US4589905A
Expired / Lapsed
US
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Herbicidal and algicidal 1-aryl-5-cyano-1H-pyrazole-4-carboxamides
Assignee: Eli Lilly and Co
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Filing: 1984-09-13
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Granted: 1986-05-20
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Expires: 2004-09-13
Abstract
Abstract The present invention is directed to compounds of the formula ##STR1## wherein R 1 is C 1 -C 6 alkyl, C 5 -C 6 cycloalkyl, ##STR2## each of R 2 and R 3 is taken separately and is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl or C 1 -C 3 alkoxy, or R 2 and R 3 are taken together with the nitrogen atom to which they are attached and form piperidine, morpholine or pyrrolidine; each R 4 independently is halogen, C 1 -C 4 alkyl, C 1 -Cphd 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or cyano; X is 0 or S; and m is 0-3; with the provisos that when R 4 is C 1 -C 4 alkyl, that substituent exists at other than the 2 or 6 position of the phenyl ring; and when R 2 is C 1 -C 3 alkoxy, R 3 is other than C 1 -C 3 alkoxy. These compounds exhibit activity as terrestrial herbicides, aquatic herbicides, and aquatic algicides.
Inventors
- 👤 James R. Beck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 23:56
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; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 46
Claim 1
Independent Claim
170 words
A compound of the formula ##STR11## wherein R 1 is C 1 -C 6 alkyl, C 5 -C 6 cycloalkyl, ##STR12## each of R 2 and R 3 is taken separately and is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl or C 1 -C 3 alkoxy, or R 2 and R 3 are taken together with the nitrogen atom to which they are attached and form piperidine, morpholine or pyrrolidine; each R 4 independently is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or cyano; X is O or S; and m is 0-3; with the provisos that when R 4 is C 1 -C 4 alkyl, that substituent exists at other than the 2 or 6 position of the phenyl ring; and when R 2 is C 1 -C 3 alkoxy R 3 is other than C 1 -C 3 alkoxy.
Claim 2
Dependent Claim
170 words
A compound of the formula ##STR11## wherein R 1 is C 1 -C 6 alkyl, C 5 -C 6 cycloalkyl, ##STR12## each of R 2 and R 3 is taken separately and is independently hydrogen, C 1 -C 4 alkyl, C 3 -C 4 alkenyl, C 3 -C 4 alkynyl, C 3 -C 4 cycloalkyl or C 1 -C 3 alkoxy, or R 2 and R 3 are taken together with the nitrogen atom to which they are attached and form piperidine, morpholine or pyrrolidine; each R 4 independently is halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy or cyano; X is O or S; and m is 0-3; with the provisos that when R 4 is C 1 -C 4 alkyl, that substituent exists at other than the 2 or 6 position of the phenyl ring; and when R 2 is C 1 -C 3 alkoxy R 3 is other than C 1 -C 3 alkoxy.
Claim 3
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is ##STR13##
Claim 4
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 5
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-phenyl-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 6
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 7
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-(4-chlorophenyl)-N-methyl-N-ethyl-1H-pyrazole-4-carboxamide.
Claim 8
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 9
Dependent Claim
8 words
The compound of claim 2 which is 5-cyano-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 10
Dependent Claim
10 words
A compound of claim 1 wherein R 1 is ##STR14##
Claim 11
Dependent Claim
8 words
The compound of claim 9 which is 5-cyano-1-(2-pyridinyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 12
Dependent Claim
8 words
The compound of claim 9 which is 5-cyano-1-(2-pyridinyl)-N-methyl-N-methoxy-1H-pyrazole-4-carboxamide.
Claim 13
Dependent Claim
8 words
The compound of claim 9 which is 5-cyano-1-(2-pyridinyl)-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 14
Dependent Claim
14 words
A compound of claim 1 wherein R 1 is C 1 -C 6 alkyl.
Claim 15
Dependent Claim
10 words
A compound of claim 13 wherein R 1 is tert-butyl.
Claim 16
Dependent Claim
8 words
The compound of claim 14 which is 5-cyano-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 17
Dependent Claim
8 words
The compound of claim 14 which is 5-cyano-1-tert-butyl-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 18
Dependent Claim
8 words
The compound of claim 14 which is 5-cyano-1-tert-butyl-N-ethyl-1H-pyrazole-4-carboxamide.
Claim 19
Dependent Claim
8 words
The compound of claim 14 which is 5-cyano-1-tert-butyl-N,N-dimethyl-1H-pyrazole-4-carboxamide.
Claim 20
Dependent Claim
23 words
A composition which comprises from about 0.1 to about 95.0 percent by weight of a compound of claim 1 and an agriculturally-acceptable carrier.
Claim 21
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 22
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-phenyl-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 23
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 24
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(4-chlorophenyl)-N-methyl-N-ethyl-1H-pyrazole-4-carboxamide.
Claim 25
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 26
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 27
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 28
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-methyl-N-methoxy-1H-pyrazole-4-carboxamide.
Claim 29
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 30
Dependent Claim
10 words
The composition of claim 19 wherein the compound is 5-cyano-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 31
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 32
Dependent Claim
11 words
The method of claim 30 wherein the active agent is 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 33
Dependent Claim
11 words
The method of claim 30 wherein the active agent is 5-cyano-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 34
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 35
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-phenyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 36
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-phenyl-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 37
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(4-chlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 38
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(4-chlorophenyl)-N-methyl-N-ethyl-1H-pyrazole-4-carboxamide.
Claim 39
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(4-bromophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 40
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(2,4-dichlorophenyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 41
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-methyl-1H-pyrazole-4-carboxamide.
Claim 42
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-methyl-N-methoxy-1H-pyrazole-4-carboxamide.
Claim 43
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-(2-pyridinyl)-N-cyclopropyl-1H-pyrazole-4-carboxamide.
Claim 44
Dependent Claim
10 words
The method of claim 33 wherein the compound is 5-cyano-1-tert-butyl-N-methyl-1H-pyrazole-4-carboxamide.
Claim 45
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 46
Dependent Claim
34 words
A method for controlling the growth of aquatic plants which comprises contacting the plants or the water in which the plants are growing with an aquatic herbicidally-effective amount of a compound of claim 1.
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) | 1989-05-19 | 1989-11-18 | 1990-05-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-05-19 | 1993-11-18 | 1994-05-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-05-19 | 1997-11-18 | 1998-05-20 | $7700.00 | Window Closed / Lapsed |