Cyclohexane dione derivatives, their use as herbicides, herbicidal compositions containing them, and methods of preparing them

Claim 2

A compound of formula I wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with a substituent selected from the group consisting of halogen, nitro, hydroxy, C 1 to C 6 alkoxy and C 1 to C 6 alkylthio; C 2 to C 6 alkenyl; C2 to C6 alkynyl; hydroxy; C 1 to C 6 alkoxy; C 1 to C 6 alkoxy substituted with a substituent selected from halogen and C 1 to C 6 alkoxy; C 2 to C 6 alkenyloxy; C 2 to C 6 alkynyloxy; C 2 to C 6 alkanoyloxy; (C 1 to C 6 alkoxy)-carbonyl; C 1 to C 6 alkylthio; C 1 to C 6 alkylsulfinyl; C 1 to C 6 alkylsulfonyl; sulfamoyl; N-(C 1 to C 6 alkyl)- sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; benzyloxy; substituted benzyloxy 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, C 1 to C 6 alkoxy and C 1 to C 6 haloalkyl; the group NR 8 R 9 wherein R 8 and R 9 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, benzoyl and benzyl; the groups formyl and C 2 to C 6 alkanoyl and the oxime, imine and Schiff base derivatives thereof; and at least one of X is not selected from the group consisting of halogen, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; R 1 is selected from the group consisting of: hydrogen; C 1 to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; substituted C 1 to C 6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of 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 consistingof halogen, nitro, cyano, 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; C 1 to C 6 (alkyl) sulfonyl; benzenesulfonyl; substituted benzenesulfonyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, cyano, C 1 to C 6 alkyl t C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy and C 1 to C 6 alkylthio; 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 2 to C 6 haloalkynyl; 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, nitro, cyano, 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 m is an integer chosen from 3 to 5.

Claim 3

A compound according to claim 1 wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with a substituent selected from the group consisting of halogen, nitro, hydroxy, C 1 to C 6 alkoxy, and C 1 to C 6 alkylthio; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; hydroxy; C 1 to C 6 alkoxy; C 1 to C 6 alkoxy substituted with a substituent selected from halogen and C 1 to C 6 alkoxy; C 2 to C 6 alkenyloxy; C 2 to C 6 alkynyloxy; C 2 to C 6 alkanoyloxy; (C 1 to C 6 alkoxy)carbonyl; C 1 to C 6 alkylthio; C 1 to C 6 alkylsulfinyl; C 1 to C 6 alkylsulfonyl; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)-sulfamoyl; benzyloxy; substituted benzyloxy 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, C 1 to C 6 alkoxy and C 1 to C 6 haloalkyl; the group NR 8 R 9 wherein R and R 9 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, benzoyl and benzyl; the group -C(R 10 )=NR 11 wherein R 10 is selected from hydrogen and C 1 to C 5 alkyl and R 11 is selected from the group consisting of hydrogen, C 1 to C 6 alkyl, phenyl, benzyl, hydroxy, C 1 to C 6 alkoxy, phenoxy and benzyloxy; and at least one of X is not selected from the group consisting of halogen, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; R 1 is selected from the group consisting of: hydrogen; C 1 to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; substituted C 1 to C 6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of 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, nitro, cyano, C1 to C6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy and C 1 to C 6 alkylthio; C 1 to C 6 (alkyl)sulfonyl; benzenesulfonyl; substituted benzenesulfonyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, cyano, 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; 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, cyano, 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; 2-furoyl; 3-furoyl; 2-thenoyl; 3-thenoyl; and an inorganic or an organic cation selected from the alkali metal ions, the alkaline earth metal ions, transition metal ions and the ammonium ion R 4 R 5 R 6 R 7 N⊕ wherein R 4 , R 5 , R and R 7 are independently selected from the group consisting of: hydrogen; C 1 to C 10 alkyl; substituted C 1 to C 10 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of hydroxy, halogen and C 1 to C 6 alkoxy; phenyl; benzyl; and the groups substituted phenyl and substituted benzyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, cyano, 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; R2 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 2 to C 6 haloalkynyl; 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, nitro, cyano, 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 m is an integer chosen from 3 to 5.

Claim 4

A compound according to claim 1 or claim 2 wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with a substituent selected from the group consisting of halogen, nitro and C 1 to C 6 alkoxy; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; hydroxy; C 1 to C 6 alkoxy; C 1 to C 6 alkoxy substituted with a substituent selected from halogen and C 1 to C 6 alkoxy; C 2 to C 6 alkanoyloxy; (C 1 to C 6 alkoxy)carbonyl; C 1 to C 6 alkylthio; C 1 to C 6 alkylsulfinyl; C 1 to C 6 alkylsulfonyl; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; benzyloxy; substituted benzyloxy 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, C 1 to C 6 alkoxy and C 1 to C 6 haloalkyl; the group NR 8 R 9 wherein R 8 and R 9 are independently selected from the group consisting of hydrogen, C 1 to C 6 alkyl, C 2 to C 6 alkanoyl, benzoyl and benzyl; the group -C(R 10 )=NR 11 wherein R 1 0 is selected from hydrogen and C 1 to C 5 alkyl and R 11 is selected from group consisting of hydrogen, C 1 to C 6 alkyl, phenyl, benzyl, hydroxy, C 1 to C 6 alkoxy, phenoxy and benzyloxy; and at least one of X is not selected from the group consistingof halogen, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; R 1 is selected from the group consisting of: hydrogen; C 1 to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 alkynyl; substituted C 1 to C 6 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of 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, nitro, cyano, 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; C 1 to C 6 (alkyl) sulfonyl; benzene sulfonyl; substituted benzenesulfonyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, cyano, 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; 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, cyano, 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; 2-furoyl; 3-furoyl; 2-thenoyl; 3-thenoyl- and an inorganic or an organic cation selected from the alkali metal ions, the alkaline earth metal ions, the transition metal ions and the ammonium ion R 4 R 5 R 6 R 7 N⊕ wherein R , R , R and R are independently selected from the group consisting of: hydrogen; C 1 to C 10 alkyl; substituted C 1 to C 10 alkyl wherein the alkyl group is substituted with a substituent selected from the group consisting of hydroxy, halogen and C 1 to C 6 alkoxy; phenyl; benzyl; and the groups substituted phenyl and substituted benzyl wherein the benzene ring is substituted with from one to three substituents selected from the group consisting of halogen, nitro, cyano, C 1 and C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkoxy and C 1 to C 6 alkylthio; R 2 is selected from the group consisting of: C l to C 6 alkyl; C 2 to C 6 alkenyl; C 2 to C 6 haloalkenyl; C 2 to C6 alkynyl; C 2 to C 6 haloalkynyl; 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, nitro, cyano, C 1 to C 6 alkyl, C 1 to C 6 haloalkyl, C 1 to C 6 alkox y 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; C2 to C 6 alkynyl; and phenyl; and m is an integer chosen from 3 to 5.

Claim 5

A compound according to any one of claims 1 to 3 inclusive wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 6 alkyl; C 1 to C 6 alkyl substituted with a substituent selected from the group consisting of halogen, nitro and C 1 to C 6 alkoxy; hydroxy; C 1 to C 6 alkoxy; C 1 to C 6 alkoxy substituted with a substituent selected from halogen and C 1 to C6 alkoxy; C2 to C6 alkanoyloxy; amino; C 1 to C 6 alkylamino; di(C 1 to C 6 alkyl)amino; C 1 to C 6 alkanoylamino; benzoylamino; formyl; C 2 to C 6 alkanoyl; (C 1 to C 6 alkoxy)carbonyl; C 1 to C 6 alkylthio; C 1 to C 6 alkylsulfinyl; C 1 to C 6 alkylsulfonyl; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; and N,N-di(C 1 to C 6 alkyl)sulfamoyl; and at least two of X are methyl and at least one of X is not selected from the group consisting of halogen, C 1 to C 6 alkyl and C 1 to C 6 alkoxy; R 1 is selected from the group consisting of hydrogen, benzoyl, 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, C 1 to C 6 alkox y , and C 1 to C 6 haloalkyl, and the group M wherein M is an alkali metal ion; 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 alkynyl, benzyl and substituted benzyl 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, C 1 to C 6 al ko xy and C 1 to C 6 haloalkoxy; R 3 is selected from C 1 to C 6 alkyl; m is an integer selected from 3 to 5.

Claim 6

A compound according to claim 1 or claim 2 wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; hydroxy; C 1 to C 4 alkyl; C 1 to C 4 alkoxy, C 2 to C 4 alkenyloxy; C 1 to C 4 alkylthio; C 1 to C 4 alkylsulfinyl; C 1 to C 4 alkylsulfonyl; formyl, C 2 to C 6 alkanoyl and the oxime O-C 1 to C4 alkyl ethers thereof; C 2 to C 6 alkanoyloxy; benzyloxy; sulfamoyl; N,N-di(C 1 to C 6 alkyl)-sulfamoyl; C 1 to C 4 alkyl substituted with a substituent selected from the group consisting of nitro, hydroxy, C 1 to C 4 alkoxy and C 1 to C 4 alkylthio; C 1 to C 4 alkoxy substituted with one or more substituents selected from halogen; the group NR 8 R 9 wherein R 8 and R 9 are independ- e ntly selected from hydrogen and C 2 to C 4 alkanoyl; and at least one of X is not selected from the group consisting of halogen, C 1 to C 4 alkyl and C 1 to C 4 alkoxy; R 1 is selected from the group consisting of: hydrogen; C 2 to C 6 alkanoyl; benzoyl; 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; 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 to C 6 alkoxy; and an inorganic or organic cation selected from the alkali metal ions, the alkaline earth metal ions, the transition metal ions, the ammonium ion, and the tri- and tetra- (alkyl)ammonium ions wherein alkyl is selected from C1 to C6 alkyl and C1 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 alkynyl; C 1 to C 6 haloalkyl; C 2 to C 6 haloalkenyl; and C 2 to C 6 haloalkynyl; R 3 is selected from C 1 to C 6 alkyl; and m is an integer selected from 3 to 5.

Claim 7

A compound according to any one of claims 1 to 5 inclusive wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; hydroxy; C 1 to C 4 alkyl; C 1 to C 4 alkoxy; C 1 to C 4 alkylthio; C 1 to C 4 alkylsulfinyl; C 1 to C 4 alkylsulfonyl; formyl; C 2 to C 6 alkanoyl; C 2 to C 6 alkanoyloxy; sulfamoyl; N,N-di (C 1 to C 6 alkyl)sulfamoyl; C 1 to C 4 alkyl substituted with a substituent selected from nitro and C 1 to C 4 alkoxy; C 1 to C 4 alkoxy substituted with one or more substituents selected from halogen; amino; C 2 to C 4 alkanoylamino and at least two of X are methyl and at least one of X is not selected from the group consisting of halogen, C 1 to C 4 alkyl and C 1 to C 4 alkoxy; R 1 is selected from the group consisting of: hydrogen, benzoyl; 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; and the alkali metal ions; R is selected from the group consisting of: C 1 to C 6 alkyl; C 2 to C 6 alkenyl and C 2 to C 6 alkynyl; R 3 is selected from C 1 to C 6 alkyl; and m is an integer selected from 3 to 5.

Claim 8

A compound according to any one of claims 1, 2 and 5 inclusive of formula wherein: X, X 2 and X 6 are independently selected from the group consisting of halogen, nitro, cyano, hydroxy, amino, methyl, ethyl, methoxy, methylmercapto, n-butylmercapto, nitromethyl, hydroxymethyl, methoxymethyl, ethoxymethyl, n-butylthiomethyl, difluoromethoxy, allyloxy, benzyloxy, methylsulfinyl, methylsulfonyl, formyl, formyl oxime O-ethyl ether, acetyl, butyryl, propionyl, acetyloxy, sulfamoyl, N,N-dimethylsulfamoyl, and acetylamino, and at least one of X, X 2 and X 6 is not selected from the group consisting of halogen, methyl, ethyl and methoxy; R 1 is selected from the group consisting of hydrogen, acetyl, benzoyl, nitrobenzoyl, methylbenzenesulfonyl and the cations of the alkali metals; R 2 is selected from the group consisting of C 1 to C 3 alkyl, 2-haloethyl, allyl and 2-haloallyl; R 3 is selected from C 1 to C 3 alkyl; and m is an integer selectee from 1 to 3.

Claim 9

A compound according to any one of claims 1 to 7 inclusive of formula wherein: X, X 2 and X 6 are independently selected from the group consisting of halogen, nitro, cyano, hydroxy, amino, methyl, ethyl, methoxy, methylmercapto, n-butylmercapto, nitromethyl, methoxymethyl, ethoxymethyl, difluoromethoxy, methylsulfinyl, methylsulfonyl, formyl, acetyl, butyryl, propionyl, acetyloxy, sulfamoyl, N,N-dimethylsulfamoyl, and acetylamino, and at least two of X , X 2 and X 6 are methyl and at least one of X, X 2 and X 6 is not selected from the group consisting of halogen, methyl, ethyl and methoxy; R 1 is selected from the group consisting of hydrogen, benzoyl, nitrobenzoyl and the cations of the alkali metals; R 2 is selected from the group consisting of C 1 to C 3 alkyl and allyl; R 3 is selected from C 1 to C 3 alkyl; and m is an integer selected from 1 to 3.

Claim 10

A compound according to claim 7 or claim 8 wherein x 2 and X 6 are independently selected from halogen, methyl, methoxy and methylmercapto.

Claim 11

A compound according to any one of claims 1, 2, 5 or 7 inclusive of formula wherein: X and X 3 are independently selected from the group consisting of halogen, methyl, ethyl, methoxy, methylmercapto, nitromethyl, hydroxymethyl, methoxymethyl, ethoxymethyl, methylsulfinyl, methylsulfonyl, acetyl, propionyl, sulfamoyl, and N,N-di(methyl)sulfamoyl, and at least one of X and X 3 is not selected from the group consisting of halogen, methyl, ethyl and methoxy; R 1 is selected from the group consisting of hydrogen, acetyl, benzoyl, nitrobenzoyl, methylbenzenesulfonyl and the cations of the alkali metals; R 2 is selected from the group consisting of C 1 to C 3 alkyl, 2-haloethyl, allyl and 2-haloallyl; R 3 is selected from C 1 to C 3 alkyl; and m is 0 or an integer selected from 1 and 2.

Claim 12

A compound according to any one of claims 1 to 10 inclusive of formula wherein: X and X 3 are independently selected from the group consisting of halogen, methyl, ethyl, methoxy, methylmercapto, nitromethyl, methoxymethyl, ethoxymethyl, methylsulfinyl, methylsulfonyl, acetyl, propionyl, sulfamoyl, and N,N-dimethylsulfamoyl, and at least one of X and X 3 is not selected from the group consisting of halogen, methyl, ethyl and methoxy; R 1 is selected from the group consisting of hydrogen, benzoyl, nitrobenzoyl and the cations of the alkali metals; R 2 is selected from the group consisting of C1 to C 3 alkyl and allyl; R 3 is selected from C 1 to C 3 alkyl; and m is 0 or an integer selected from 1 and 2.

Claim 13

A compound according to any one of claims 1 to 11 inclusive of formula wherein: X 3 is selected from the group consisting of methylmercapto, nitromethyl, methoxymethyl, ethoxymethyl, methylsulfinyl, methylsulfonyl, acetyl, propionyl, sulfamoyl and N,N-di(methyl)sulfamoyl: X 4 is selected from hydrogen and methyl; X 5 is selected from hydrogen, methyl and ethyl; R 1 is selected from hydrogen, sodium and potassium; R 2 is selected from ethyl and allyl; and R 3 is selected from ethyl and n-propyl.

Claim 14

A compound according to any one of claims 1 to 12 inclusive selected from the group consisting of: 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,6-dimethyl-3-(N,N-dimethylsulfamoyl)phenyl]cyclohex-2-en-1-one; 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-[2,4,6-trimethyl-3-(N,N-dimethylsulfamoyl)phenyl]cyclohex-2-en-1-one; 2-[1-(ethoxyimino)propyl]-3-hydroxy-5-(2,4,6-trimethyl-3-sulfamoylphenyl) cyclohex-2-en-1-one; 5-(3-acetyl-2,-4,6-trimethylphenyl)-2-[1-(ethoxyimino)-propyl]-3-hydroxycyclohex-2-en-1-one; 5-(3-acetyl-5-ethyl-2,4,b-trimethylphenyl)-2-[1-(ethoxy- imino)propyl]-3-hydroxycyclohex-2-en-1-one; 5-(3-acetyl-2,4,5,6-tetramethylphenyl)-2-[1-ethoxyimino)-propyl7-3-hydroxycyclohex-2-en-l-one; and 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-ethoxyimino)-butyl]-3-hydroxycyclohex-2-en-1-one.

Claim 15

A compound of formula IX wherein m is as defined according to any one of claims 1 to 11 inclusive.

Claim 16

A compound of formula XIII wherein m and R are as defined according to any one of claims 1 to 11 inclusive.

Claim 17

A herbicidal composition comprising as active ingredient a compound as defined according to any one of claims 1 to 13 inclusive and a carrier therefor.

Claim 18

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 any one of claims 1 to 13 inclusive or an effective amount of a composition as defined according to claim 16.

Claim 19

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 any one of claims 1 to 13 inclusive or a composition as defined according to claim 16 in an amount sufficient to severely damage or kill said weeds but insufficient to substantially damage said crop.

Claim 20

A process according to claim 17 or claim 18 wherein the compound is applied at a rate in the range of from 0.005 to 20 kilograms per hectare.

Claim 21

A process for the synthesis of a compound of formula I as defined according to any one of claims 1 to 13 inclusive which process comprises; a) reacting a benzaldehyde derivative of formula V with acetone to give a ketone derivative of formula VI and reacting the ketone derivative of formula VI with a malonic acid ester of formula VII, wherein R is C 1 to C 6 alkyl, to give a 5-(substituted phenyl)-cyclohexane-l,3-dione derivative of formula IX b) acylating the 5-(substituted phenyl)cyclohexane-1,3-dione derivative of formula IX with an acid anhydride of formula XIV or an acid halide of formula XV to give a 2-acyl-5-(substituted phenyl)cyclohexane-1,3-dione derivative of formula XIII; c) reacting the 2-acyl-5-(substituted phenyl)-cyclohexane-1,3-dione derivative of formula XIII with an alkoxyamine derivative of formula XVII to give a compound of the invention of formula II (formula I wherein R l = H ); and optionally d) reacting the compound of the invention of formula II with a compound of formula XX to give a compound of the invention of formula I

Claim 22

A compound of formula I as defined according to any one of claims 1 to 13 inclusive substantially as herein described with reference to any one of Examples 1 to 33 inclusive.

Claim 23

A composition as defined according to claim 16 substantially as herein described with reference to any one of Examples 38 to 42 inclusive.

Claim 24

A process as defined according to any one of claims 17 to 19 inclusive substantially as herein described with reference to any one of Examples 39 to 42 inclusive.

Claim 25

A process as defined according to claim 20 substantially as herein described with reference to any one of Examples 1 to 33 inclusive.