US4620865A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal and algicidal 1,5-disubstituted-1H-pyrazole-4-carboxamides
Assignee: Eli Lilly and Co
•
Filing: 1986-02-24
•
Granted: 1986-11-04
•
Expires: 2006-02-24
Abstract
Abstract 1,5-Disubstituted-1H-pyrazole-4-carboxamide derivatives, useful as herbicides and aquatic algicides.
Inventors
- 👤 James R. Beck
- 👤 Michael P. Lynch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 06:15
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/38; A; A01; A01N; A01N43/00; A01N43/48; A01N43/56; C07D231/16; C07D231/18; C07D231/20; C07D231/22; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 49
Claim 1
Independent Claim
219 words
A compound of the formula ##STR10## wherein R 1 is tert-butyl, C 5 -C 6 cycloalkyl, ##STR11## R 2 is halogen, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl; R 3 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; R 4 is cyclopropyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; R 5 is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or nitro; X is O or S; and n is 0-3; with the following provisos: the combined total of carbon atoms for R 3 and R 4 does not exceed 5; when R 1 is phenyl, R 5 is C 1 -C 4 alkyl, and R 2 is halogen, alkoxy, alkylthio, or alkylsulfonyl, the R 5 substituent exists at other than the 2 or 6 position of the phenyl ring; when R 3 is C 1 -C 4 alkoxy, R 4 is other than C 1 -C 4 alkoxy; and when R 1 is phenyl, R 5 is C 1 -C 4 alkoxy and R 2 is other than bromine, the R 5 substituent exists at other than the 3 or 5 position of the phenyl ring.
Claim 2
Dependent Claim
219 words
A compound of the formula ##STR10## wherein R 1 is tert-butyl, C 5 -C 6 cycloalkyl, ##STR11## R 2 is halogen, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkylthio or C 1 -C 4 alkylsulfonyl; R 3 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; R 4 is cyclopropyl, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; R 5 is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or nitro; X is O or S; and n is 0-3; with the following provisos: the combined total of carbon atoms for R 3 and R 4 does not exceed 5; when R 1 is phenyl, R 5 is C 1 -C 4 alkyl, and R 2 is halogen, alkoxy, alkylthio, or alkylsulfonyl, the R 5 substituent exists at other than the 2 or 6 position of the phenyl ring; when R 3 is C 1 -C 4 alkoxy, R 4 is other than C 1 -C 4 alkoxy; and when R 1 is phenyl, R 5 is C 1 -C 4 alkoxy and R 2 is other than bromine, the R 5 substituent exists at other than the 3 or 5 position of the phenyl ring.
Claim 3
Dependent Claim
12 words
A compound of claim 1 wherein R 2 is chlorine or bromine.
Claim 4
Dependent Claim
8 words
The compound of claim 2 which is 5-bromo-1-(3-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 5
Dependent Claim
8 words
A compound of claim 2 which is 5-chloro-1-(4-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 6
Dependent Claim
8 words
The compound of claim 2 which is 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 7
Dependent Claim
8 words
The compound of claim 2 which is 5-chloro-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 8
Dependent Claim
8 words
The compound of claim 2 which is 5-bromo-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 9
Dependent Claim
8 words
The compound of claim 2 which is 5-chloro-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 10
Dependent Claim
10 words
A compound of claim 1 wherein R 2 is trifluoromethyl.
Claim 11
Dependent Claim
8 words
The compound of claim 9 which is 5-(trifluoromethyl)-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 12
Dependent Claim
8 words
The method of claim 9 which is 5-(trifluoromethyl)-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 13
Dependent Claim
8 words
The compound of claim 9 which is 5-trifluoromethyl)-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 14
Dependent Claim
8 words
The compound of claim 9 which is 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 15
Dependent Claim
22 words
A method for controlling undesired plants which comprises applying to the plants a growth inhibiting amount of a compound of claim 1.
Claim 16
Dependent Claim
12 words
A method of claim 14 wherein R 2 is chlorine or bromine.
Claim 17
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-bromo-1-(3-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 18
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-chloro-1-(4-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 19
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 20
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-chloro-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 21
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-bromo-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 22
Dependent Claim
11 words
The method of claim 15 in which the compound is 5-chloro-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 23
Dependent Claim
10 words
A method of claim 14 wherein R 2 is trifluoromethyl.
Claim 24
Dependent Claim
11 words
The method of claim 22 in which the compound is 5-(trifluoromethyl)-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 25
Dependent Claim
11 words
The method of claim 22 in which the compound is 5-(trifluoromethyl)-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 26
Dependent Claim
11 words
The method of claim 22 in which the compound is 5-(trifluoromethyl)-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 27
Dependent Claim
11 words
The method of claim 22 in which the compound is 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 28
Dependent Claim
28 words
A method for controlling the growth of aquatic algae which comprises applying to the water containing said algae a growth inhibiting amount of a compound of claim 1.
Claim 29
Dependent Claim
19 words
A composition which comprises a plant growth inhibiting amount of a compound of claim 1 and an agriculturally-acceptable carrier.
Claim 30
Dependent Claim
12 words
A composition of claim 28 wherein R 2 is chlorine or bromine.
Claim 31
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-bromo-1-(3-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 32
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-chloro-1-(4-fluorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 33
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-chloro-1-(3-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 34
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-chloro-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 35
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-bromo-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 36
Dependent Claim
11 words
The composition of claim 29 in which the compound is 5-chloro-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 37
Dependent Claim
10 words
The composition of claim 28 wherein R 2 is trifluoromethyl.
Claim 38
Dependent Claim
11 words
The composition of claim 36 in which the compound is 5-(trifluoromethyl)-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 39
Dependent Claim
11 words
The composition of claim 36 in which the compound is 5-(trifluoromethyl)-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 40
Dependent Claim
11 words
The composition of claim 36 in which the compound is 5-(trifluoromethyl)-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 41
Dependent Claim
11 words
The composition of claim 36 in which the compound is 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 42
Dependent Claim
16 words
A herbicidal combination comprising one or more herbicidal 2,6-dinitroanilines together with a compound of claim 1.
Claim 43
Dependent Claim
10 words
A combination of claim 41 wherein the dinitroaniline is trifluralin.
Claim 44
Dependent Claim
22 words
A method for controlling undesired plants which comprises applying to the plants a growth inhibiting amount of a combination of claim 41.
Claim 45
Dependent Claim
29 words
A method of controlling weeds in a wheat or corn crop which comprises applying preemergently an effective amount of an active agent which is a compound of claim 1.
Claim 46
Dependent Claim
11 words
The method of claim 44 wherein the active agent is 5-chloro-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 47
Dependent Claim
11 words
The method of claim 44 wherein the active agent is 5-(trifluoromethyl)-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 48
Dependent Claim
11 words
The method of claim 44 wherein the active agent is 5-(trifluoromethyl)-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 49
Dependent Claim
11 words
The method of claim 44 wherein the active agent is 5-(trifluoromethyl)-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
References Cited (Backward Citations)
US2925418A
Cited
US2965643A
Cited
US3187006A
Cited
DE1058519B
Cited
GB884851A
Cited
US3567735A
Cited
US3732225A
Cited
US3760084A
Cited
JPS4970966A
Cited
US3953467A
Cited
GB1488285A
Cited
US4134987A
Cited
GB1573942A
Cited
US4316039A
Cited
US4298749A
Cited
US4316040A
Cited
US4245106A
Cited
GB2070604A
Cited
US4346094A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-11-03 | 1990-05-05 | 1990-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-03 | 1994-05-05 | 1994-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-03 | 1998-05-05 | 1998-11-04 | $7700.00 | Window Closed / Lapsed |