Patent GB-546018-A (GB)
Title: Improvements in or relating to the manufacture of insecticidal and fungicidal amine salts of dinitro-phenols
IPC: B27K3/42
Filed: 1940-09-19
Abstract: 546,018. Phenol-amine salts; insecticides and fungicides. ABBEY, A. (Dow Chemical Co.). Sept. 19, 1940, No. 14352. [Class 2 (iii)] [Also in Group VI] Salts of dinitro-phenols and cyclohexylamine which may be substituted or not and which are suitable as insecticides and fungicides are prepared by reacting the amine compound with a substantially equimolecular proportion of the phenol in an organic solvent such as benzene, chlorbenzene or alcohol. The sparingly soluble salt which separates is freed from an excess of either component by washing with an organic solvent. The preferred raction temperature is between 40‹ C. - 120‹ C. The dinitro-phenols which are used in the present invention are characterized by the presence of one nitro group in the para position and another in one of the ortho positions to the hydroxyl group. In addition there may be present as additional substituents an aryl, cycloalkyl, or a lower alkyl radical containing at least two carbon atoms. The amine compound may comprise unsubstituted cyclohexylamine, methylcyclohexylamine, or dicyclo-hexylamine. In addition, there may be present as substituents halogen atoms and aryl, aralkyl, cycloalkyl, or alkyl groups. When alkyl groups are present these may contain from 1-8 carbon atoms. Examples are given of the preparation of salts from the following pairs of substituents. (1) 2:4 - dinitro - 6 - cyclohexyl phenol and dicyclohexylamine. (2) 2:4 - dinitro - 6 - cyclohexyl phenol and 2-methyl-cyclohexylamine. (3) 2:4-dinitro-6-cyclohexyl phenol and di- (2-methyl-cyclohexyl) amine. (4) 2:4-dinitro - 6- cyclohexyl phenol and cyclohexylamine. (5) 2:4-dinitro-6-ethyl phenol and dicyclohexylamine. (6) 2:4-dinitro-6-n-hexyl phenyl and dicyclohexylamine. (7) 2:4-dinitro-6-phenyl phenol and dicyclohexylamine. (8) 2:4-dinitroalpha-naphthol and dicyclohexylamine. (9) 2:4-dinitro-6-chloro-phenol and dicyclohexylamine. (10) 2:4-dinitro-6-methyl phenol and dicyclohexylamine. (11) 2:4-dinitro-phenol and di-cyclohexylamine. Other 2:4-di-nitrophenols mentioned include the 5-anilino-, 5- naphthylamino-, 5-cyclohexyl-, 6-cyclo-pentyl-, 6-tertiary-octyl-, 6-bromo-phenol, and 2:4- dinitro-carvacrol. Additional cyclohexylamines mentioned include the 3-bromo-, mono-, and di-3:5-dimethyl-, mono-, and di-3 methyl-, mono-, and di-4 methyl-, mono-, and di-3 phenyl-, mono-, and di-2-benzyl-, mono-, and di-2-cyclohexyl-, mono-, and di-2-ethyl-, mono-, and di-2:6-diethyl-, and mono-, and di-4- phenyl-cyclo-hexylamines. The salts have in all cases a very low solubility in organic solvents, and a water solubility consistently below 0.05 gram per 100 grams of water at 25‹ C. The compounds have also a high melting point, stability and low vapour pressure. The compounds may be employed as constituents of both spray and dust compositions and may be compounded with carriers such as diatomaceous earth, bentonite, talc, sulphur, wood flours, inorganic phosphates or lime. Wetting, dispersing, or sticking agents may be added and the salts may be employed in combination with oil emulsions. The preferred concentration of the amine salt when applied to living vegetation is between 0.01 per cent. and 5 per cent. by weight. Additional compounding ingredients referred to include inorganic pigments, organic dyes, lead arsenate, pyrethrum, rotenone, organic thiocyanates, sulphur, cryolite, and copper sprays. Numerous examples of specific compositions are included. U.S.A. Specification 2,029,960 is referred to.