Patent GB-781413-A (GB)
Title: New ethers and thioethers and processes for their preparation
IPC: C07D309/40
Filed: 1955-12-23
Abstract: The invention comprises compounds of the formula <FORM:0781413/IV (a)/1> where R is alkyl, X is O or NH, Y is O or S, and Ar is aryl, which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms.  The compounds are prepared (1) by the action of H-Y-Ar on the appropriate pyrones or pyridones having a -CH2Z substituent where Z is a reactive ester group such as halide, sulphuric or sulphonic ester, preferably in a solvent at 50-100 DEG C. in the presence of a basic condensing agent, or (2) by the alkylation of the corresponding 5-hydroxy compounds.  In addition the pyridones may be made from the pyrones by heating with ammonia. Examples show the preparation by method (1) of 2-aryloxymethyl-5 - methoxy - 4 - pyrones where aryl group is phenyl, b -naphthyl, and the following substituted phenyl groups:-chloro (3 isomers), 2:4-dichloro, 2:4:6-trichloro, pentachloro, methyl (3 isomers), dimethyl (6 isomers), 2:4:6-trimethyl, 2-methyl-4- and -6-chloro, 3-methyl-4-chloro, 4-methyl-2-chloro, 2-methyl-4:6-dichloro, 4 - methyl - 2:6 - dichloro, 2:4 - dimethyl-6-chloro, 3:5-dimethyl-4-chloro, 4-isopropyl, 4-cyclohexyl, 2- and 4-nitro, 2-methylol, 2:4 - dichloro - 6 - methylol, 2 - chloro - 4:6 - dimethylol, 4 - chloro - 2:6 - dimethylol, 4 - methyl - 2 - methylol, 4 - methyl - 2:6 - dimethylol, 2:5 - dimethyl - 4 - methylol, 3:4 - dimethyl - 6 - methylol, 3 - methoxy, and 2 - methoxy-4-, -5- and -6-methyl; also 2-(21-methylolphenoxymethyl) - 5 - ethoxy - 4 - pyrone and 2-(41-chlorophenylthiomethyl) - 5 - methoxy-4-pyrone.  I further examples 2-(41 chlorophenoxymethyl) - 5 - methoxy - 4 - pyridone (hydrochloride described) and 2-(21-methyl - 61 - chlorophenoxymethyl) - 5 - methoxy-4-pyridone are made from the corresponding pyrones and ammonia.  It is also stated that Ar may also be ethylphenyl, ethoxyphenyl or hydroxy-ethyl-phenyl.ALSO:Compositions for use as plant growth regulants contain as active ingredient a compound of the formula: <FORM:0781413/I/1> where R is alkyl, X is O or NH, Y is O or S and Ar is aryl which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms.  The compositions may be in the form of powders, sprays, aerosols, emulsions or solutions in organic or aqueous organic solvents.  There may also be present wetting agents, synergists and other plant growth regulants.  In an example 2-(21 : 41-dichlorophenoxymethyl)-5-methoxy-4-pyrone is dissolved in dimethylformamide and diluted with water to give a solution which enhances root formation when plant stems are soaked with it.  Many other suitable compounds are mentioned.ALSO:Compositions for use as systemic fungicides or herbicides contain as essential ingredient a compound of the formula <FORM:0781413/VI/1> where R is alkyl, X is O or NH, Y is O or S and Ar is aryl which may have one or more alkyl, alkoxy, hydroxyalkyl, nitro or halogen substituents; the alkyl and alkoxy groups have not more than 4 carbon atoms.  The compositions may be in the form of powders, sprays, aerosols, emulsions or solutions in organic or aqueous organic solvents.  There may also be present wetting agents, synergists, and other plant-growth regulants or fungicides.  In examples, fungicides are made of (1) 2-(21-methyl - 41 - chlorophenoxymethyl) - 5 - methoxy-4-pyrone dispersed in water with the aid of a wetting agent; and (2) 2-(31:51-dimethylphenoxy - methyl) - 5 - methoxy - 4 - pyrone and talc similarly dispersed; herbicides are made from (3) 2-(2-(21:41-dichlorophenoxymethyl) - 5 - methoxy - 4 - pyrone; and (4) 2-(41 - chlorophenoxymethyl) - 5 - methoxy - 4-pyrone, in each case dissolved in toluene and acetone and dispersed in water with the aid of a wetting agent. Many other suitable compounds are mentioned.