Patent GB-698971-A (GB)
Title: Improvements relating to fungicidal compositions
IPC: C07D215/24
Filed: 1951-05-18
Abstract: A fungicidal composition comprises the product of reaction of a phenol and a water-insoluble metal quinolinolate.  Any desired proportion of reactants may be used, whether or not the resulting mass contains an unreacted quantity of a reactant employed in excess. Phenols solid at room temperature are preferably melted, and those liquid at room temperature are reacted at or below the boiling point of the phenol.  Metal quinolinolates specified are the calcium, barium, magnesium, beryllium, lead, mercury, manganese, cobalt, nickel, iron copper, cadmium, silver, thallium, tin, zinc and aluminium salts of 2-hydroxyquinoline, 4-methyl 2-hydroxyquinoline, 4-hydroxyquinoline, 2 - methyl - 4 - hydroxyquinoline, 5 - hydroxyquinoline, 6 - hydroxyquinoline, 7 - hydroxyquinoline and 8-hydroxyquinoline.  Preferred salts are copper 5,7-dichloro- and 5,7-dibromo-8-quinolinolate.  Preferred phenols have the general formula <FORM:0698971/IV (b)/1> where X represents H, OH, CHO, NO2, Cl, Br, alkyl, aryl, alkaryl, aralkyl, CONH2, COOR (R being H, alkyl or aryl) or OR1 (R1 being alkyl or aryl) and n represents an integer from 1 to 5, and where n is greater than 1 the radicals X are either alike or dissimilar.  Examples are phenol, o-amyl phenol, o-m-p-cresols, p-chloro-m-cresol, tert-butyl m-cresol, p-nitrophenol, salicylaldehyde, salicylamide, o-cyclohexyl phenol, resorcinol, pyrogallol, 2,4-dichlorophenol, pentachlorophenol, picric acid, 5-methyl-2-isopropyl phenol, 2,3,4,6-tetrachlorophenol, tetrachlorohydroquinone, 6-tert-butyl-3 methyl phenol, xylenol, chloroxylenol, 4-phenyl phenol, 2,4,6-tribromophenol, p-tolyl phenol, xylyl phenol, phenyl salicylate, methyl salicylate, p-hydroxypropiophenone, bis (5-chloro-2-hydroxy phenyl) methane.ALSO:A fungicidal composition comprises the product of reaction of a phenol and a water-insoluble metal quinolinolate.  Any desired proportions of reactants may be used, whether or not the resulting mass contains an unreacted quantity of a reactant employed in excess.  Phenols solid at room temperature are preferably melted, and those liquid at room temperature are reacted at or below the boiling point of the phenol.  Metal quinolinolates specified are the calcium, barium, magnesium, beryllium, lead, mercury, manganese, cobalt, nickel, iron, copper, cadmium, silver, thallium, tin, zinc and aluminium salts of 2-hydroxyquinoline, N-methyl 2-hydroxyquinoline, N-hydroxyquinoline, 2-methyl-4-hydroxyquinoline, 5-hydroxyquinoline, 6-hydroxyquinoline, 7-hydroxyquinoline and 8-hydroxyquinoline.  Preferred salts are copper, 5,7-dichloro- and 5,7-dibromo-8-quinolinolate.  Preferred phenols have the general formula <F\1> where X represents H, OH, CHO, NO2, Cl, Br, alkyl, aryl, alkaryl, aralkyl, CONH2, COOR (R being H, alkyl or aryl) or OR1 (R1 being alkyl or aryl) and n represents an integer from 1 to 5, and where n is greater than 1 the radicals X are either alike or dissimilar.  Examples are phenol, o-amyl phenol, o-m-p-cresols, p-chloro-m-cresol, tert-butyl m-cresol, p-nitrophenol, salicylaldehyde, salicylamide, o-cyclohexyl phenol, resorcinol, pyrogallol, 2,4-dichlorophenol, pentachlorophenol, picric acid, 5-methyl-2-isopropyl phenol, 2,3,4,6-tetrachlorophenol, tetrachlorohydroquinone, 6-tert-butyl-3 methyl phenol, xylenol, chloroxylenol, 4-phenyl phenol, 2,4,6-tribromophenol, p-tolyl phenol, xylyl phenol, phenyl salicylate, methyl salicylate, p-hydroxypropiophenone, bis(5-chloro-2-hydroxyphenyl) methane. The reaction products may be dissolved or dispersed in a solvent such as benzol, toluol, methanol, acetone; vegetable oils, mineral oils, fish oils, molten resin, saturated and unsaturated aliphatic acids of C8-18, and mixtures thereof.  They may be used as sprays, impregnants and coating in the treatment of canvas, webbing, threads, yarns, rope, cord, wood, paper, leather and resins.  They may be incorporated in varnishes, sealers, lacquers, paints and the like; mineral and synthetic waxes and greases; resins such as phenol-aldehyde, urea-aldehyde, melamine-aldehyde; polymerizable polyester resins, alkyds including unsaturated alkyl resins, vinyl resins and polyethylene resins.  Other additions are plasticizers e.g. glycol, glycerin, sorbitol, pentaerythritol and mannitol; driers e.g. zinc naphthenate, lead naphthenate, cobalt naphthenate and zinc octoate; anti-oxidants e.g. phenyl salicylate, tert-butyl catechol and guaicol; cellulose derivatives e.g. nitrocellulose, cellulose acetate and ethyl cellulose.  Solutions may be rendered water proofing by the addition of paraffin wax, beeswax, carnauba wax, spermaceti wax, synthetic wax or mixtures thereof.