US4249931A
Expired / Lapsed
US
⏱️ 0.0 years remaining
5-Oxy or thiomethyl substituted oxazolidine herbicide antidotes
Assignee: Zeneca Inc
•
Filing: 1979-06-18
•
Granted: 1981-02-10
•
Expires: 1999-06-18
Abstract
Abstract Substituted N-haloacyl oxazolidines as new compositions of matter useful as active herbicidal antidotes to protect against and decrease crop injury when used with thiolcarbamate herbicides when applied in various methods; improved herbicidal compositions and utility of said compositions to protect against and decrease phytotoxic crop injury when employing thiolcarbamate herbicides, and a two-part herbicide system consisting essentially of a first-part of one or more thiolcarbamate herbicides and a second-part of an effective antidote compound therefor, said antidote compounds of the class 5-substituted 3-acyl oxazolidines having the formula <IMAGE> wherein X is oxygen or sulfur and R1 is alkyl; R is selected from the group consisting of haloalkyl, and alkoxy carboalkyl; R2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R3 is selected from the group consisting of hydrogen and methyl.
Inventors
- 👤 Eugene G. Teach
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 02:59
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/04; A; A01; A01N; A01N25/00; A01N25/32; C07C; C07C323/00; C07C323/23; C07C323/24; C07C323/25; C07D263/06; C07D303/00; C07D303/02; C07D303/34
Claims Analysis
Total Claims: 113
Claim 1
Independent Claim
85 words
Compounds according to the formula ##STR7## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 2
Dependent Claim
85 words
Compounds according to the formula ##STR7## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 3
Dependent Claim
27 words
A compound according to claim 1 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 4
Dependent Claim
16 words
A compound according to claim 2 in which R is dichloromethyl and R 1 is methyl.
Claim 5
Dependent Claim
16 words
A compound according to claim 2 in which R is 1,2-dibromoethyl and R 1 is methyl.
Claim 6
Dependent Claim
16 words
A compound according to claim 2 in which R is 2-bromoethyl and R 1 is methyl.
Claim 7
Dependent Claim
16 words
A compound according to claim 2 in which R is 2-chloroethyl and R 1 is methyl.
Claim 8
Dependent Claim
16 words
A compound according to claim 2 in which R is dichloromethyl and R 1 is propyl.
Claim 9
Dependent Claim
16 words
A compound according to claim 2 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 10
Dependent Claim
16 words
A compound according to claim 2 in which R is 2-bromoethyl and R 1 is propyl.
Claim 11
Dependent Claim
16 words
A compound according to claim 2 in which R is 2-chloroethyl and R 1 is propyl.
Claim 12
Dependent Claim
27 words
A compound according to claim 1 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 13
Dependent Claim
16 words
A compound according to claim 11 in which R is methoxypropanoyl and R 1 is methyl.
Claim 14
Dependent Claim
16 words
A compound according to claim 11 in which R is methoxypropanoyl and R 1 is propyl.
Claim 15
Dependent Claim
27 words
A compound according to claim 1 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 16
Dependent Claim
16 words
A compound according to claim 14 in which R is dichloromethyl and R 1 is methyl.
Claim 17
Dependent Claim
16 words
A compound according to claim 14 in which R is 2-chloroethyl and R 1 is methyl.
Claim 18
Dependent Claim
16 words
A compound according to claim 14 in which R is 1-chloroethyl and R 1 is methyl.
Claim 19
Dependent Claim
16 words
A compound according to claim 14 in which R is dichloromethyl and R 1 is propyl.
Claim 20
Dependent Claim
16 words
A compound according to claim 14 in which R is 2-bromomethyl and R 1 is propyl.
Claim 21
Dependent Claim
16 words
A compound according to claim 14 in which R is 2-chloroethyl and R 1 is propyl.
Claim 22
Dependent Claim
16 words
A compound according to claim 14 in which R is 1-chloroethyl and R 1 is propyl.
Claim 23
Dependent Claim
16 words
A compound according to claim 14 in which R is dichloroethyl and R 1 is methyl.
Claim 24
Dependent Claim
16 words
A compound according to claim 14 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 25
Dependent Claim
24 words
A compound according to claim 1 in which X is oxygen, R 1 is carboalkoxyalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 26
Dependent Claim
16 words
A compound according to claim 24 in which R is methoxypropanoyl and R 1 is methyl.
Claim 27
Dependent Claim
16 words
A compound according to claim 24 in which R is methoxypropanoyl and R 1 is propyl.
Claim 28
Dependent Claim
16 words
A compound according to claim 24 in which R is methoxypropanoyl and R 1 is pentyl.
Claim 29
Dependent Claim
27 words
A compound according to claim 2 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 30
Dependent Claim
16 words
A compound according to claim 28 in which R is dichloromethyl and R 1 is methyl.
Claim 31
Dependent Claim
16 words
A compound according to claim 28 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 32
Dependent Claim
27 words
A compound according to claim 1 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 33
Dependent Claim
16 words
A compound according to claim 31 in which R is methoxypropanoyl and R 1 is propyl.
Claim 34
Dependent Claim
27 words
A compound according to claim 1 in which X is sulfur, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 35
Dependent Claim
16 words
A compound according to claim 33 in which R is dichloromethyl and R 1 is ethyl.
Claim 36
Dependent Claim
16 words
A compound according to claim 33 in which R is 1,2-dibromoethyl and R 1 is ethyl.
Claim 37
Dependent Claim
16 words
A compound according to claim 31 in which R is 2-bromoethyl and R 1 is ethyl.
Claim 38
Dependent Claim
104 words
A herbicidal composition consisting essentially of a thiolcarbamate herbicide and a non-phytotoxic antidotally effective amount of an antidote compound therefor corresponding to the formula ##STR8## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 39
Dependent Claim
104 words
A herbicidal composition consisting essentially of a thiolcarbamate herbicide and a non-phytotoxic antidotally effective amount of an antidote compound therefor corresponding to the formula ##STR8## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 40
Dependent Claim
28 words
The herbicidal composition according to claim 27 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 41
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is dichloromethyl and R 1 is methyl.
Claim 42
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 1,2-dibromoethyl and R 1 is methyl.
Claim 43
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 2-bromoethyl and R 1 is methyl.
Claim 44
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 2-chloroethyl and R 1 is methyl.
Claim 45
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is dichloromethyl and R 1 is propyl.
Claim 46
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 47
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 2-bromoethyl and R 1 is propyl.
Claim 48
Dependent Claim
17 words
The herbicidal composition according to claim 38 in which R is 2-chloroethyl and R 1 is propyl.
Claim 49
Dependent Claim
28 words
The herbicidal composition according to claim 37 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 50
Dependent Claim
17 words
The herbicidal composition according to claim 47 in which R is methoxypropanoyl and R 1 is methyl.
Claim 51
Dependent Claim
17 words
The herbicidal composition according to claim 47 in which R is methoxypropanoyl and R 1 is propyl.
Claim 52
Dependent Claim
28 words
The herbicidal composition according to claim 37 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is oxygen.
Claim 53
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is dichloromethyl and R 1 is methyl.
Claim 54
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 2-chloroethyl and R 1 is methyl.
Claim 55
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 1-chloroethyl and R 1 is methyl.
Claim 56
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is dichloromethyl and R 1 is propyl.
Claim 57
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 2-bromoethyl and R 1 is propyl.
Claim 58
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 2-chloroethyl and R 1 is propyl.
Claim 59
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 1-chloroethyl and R 1 is propyl.
Claim 60
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is dichloromethyl and R 1 is methyl.
Claim 61
Dependent Claim
17 words
The herbicidal composition according to claim 50 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 62
Dependent Claim
25 words
The herbicidal composition according to claim 37 in which X is oxygen, R 1 is carboalkoxyalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 63
Dependent Claim
17 words
The herbicidal composition according to claim 60 in which R is methoxypropanoyl and R 1 is methyl.
Claim 64
Dependent Claim
17 words
The herbicidal composition according to claim 60 in which R is methoxypropanoyl and R 1 is propyl.
Claim 65
Dependent Claim
17 words
The herbicidal composition according to claim 60 in which R is methoxypropanoyl and R 1 is pentyl.
Claim 66
Dependent Claim
28 words
The herbicidal composition according to claim 37 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 67
Dependent Claim
17 words
The herbicidal composition according to claim 64 in which R is dichloromethyl and R 1 is methyl.
Claim 68
Dependent Claim
17 words
The herbicidal composition according to claim 64 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 69
Dependent Claim
28 words
The herbicidal composition according to claim 37 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 70
Dependent Claim
17 words
The herbicidal composition according to claim 67 in which R is methoxypropanoyl and R 1 is propyl.
Claim 71
Dependent Claim
28 words
The herbicidal composition according to claim 37 in which X is sulfur, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 72
Dependent Claim
17 words
The herbicidal composition according to claim 69 in which R is dichloromethyl and R 1 is ethyl.
Claim 73
Dependent Claim
17 words
The herbicidal composition according to claim 69 in which R is 1,2-dibromoethyl and R 1 is ethyl.
Claim 74
Dependent Claim
17 words
The herbicidal composition according to claim 69 in which R is 2-bromoethyl and R 1 is ethyl.
Claim 75
Independent Claim
122 words
The method of decreasing injury to crops, said injury due to a thiolcarbamate herbicide comprising application to the soil in which said crop is to be planted and grown, a non-phytotoxic antidotally effective amount of an antidote compound corresponding to the formula ##STR9## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo include chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 76
Independent Claim
122 words
The method of decreasing injury to crops, said injury due to a thiolcarbamate herbicide comprising application to the soil in which said crop is to be planted and grown, a non-phytotoxic antidotally effective amount of an antidote compound corresponding to the formula ##STR9## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo include chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 77
Dependent Claim
27 words
The method according to claim 73 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 78
Dependent Claim
16 words
The method according to claim 74 in which R is dichloromethyl and R 1 is methyl.
Claim 79
Dependent Claim
16 words
The method according to claim 74 in which R is 1,2-dibromoethyl and R 1 is methyl.
Claim 80
Dependent Claim
16 words
The method according to claim 74 in which R is 2-bromoethyl and R 1 is methyl.
Claim 81
Dependent Claim
16 words
The method according to claim 74 in which R is 2-chloroethyl and R 1 is methyl.
Claim 82
Dependent Claim
16 words
The method according to claim 74 in which R is dichloromethyl and R 1 is propyl.
Claim 83
Dependent Claim
16 words
The method according to claim 74 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 84
Dependent Claim
16 words
The method according to claim 74 in which R is 2-bromoethyl and R 1 is propyl.
Claim 85
Dependent Claim
16 words
The method according to claim 74 in which R is 2-chloroethyl and R 1 is propyl.
Claim 86
Dependent Claim
27 words
The method according to claim 73 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-chlorophenyl and R 3 is hydrogen.
Claim 87
Dependent Claim
16 words
The method according to claim 83 in which R is methoxypropanoyl and R 1 is methyl.
Claim 88
Dependent Claim
16 words
The method according to claim 83 in which R is methoxypropanoyl and R 1 is propyl.
Claim 89
Dependent Claim
27 words
The method according to claim 73 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 90
Dependent Claim
16 words
The method according to claim 86 in which R is dichloromethyl and R 1 is methyl.
Claim 91
Dependent Claim
16 words
The method according to claim 86 in which R is 2-chloroethyl and R 1 is methyl.
Claim 92
Dependent Claim
16 words
The method according to claim 86 in which R is 1-chloroethyl and R 1 is methyl.
Claim 93
Dependent Claim
16 words
The method according to claim 86 in which R is dichloromethyl and R 1 is propyl.
Claim 94
Dependent Claim
16 words
The method according to claim 86 in which R is 2-bromoethyl and R 1 is propyl.
Claim 95
Dependent Claim
16 words
The method according to claim 86 in which R is 2-chloroethyl and R 1 is propyl.
Claim 96
Dependent Claim
16 words
The method according to claim 86 in which R is 1-chloroethyl and R 1 is propyl.
Claim 97
Dependent Claim
16 words
The method according to claim 86 in which R is dichloroethyl and R 1 is methyl.
Claim 98
Dependent Claim
16 words
The method according to claim 86 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 99
Dependent Claim
24 words
The method according to claim 73 in which X is oxygen, R 1 is carboalkoxyalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 100
Dependent Claim
16 words
The method according to claim 96 in which R is methoxypropanoyl and R 1 is methyl.
Claim 101
Dependent Claim
16 words
The method according to claim 96 in which R is methoxypropanoyl and R 1 is propyl.
Claim 102
Dependent Claim
16 words
The method according to claim 96 in which R is methoxypropanoyl and R 1 is pentyl.
Claim 103
Dependent Claim
27 words
The method according to claim 73 in which X is oxygen, R 1 is alkyl, R is haloalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 104
Dependent Claim
16 words
The method according to claim 100 in which R is dichloromethyl and R 1 is methyl.
Claim 105
Dependent Claim
16 words
The method according to claim 100 in which R is 1,2-dibromoethyl and R 1 is propyl.
Claim 106
Dependent Claim
27 words
The method according to claim 73 in which X is oxygen, R 1 is alkyl, R is alkoxycarboalkyl, R 2 is p-bromophenyl and R 3 is hydrogen.
Claim 107
Dependent Claim
16 words
The method according to claim 103 in which R is methoxypropanoyl and R 1 is propyl.
Claim 108
Dependent Claim
27 words
The method according to claim 73 in which X is sulfur, R 1 is alkyl, R is haloalkyl, R 2 is phenyl and R 3 is hydrogen.
Claim 109
Dependent Claim
16 words
The method according to claim 105 in which R is dichloromethyl and R 1 is ethyl.
Claim 110
Dependent Claim
16 words
The method according to claim 105 in which R is 1,2-dibromoethyl and R 1 is ethyl.
Claim 111
Dependent Claim
16 words
The method according to claim 105 in which R is 2-bromoethyl and R 1 is ethyl.
Claim 112
Independent Claim
130 words
The method of decreasing injury to crops, said injury due to a thiolcarbamate herbicide, comprising applying into the seed furrow to the seed and adjacent soil in the open furrow prior to covering to achieve a planted state, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR10## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
Claim 113
Independent Claim
130 words
The method of decreasing injury to crops, said injury due to a thiolcarbamate herbicide, comprising applying into the seed furrow to the seed and adjacent soil in the open furrow prior to covering to achieve a planted state, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##STR10## wherein X is oxygen or sulfur and R 1 is alkyl containing from 1 to 6 carbon atoms, inclusive; R is selected from the group consisting of haloalkyl containing from 1 to 4 carbon atoms, inclusive, and the term halo includes chloro and bromo and alkoxycarboalkyl containing 3 to 6 carbon atoms, inclusive; R 2 is selected from the group consisting of phenyl, p-chlorophenyl and p-bromophenyl; and R 3 is selected from the group consisting of hydrogen and methyl.
References Cited (Backward Citations)
US3989503A
Cited
US4072688A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-02-10 | 1984-08-11 | 1985-02-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-02-10 | 1988-08-11 | 1989-02-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-02-10 | 1992-08-11 | 1993-02-10 | $7700.00 | Window Closed / Lapsed |