A PROCESS FOR THE PREPARATION OF 4 SUBSTITUTED PYRIDYL 2 OXY PHENOXY ALKANE CARBOXYLIC ACIDS AND DERIVATIVES THEREOF

摘要

1491274α- [4 - (5 - mono-substituted or 3,5 - di - substituted - pyridyl - 2 - oxy)phenoxy]- alkanecarboxylic acid derivatives ISHIHARA SANGYO KAISHA Ltd 10 Oct 1975 [17 Oct 1974 13 March 1975] 41560/75 Heading C2C Novelα- [4 - (5 - mono-substituted or 3,5 - di - substituted - pyridyl - 2 - oxy)- phenoxy] - alkanecarboxylic acid derivatives of the formula wherein X is a halogen atom; Y is a hydrogen atom, a halogen atom or a methyl group; R is a hydrogen atom or a straight or branched chain (C 1 -C 6 ) alkyl group; and R1 is a hydroxy group; a (C 1 -C 9 ) alkoxy group in which the alkyl moiety thereof may have a straight or a branched chain and may be substituted with one or more of a halogen atom or a hydroxy group; an -(OC 2 H 4 ) n -O- (C 1 -C 4 ) alkyl group in which the alkyl moiety thereof may have a straight or a branched chain and n is 1, 2, 3, 4 or 5; a (C 1 -C 4 ) alkylthio group in which the alkyl moiety thereof may have a straight or a branched chain; a (C 2 -C 4 ) alkenyloxy group; a cyclohexyloxy group in which the cyclohexyl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a phenoxy group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a phenylthio group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a benzyloxy group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; an amino group which may be substituted with one or more of a (C 1 -C 4 ) alkyl group in which the alkyl moiety thereof may have a straight or a branched chain and may be substituted with a hydroxy group; a mono-(C 1 -C 4 ) alkylamino group in which the alkyl moiety thereof may have a straight or a branched chain and is substituted with a -COOR4 group in which R4 is a hydrogen atom, a cation or a straight or branched chain (C 1 -C 4 ) alkyl group; an anilino group in which the aryl moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a benzylamino group; an amino group substituted with a heterocyclic group in which the heterocyclic moiety thereof may be substituted with one or more of a halogen atom or a methyl group; a morpholino group; a piperidino group; an -OM group where M is a cation; or a halogen atom, are prepared by reacting a substituted pyridine of the formula with a substituted phenol of the formula wherein Z is a hydroxy group; a (C 1 -C 5 ) alkoxy group or a group of the formula wherein R3 is a hydroxy group; a (C 1 -C 9 ) alkoxy group or an amino group, in the presence of an alkaline material in an amount of from 1 to 1À2 moles per mole of compound III at a temperature of at least 50‹ C. for 1 to 20 hours to give a substituted pyridyl phenyl ether of the formula and, when Z is other than optionally dealkylating the compound of Formula IV and reacting this compound with anα-haloalkanecarboxylic acid or a derivative thereof having the formula in the presence of an alkaline material in an amount of from 1 to 1À2 moles per mole of compound IV to give a compound of the formula and optionally converting the R3 moiety into R1. The novel compounds possess herbicidal properties.