초록 ▼

Herbicides derived from 2-cyano-1,3-diones have the formula: [ STR 1 ] wherein R, R.sup.1, R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are as defined in the description. The compounds are intended for use pre- and post-emergence as selective herbicides in maize and a large number of other monocotyledon cro

Herbicides derived from 2-cyano-1,3-diones have the formula: [ STR 1 ] wherein R, R.sup.1, R.sup.2 R.sup.3, R.sup.4 and R.sup.5 are as defined in the description. The compounds are intended for use pre- and post-emergence as selective herbicides in maize and a large number of other monocotyledon crops.

대표청구항 ▼

[ What is claimed is:] [1.] A compound of the formula [ STR 54 ] wherein: R is:straight- or branched-chain alkyl having up to six carbon atoms, optionally substituted by one or more halogen; orcycloalkyl having from three to six carbon atoms, optionally bearing one or more R.sup.7 substituents;R.sup

[ What is claimed is:] [1.] A compound of the formula [ STR 54 ] wherein: R is:straight- or branched-chain alkyl having up to six carbon atoms, optionally substituted by one or more halogen; orcycloalkyl having from three to six carbon atoms, optionally bearing one or more R.sup.7 substituents;R.sup.1 is hydrogen;each of R.sup.2, R.sup.3, R.sup.4 and R.sup.5, which can be the same or different, is:hydrogen;straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;straight- or branched-chain alkyl having up to six carbon atoms, substituted by an --OR.sup.6 group;halogen;phenyl, optionally substituted by from one to three R.sup.21 groups, which can be the same or different; or--COR.sup.7, nitro, cyano, --CO.sub.2 R.sup.6, --S(O).sub.n R.sup.9, --O(CH.sub.2).sub.m OR.sup.6, --N(R.sup.12)SO.sub.2 R.sup.8, --CONR.sup.10 R.sup.15 or --OR.sup.61 ;provided that at least one of R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is --N(R.sup.12)SO.sub.2 R.sup.8 ;R.sup.6 is:straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen; orcycloalkyl having from three to six carbon atoms;R.sup.61 is:straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;cycloalkyl having from three to six carbon atoms; orphenyl, optionally substituted by from one to five R.sup.21 groups, which can be the same or different;R.sup.7 is:straight- or branched-chain alkyl having up to six carbon atoms, optionally substituted by one or more halogen; orcycloalkyl having from three to six carbon atoms;R.sup.8 is:straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;cycloalkyl having from three to six carbon atoms;phenyl, optionally substituted by from one to five R.sup.21 groups, which can be the same or different; or--NR.sup.10 R.sup.11 ;R.sup.9 is:straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;cycloalkyl having from three to six carbon atoms; orphenyl, optionally substituted by from one to five R.sup.21 groups, which can be the same or different;R.sup.10 is:hydrogen; orstraight- or branched-chain alkyl having up to six carbon atoms, optionally substituted by one or more halogen;R.sup.11 is:straight- or branched-chain alkyl having up to six carbon atoms, optionally substituted by one or more halogen;provided that when R.sup.10 and R.sup.11 are part of a group --NR.sup.10 R.sup.11 they can, together with the nitrogen to which they are attached, form a five or six membered ring optionally having one additional hetero ring atom which is oxygen or nitrogen, said ring being optionally substituted by one or more alkyl, each having up to three carbon atoms;R.sup.12 is:hydrogen;straight- or branched-chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;cycloalkyl having from three to six carbon atoms;phenyl, optionally substituted by from one to five R.sup.21 groups, which can be the same or different; or--OR.sup.17 ;R.sup.15 is:R.sup.7 or --OR.sup.17 ;provided that when R.sup.10 and R.sup.15 are part of a group --CONR.sup.10 R.sup.15 they can, together with the nitrogen to which they are attached, form a 5 or 6 membered ring optionally having one additional hetero ring atom which is oxygen or nitrogen, said ring being optionally substituted by one or more alkyl, each having up to 3 carbon atoms;R.sup.17 is:straight- or branched-chain alkyl having up to six carbon atoms;R.sup.21 is:halogen;straight- or branched-chain alkyl having up to three carbon atoms, optionally substituted by one or more halogen; ornitro, cyano, --S(O).sub.n R.sup.7 or --OR.sup.7 ;m is one, two or three; andn is zero, one or two;or an agriculturally acceptable salt, metal complex or enolic tautomeric form thereof. [13.] A compound of formula: [ STR 56 ] wherein: R represents:straight- or branched-chain alkyl having from 1 to 6 carbon atoms, optionally substituted by one or more halogen which may be the same or different; orcycloalkyl having from 3 to 6 carbon atoms, optionally bearing one or more substituents which may be the same or different selected from the group consisting of R.sup.51 and halogen, wherein R.sup.51 is as defined below;R.sup.1 represents hydrogen;R.sup.2 represents --S(O).sub.n CH.sub.3 or --S(O).sub.n CH.sub.2 CH.sub.3R.sup.3 and R.sup.5, which may be the same or different, each represents:halogen or hydrogen, orstraight- or branched-chain alkyl having from 1 to 6 carbon atoms, bearing a substituent --OR.sup.51, wherein R.sup.51 is as defined below;or a member selected from the group consisting of R.sup.51, cyano, --OR.sup.51, --O(CH.sub.2).sub.m OR.sup.51 and --CO.sub.2 R.sup.51, wherein R.sup.51 and m are as defined below;provided that at least one of R.sup.3 and R.sup.5 is hydrogen;R.sup.4 represents:halogen or hydrogen, orstraight- or branched-chain alkyl having from 1 to 6 carbon atoms bearing a substituent --OR.sup.51, wherein R.sup.51 is as defined below; ora member selected from the group consisting of R.sup.51, cyano, --SR.sup.41, --OR.sup.51, --O(CH.sub.2).sub.m OR.sup.51 and --CO.sub.2 R.sup.51, wherein R.sup.51, R.sup.41 and m are as defined below;R.sup.41 and R.sup.51, which may be the same or different, each represents:straight- or branched-chain alkyl having from 1 to 6 carbon atoms; R.sup.51 is optionally substituted by one or more halogen which may be the same or different;m is an integer from 1 to 3; andn is zero, 1 or 2;with the proviso that when n is zero, R.sup.4 does not represent --SR.sup.41 ;an enolic tautomeric form thereof,or an agriculturally acceptable salt of said enolic tautomeric form. The compound according to claim 13, wherein R.sup.4 is halogen, hydrogen, or --OR.sup.51 or R.sup.51, wherein R.sup.51 is as defined in claim 60. The compound according to claim 14, wherein halogen is chlorine, bromine or fluorine. The compound according to claim 14, wherein R.sup.51 is straight- or branched-chain alkyl having from 1 to 4 carbon atoms, optionally substituted by one or more halogen, which may be the same or different. The compound according to claim 16, wherein halogen is chlorine, bromine or fluorine. The compound according to claim 13, wherein R represents methyl, isopropyl, t-butyl, cyclopropyl or 1-methylcyclopropyl. The compound according to claim 13, wherein R.sup.4 is halogen, methoxy, ethoxy, trifluoromethoxy, methyl or trifluoromethyl. [33.] A compound of formula: [ STR 57 ] wherein: R represents cyclopropyl or methylcyclopropyl;R.sup.1 represents hydrogen;R.sup.2 represents:halogen, orstraight- or branched-chain alkyl having from 1 to 6 carbon atoms, bearing a substituent --OR.sup.51 ; wherein R.sup.51 is as defined below;or a member selected from the group consisting of R.sup.51, cyano, --SR.sup.51, --OR.sup.51, --O(CH.sub.2).sub.m OR.sup.51, and --CO.sub.2 R.sup.51, wherein R.sup.51 and m are as defined below;R.sup.3 and R.sup.5, which may be the same or different, each represents:halogen or hydrogen, orstraight- or branched-chain alkyl having from 1 to 6 carbon atoms, bearing a substituent --OR.sup.51, wherein R.sup.51 is as defined below;or a member selected from the group consisting of R.sup.51, cyano, --OR.sup.51, --O(CH.sub.2).sub.m OR.sup.51 and --CO.sub.2 R.sup.51, wherein R.sup.51 and m are as defined below;provided that at least one of R.sup.3 and R.sup.5 is hydrogen;R.sup.4 represents --S(O).sub.n R.sup.41, wherein R.sup.41 and n are as defined below;R.sup.41 and R.sup.51, which may be the same or different, each represents:straight- or branched-chain alkyl having from 1 to 6 carbon atoms, R.sup.51 is optionally substituted by one or more halogen which may be the same or different;n is zero, 1 or 2; m is an integer from 1 to 3;an enolic tautomeric form thereof,or an agriculturally acceptable salt of said enolic tautomeric form.