US4666510A
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US
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Cyclohexenone derivatives and their herbicidal use.
Assignee: Orica Ltd
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Filing: 1983-01-25
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Granted: 1987-05-19
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Expires: 2003-01-25
Abstract
Abstract The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, hydroxy, alkoxy, substituted alkoxy, alkenyl, alkynyl, alkenyloxy, alkynyloxy, acyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof; R 1 is selected from hydrogen, alkyl, alkenyl, alkynyl, substituted alkyl, alkylsulfonyl, arylsulfonyl, acyl and an inorganic or organic cation; R 2 is selected from alkyl, substituted alkyl, alkenyl, haloalkenyl, alkynyl and haloalkynyl; R 3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl, and phenyl; m is an integer chosen from 3 to 5. The compounds of the invention show herbicidal properties and plant growth regulating properties and in further embodiments the invention provides processes for the preparation of compounds of formula I, intermediates useful in the preparation of the compounds of formula I, compositions containing as active ingredient a compound of formula I, and herbicidal and plant growth regulating processes utilizing compounds of formula I.
Inventors
- 👤 Keith G. Watson
- 👤 Lynette A. Garson
- 👤 Graham J. Bird
- 👤 Lindsay E. Cross
- 👤 Graeme J. Farquharson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 21:09
CPC Classifications
C; C07; C07C; C07C205/00; C07C205/45; A; A01; A01N; A01N35/00; A01N35/08; A01N35/10; A01N37/00; A01N37/02; A01N37/10; A01N37/18; A01N37/22; A01N37/44; A01N37/48; A01N41/00; A01N41/02; A01N41/04; A01N41/06; A01N41/10; C07C255/00; C07C323/00; C07C45/00; C07C45/45; C07C45/455; C07C45/51; C07C45/511; C07C45/513; C07C45/61; C07C45/67; C07C45/673; C07C45/68; C07C45/70; C07C45/71; C07C45/72; C07C45/74; C07C47/00; C07C47/52; C07C47/542; C07C47/575; C07C49/00; C07C49/20; C07C49/255; C07C49/587; C07C49/703; C07C49/747; C07C49/753; C07C49/76; C07C49/86
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
299 words
A compound of formula I ##STR15## wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 4 alkyl; C 1 to C 4 alkoxy; C 1 to C 4 alkylsulfinyl; C 1 to C 4 alkylsulfonyl; C 2 to C 6 alkanoyl; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; C 1 to C 4 alkyl substituted with C 1 to C 4 alkoxy; (C 1 to C 6 alkoxy)carbonyl; 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, C 1 to C 4 alkoxy and nitro; 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; 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 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 alkynyl; C 1 to C 6 haloalky; 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 2
Dependent Claim
299 words
A compound of formula I ##STR15## wherein: X, which may be the same or different, are selected from the group consisting of: halogen; nitro; cyano; C 1 to C 4 alkyl; C 1 to C 4 alkoxy; C 1 to C 4 alkylsulfinyl; C 1 to C 4 alkylsulfonyl; C 2 to C 6 alkanoyl; sulfamoyl; N-(C 1 to C 6 alkyl)sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; C 1 to C 4 alkyl substituted with C 1 to C 4 alkoxy; (C 1 to C 6 alkoxy)carbonyl; 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, C 1 to C 4 alkoxy and nitro; 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; 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 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 alkynyl; C 1 to C 6 haloalky; 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 3
Dependent Claim
220 words
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 4 alkyl; C 1 to C 4 alkoxy; C 1 to C 4 alkylsulfinyl; C 1 to C 4 alkylsulfonyl; C 2 to C 6 alkanoyl; sulfamoyl; N,N-di(C 1 to C 6 alkyl)sulfamoyl; C 1 to C 4 alkyl substituted with C 1 to C 4 alkoxy; 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, C 1 to C 4 alkoxy and nitro; 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 2 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 4
Dependent Claim
127 words
A compound according to claim 1 of formula ##STR16## wherein: X, X 2 and X 6 are independently selected from the group consisting of halogen, nitro, cyano, amino, methyl, ethyl, methoxy, methoxymethyl, ethoxymethyl, methylsulfinyl, methylsulfonyl, acetyl, butyryl, propionyl, 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, methoxy and nitro; R 1 is selected from the group consisting of hydrogen, acetyl, benzoyl, nitrobenzoyl, 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 selected from 1 to 3.
Claim 5
Dependent Claim
137 words
A compound according to claim 3 of formula ##STR17## wherein: X, X 2 and X 6 are independently selected from the group consisting of halogen, nitro, cyano, amino, methyl, ethyl, methoxy, methoxymethyl, ethoxymethyl, methylsulfinyl, methylsulfonyl, acetyl, butyryl, propionyl, 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, methoxy and nitro; 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 6
Dependent Claim
23 words
A compound according to claim 3 or claim 4 wherein X 2 and X 6 are independently selected from halogen, methyl and methoxy.
Claim 7
Dependent Claim
120 words
A compound according to claim 3 of formula ##STR18## wherein: X and X 3 are independently selected from the group consisting of halogen, methyl, ethyl, methoxy, 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, methoxy and nitro; R 1 is selected from the group consisting of hydrogen, acetyl, benzoyl, nitrobenzoyl, 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 8
Dependent Claim
117 words
A compound according to claim 6 of formula ##STR19## wherein: X and X 3 are independently selected from the group consisting of halogen, methyl, ethyl, methoxy, 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, methoxy and nitro; 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 0 or an integer selected from 1 and 2.
Claim 9
Dependent Claim
71 words
A compound according to claim 7 of formula ##STR20## wherein: X 3 is selected from the group consisting of 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 10
Dependent Claim
54 words
A compound according to claim 1 of formula ##STR21## wherein: R 2 is selected from C 1 to C 3 alkyl, 2-haloethyl, allyl, 3-chloro allyl and C 3 to C 4 alkynyl; R 3 is selected from C 1 to C 4 alkyl; R 4 is selected from C 1 to C 4 alkyl.
Claim 11
Dependent Claim
16 words
A compound 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-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-en-1-one; 5-(3-acetyl-2,4,5,6-tetramethylphenyl)-2-[1-ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one; and 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-ethoxyimino)butyl]-3-hydroxycyclohex-2-en-1-one.
Claim 12
Dependent Claim
16 words
A compound 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-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-en-1-one; 5-(3-acetyl-2,4,5,6-tetramethylphenyl)-2-[1-ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one; and 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-ethoxyimino)butyl]-3-hydroxycyclohex-2-en-1-one.
Claim 13
Dependent Claim
10 words
A compound according to claim 10, said compound being 5-(3-acetyl-2,4,6-trimethylphenyl)-2-[1-(ethoxyimino)propyl]-3-hydroxycyclohex-2-en-1-one.
Claim 14
Dependent Claim
24 words
A herbicidal composition comprising as active ingredient a herbicidal effective amount of a compound as defined according to claim 1 and a carrier therefor.
Claim 15
Dependent Claim
35 words
A process for severely damaging or killing unwanted plants which process comprises applying to said plant, or the growth medium of said plants, an effective amount of a compound as defined according to claim 1.
Claim 16
Dependent Claim
54 words
A process for selectively controlling the growth of monocotyledenous weeds in dicoytledonous crops which process comprises applying to said crop, or to the growth medium of said crop, a compound as defined according to claim 1 in an amount sufficient to severly damage or kill said weeds but insufficiently to substantially damage said crop.
Claim 17
Dependent Claim
25 words
A process according to claim 14 wherein the compound is applied at a rate in the range of from 0.005 to 20 kilograms per hectare.
References Cited (Backward Citations)
US3950420A
Cited
US3989737A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 7.5 Years (Year 8) | 1994-05-18 | 1994-11-17 | 1995-05-19 | $3760.00 | Window Closed / Lapsed |
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