO:An insecticidal and fungicidal composition comprises as an active toxicant an aralkylamine salt of a hydrocarbon substituted 2.4-dinitro-phenol having the formula: <FORM:0593331/VI/1> wherein R represents an aralkyl radical, n represents an integer not greater than 3, and Y represents an alkyl, cycloalkyl, aralkyl, or aryl radical, together with a known insecticide or an inert diluent.  In Examples: (8) the benzylamine salt of 2.4-dinitro-6-cyclohexyl-phenol and sodium lauryl sulphate are ground together and the mixture is dispersed in water; (9) the dibenzylamine salt of 2.4-dinitro-6-cyclohexyl-phenol, diatomaceous earth and sodium lauryl sulphate are ground together and the mixture is dispersed in water; (10) the dibenzylamine salt of 2.4-dinitro-6-cyclohexyl phenol is ground with diatomaceous earth to obtain an insecticidal dust; (11) the benzylamine salt of 2.4-dinitro-6-phenyl-phenol is ground with powdered gypsum and sodium lauryl sulphate and the mixture is dispersed in water; (12) the alpha-phenyl ethylamine salt of 2.4-dinitro-6-cyclohexyl-phenol, diatomaceous earth and sodium lauryl sulphate are ground together and the mixture is dispersed in aqueous solution; (13) the dibenzylamine salt of 2.4-dinitro-6-benzyl alcohol is ground with sodium lauryl sulphate and the mixture is dispersed in water; (14) beta-phenylethylamine salt of 2.4-dinitro-6-cyclohexyl-phenol is dispersed in water; (15) the toxicant of (14) is mixed with talc to obtain a dust; (16) the tri-benzylamine salt of 2.4-dinitro-6-methyl-phenol is dispersed in water containing rotenone; (17) the alpha-naphthylmethylamine salt or 2.4-dinitro-6-cyclohexyl-phenol is mixed with diatomaceous earth and sodium lauryl sulphate and the product is mixed with water to obtain a spraying composition; (18) the alpha-naphthylmethylamine salt of 2.4 dinitro-6-cyclohexyl phenol is ground with diatomaceous earth to obtain a dust.  Other specified inert carriers are: volcanic ash, bentonite and finely divided wood flour.  Other specified solvents are: alcohol, carbon tetrachloride and petroleum distillate in which liquids also the toxicants may be dispersed.  Other specified wetting, sticking and dispersing agents are: glyceryl oleate, alkali metal caseinates, aluminium naphthenate, alkali metal salts of sulphonated aromatic hydrocarbons and phenols, partially neutralized sulphuric acid derivatives of fatty acid and oils blood albumen, and soap.  Other parasiticides which may be added to the compositions include: petroleum, fish and vegetable oils; lead arsenate, cryolite, sulphur, copper sprays and pyrethums.