Heterocyclic phenyl ethers and herbicides containing same

An herbicidal composition consisting essentially of an inert carrier and an herbicidally effective amount of a compound of the formula ##STR90## in which R is halogen, CF.sub.3, NO.sub.2, CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,

• A is O, S, NH, or N-(C.sub.1 -C.sub.4)alkyl,
• R.sub.1 is H or C.sub.1 -C.sub.4 alkyl,
• Z is a group of the formula ##STR91## n is zero or 1 or 2, R.sub.2 is H, C.sub.1 -C.sub.12 alkyl (optionally substituted by 1 to 6 halogen atoms, OH, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.6 alkoxy-C.sub.2 -C.sub.6 alkoxy, halo-C.sub.1 -C.sub.2 alkoxy, methoxyethoxy-ethoxy, C.sub.1 -C.sub.4 alkylamino, di-C.sub.1 -C.sub.4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C.sub.1 -C.sub.4 alkyl);
• C.sub.5 -C.sub.6 cycloalkyl (optionally substituted by halogen or methyl);
• C.sub.3 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.6 alkenyl or C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.4 -alkinyl (optionally substituted once or twice by C.sub.1 -C.sub.6 alkyl, phenyl, halogen or C.sub.1 -C.sub.2 alkoxy);
• phenyl (optionally substituted one to three times by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, NO.sub.2, or CF.sub.3);
• furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base;
• R.sub.3 is C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.2)-alkyl, the phenyl radical optionally being substituted once or twice by C.sub.1 -C.sub.4 alkyl and/or halogen, C.sub.3 -C.sub.6 alkenyl, or phenyl (optionally substituted once or twice by C.sub.1 -C.sub.4 alkyl and/or halogen),
• R.sub.4 and R.sub.5, which are identical or different, are H, C.sub.1 -C.sub.6 alkyl, hydroxy-(C.sub.1 -C.sub.6)-alkyl, C.sub.5 -C.sub.6 cycloalkyl, or phenyl (optionally substituted one to three times by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or CF.sub.3), with the proviso that R.sub.4 and R.sub.5 cannot be phenyl at the same time;
• or wherein R.sub.4 and R.sub.5 together form a methylene chain having 2, 4 or 5 CH.sub.2 -groups in which one CH.sub.2 group may be replaced by O, NH, or N(CH.sub.3);
• R.sub.6 is H or CH.sub.3,
• R.sub.7 is H, CH.sub.3, or C.sub.2 H.sub.5,
• R.sub.8 is H, CH.sub.3, C.sub.2 H.sub.5 or phenyl,
• R.sub.9 is C.sub.1 -C.sub.6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C.sub.3 -C.sub.6 alkenyl, phenyl, C.sub.1 -C.sub.4 alkylphenyl C.sub.1 -C.sub.4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and
• R.sub.10 is C.sub.1 -C.sub.4 alkyl or phenyl (optionally substituted once or twice by halogen, CF.sub.3, NO.sub.2, or C.sub.1 -C.sub.4 alkyl).

A method for controlling the growth of undesired weed grasses which comprises treating the infested area with an herbicidally effective amount of a compound of the formula ##STR92## in which R is halogen, CF.sub.3, NO.sub.2, CN, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkylthio,

• A is O, S, NH, or N-(C.sub.1 -C.sub.4)alkyl,
• R is H or C.sub.1 -C.sub.4 alkyl,
• Z is a group of the formula ##STR93## n is zero or 1 or 2, R.sub.2 is H, C.sub.1 -C.sub.12 alkyl (optionally substituted by 1 to 6 halogen atoms), OH, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.6 alkoxy-C.sub.2 -C.sub.6 -alkoxy, halo-C.sub.1 -C.sub.2 alkoxy, methoxyethoxy-ethoxy, C.sub.1 -C.sub.4 alkylamino, di-C.sub.1 -C.sub.4 alkylamino, phenyl, oxiranyl and/or phenoxy which latter may be substituted once or twice by halogen or C.sub.1 -C.sub.4 alkyl;
• C.sub.5 -C.sub.6 cycloalkyl (optionally substituted by halogen or methyl);
• C.sub.3 -C.sub.6 alkenyl, halo-C.sub.3 -C.sub.6 alkenyl or C.sub.5 -C.sub.6 cycloalkenyl, C.sub.3 -C.sub.4 alkinyl (optionally substituted once or twice by C.sub.1 -C.sub.6 alkyl, phenyl, halogen or C.sub.1 -C.sub.2 alkoxy);
• phenyl (optionally substituted one to three times by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen NO.sub.2, or CF.sub.3);
• furfuryl, tetrahydrofurfuryl, or the cation equivalent of an organic or inorganic base;
• R.sub.3 is C.sub.1 -C.sub.6 alkyl, phenyl-(C.sub.1 -C.sub.2)-alkyl, the phenyl radical optionally being substituted once or twice by C.sub.1 -C.sub.4 alkyl and/or halogen, C.sub.3 -C.sub.6 alkenyl, or phenyl (optionally substituted once or twice by C.sub.1 -C.sub.4 alkyl and/or halogen);
• R.sub.4 and R.sub.5, which are identical or different, are H, C.sub.1 -C.sub.6 alkyl, hydroxy-(C.sub.1 -C.sub.6)-alkyl, C.sub.5 -C.sub.6 cycloalkyl, or phenyl (optionally substituted one to three times by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen or CF.sub.3), with the proviso that R.sub.4 and R.sub.5 cannot be phenyl at the same time;
• or wherein R.sub.4 and R.sub.5 together form a methylene chain having 2, 4 or 5 CH.sub.2 -groups in which one CH.sub.2 group may be replaced by O, NH, or N(CH.sub.3);
• R.sub.6 is H or CH.sub.3,
• R.sub.7 is H, CH.sub.3, or C.sub.2 H.sub.5,
• R.sub.8 is H, CH.sub.3, C.sub.3 H.sub.5 or phenyl,
• R.sub.9 is C.sub.1 -C.sub.6 alkyl (optionally substituted one to three times by halogen), cyclopropyl, C.sub.3 -C.sub.6 alkenyl, phenyl, C.sub.1 -C.sub.4 alkylphenyl C.sub.1 -C.sub.4 alkoxyphenyl, halophenyl, trifluoromethylphenyl or nitrophenyl and
• R.sub.10 is C.sub.1 -C.sub.4 alkyl or phenyl (optionally substituted once or twice by halogen, CF.sub.3, NO.sub.2, or C.sub.1 -C.sub.4 alkyl).