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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
•
Expires: 2005-04-26
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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)

GB1521092A Cited
GB2080289A Cited
US4441910A Cited
US4537623A Cited

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

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