US4110105A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Aromatic N-substituted halo-substituted-2-pyrrolidinones and their utility as herbicides
Assignee: Zeneca Inc
•
Filing: 1976-01-09
•
Granted: 1978-08-29
•
Expires: 1996-01-09
Abstract
Abstract Monocyclic aromatic N-substituted halo-2-pyrrolidinones having the formula <IMAGE> in which X is hydrogen, chlorine or methyl; Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R2 is alkyl or hydrogen; R is hydrogen, alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoropropionamido, or 3-methylureido; and R1 is hydrogen, alkyl, chlorine or trifluoromethyl. The compounds of this invention are prepared by a novel process and are useful as herbicides.
Inventors
- 👤 Eugene G. Teach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 21:17
CPC Classifications
C; C07; C07D; C07D207/00; C07D207/02; C07D207/18; C07D207/22; C07D207/24; C07D207/26; C07D207/273
Claims Analysis
Total Claims: 100
Claim 1
Independent Claim
111 words
A compound having the formula ##STR6## in which X is hydrogen, chlorine or methyl; Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R 2 is alkyl having from 1 to 4 carbon atoms, inclusive, or hydrogen; R is hydrogen, alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, alkoxy having from 1 to 4 carbon atoms, inclusive, alkylthio having from 1 to 4 carbon atoms, inclusive, alkylsulfinyl having from 1 to 4 carbon atoms, inclusive, alkylsulfonyl having from 1 to 4 carbon atoms, inclusive, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, penta fluoropropionamido or 3-methylureido; and R 1 is hydrogen, alkyl having from 1 to 4 carbon atoms, inclusive, chlorine or trifluoromethyl.
Claim 2
Dependent Claim
111 words
A compound having the formula ##STR6## in which X is hydrogen, chlorine or methyl; Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R 2 is alkyl having from 1 to 4 carbon atoms, inclusive, or hydrogen; R is hydrogen, alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, alkoxy having from 1 to 4 carbon atoms, inclusive, alkylthio having from 1 to 4 carbon atoms, inclusive, alkylsulfinyl having from 1 to 4 carbon atoms, inclusive, alkylsulfonyl having from 1 to 4 carbon atoms, inclusive, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, penta fluoropropionamido or 3-methylureido; and R 1 is hydrogen, alkyl having from 1 to 4 carbon atoms, inclusive, chlorine or trifluoromethyl.
Claim 3
Dependent Claim
26 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 4
Dependent Claim
26 words
The compound according to claim 1 in which X is chlorine, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 5
Dependent Claim
26 words
The compound according to claim 1 in which X is methyl, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 6
Dependent Claim
46 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is methyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, pentafluoropropionamido, or 3-methylureido, and R 1 is hydrogen.
Claim 7
Dependent Claim
11 words
The compound according to claim 5 in which R is 4-methyl.
Claim 8
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-fluorine.
Claim 9
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-chlorine.
Claim 10
Dependent Claim
11 words
The compound according to claim 5 in which R is 4-chlorine.
Claim 11
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-trifluoromethyl.
Claim 12
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-nitro.
Claim 13
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-cyano.
Claim 14
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-trifluorothio.
Claim 15
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-trifluorosulfinyl.
Claim 16
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-trifluorosulfonyl.
Claim 17
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-methylthio.
Claim 18
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-methylsulfinyl.
Claim 19
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-methylsulfonyl.
Claim 20
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-methoxy.
Claim 21
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-acetyl.
Claim 22
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-methyl.
Claim 23
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-bromine.
Claim 24
Dependent Claim
11 words
The compound according to claim 5 in which R is 2-chlorine.
Claim 25
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-iodine.
Claim 26
Dependent Claim
11 words
The compound according to claim 5 in which R is 4-methoxy.
Claim 27
Dependent Claim
11 words
The compound according to claim 5 in which R is 2-trifluoromethyl.
Claim 28
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-pentafluoropropionamido.
Claim 29
Dependent Claim
11 words
The compound according to claim 5 in which R is 3-(3-methylureido).
Claim 30
Dependent Claim
14 words
The compound according to claim 5 in which said compound is the cis-isomer configuration.
Claim 31
Dependent Claim
11 words
The compound according to claim 29 in which R is 3-trifluoromethyl.
Claim 32
Dependent Claim
14 words
The compound according to claim 5 in which said compound is the trans-isomer configuration.
Claim 33
Dependent Claim
11 words
The compound according to claim 31 in which R is 3-trifluoromethyl.
Claim 34
Dependent Claim
29 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is alkyl and R 1 is alkyl.
Claim 35
Dependent Claim
16 words
The compound according to claim 33 in which R is 2-methyl and R 1 is 6-methyl.
Claim 36
Dependent Claim
34 words
The compound according to claim 1 in which X is chlorine, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is chlorine, trifluoromethyl or cyano, and R 1 is hydrogen or chlorine.
Claim 37
Dependent Claim
16 words
The compound according to claim 35 in which R is 3-chlorine, and R 1 is 4-chlorine.
Claim 38
Dependent Claim
16 words
The compound according to claim 35 in which R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 39
Dependent Claim
16 words
The compound according to claim 35 in which R is 3-chlorine and R 1 is 5-chlorine.
Claim 40
Dependent Claim
16 words
The compound according to claim 35 in which R is 3-cyano and R 1 is hydrogen.
Claim 41
Dependent Claim
16 words
The compound according to claim 35 in which R is 3-trifluoromethyl and R 1 is 4-chlorine.
Claim 42
Dependent Claim
29 words
The compound according to claim 1 in which X is hydrogen, Y is bromine, Z is bromine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 43
Dependent Claim
29 words
The compound according to claim 1 in which X is methyl, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 44
Dependent Claim
29 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-chlorine and R 1 is 5-chlorine.
Claim 45
Dependent Claim
29 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is methyl, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 46
Dependent Claim
29 words
The compound according to claim 1 in which X is chlorine, Y is chlorine, Z is chlorine, R 2 is methyl, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 47
Dependent Claim
25 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R is 3-chlorine and R 1 is 4-chlorine.
Claim 48
Dependent Claim
25 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R is 3-trifluoromethyl and R 1 is 4-chlorine.
Claim 49
Dependent Claim
25 words
The compound according to claim 1 in which X is hydrogen, Y is chlorine, Z is chlorine, R is 3-trifluoromethyl and R 1 is 5-trifluoromethyl.
Claim 50
Dependent Claim
46 words
The compound according to claim 1 in which X is hydrogen, Y is hydrogen, Z is chlorine, R is methyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, pentafluoropropionamido, or 3-methylureido, and R 1 and R 2 are each hydrogen.
Claim 51
Dependent Claim
11 words
The compound according to claim 49 in which R is 3-trifluoromethyl.
Claim 52
Independent Claim
140 words
A method for controlling the growth of undesirable vegetation which comprises applying to at least one of (a) such undesirable vegetation and (b) their habitat, an herbicidally effective amount of a compound having the formula ##STR7## in which X is hydrogen, chlorine or methyl; Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R 2 is alkyl having from 1 to 4 carbon atoms, inclusive, or hydrogen; R is hydrogen, alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, alkoxy having from 1 to 4 carbon atoms, inclusive, alkylthio having from 1 to 4 carbon atoms, inclusive, alkylsulfinyl having from 1 to 4 carbon atoms, inclusive, alkylsulfonyl having from 1 to 4 carbon atoms, inclusive, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoroproprionamido, or 3-methylureido; and R 1 is hydrogen, alkyl having from 1 to 4 carbon atoms, inclusive, chlorine or trifluoromethyl.
Claim 53
Independent Claim
140 words
A method for controlling the growth of undesirable vegetation which comprises applying to at least one of (a) such undesirable vegetation and (b) their habitat, an herbicidally effective amount of a compound having the formula ##STR7## in which X is hydrogen, chlorine or methyl; Y is hydrogen, chlorine or bromine, Z is chlorine or bromine; R 2 is alkyl having from 1 to 4 carbon atoms, inclusive, or hydrogen; R is hydrogen, alkyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, alkoxy having from 1 to 4 carbon atoms, inclusive, alkylthio having from 1 to 4 carbon atoms, inclusive, alkylsulfinyl having from 1 to 4 carbon atoms, inclusive, alkylsulfonyl having from 1 to 4 carbon atoms, inclusive, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, pentafluoroproprionamido, or 3-methylureido; and R 1 is hydrogen, alkyl having from 1 to 4 carbon atoms, inclusive, chlorine or trifluoromethyl.
Claim 54
Dependent Claim
26 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 55
Dependent Claim
26 words
The method according to claim 51 in which X is chlorine, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 56
Dependent Claim
26 words
The method according to claim 51 in which X is methyl, Y is chlorine, Z is chlorine, R, R 1 and R 2 are each hydrogen.
Claim 57
Dependent Claim
46 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is methyl, acetyl, chlorine, bromine, fluorine, iodine, trifluoromethyl, nitro, cyano, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, pentafluoropropionamido, or 3-methylureido; and R 1 is hydrogen.
Claim 58
Dependent Claim
11 words
The method according to claim 55 in which R is 4-methyl.
Claim 59
Dependent Claim
11 words
The method according to claim 55 in which R is 3-fluorine.
Claim 60
Dependent Claim
11 words
The method according to claim 55 in which R is 3-chlorine.
Claim 61
Dependent Claim
11 words
The method according to claim 55 in which R is 4-chlorine.
Claim 62
Dependent Claim
11 words
The method according to claim 55 in which R is 3-trifluoromethyl.
Claim 63
Dependent Claim
11 words
The method according to claim 55 in which R is 3-nitro.
Claim 64
Dependent Claim
11 words
The method according to claim 55 in which R is 3-cyano.
Claim 65
Dependent Claim
11 words
The method according to claim 55 in which R is 3-trifluorothio.
Claim 66
Dependent Claim
11 words
The method according to claim 55 in which R is 3-trifluorosulfinyl.
Claim 67
Dependent Claim
11 words
The method according to claim 55 in which R is 3-trifluorosulfonyl.
Claim 68
Dependent Claim
11 words
The method according to claim 55 in which R is 3-methylthio.
Claim 69
Dependent Claim
11 words
The method according to claim 55 in which R is 3-methylsulfinyl.
Claim 70
Dependent Claim
11 words
The method according to claim 55 in which R is 3-methylsulfonyl.
Claim 71
Dependent Claim
11 words
The method according to claim 55 in which R is 3-methoxy.
Claim 72
Dependent Claim
11 words
The method according to claim 55 in which R is 3-acetyl.
Claim 73
Dependent Claim
11 words
The method according to claim 55 in which R is 3-methyl.
Claim 74
Dependent Claim
11 words
The method according to claim 55 in which R is 3-bromine.
Claim 75
Dependent Claim
11 words
The method according to claim 55 in which R is 2-chlorine.
Claim 76
Dependent Claim
11 words
The method according to claim 55 in which R is 3-iodine.
Claim 77
Dependent Claim
11 words
The method according to claim 55 in which R is 4-methoxy.
Claim 78
Dependent Claim
11 words
The method according to claim 55 in which R is 2-trifluoromethyl.
Claim 79
Dependent Claim
11 words
The method according to claim 55 in which R is 3-pentafluoropropionamido.
Claim 80
Dependent Claim
11 words
The method according to claim 55 in which R is 3-(3-methylureido).
Claim 81
Dependent Claim
14 words
The method according to claim 55 in which said compound is the cis-isomer configuration.
Claim 82
Dependent Claim
11 words
The method according to claim 79 in which R is 3-trifluoromethyl.
Claim 83
Dependent Claim
14 words
The method according to claim 55 in which said compound is the trans-isomer configuration.
Claim 84
Dependent Claim
11 words
The method according to claim 81 in which R is 3-trifluoromethyl.
Claim 85
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is alkyl and R 1 is alkyl.
Claim 86
Dependent Claim
16 words
The method according to claim 83 in which R is 2-methyl and R 1 is 6-methyl.
Claim 87
Dependent Claim
34 words
The method according to claim 51 in which X is chlorine, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is chlorine, trifluoromethyl or cyano, and R 1 is hydrogen or chlorine.
Claim 88
Dependent Claim
16 words
The method according to claim 85 in which R is 3-chlorine, and R 1 is 4-chlorine.
Claim 89
Dependent Claim
16 words
The method according to claim 85 in which R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 90
Dependent Claim
16 words
The method according to claim 85 in which R is 3-chlorine and R 1 is 5-chlorine.
Claim 91
Dependent Claim
16 words
The method according to claim 85 in which R is 3-cyano and R 1 is hydrogen.
Claim 92
Dependent Claim
16 words
The method according to claim 85 in which R is 3-trifluoromethyl and R 1 is 4-chlorine.
Claim 93
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is bromine, Z is bromine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 94
Dependent Claim
29 words
The method according to claim 51 in which X is methyl, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 95
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-chlorine and R 1 is 5-chlorine.
Claim 96
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is methyl, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 97
Dependent Claim
29 words
The method according to claim 51 in which X is chlorine, Y is chlorine, Z is chlorine, R 2 is methyl, R is 3-trifluoromethyl and R 1 is hydrogen.
Claim 98
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-chlorine and R 1 is 4-chlorine.
Claim 99
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is 4-chlorine.
Claim 100
Dependent Claim
29 words
The method according to claim 51 in which X is hydrogen, Y is chlorine, Z is chlorine, R 2 is hydrogen, R is 3-trifluoromethyl and R 1 is 5-trifluoromethyl.
References Cited (Backward Citations)
US3488732A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-08-28 | 1982-02-27 | 1982-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-08-28 | 1986-02-27 | 1986-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-08-28 | 1990-02-27 | 1990-08-29 | $7700.00 | Window Closed / Lapsed |