US4568377A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran
Assignee: Chevron USA Inc
•
Filing: 1985-04-26
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Granted: 1986-02-04
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Expires: 2005-04-26
Abstract
Abstract 5-Amino-2-aryl-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof. The compounds generally exhibit both pre-emergence and post-emergence phytotoxicity with respect to grassy and broadleaf weeds and have improved crop safety.
Inventors
- 👤 Carl E. Ward
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 20:06
CPC Classifications
A; A01; A01N; A01N43/00; A01N43/02; A01N43/04; A01N43/06; A01N43/08; C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/56; C07D307/66
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
281 words
A compound having the formula: ##STR13## wherein R is phenyl, naphth-1-yl, inden-1-yl; 4-fluorophenyl; or R is a substituted aryl selected from the group having the formulas: ##STR14## wherein one, two or three of R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group of lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 through 3 carbon atoms and 1 through 3 of the same or different halo atoms, and the remainder are hydrogen; R 1 is hydrogen or alkyl having 1 through 4 carbon atoms; R 2 is hydrogen, alkyl having 1 through 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; R 1 and R 2 together with the nitrogen atom to which they are joined form a saturated or unsaturated nitrogen heterocycle having 5 or 6 ring atoms one of which is nitrogen and the remainder are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl and can be at any available position on the phenyl ring; and Y is cyano; nitro; alkoxycarbonyl having 2 through 9 carbon atoms; cyclopentyloxycarbonyl; cyclohexyloxycarbonyl; phenoxycarbonyl; substituted phenoxycarbonyl having 1 or 2 substituents independently selected from the group of lower alkyl having 1 through 6 carbon atoms, lower alkoxy having 1 through 6 carbon atoms, halo, haloalkyl having 1 through 3 carbon atoms and 1 through 4 of the same or different halo atoms, nitro or cyano; alkylthiocarbonyl having 2 through 9 carbon atoms, or ##STR15## wherein R 10 and R 11 are independently hydrogen or alkyl having 1 through 8 carbon atoms; and compatible salts thereof.
Claim 2
Dependent Claim
281 words
A compound having the formula: ##STR13## wherein R is phenyl, naphth-1-yl, inden-1-yl; 4-fluorophenyl; or R is a substituted aryl selected from the group having the formulas: ##STR14## wherein one, two or three of R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group of lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 through 3 carbon atoms and 1 through 3 of the same or different halo atoms, and the remainder are hydrogen; R 1 is hydrogen or alkyl having 1 through 4 carbon atoms; R 2 is hydrogen, alkyl having 1 through 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; R 1 and R 2 together with the nitrogen atom to which they are joined form a saturated or unsaturated nitrogen heterocycle having 5 or 6 ring atoms one of which is nitrogen and the remainder are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl and can be at any available position on the phenyl ring; and Y is cyano; nitro; alkoxycarbonyl having 2 through 9 carbon atoms; cyclopentyloxycarbonyl; cyclohexyloxycarbonyl; phenoxycarbonyl; substituted phenoxycarbonyl having 1 or 2 substituents independently selected from the group of lower alkyl having 1 through 6 carbon atoms, lower alkoxy having 1 through 6 carbon atoms, halo, haloalkyl having 1 through 3 carbon atoms and 1 through 4 of the same or different halo atoms, nitro or cyano; alkylthiocarbonyl having 2 through 9 carbon atoms, or ##STR15## wherein R 10 and R 11 are independently hydrogen or alkyl having 1 through 8 carbon atoms; and compatible salts thereof.
Claim 3
Dependent Claim
19 words
The compound of claim 1 wherein one of R 1 or R 2 is hydrogen, methyl, ethyl or propyl.
Claim 4
Dependent Claim
25 words
The compound of claim 1 wherein one of R 1 or R 2 is methyl or ethyl and the other is hydrogen, methyl or ethyl.
Claim 5
Dependent Claim
23 words
The compound of claim 1 wherein one of R 1 or R 2 is hydrogen and the other is methyl, ethyl or propyl.
Claim 6
Dependent Claim
9 words
The compound of claim 1 wherein X is hydrogen.
Claim 7
Dependent Claim
9 words
The compound of claim 2 wherein X is hydrogen.
Claim 8
Dependent Claim
9 words
The compound of claim 3 wherein X is hydrogen.
Claim 9
Dependent Claim
14 words
The compound of claim 1 wherein R is phenyl, naphth-1-yl, 4-fluorophenyl or substituted aryl.
Claim 10
Dependent Claim
14 words
The compound of claim 8 wherein R is phenyl, naphthyl or a monosubstituted phenyl.
Claim 11
Dependent Claim
13 words
The compound of claim 9 wherein R is phenyl, halophenyl, or lower alkylphenyl.
Claim 12
Dependent Claim
14 words
The compound of claim 10 wherein R is phenyl, 4-fluorophenyl, 2-halophenyl, or 2-lower alkylphenyl.
Claim 13
Dependent Claim
26 words
The compound of claim 11 wherein X is hydrogen and R 1 and R 2 are independently selected from the group of hydrogen, methyl or ethyl.
Claim 14
Dependent Claim
199 words
A compound having the formula: ##STR16## wherein R is phenyl, naphth-1-yl, inden-1-yl; 4-fluorophenyl; or R is a substituted aryl selected from the group having the formulas: ##STR17## wherein one, two or three of R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group of lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 through 3 carbon atoms and 1 through 3 of the same or different halo atoms, and the remainder are hydrogen; R 1 is hydrogen or alkyl having 1 through 4 carbon atoms; R 2 is hydrogen, alkyl having 1 through 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; R 1 and R 2 together with the nitrogen atom to which they are joined form a saturated or unsaturated nitrogen heterocycle having 4 through 6 ring atoms one of which is nitrogen and the remainder are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl and can be at any available position on the phenyl ring; and R" is alkyl having 1 through 7 carbon atoms; and compatible salts thereof.
Claim 15
Dependent Claim
199 words
A compound having the formula: ##STR16## wherein R is phenyl, naphth-1-yl, inden-1-yl; 4-fluorophenyl; or R is a substituted aryl selected from the group having the formulas: ##STR17## wherein one, two or three of R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 are independently selected from the group of lower alkyl, lower alkoxy, halo, nitro, or haloalkyl having 1 through 3 carbon atoms and 1 through 3 of the same or different halo atoms, and the remainder are hydrogen; R 1 is hydrogen or alkyl having 1 through 4 carbon atoms; R 2 is hydrogen, alkyl having 1 through 4 carbon atoms, alkenyl having 3 or 4 carbon atoms, lower alkoxycarbonylalkyl, lower alkoxyalkyl or lower alkylthioalkyl; R 1 and R 2 together with the nitrogen atom to which they are joined form a saturated or unsaturated nitrogen heterocycle having 4 through 6 ring atoms one of which is nitrogen and the remainder are carbon atoms; X is hydrogen, lower alkyl, lower alkoxy, halo, or trifluoromethyl and can be at any available position on the phenyl ring; and R" is alkyl having 1 through 7 carbon atoms; and compatible salts thereof.
Claim 16
Dependent Claim
17 words
The compound of claim 13 wherein R 1 and R 2 are independently hydrogen, methyl or ethyl.
Claim 17
Dependent Claim
24 words
The compound claim 14 wherein one of R 1 or R 2 is methyl or ethyl and the other is hydrogen, methyl or ethyl.
Claim 18
Dependent Claim
22 words
The compound of claim 13 wherein one of R 1 or R 2 is methyl or ethyl and the other is hydrogen.
Claim 19
Dependent Claim
19 words
The compound of claim 14 wherein X is hydrogen and R is phenyl, naphthyl, 4-fluorophenyl, 2-halophenyl or 2-lower alkylphenyl.
Claim 20
Dependent Claim
23 words
The compound of claim 17 wherein one of R 1 or R 2 is hydrogen and the other is hydrogen methyl or ethyl.
Claim 21
Dependent Claim
13 words
The compound of claim 18 wherein R is phenyl, 2-fluorophenyl 2-chlorophenyl or 2-methylphenyl.
Claim 22
Dependent Claim
9 words
The compound of claim 18 wherein R is phenyl.
Claim 23
Dependent Claim
24 words
The compound of claim 18 wherein R is phenyl and one of R 1 or R 2 is hydrogen and the other is methyl.
Claim 24
Dependent Claim
24 words
The compound of claim 18 wherein R is phenyl and one of R 1 or R 2 is hydrogen and the other is ethyl.
Claim 25
Dependent Claim
9 words
The compound of claim 13 wherein X is hydrogen.
Claim 26
Dependent Claim
17 words
The compound of claim 5 wherein Y is a lower haloalkyl having 1 or 2 carbon atoms.
Claim 27
Dependent Claim
24 words
A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1, or mixtures of such compounds, and a compatible carrier.
Claim 28
Dependent Claim
22 words
A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 20, or mixtures thereof, and a compatible carrier.
Claim 29
Dependent Claim
32 words
A method for controlling plants which comprises applying a herbicidally effective amount of a compound according to claim 1, or mixtures thereof, to the foliage or potential growth medium of said plants.
Claim 30
Dependent Claim
32 words
A method for controlling plants which comprises applying a herbicidally effective amount of a compound according to claim 20, or mixtures thereof, to the foliage or potential growth medium of said plants.
Claim 31
Dependent Claim
42 words
A method for regulating the growth of plants which comprises applying to the foliage of said plants or their growth medium an amount of a compound according to claim 1, or mixtures thereof, effective to alter the growth pattern of such plants.
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) | 1989-02-03 | 1989-08-05 | 1990-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-02-03 | 1993-08-05 | 1994-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-02-03 | 1997-08-05 | 1998-02-04 | $7700.00 | Window Closed / Lapsed |