OPTICALLY ACTIVE ALPHA-PHENOXYPROPIONIC ACID DERVATIVES

摘要

Optically active phenoxypropionic acid derivs. of formula (I) are new. In (I) R is phenoxy, 2-pyridyloxy, 2-benzoxazolyloxy, 2-benzothiazolyloxy or benzyl, all substd. by R1 and R2, R1 is H, halo or CF3 (not H if R is phenoxy, pyridyl oxy or benzyl). R2=H, 1-4C alkyl, halo or NO2, Z is COOR3, COSR4, CONR5R6, CONR7NR8R9 or CSNH2, R3 is H, 1-12C alkyl (opt. substd. by 1-6 halo and/or an OH, 1-6C alkoxy, 1-4C alkylthio, 1-6C alkoxy-(2-6C) alkoxy, 1-2C haloalkoxy, methoxyethoxyethoxy, mono- or di-(1-4C) alkylamino, phenyl, oxiranyl or phenoxy, the last opt. substd. by 1 or 2 halo or 1-4C alkyl), 5-6C cycloalkyl (opt. halogenated), 3-6C alkenyl (opt. halogenated), 5-6C cycloalkenyl, 3-4C alkynyl (opt. substd. by 1 or 2 1-6C alkyl, phenyl, halo or 1-2C alkoxy), phenyl (opt. substd. by 1-3 1-4C alkyl or alkoxy, halo, NO2 and CF3), furfuryl, tetrahydrofurfuryl or the equiv of a base. R4 is 1-6C alkyl (opt. substd. by 1-4C alkoxy, halo or phenyl the phenyl itself opt. substd. by 1-4C alkyl or halo), 3-6C alkenyl, or phenyl opt. substd. by 1-3 halo or 1-4C alkyl, R5 and R6=H, 1-6C alkyl (opt. substd. by OH), 5-6C cycloalkyl, or phenyl (opt. substd. by 1-3 1-4C alkyl or alkoxy, halo or CF3), or together they complete a 2,4 or 5 membered methylene chain in which one CH2 can be replaced by O, NH or NCH3. R5 and R6 cannot both be phenyl, R7 is H or CH3, R8 is H, CH3 or C2H5, R9 is H, CH3, C2H5 or phenyl, Proviso is that when R1=CH3, R2=H and R is phenoxy, then R3 cannot be H. (I) are herbicides useful e.g. for control of Alopecurus myosuroides, Echinochloa crus-galli and Avena fatua in sugar beet and wheat. The D-enantiomer is about twice as active as the racemate.