Herbicidal cyclohexane-1,3-dione derivatives

Claim 2

A compound of formula I, ##STR10## wherein: Y is a linking group selected from the group consisting of: --(CH 2 ) 1 --;--CH(CH 3 )--;--C(CH 3 ) 2 --; --CH(CH 3 )CH 2 --; --G(CH 2 ) m --;--CH 2 GCH 2 --;--C(G)(CH 2 ) m --;--GC(G)--; and --NHC(G)--; wherein: G is selected from oxygen and sulfur; 1is an integer selected from 1 to 3; and m is zero or an integer selected from 1 and 2; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with halogen or cyano; hydroxy; C 1 to C 6 alkoxy; C 1 to C 6 alkylthio; sulfamoyl; N--(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; the group --(CH 2 ) p C(═A)Z wherein p is zero or one, A is selected from oxygen and sulfur, and Z is selected from the group consisting of hydrogen, hydroxy, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, amino, N-(C 1 to C 6 alkyl) amino, N,N-di(C 1 to C 6 alkylamino, N-(C 1 to C 6 alkanoyl)amino, C 1 to C 6 alkyl, and C 1 to C 6 haloalkyl; the group --NR 5 R 6 wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, C 2 to C 6 haloalkanoyl, C 1 to C 6 alkylsulfonyl, and benzoyl; the group --NHC(═B)NR 7 R 8 wherein B is selected from oxygen and sulfur and R 7 and R 8 are independently selected from hydrogen and C 1 to C 6 alkyl; and the group --(CH 2 )q--which bridges two adjacent carbon atoms of the benzene ring and wherein q is an integer selected from 3 or 4; R 1 is selected from the group consisting of: hydrogen; an acyl group; and an inorganic or organic cation; R 2 is selected from the group consisting of: C 1 to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 haloalkenyl; C 2 to C 6 alkynyl; C 3 to C 6 haloalkynyl; and substituted C 1 to C 6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of halogen, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, phenyl and substituted phenyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, and C 1 to C 6 alkylthio; R 3 is selected from the group consisting of: C 1 to C 6 alkyl; C 1 to C 6 fluoroalkyl; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; and phenyl; and R 4 is selected from the group consisting of: hydrogen; halogen; cyano; C 1 to C 6 alkyl; and (C 1 to C 6 alkoxy) carbonyl.

Claim 3

A Compound according to claim 1 wherein: Y is a linking group selected form the group consisting of: --(CH 2 ) 1 --;--CH(CH 3 )--; --C(CH 3 ) 2 --;--CH(CH 3 )CH 2 --; --G(CH 2 ) m --;--CH 2 GCH 2 --;--C(G)(CH 2 ) m --;--GC(G)--; and G--NHC(G)--; wherein: G is selected from oxygen and sulfur; 1 is an integer selected from 1 to 3; and m is zero or an integer selected from 1 and 2; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with halogen or cyano; hydroy; C 1 to C 6 alkoxy; C 1 to C 6 alkylthio; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; the group --(CH 2 ) p C(═A)Z wherein p is zero or one, A is selected from oxygen and sulfur, and Z is selected from the group consisting of hydrogen, hydroxy, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, amino, N-(C 1 to C 6 alkyl)amino, N,N-di(C 1 to C 6 alkyl)amino, N-(C 1 to 6 alkanoyl)amino, C 1 to C 6 alkyl, and C 1 to C 6 haloalkyl; the group --NR 5 R 6 wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, C 2 to C 6 haloalkanoyl, C 1 to C 6 alkylsulfonyl, and benzoyl; the group --NHC(═B)NR 7 R 8 wherein B is selected from oxygen and sulfur and R 7 and R 8 are independently selected from hydrogen and C 1 to C 6 alkyl; and the group --(CH 2 )q-- which bridged two adjacent carbon atoms of the benzene ring and wherein q is an integer selected from 3 or 4; R 1 is selected from the group consisting of: hydrogen; C 2 to C 6 alkanoyl; benzoyl and substituted benzoyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; benzenesulfonyl and substituted benzenesulfonyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, C 1 to C 6 alkyl and C 1 C 6 alkoxy; and an inorganic or an organic cation selected from the alkali metals, the alkaline earth metals the transition metals the ammonium ion and the tri- and tetra(alkyl) ammonium ions wherein alkyl is selected from C 1 to C 6 alkyl and C 1 to C 6 hydroxyalkyl; R 2 is selected from the group consisting of: C 1 to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 haloalkenyl; C 2 to C 6 alkynyl, C 3 to C 6 haloalkynyl; and substituted C 1 to C 6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of halogen, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, phenyl and substituted phenyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy, and C 1 to C 6 alkylthio; R 3 is selected from the group consisting of: C 1 to C 6 alkyl; C 1 to C 6 fluoroalkyl; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; and phenyl; and R 4 is selected from the group consisting of: hydrogen; halogen; cyano; C 1 to C 6 alkyl; and (C 1 to C 6 alkoxy) carbonyl.

Claim 4

A compound according to claim 2 wherein: Y is a linking group selected form the group consisting of: --(CH 2 ) 1 --;--CH(CH 3 )--;--C(CH 3 ) 2 --;--CH(CH 3 )CH 2 --; --G(CH 2 ) m --;--CH 2 GCH 2 --;--C(G)(CH 2 ) m --;--GC(G)--; and --NHC(G)--; wherein: G is selected from oxygen and sulfur; 1 is an integer selected from 1 to 3; and m is zero or an integer selected from 1 and 2; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkoxy; C 1 to C 6 alkylthio; sulfamoyl; N-(C 1 to C 6 alkyl)- sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; the group -(CH 2 ) p C(═A)Z wherein p is zero or one, A is selected from oxygen and sulfur, and Z is selected from the group consisting of hydrogen, hydroxy, C1 to C6 alkoxy, C 1 to C 6 alkylthio, amino, N-(C 1 to C 6 alkyl)amino, N,N-di(C 1 to C 6 alkyl)amino, N-(C 1 to C 6 alkanoyl)amino, C 1 to C 6 alkyl, and C 1 to C 6 haloalkyl; the group --NR 5 R 6 wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, C 2 to C 6 haloalkanoyl, C 1 to C 6 alkylsulfonyl, and benzoyl; the group --NHC(═B)NR 7 R 8 wherein B is selected from oxygen and sulfur and R 7 and R 8 are independently selected from hydrogen and Chd 1 to C 6 alkyl; and the group (CH 2 )q- which bridges two adjacent carbon atoms of the benzene ring and wherein q is an integer selected from 3 or 4; R 1 , is selected from the group consisting of: hydrogen; C 1 to C 6 alkanoyl; benzoyl and substituted benzoyl wherein the benzene ring is substituted with from one to two substituents selected from the group consisting of halogen, nitro, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; an alkali metal cation; an alkaline earth cation; a transition metal cation; the ammonium ion and the tri and tetra(alkyl) ammonium ions wherein alkyl is selected from C 1 to C 6 alkyl and C 1 to C 6 hydroxy-alkyl; R 2 is selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl and C 3 to C 6 alkynyl; R 3 is selected from the group consisting of C 1 to C 6 alkyl; R 4 is selected from the group consisting hydrogen, halogen, C 1 to C 6 alkyl; and (C 1 to C 6 alkoxy) carbonyl.

Claim 5

A compound according to claim 3 wherein: Y is a linking group selected form the group consisting of: --(CH 2 ) 1 --;--CH(CH 3 )--;--C(CH 3 ) 2 --;--CH(CH 3 )CH 2 --; --G(CH 2 ) m --;--CH 2 GCH 2 --;--C(G)(CH 2 ) m--;--GC (G)--; and --NHC(G)--; wherein: G is selected from oxygen and sulfur; 1 is an integer selected from 1 to 3; and m is zero or an integer selected from 1 and 2; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of: halogen; nitro; C 1 to C 6 alkyl; C 1 to C 6 alkoxy; C 1 to C 6 alkylthio; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl) sulfamoyl; the group --(CH 2 ) p --C(═A)Z wherein p is zero or one, A is either oxygen or sulfur, and Z is selected from the group consisting of hydroxy, C 1 to C 6 alkoxy, C 1 to C 6 alkylthio, amino, N-(C 1 to C 6 alkyl) amino, N,N-di(C 1 to C 6 alkyl) amino, C 1 to C 6 alkyl and C 1 to C 6 haloalkyl; the group --NR 5 R 6 wherein R 5 and R 6 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, C 2 to C 6 haloalkanoyl, C 1 to C 6 alkylsulfonyl; and the group --(CH 2 )q--which bridges two adjacent carbon atoms of the benzene ring and wherein q is an integer selected from 3 or 4; R 1 is selected from the group consisting of hydrogen; C 2 to C 6 alkanoyl; benzoyl and substituted benzoyl wherein the benzene ring is substituted with from one to two substituents selected from the group consisting of halogen, nitro, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; an alkali metal cation; an alkaline earth cation; a transition metal cation; the ammonium ion and the tri and tetra(alkyl) ammonium ions wherein alkyl is selected from C 1 to C 6 alkyl and C 1 to C 6 hydroxy alkyl; R 2 is selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl and C 3 to C 6 alkynyl; R 3 is selected from the group consisting of C 1 to C 6 alkyl; and R 4 is hydrogen.

Claim 6

A compound according to claim 4 wherein: Y is a linking group selected form the group consisting of: --(CH 2 ) 1 --;--G(CH 2 ) m --;--CH 2 GCH 2 --; --C(G)(CH 2 ) m --; and --GC(G)--; wherein: G is selected from oxygen and sulfur; 1 is an integer selected from 1 to 3; and m is zero or an integer selected from 1 and 2; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of halogen; C 1 to C 6 alkyl; C 1 to C 6 alkoxy, C 1 to C 6 alkythio; sulfamoyl; N-(C 1 to C 6 alkyl) sulfamoyl; N,N-di(C 1 to C 6 alkyl) sulfamoyl; (C 2 to C 6 alkanoyl; C 2 to C 6 haloalkanoyl; and C 2 to C 6 haloalkanoylamino; R 1 is selected form the group consisting of: hydrogen; C 2 to C 6 alkanoyl; benzoyl; an alkali metal cation; an alkaline earth metal cation; a transition metal cation; the ammonium ion and the tri and tetra (alkyl) ammonium ions wherein alkyl is selected from C 1 to C 6 alkyl and C 1 to C 6 hydroxyalkyl; R 2 is selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl and C 3 to C 6 alkynyl; R 3 is selected from the group consisting of C 2 to C 6 alkyl; and R 4 is hydrogen.

Claim 7

A compound according to claim 5 wherein: Y is a linking group selected from the group consisting of:

Claim 8

--CH 2 --;--CH 2 CH 2 --;--CH 2 CH 2 CH 2 --;--0--;--S--;

Claim 9

--CH 2 --;--CH 2 CH 2 --;--CH 2 CH 2 CH 2 --;--0--;--S--;

Claim 10

--0--CH 2 --;--OCH 2 CH 2 --;--SCH 2 --;

Claim 11

--0--CH 2 --;--OCH 2 CH 2 --;--SCH 2 --;

Claim 12

--CH 2 OCH 2 --;--CH 2 SCH 2 --;--CO--;

Claim 13

--CH 2 OCH 2 --;--CH 2 SCH 2 --;--CO--;

Claim 14

--COCH 2--; --COCH 2 CH 2 --; and --OCO--; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of halogen; C 1 to C 6 alkyl; C 1 to C 6 alkoxy; sulfamoyl; N-(C 1 to C 6 alkyl) sulfamoyl; N,N-di(C 1 to C 6 alkyl) sulfamoyl and C 2 to C 6 alkanoyl; R 1 is selected from the group consisting of hydrogen; C 2 to C 6 alkanoyl; benzoyl, the alkali metal cations; the alkaline earth metal cations and the transition metal cations; R 2 is selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 halo alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl and C 3 to C 6 alkynyl; R 3 is selected from C 1 to C 6 alkyl; and R 4 is hydrogen.

Claim 15

--COCH 2--; --COCH 2 CH 2 --; and --OCO--; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of halogen; C 1 to C 6 alkyl; C 1 to C 6 alkoxy; sulfamoyl; N-(C 1 to C 6 alkyl) sulfamoyl; N,N-di(C 1 to C 6 alkyl) sulfamoyl and C 2 to C 6 alkanoyl; R 1 is selected from the group consisting of hydrogen; C 2 to C 6 alkanoyl; benzoyl, the alkali metal cations; the alkaline earth metal cations and the transition metal cations; R 2 is selected from the group consisting of C 1 to C 6 alkyl, C 1 to C 6 halo alkyl, C 2 to C 6 alkenyl, C 2 to C 6 haloalkenyl and C 3 to C 6 alkynyl; R 3 is selected from C 1 to C 6 alkyl; and R 4 is hydrogen.

Claim 16

A compound according to claim 6 wherein: Y is a linking group selected from the group consisting of: --CH 2 --;--CH 2 CH 2 --;--CH 2 CH 2 CH 2 --;--0--; --0CH 2 --;--0CH 2 CH 2 --;--SCH 2 --; and --COCH 2 --; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of C 1 to C 6 alkyl; C 1 to C 6 alkoxy; N(C 1 to C 6 alkyl) sulfamoyl; N,N-di (C 1 to C 6 alkyl) sulfamoyl and C 1 to C 6 alkanoyl; R 1 is selected from the group consisting of hydrogen; C 2 to C 6 alkanoyl; benzoyl; the alkali metal cations; the alkaline earth metal cations and the transition metal cations; R 2 is selected from C 1 to C 4 alkyl, C 1 to C 4 haloalkyl, C 2 to C 4 alkenyl, C 2 to C 4 haloalkenyl and C 3 to C 4 alkynyl; R 3 is selected from C 1 to C 4 alkyl; and R 4 is hydrogen.

Claim 17

A compound according to claim 7 wherein: Y is a linking group selected from the group consisting of:

Claim 18

--CH 2 --; --CH 2 CH 2 --;--CH 2 CH 2 CH 2 --;--0--;

Claim 19

--CH 2 --; --CH 2 CH 2 --;--CH 2 CH 2 CH 2 --;--0--;

Claim 20

--OCH 2 --;--OCH 2 CH 2 --;--SCH 2 --; and --COCH 2 --; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of methyl, methoxy N-methylsulfamoyl, N,N-dimethyl-sulfamoyl, acetyl and propionyl; R 1 is selected from the group consisting of hydrogen, C 2 to C 6 alkanoyl, and the alkali metal cations; R 2 is selected from the group consisting of C 1 to C 3 alkyl, 2-haloethyl, allyl, 3-halo-allyl and propargyl; and R 3 is selected from C 1 to C 4 alkyl; and R 4 is hydrogen.

Claim 21

--OCH 2 --;--OCH 2 CH 2 --;--SCH 2 --; and --COCH 2 --; n is zero or an integer selected from 1 to 4; X, which may be the same or different, are independently selected from the group consisting of methyl, methoxy N-methylsulfamoyl, N,N-dimethyl-sulfamoyl, acetyl and propionyl; R 1 is selected from the group consisting of hydrogen, C 2 to C 6 alkanoyl, and the alkali metal cations; R 2 is selected from the group consisting of C 1 to C 3 alkyl, 2-haloethyl, allyl, 3-halo-allyl and propargyl; and R 3 is selected from C 1 to C 4 alkyl; and R 4 is hydrogen.

Claim 22

A compound according to claim 1 selected from the group consisting of: 2-[1-(Ethoxyimino)propyl]-5,6,7,8-tetramethyl-1,3-dioxa -1,2,3,4,4a,9,10,10a-octahydrophenanthrene; 2-[1-(Ethoxyimino)propyl]-5,8-dimethyl-6,7-trimethylene-1,3-dioxa-1,2,3,4,4a,9,10,10a-octahydrophenanthrene; 2-[1-(Ethoxyimino)propyl]-5,6,7-trimethyl-1,3-dioxa-1,2,3,4,4a,9,10,10a-octahydrophenanthrene; 8-Acetyl-2-[ethoxyimino)propyl]-5,6,7-trimethyl-1,3-dioxa-1,2,3,4,4a,9,10,10a-octahydrophenanthrene.

Claim 23

A herbicidal composition comprising as active ingredient a herbicidally effective amount of a compound as defined according to claim 1 and an inert carrier therefor.

Claim 24

A process for severely damaging or killing unwanted plants which process comprises applying to said plants, or to the growth medium of said plants, an effective amount of a compound as defined according to claim 1 or an effective amount of a composition as defined according to claim 10.

Claim 25

A process for selectively controlling the growth of monocotyledonous weeds in dicotyledonous crops which process comprises applying to said crop, or to the growth medium of said crop, a compound as defined according to claim 1 or a composition as defined according to claim 10 in a amount sufficient to severely damage or kill said weeds but insufficient to substantially damage said crop.

Claim 26

A process according to claim 11 or claim 12 wherein the compound is applied at a rate in the range of from 0.005 to 20 kilograms per hectare.