Patent GB-843883-A (GB)
Title: New aromatic ethers
IPC: C07C59/70
Filed: 1958-05-23
Abstract: The invention comprises compounds of the formula: <FORM:0843883/IV(b)/1> where Y represents a hydrogen or chlorine atom or a methyl, formyl or hydroxymethyl group, A represents a divalent aliphatic hydrocarbon group containing two or three carbon atoms and R represents a carboxyl, alkoxycarbonyl carbamoyl or cyano group, including, where R is a carboxyl group, salts thereof; and a process for their preparation by reacting an alkali metal derivative of an alcohol of the formula: <FORM:0843883/IV(b)/2> with a compound of the formula X-CH2-R, or an alkali metal derivative of a phenol of the formula: <FORM:0843883/IV(b)/3> with a compound of the formula X-A-O-CH2-R, where X is a halogen atom or a sulphonic acid residue, preferably carrying out the reaction in an inert organic solvent, and followed if desired, by conversion by known methods of the group R into another group R or in the case of a starting material in which Y is a formyl group, of this formyl group into a hydroxymethyl group. The examples describe the preparation of 2 - (4 - chlorophenoxy) ethoxyacetic acetic, its nitrile and methyl ester; 2-(2,4-dichlorophenoxy) - ethoxyacetic acid; its diethylamine and triethanolamine salt, amide, nitrile and isopropyl ester; 2-(2-methyl-4-chloro-phenoxy) ethoxyacetic acid and its nitrile; 3-(4:chlorophenoxy)-propoxyacetic acid and its nitrile; 2 - (4 - chlorophenoxy) - propoxyacetic acid and its nitrile; 2-(2-formyl-4-chlorophenoxy)-ethoxyacetic acid and its nitrile and 2-(2-hydroxymethyl - 4 - chlorophenoxy) ethexyacetic acid.  The acids may be converted into their acid chlorides and these may be reacted with alcohols to form the esters.ALSO:Plant growth regulant composition comprise as active ingredient a compound of the formula: <FORM:0843883/I/1> where Y represents a hydrogen or chlorine atom or a methyl, formyl or hydroxymethyl group, A represents a divalent aliphatic hydrocarbon group containing 2 or 3 carbon atoms and R represents a carboxyl (including salts thereof), alkoxy-carboxyl, carbamoyl or cyano group; in association with an inert carrier or diluent, the concentration of the active compound being at least 0,1 p.p.m. by weight of the carrier.  The composition may be in solid or liquid form using for example water, talc or clay together with a wetting, dispersing or emulsifying agent.  The examples describe aqueous solutions of 2-(4-chlorophenoxy) ethoxy-acetic acid sodium salt and 2-(2, 4-dichlorophenoxy) ethoxy-acetic acid diethylamine and triethanolamine salt together with a wetting agent and a xylene solution of isopropyl 2-(2, 4-dichlorophenoxy) ethoxy-acetate together with a phenol-ethylene oxide condensate.ALSO:Herbicidal and plant growth regulant compositions comprise as active ingredient an aryloxyalkoxyaliphatic compound of the formula:  <FORM:0843883/VI/1> where Y represents a hydrogen or chlorine atom or a methyl, formyl or hydroxymethyl group, A represents a divalent aliphatic hydrocarbon group containing 2 or 3 carbon atoms and R represents a carboxyl, (including salts thereof), alkoxycarbonyl, carbamoyl or cyano group; in association with an inert carrier or diluent, the concentration of the active ingredient being at least 0,1 part per million parts by weight of carrier or diluent.  The composition may be in solid or liquid form using for example water, talc or clay together with a wetting, dispersing or emulsifying agent.  The examples describe aqueous solutions of 2-(4-chlorophenoxy) ethoxyacetic acid sodium salt and 2-(2,4 . dichlorophenoxy) ethoxyacetic acid diethylamine and triethanolamine salt together with a wetting agent and a xylene solution of isopropyl 2-(2,4 - dichlorophenoxy) - ethoxyacetate together with a phenol-ethylene oxide condensate.