Herbicidally active phenylsubstituted 5-and 6-membered heterocyclic compounds

A compound of formula (I):

• where E is oxygen or sulphur;
• A is CR.sup.3 or N where R.sup.3 is hydrogen;
• alkyl;
• alkenyl;
• alkynyl;
• cyclopropyl;
• cyclopropylmethyl;
• cyclobutyl;
• cyclopentyl;
• cyclohexyl;
• adamantyl or phenyl;
• D completes a 5 or 6-membered non-aromatic heterocyclic ring which optionally contains additional heteroatoms selected from oxygen, nitrogen or sulphur and which is unsubstituted or is substituted by a C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, pyridyl, pyrimidyl, triazinyl, thienyl, furyl or thiazolyl group each of which may be substituted by halogen, cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, aryl such as phenyl, carboxy or carboxyamide in which the groups attached to the N atom may be hydrogen, C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl or phenyl;
• R.sup.1 and R.sup.2 are each independently hydrogen;
• a C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, pyridyl, pyrimidyl, triazinyl, thienyl, furyl or thiazolyl group each of which may be substituted by halogen, cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, aryl such as phenyl, carboxy or carboxyamide in which the groups attached to the N atom may be hydrogen, alkyl, alkenyl, alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl or phenyl;
• or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached, form a pyrrolidino, piperidino, thiomorpholino or morpholino ring each of which may be substituted by one or more methyl groups;
• or R.sup.1 may also be a 3-6 membered cycloalkyl ring substituted by CH.sub.3 or C.ident.CH at the alpha position of the cycloalkyl ring;
• Z represents halogen;
• cyano;
• nitro;
• CHO;
• NHOH;
• ONR.sup.7' R.sup.7" ;
• SF.sub.5 ;
• acylamino;
• COOR.sup.7 ;
• SO.sub.2 NR.sup.8 R.sup.9 ;
• CONR.sup.10 R.sup.11 ;
• OR.sup.12 ;
• NR.sup.13 R.sup.14 or a C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, C.sub.1-10 alkyoxy, C.sub.2-10 alkenyloxy, C.sub.2-10 alkynyloxy, cyclopropyloxy, cyclopropylmethyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, adamantyloxy, phenoxy, C.sub.1-10 alkylthio, C.sub.2-10 alkenylthio, C.sub.2-10 alkynylthio, cyclopropylthio, cyclopropylmethylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, adamantylthio, phenylthio, C.sub.1-10 alkylsulphinyl, C.sub.2-10 alkenylsulphinyl, C.sub.2-10 alkynylsulphinyl, cyclopropylsulphinyl, cyclopropylmethylsulphinyl, cyclobutylsulphinyl, cyclopentylsulphinyl, cyclohexylsulphinyl, adamantylsulphinyl, phenylsulphinyl, C.sub.1-10 alkylsulphonyl, C.sub.2-10 alkenylsulphonyl, C.sub.2-10 alkynylsulphonyl, cyclopropylsulphonyl, cyclopropylmethylsulphonyl, cyclobutylsulphonyl, cyclopentylsulphonyl, cyclohexylsulphonyl, adamantylsulphonyl, phenylsulphonyl, CO C.sub.1-10 alkyl, CO C.sub.2-10 alkenyl, CO C.sub.2-10 alkynyl, CO cyclopropyl, CO cyclopropylmethyl, CO cyclobutyl, CO cyclopentyl, CO cyclohexyl, CO adamantyl, COphenyl, pyridyl, pyrimidyl, triazinyl, thienyl, furyl or thiazolyl group each of which may be substituted by halogen, cyano, nitro, amino, mono- and dialkylamino in which the alkyl groups have from 1 to 6 or more carbon atoms, acylamino, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 alkylsulphonyl, alkoxy carbonyl wherein the alkoxy group may have from 1 to 6 or more carbon atoms, aryl such as phenyl, carboxy or carboxyamide in which the groups attached to the N atom may be hydrogen, alkenyl, alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl or phenyl;
• where R.sup.7, R.sup.7',R.sup.7", R.sup.8, R.sup.9, R.sup.10 and R.sup.11 are independently H or C.sub.1-10 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl or phenyl;
• R.sup.12 is hydrogen;
• SO.sub.2 C.sub.1-10 alkyl;
• SO.sub.2 C.sub.2-10 alkenyl;
• SO.sub.2 C.sub.2-10 alkynyl;
• SO.sub.2 cyclopropyl;
• SO.sub.2 cyclopropylmethyl;
• SO.sub.2 cyclobutyl;
• SO.sub.2 cyclopentyl;
• SO.sub.2 cyclohexyl;
• SO.sub.2 adamantyl;
• SO.sub.2 phenyl or COR.sup.15 ;
• R.sup.13 and R.sup.14 are independently C.sub.1-10 alkyl;
• C.sub.2-10 alkenyl;
• C.sub.2-10 alkynyl;
• cyclopropyl;
• cyclopropylmethyl;
• cyclobutyl;
• cyclopentyl;
• cyclohexyl;
• adamantyl;
• phenyl;
• C.sub.1-10 alkyoxy;
• C.sub.2-10 alkenyloxy;
• C.sub.2-10 alkynyloxy;
• cyclopropyloxy;
• cyclopropylmethyloxy;
• cyclobutyloxy;
• cyclopentyloxy;
• cyclohexyloxy;
• adamantyloxy;
• phenoxy or a group R.sup.12 ;
• R.sup.15 is OR.sup.16 ;
• NR.sup.17 R.sup.18 ;
• hydrogen;
• C.sub.1-10 alkyl;
• C.sub.2-10 alkenyl;
• C.sub.2-10 alkynyl;
• cyclopropyl;
• cyclopropylmethyl;
• cyclobutyl;
• cyclopentyl;
• cyclohexyl;
• adamantyl or phenyl;
• R.sup.16 is C.sub.1-10 alkyl;
• C.sub.2-10 alkenyl;
• C.sub.2-10 alkynyl;
• cyclopropyl;
• cyclopropylmethyl;
• cyclobutyl;
• cyclopentyl;
• cyclohexyl;
• adamantyl or phenyl;
• R.sup.17 and R.sup.18 are independently hydrogen;
• C.sub.1-10 alkyl;
• C.sub.2-10 alkenyl;
• C.sub.2-10 alkynyl;
• cyclopropyl;
• cyclopropylmethyl;
• cyclobutyl;
• cyclopentyl;
• cyclohexyl;
• adamantyl or phenyl provided that when there are two or more substituents Z, they may be the same or different;
• and m is 0 or an integer from 1 to 5.