US4036631A
Expired / Lapsed
US
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Pyrazolone derivatives and their use as herbicides
Assignee: Sankyo Co Ltd
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Filing: 1976-08-12
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Granted: 1977-07-19
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Expires: 1996-08-12
Abstract
Abstract Pyrazolone compounds of the formula ##STR1## WHEREIN R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different. These compounds are useful as herbicides and obtainable by reacting the corresponding 5-pyrazolone derivatives with a halogenating agent.
Inventors
- 👤 Takuo Konotsune
- 👤 Katsuhiko Kawakubo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 02:01
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/18; C07D231/20
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
74 words
A compound having the formula ##STR5## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 2
Dependent Claim
74 words
A compound having the formula ##STR5## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 3
Dependent Claim
99 words
The compound according to claim 1 wherein R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 3 to 6 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 4
Dependent Claim
81 words
The compound according to claim 1 wherein R 1 is an alkyl group having 1 to 3 carbon atoms, R 2 is an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 3 or 4 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, a methyl group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 5
Dependent Claim
67 words
The compound according to claim 1 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromine atom, Y is a chlorine atom, a methyl group, a nitro group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 6
Dependent Claim
73 words
The compound according to claim 1 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromine atom, n is 2 and Y's are attached to the phenyl group at 2 and 4 positions and each Y represents a chlorine atom or Y at the 2-position is a chlorine atom and Y at the 4-position is a nitro group.
Claim 7
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 8
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 9
Dependent Claim
1 words
1,3-Dimethyl-4-bromo-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 10
Dependent Claim
1 words
1,3-Dimethyl-4-bromo-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 11
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2-chloro-4-nitrobenzoyl)-5-pyrazolone.
Claim 12
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2-chloro-4-nitrobenzoyl)-5-pyrazolone.
Claim 13
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2-nitro-5-methylbenzoyl)-5-pyrazolone.
Claim 14
Dependent Claim
1 words
1,3-Dimethyl-4-chloro-4-(2-nitro-5-methylbenzoyl)-5-pyrazolone.
Claim 15
Dependent Claim
1 words
1-Ethyl-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 16
Dependent Claim
1 words
1-Ethyl-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 17
Dependent Claim
1 words
1-(2-Propenyl)-3-methyl-4-chloro-4-(2,4-dichlorobenzyl)-5-pyrazolone.
Claim 18
Dependent Claim
1 words
1-(2-Propenyl)-3-methyl-4-chloro-4-(2,4-dichlorobenzyl)-5-pyrazolone.
Claim 19
Dependent Claim
88 words
A herbicidal composition which comprises as an active ingredient a compound having the formula ##STR6## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different and an agriculturally acceptable carrier.
Claim 20
Dependent Claim
88 words
A herbicidal composition which comprises as an active ingredient a compound having the formula ##STR6## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different and an agriculturally acceptable carrier.
Claim 21
Dependent Claim
99 words
The composition according to claim 12 wherein R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R 2 is an alkyl group having 1 to 6 carbon atoms or an alkenyl group having 3 to 6 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 22
Dependent Claim
81 words
The composition according to claim 12 wherein R 1 is an alkyl group having 1 to 3 carbon atoms, R 2 is an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 3 to 4 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, a methyl group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 23
Dependent Claim
67 words
The composition according to claim 12 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromide atom, Y is a chlorine atom, a methyl group, a nitro group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 24
Dependent Claim
73 words
The composition according to claim 12 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromine atom, n is 2 and Y's are attached to the phenyl group at 2 and 4 positions and each Y represents a chlorine atom or Y at the 2-position is a chlorine atom and Y at the 4-position is a nitro group.
Claim 25
Dependent Claim
23 words
The composition according to claim 12 wherein said compound is selected from the group consisting of 1,3-dimethyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-bromo-4-(2,4-dichlorobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-chloro-4-(2-chloro-4-nitrobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-chloro-4-(2-nitro-5-methylbenzoyl)-5-pyrazolone, 1-ethyl-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone and 1-(2-propenyl)-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 26
Dependent Claim
24 words
The composition according to claim 12 wherein said compound is contained in an amount of 0.1 - 99% by weight, based upon the composition.
Claim 27
Independent Claim
92 words
A method for the destruction of undesirable weeds which comprises applying to said weeds a herbicidal amount of a compound having the formula ##STR7## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 28
Independent Claim
92 words
A method for the destruction of undesirable weeds which comprises applying to said weeds a herbicidal amount of a compound having the formula ##STR7## wherein R 1 represents a hydrogen atom or a lower alkyl group, R 2 represents a lower alkyl group or a lower alkenyl group, X represents a halogen atom, Y represents a halogen atom, a nitro group, a lower alkyl group or a lower alkoxy group, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 29
Dependent Claim
99 words
The method according to claim 19 wherein R 1 is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R 2 is an aklyl group having 1 to 6 carbon atoms or an alkenyl group having 3 to 6 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, n is an integer of 1 to 3 and when n is 2 or 3, Y's may be the same or different.
Claim 30
Dependent Claim
81 words
The method according to claim 19 wherein R 1 is an alkyl group having 1 to 3 carbon atoms, R 2 is an alkyl group having 1 to 3 carbon atoms or an alkenyl group having 3 to 4 carbon atoms, X is a halogen atom, Y is a halogen atom, a nitro group, a methyl group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 31
Dependent Claim
67 words
The method according to claim 19 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromine atom, Y is a chlorine atom, a methyl group, a nitro group or a methoxy group, n is an integer of 1 or 2 and when n is 2, Y's may be the same or different.
Claim 32
Dependent Claim
73 words
The method according to claim 19 wherein R 1 is a methyl group, R 2 is a methyl group or a 2-propenyl group, X is a chlorine atom or a bromine atom, n is 2 and Y's are attached to the phenyl group at 2 and 4 positions and each Y represents a chlorine atom or Y at the 2-position is a chlorine atom and Y at the 4-position is a nitro group.
Claim 33
Dependent Claim
23 words
The method according to claim 19 wherein said compound is selected from the group consisting of 1,3-dimethyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-bromo-4-(2,4-dichlorobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-chloro-4-(2-chloro-4-nitrobenzoyl)-5-pyrazolone, 1,3-dimethyl-4-chloro-4-(2-nitro-5-methylbenzoyl)-5-pyrazolone, 1-ethyl-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone and 1-(2-propenyl)-3-methyl-4-chloro-4-(2,4-dichlorobenzoyl)-5-pyrazolone.
Claim 34
Dependent Claim
26 words
The method according to claim 19 wherein said herbicidal amount is within the range of 10 g to 4000 g of said compound per 10 ares.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-18 | 1981-01-17 | 1981-07-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-18 | 1985-01-17 | 1985-07-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-18 | 1989-01-17 | 1989-07-19 | $7700.00 | Window Closed / Lapsed |