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US4065290A
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Herbicidal β-phenyl-4-piperidinones
Assignee: Eli Lilly and Co
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Filing: 1976-05-20
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Granted: 1977-12-27
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Expires: 1996-05-20
Abstract
Abstract A class of 4-piperidinones and corresponding dihydropyridinones having a phenyl substituent at one β-position, an alkyl, alkenyl or propargyl group at the 1-position and an optional substituent at the other β-position are broad-spectrum herbicides. The compounds bear a meta-substituent on the phenyl ring, and are particularly suited for use as herbicides in cotton culture.
Inventors
- 👤 Harold Mellon Taylor
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:30
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/63; C07D213/68; C07D211/00; C07D211/04; C07D211/68; C07D211/72; C07D211/74; C07D211/80; C07D211/84; C07D211/86
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
120 words
A method of reducing the vigor of unwanted herbaceous plants which comprises contacting the plants with a herbicidally-effective amount of a compound of the formula ##STR43## wherein R 6 represents C 1 -C 3 alkyl, C 2 -C 3 alkenyl or propargyl; R 7 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkyl, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; R 8 represents chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; each of X 4 and X 5 represents hydrogen; and each of X 6 and X 7 represents hydrogen.
Claim 2
Independent Claim
120 words
A method of reducing the vigor of unwanted herbaceous plants which comprises contacting the plants with a herbicidally-effective amount of a compound of the formula ##STR43## wherein R 6 represents C 1 -C 3 alkyl, C 2 -C 3 alkenyl or propargyl; R 7 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkyl, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; R 8 represents chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; each of X 4 and X 5 represents hydrogen; and each of X 6 and X 7 represents hydrogen.
Claim 3
Dependent Claim
19 words
A method of claim 1 wherein the amount of the compound is from about 0.25 to about 20 kg./ha.
Claim 4
Dependent Claim
19 words
A method of claim 2 wherein the amount of the compound is from about 1 to about 10 kg./ha.
Claim 5
Dependent Claim
10 words
A method of claim 2 wherein the contacting is preemergence.
Claim 6
Dependent Claim
12 words
A method of claim 2 wherein the plants are in cotton cropland.
Claim 7
Dependent Claim
12 words
A method of claim 1 wherein R 6 represents alkyl or alkenyl.
Claim 8
Dependent Claim
23 words
A method of claim 6 wherein R 7 represents hydrogen, alkyl, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, methyl or methoxy.
Claim 9
Dependent Claim
16 words
A method of claim 7 wherein R 8 represents chloro, bromo, fluoro, trifluoromethyl, methyl or methoxy.
Claim 10
Dependent Claim
10 words
The method of claim 1 wherein the compound is 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone.
Claim 11
Dependent Claim
48 words
A compound of the formula ##STR44## wherein R represents methyl or ethyl; R 1 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, C 1 -c 4 alkyl, phenyl or phenyl monosubstituted with chloro or fluoro; R 2 represents bromo, fluoro or trifluoromethyl.
Claim 12
Dependent Claim
48 words
A compound of the formula ##STR44## wherein R represents methyl or ethyl; R 1 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, C 1 -c 4 alkyl, phenyl or phenyl monosubstituted with chloro or fluoro; R 2 represents bromo, fluoro or trifluoromethyl.
Claim 13
Dependent Claim
15 words
A compound of claim 10 wherein R 1 represents hydrogen, alkyl, phenyl or substituted phenyl.
Claim 14
Dependent Claim
8 words
The compound of claim 11 which is 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone.
Claim 15
Dependent Claim
109 words
A herbicidal composition which comprises an inert carrier and a compound of the formula ##STR45## wherein R 6 represents C 1 -C 3 alkyl, C 2 -C 3 alkenyl or propargyl; R 7 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkyl, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; R 8 represents chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; each of X 4 and X 5 represents hydrogen; and each of X 6 and X 7 represents hydrogen.
Claim 16
Dependent Claim
109 words
A herbicidal composition which comprises an inert carrier and a compound of the formula ##STR45## wherein R 6 represents C 1 -C 3 alkyl, C 2 -C 3 alkenyl or propargyl; R 7 represents hydrogen, phenoxy, phenylthio, C 1 -c 4 alkyl, C 1 -c 4 alkoxy, C 1 -c 4 alkylthio, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; R 8 represents chloro, bromo, fluoro, trifluoromethyl, C 1 -c 3 alkyl or C 1 -c 3 alkoxy; each of X 4 and X 5 represents hydrogen; and each of X 6 and X 7 represents hydrogen.
Claim 17
Dependent Claim
12 words
A composition of claim 13 wherein R 6 represents alkyl or alkenyl.
Claim 18
Dependent Claim
23 words
A composition of claim 14 wherein R 7 represents hydrogen, alkyl, phenyl or phenyl monosubstituted with chloro, bromo, fluoro, trifluoromethyl, methyl or methoxy.
Claim 19
Dependent Claim
16 words
A composition of claim 15 wherein R 8 represents chloro, bromo, fluoro, trifluoromethyl, methyl or methoxy.
Claim 20
Dependent Claim
10 words
The composition of claim 13 wherein the compound is 1-methyl-3-phenyl-5-(3-trifluoromethylphenyl)-4-piperidinone.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-26 | 1981-06-27 | 1981-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-26 | 1985-06-27 | 1985-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-26 | 1989-06-27 | 1989-12-27 | $7700.00 | Window Closed / Lapsed |