Patent GB-593957-A (GB)
Title: Improvements in or relating to the manufacture of insecticidal and fungicidal amine salts of dinitrophenols
IPC: C07C205/23
Filed: 1945-05-29
Abstract: Insecticidal and fungicidal amine salts of dinitrophenols are obtained by reacting an amine having the formula <FORM:0593957/IV/1> wherein n represents an integer, and each R represents a hydrogen atom or an alkyl, hydroxy-alkyl, or cycloalkyl radical with a phenol, characterised by the formula <FORM:0593957/IV/2> wherein Y represents an aryl cycloalkyl or alkyl radical.  A mono-salt (examples 1 and 3) or a di-salt (examples 2 and 4 to 6) is formed, depending upon the proportions of the reactants.  In examples 1 to 4, there are reacted in hot benzene solution: (1) 2.4-dinitro-6-cyclohexylphenol and ethylene diamine; (2) 2.4-dinitro-6-cyclohexyl-phenol and N.N1-di-(2-methyl-cyclo-hexyl)-ethylene diamine; (3) 2.4-dinitro-6-methyl-phenol and propylene diamine; (4) 2.4-dinitro-6-methyl-phenol and N.N1-di-(2-methyl-cyclohexyl)-ethylene diamine.  In examples 5 and 6, there are reacted in hot ethanol solution: (5) 2.4-dinitro-6-phenyl-phenol and propylene diamine; (6) 2.4 - dinitro - 6 - cyclohexyl-phenol and N-(2)-hydroxy-ethyl)-ethylene diamine: in each instance the product is filtered from the cooled reaction mixture.  Other specified amines are: 1.6-diamino-hexane, 1.4-diamino-butane, 1.10-diamino-decane, 1.6-diamino-3-tertiary-butyl-hexane, 1.8-diamino-octane, 1.6-diamino-2.5-dimethylhexane, heptamethylene - diamine, butylene - diamine, N-cyclohexyl-ethylene-diamine, N-(3-hydroxy - propyl) - ethylene - diamine, N.N1 - diethyl - octamethylene - diamine, N - isobutyl - propylene-diamine and N.N1-dipropyl-ethylene-diamine. Other specified diamines are: those having formula wherein Y represents (6-position): ethyl, normal hexyl, normal octyl, and (41-methyl-phenyl); and (5-position): secondary-butyl, phenyl.  Other specified solvents are: chlorobenzene and toluene.  The reactants may also be dispersed in water.  N.N1 - Di - (2 - methyl - cyclohexyl) - ethylene - diamine, used in example 2, is prepared by reacting 2-methyl-cyclohexyl-amine with ethylene chloride or ethylene bromide and neutralizing the resulting hydrohalide with aqueous sodium hydroxide.ALSO:An insecticidal and fungicidal composition comprises an active toxicant, viz., an amine salt of a dinitro-phenol having the formula: <FORM:0593957/VI/1> wherein: n represents an integer, W represents an integer not greater than 2, each R represents a hydrogen atom or an alkyl, hydroxy-alkyl, or cyclo-alkyl radical, and Y represents an aryl, cycloalkyl, or alkyl radical, and a known insecticide or an inert diluent.  In examples 7, 8, 10, 11 and 13 there are ground together to obtain a concentrate suitable for adding to water to prepare a spray composition: (7) ethylene-diamine mono-salt of 2.4- dinitro-6-cyclohexyl-phenol, bentonite and sodium lauryl sulphate; (8) propylene-diamine mono-salt of 2.4-dinitro-6-methyl-phenol, diatomaceous earth and sodium lauryl sulphate; (10) propylene-diamine di-salt of a.4-dinitro-6-phenyl-phenol and sodium lauryl sulphate; (11) as in (7) followed by preparation of spray composition; (13) N-(2-hydroxy-ethyl)-ethylene-diamine di-salt of 2.4-dinitro-6-cyclohexyl-phenol and sodium lauryl sulphate.  In example (9) N-(2-hydroxy-ethyl)-ethylene-diamine di-salt of 2.4-dinitro-6-cyclohexyl-phenol is ground with diatomaceous earth to obtain a fungicidal dust.  In example 12 the ethylene diamine mono salt of the phenol of (9) is treated as in (9).  Other specified inert carriers are: volcanic ash, bentonite, talc and finely divided wood flour.  Other components are: wetting, sticking and dispersing agents such as glyceryl oleate, alkali metal caseinates, aluminium naphthenate, alkali metal salts of sulphonated aromatic hydrocarbons and phenols, partially neutralized sulphuric acid derivatives of fatty acids and oils, blood albumen, and soap; other insecticidal and fungicidal agents are: petroleum, fish and vegetable oils; lead arsenate, sulphur and copper sprays.