US4124374A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Alkyl-substituted cycloalkanapyrazole herbicides
Assignee: Marley Wylain Co LLC
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Filing: 1976-09-27
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Granted: 1978-11-07
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Expires: 1996-09-27
Abstract
Abstract Herbicidal alkyl-substituted cycloalkanapyrazoles of the formula: ##STR1## where N IS 3, 4 OR 5; R 1 is hydrogen or methyl; Q is methyl; X is fluorine, chlorine, bromine, iodine, cyano or methoxy; Y is hydrogen, fluorine or chlorine; Z is hydrogen or fluorine; V is hydrogen, fluorine, chlorine or OR; and R is alkyl of 1 to 4 carbon atoms; with the proviso that A. when n is 3, R 1 is hydrogen; B. when n is 5, R 1 is hydrogen, Y is hydrogen or fluorine, Z and V are hydrogen and X is fluorine, chlorine or bromine; C. when V is OR, X and Y are chlorine and Z is hydrogen; D. when V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen. Preferred for their higher activity or favorable cost or both are those compounds of formula I where, independently, 1. R 1 is hydrogen and n is 4, 2. Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen. Most preferred for their outstanding herbicidal activity are those compounds of formula I where n is 4, R 1 is hydrogen, X is fluorine, chlorine or bromine, Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen.
Inventors
- 👤 Anthony D. Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 00:11
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/54; C07D231/56; C07C; C07C243/00
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
127 words
A compound of the formula ##STR50## where n is 3, 4 or 5; R 1 is hydrogen or methyl; Q is methyl; X is fluorine, chlorine, bromine, iodine, cyano or methoxy; Y is hydrogen, fluorine or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine or chlorine; with the proviso that a. when n is 3, R 1 is hydrogen; and when V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen; b. when n is 4 and V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen; and c. when n is 5, R 1 is hydrogen, Y is hydrogen or fluorine, Z and V are hydrogen and X is fluorine, chlorine or bromine.
Claim 2
Dependent Claim
127 words
A compound of the formula ##STR50## where n is 3, 4 or 5; R 1 is hydrogen or methyl; Q is methyl; X is fluorine, chlorine, bromine, iodine, cyano or methoxy; Y is hydrogen, fluorine or chlorine; Z is hydrogen or fluorine; and V is hydrogen, fluorine or chlorine; with the proviso that a. when n is 3, R 1 is hydrogen; and when V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen; b. when n is 4 and V is fluorine or chlorine, X is fluorine, chlorine or bromine and Z is hydrogen; and c. when n is 5, R 1 is hydrogen, Y is hydrogen or fluorine, Z and V are hydrogen and X is fluorine, chlorine or bromine.
Claim 3
Dependent Claim
14 words
A compound of claim 1 wherein R 1 is hydrogen and n is 4.
Claim 4
Dependent Claim
18 words
A compound of claim 1 wherein Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen.
Claim 5
Dependent Claim
31 words
A compound of claim 1 wherein n is 4, R 1 is hydrogen, X is fluorine, chlorine or bromine, Y is hydrogen or fluorine, V is hydrogen and Z is hydrogen.
Claim 6
Dependent Claim
6 words
A compound of claim 1, 2-(4-chloro-2-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole.
Claim 7
Dependent Claim
6 words
A compound of claim 1, 2-(4-bromo-2-fluorophenyl)-3-methyl-4,5,6,7-tetrahydro-2H-indazole.
Claim 8
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of a compound of claim 1 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 9
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of a compound of claim 2 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 10
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of a compound of claim 3 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 11
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of a compound of claim 4 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 12
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of the compound of claim 5 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 13
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbicidally effective amount of the compound of claim 6 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 14
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 15
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 16
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 17
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 18
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 5.
Claim 19
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 6.
Claim 20
Dependent Claim
30 words
A method for the control of undesirable vegetation in rice, which comprises applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 21
Dependent Claim
30 words
A method for the control of undesirable vegetation in rice, which comprises applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 5.
Claim 22
Dependent Claim
11 words
The method of claim 19 wherein the undesirable vegetation is barnyardgrass.
Claim 23
Dependent Claim
29 words
A method for the control of undesirable vegetation in wheat comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 24
Dependent Claim
29 words
A method for the control of undesirable vegetation in wheat comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 5.
Claim 25
Dependent Claim
29 words
A method for the control of undesirable vegetation in paddyrice comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 26
Dependent Claim
29 words
A method for the control of undesirable vegetation in paddyrice comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 5.
Claim 27
Dependent Claim
30 words
A method for the control of undesirable vegetation in transplanted crops comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 28
Dependent Claim
30 words
A method for the control of undesirable vegetation in transplanted crops comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of the compound of claim 5.
Claim 29
Dependent Claim
11 words
The method of claim 24 wherein the undesirable vegetation is barnyardgrass.
Claim 30
Dependent Claim
56 words
A compound of the formula ##STR51## where n is 3 or 4; R 1 is hydrogen or methyl; Q is methyl; X is chlorine; Y is chlorine; Z is hydrogen; V is OR; and R is alkyl of 1 to 4 carbon atoms, with the proviso that a. when n is 3, R 1 is hydrogen.
Claim 31
Dependent Claim
56 words
A compound of the formula ##STR51## where n is 3 or 4; R 1 is hydrogen or methyl; Q is methyl; X is chlorine; Y is chlorine; Z is hydrogen; V is OR; and R is alkyl of 1 to 4 carbon atoms, with the proviso that a. when n is 3, R 1 is hydrogen.
Claim 32
Dependent Claim
14 words
A compound of claim 29 wherein R 1 is hydrogen and n is 4.
Claim 33
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbidically effective amount of a compound of claim 29 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 34
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 29.
Claim 35
Dependent Claim
30 words
A method for the control of undesirable vegetation in rice, which comprises applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 29.
Claim 36
Dependent Claim
11 words
The method of claim 32 wherein the undesirable vegetation is barnyardgrass.
Claim 37
Dependent Claim
29 words
A method for the control of undesirable vegetation in wheat comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 29.
Claim 38
Dependent Claim
29 words
A method for the control of undesirable vegetation in paddyrice comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 29.
Claim 39
Dependent Claim
11 words
The method of claim 35 wherein the undesirable vegetation is barnyardgrass.
Claim 40
Dependent Claim
30 words
A method for the control of undesirable vegetation in transplanted crops comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 29.
Claim 41
Dependent Claim
37 words
A composition for the control of undesirable vegetation consisting essentially of a herbidically effective amount of a compound of claim 30 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 42
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 30.
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) | 1981-11-06 | 1982-05-08 | 1982-11-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-11-06 | 1986-05-08 | 1986-11-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-11-06 | 1990-05-08 | 1990-11-07 | $7700.00 | Window Closed / Lapsed |