US4059434A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Cycloalkanapyrazole herbicides
Assignee: EIDP Inc
•
Filing: 1976-08-26
•
Granted: 1977-11-22
•
Expires: 1996-08-26
Abstract
Abstract Herbicidal cycloalkanapyrazoles of the formula: ##STR1## where N IS 3, 4 OR 5; R 1 is hydrogen or methyl; Q is fluorine, chlorine, bromine or iodine; X is fluorine, chlorine, bromine, iodine, cyano, methoxy or nitro; Y is hydrogen, fluorine, or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine, chlorine or methoxy with the proviso that A. when n is 5, R 1 must be hydrogen, Q must be chlorine or bromine, Z and V must both be hydrogen and Y must be hydrogen or fluorine; B. when n is 3 or 4 and Q is fluorine or iodine, R 1 , Z and V must be hydrogen and Y must be hydrogen or fluorine; C. when n is 3 and R 1 is methyl, Q must be chlorine or bromine, Y must be hydrogen or fluorine and Z and V must both be hydrogen; and, D. when V is other than hydrogen, X must be fluorine, chlorine or bromine and Z must be hydrogen.
Inventors
- 👤 Anthony David Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:18
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/54; C07D231/56; C07C; C07C243/00
Claims Analysis
Total Claims: 106
Claim 1
Independent Claim
167 words
A compound of the formula ##STR247## where n is 3, 4 or 5; R 1 is hydrogen or methyl; Q is fluorine, chlorine, bromime or iodine; X is fluorine, chlorine, bromine, iodine, cyano, methoxy or nitro; Y is hydrogen, fluorine or chlorine; Z is hydrogen or flurorine; and V is hydrogen, fluorine, chlorine or methoxy; with the proviso that a. when n is 5, R 1 must be hydrogen, Q must be chlorine or bromine, Z and V must both be hydrogen and Y must be hydrogen or fluorine; b. when n is 3 or 4 and Q is fluorine or iodine, R 1 , Z and Y must be hydrogen and Y must be hydrogen or fluorine; c. when n is 3 and R 1 is methyl, Q must be chlorine or bromine, Y must be hydrogen or fluorine and Z and V must be hydrogen; and d. when V is other than hydrogen, X must be fluorine, chlorine or bromine and Z must be hydrogen.
Claim 2
Dependent Claim
167 words
A compound of the formula ##STR247## where n is 3, 4 or 5; R 1 is hydrogen or methyl; Q is fluorine, chlorine, bromime or iodine; X is fluorine, chlorine, bromine, iodine, cyano, methoxy or nitro; Y is hydrogen, fluorine or chlorine; Z is hydrogen or flurorine; and V is hydrogen, fluorine, chlorine or methoxy; with the proviso that a. when n is 5, R 1 must be hydrogen, Q must be chlorine or bromine, Z and V must both be hydrogen and Y must be hydrogen or fluorine; b. when n is 3 or 4 and Q is fluorine or iodine, R 1 , Z and Y must be hydrogen and Y must be hydrogen or fluorine; c. when n is 3 and R 1 is methyl, Q must be chlorine or bromine, Y must be hydrogen or fluorine and Z and V must be hydrogen; and d. when V is other than hydrogen, X must be fluorine, chlorine or bromine and Z must be hydrogen.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein n is 4.
Claim 4
Dependent Claim
9 words
A compound of claim 1 wherein n is 3.
Claim 5
Dependent Claim
17 words
A compound of claim 1 wherein Y is hydrogen or fluorine and Z and V are hydrogen.
Claim 6
Dependent Claim
9 words
A compound of claim 1 wherein Q is chlorine.
Claim 7
Dependent Claim
15 words
A compound of claim 1 wherein n is 4 and Q is chlorine or bromine.
Claim 8
Dependent Claim
13 words
A compound of claim 1 wherein n is 4 and Q is chlorine.
Claim 9
Dependent Claim
19 words
A compound of claim 1 wherein n is 4, Q is chlorine or bromine and R 1 is hydrogen.
Claim 10
Dependent Claim
17 words
A compound of claim 1 wherein n is 4, Q is chlorine and R 1 is hydrogen.
Claim 11
Dependent Claim
17 words
A compound of claim 1 wherein n is 4, Q is bromine and R 1 is hydrogen.
Claim 12
Dependent Claim
15 words
A compound of claim 1 wherein n is 3 and Q is chlorine or bromine.
Claim 13
Dependent Claim
19 words
A compound of claim 1 wherein n is 3, Q is chlorine or bromine and R 1 is hydrogen.
Claim 14
Dependent Claim
17 words
A compound of claim 1 wherein n is 3, Q is chlorine and R 1 is hydrogen.
Claim 15
Dependent Claim
20 words
A compound of claim 1 wherein Q is chlorine, Z and V are hydrogen and Y is hydrogen or fluorine.
Claim 16
Dependent Claim
23 words
A compound of claim 1 wherein n is 4, Q is chlorine, R 1 is hydrogen, Z is hydrogen and V is hydrogen.
Claim 17
Dependent Claim
36 words
A compound of claim 1 wherein n is 4, Q is chlorine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine and X is fluorine, chlorine, bromine, cyano or methoxy.
Claim 18
Dependent Claim
33 words
A compound of claim 1 wherein n is 4, Q is chlorine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine and X is chlorine or bromine.
Claim 19
Dependent Claim
23 words
A compound of claim 1 wherein n is 4, Q is bromine, R 1 is hydrogen, Z is hydrogen and V is hydrogen.
Claim 20
Dependent Claim
36 words
A compound of claim 1 wherein n is 4, Q is bromine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine, and X is fluorine, chlorine, bromine, cyano or methoxy.
Claim 21
Dependent Claim
33 words
A compound of claim 1 wherein n is 4, Q is bromine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine, and X is chlorine or bromine.
Claim 22
Dependent Claim
23 words
A compound of claim 1 wherein n is 3, Q is chlorine, R 1 is hydrogen, Z is hydrogen and V is hydrogen.
Claim 23
Dependent Claim
36 words
A compound of claim 1 wherein n is 3, Q is chlorine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine, and X is fluorine, chlorine, bromine, cyano or methoxy.
Claim 24
Dependent Claim
33 words
A compound of claim 1 wherein n is 3, Q is chlorine, R 1 is hydrogen, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine, and X is chlorine or bromine.
Claim 25
Dependent Claim
26 words
A compound of claim 1 wherein Q is chlorine, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine and X is chlorine or bromine.
Claim 26
Dependent Claim
29 words
A compound of claim 1 wherein n is 3, Q is bromine, Z is hydrogen, V is hydrogen, Y is hydrogen or fluorine and X is chlorine or bromine.
Claim 27
Dependent Claim
6 words
The compound of claim 1, 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 28
Dependent Claim
6 words
The compound of claim 1, 3-chloro-2-(4-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 29
Dependent Claim
6 words
The compound of claim 1, 3-bromo-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 30
Dependent Claim
6 words
The compound of claim 1, 3-chloro-2-(4-bromo-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 31
Dependent Claim
6 words
The compound of claim 1, 3-chloro-2-(4-chloro-2-fluorophenyl)-2,4,5,6-tetrahydrocyclopentapyrazole.
Claim 32
Dependent Claim
6 words
The compound of claim 1, 3-chloro-2-(4-chlorophenyl)-2,4,5,6-tetrahydrocyclopentapyrazole.
Claim 33
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 1 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 34
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 2 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 35
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 3 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 36
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 4 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 37
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 5 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 38
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 6 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 39
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 7 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 40
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 8 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 41
Dependent Claim
38 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 9 and at least one of (a) an inert surface active agent and (b) a solid or liquid diluent.
Claim 42
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 10 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 43
Dependent Claim
34 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of claim 11 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 44
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 12 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 45
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 13 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 46
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 14 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 47
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 15 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 48
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 16 and at least one of (a) an inert surfact-active agent, and (b) a solid or liquid diluent.
Claim 49
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 17 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 50
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 18 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 51
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 19 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 52
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 20 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 53
Dependent Claim
34 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of claim 21 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 54
Dependent Claim
37 words
A compositon for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 22 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 55
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 23 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 56
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 24 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 57
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of a compound of claim 25 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 58
Dependent Claim
37 words
A compositon for the control of undesirable vegetation consisting essentially of an effective amount of the compound of claim 26 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 59
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of the compound of claim 27 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 60
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of the compound of claim 28 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 61
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of the compound of claim 29 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 62
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of the compound of an effective amount of claim 30 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 63
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of an effective amount of the compound of claim 31 and at least one of (a) an inert surface-active agent, and (b) a solid or liquid diluent.
Claim 64
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 65
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 2.
Claim 66
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 3.
Claim 67
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 4.
Claim 68
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 5.
Claim 69
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 6.
Claim 70
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 7.
Claim 71
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 8.
Claim 72
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 9.
Claim 73
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 10.
Claim 74
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 11.
Claim 75
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 12.
Claim 76
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 13.
Claim 77
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 14.
Claim 78
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 15.
Claim 79
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 16.
Claim 80
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbidically effective amount of a compound of claim 17.
Claim 81
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbidically effective amount of a compound of claim 18.
Claim 82
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 19.
Claim 83
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 20.
Claim 84
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 21.
Claim 85
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 22.
Claim 86
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 23.
Claim 87
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbidically effective amount of a compound of claim 24.
Claim 88
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 25.
Claim 89
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 26.
Claim 90
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 27.
Claim 91
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 28.
Claim 92
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 29.
Claim 93
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 30.
Claim 94
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 31.
Claim 95
Dependent Claim
31 words
A method for the control of undesirable vegetation in rice consisting essentially of applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 96
Dependent Claim
12 words
The method of claim 94, wherein said undesirable vegetation is barnyard grass.
Claim 97
Dependent Claim
10 words
The method of claim 94, wherein the compound is 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 98
Dependent Claim
10 words
The method of claim 94, wherein the compound is 3-chloro-2-(4-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 99
Dependent Claim
10 words
The method of claim 96, wherein the rice is paddyrice.
Claim 100
Dependent Claim
10 words
The method of claim 97, wherein the rice is paddyrice.
Claim 101
Dependent Claim
30 words
A method for the control of undesirable vegetation in wheat which comprises applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 1.
Claim 102
Dependent Claim
10 words
The method of claim 100, wherein the compound is 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 103
Dependent Claim
10 words
The method of claim 100, wherein the compound is 3-chloro-2-(4-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 104
Dependent Claim
32 words
A method for the control of undesirable vegetation in transplanted crops consisting essentially of applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 1.
Claim 105
Dependent Claim
10 words
The method of claim 103, wherein the compound is 3-chloro-2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
Claim 106
Dependent Claim
10 words
The method of claim 103, wherein the compound is 3-chloro-2-(4-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazole.
References Cited (Backward Citations)
US3364227A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-11-21 | 1981-05-23 | 1981-11-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-21 | 1985-05-23 | 1985-11-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-21 | 1989-05-23 | 1989-11-22 | $7700.00 | Window Closed / Lapsed |