US3989503A
Expired / Lapsed
US
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Herbicidal antidote compositions with substituted oxazolidines and thiazolidines
Assignee: Zeneca Inc
•
Filing: 1973-05-02
•
Granted: 1976-11-02
•
Expires: 1993-05-02
Abstract
Abstract Herbicidal compositions comprising an active herbicidal compound and antidote therefor and the methods of use; the antidote compound corresponds to substituted oxazolidines and thiazolidines having the formula +q,10 IN WHICH X is oxygen or sulfur; R is haloalkyl, alkyl or alkylthio; and R1, R2, R3, R4, R5 and R6 are independently selected from the group consisting of hydrogen, lower alkyl, alkoxyalkyl and lower alkylol.
Inventors
- 👤 Ferenc M. Pallos
- 👤 Mervin E. Brokke
- 👤 Duane R. Arneklev
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 10:50
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/04; C07D263/06; C07D277/00; C07D277/02; C07D277/04
Claims Analysis
Total Claims: 70
Claim 1
Independent Claim
117 words
An herbicidal composition comprising an active thiocarbamate herbicidal compound and an antidote therefor corresponding to the formula ##SPC4## in which X is oxygen or sulfur, R is haloalkyl having 1 to 10 carbon atoms, inclusive, and the term halo includes chloro and bromo substitutions, alkyl having 1 to 10 carbon atoms, inclusive, or alkylthio having 1 to 4 carbon atoms, inclusive; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive, alkoxyalkyl having a total of 2 to 4 carbon atoms, inclusive, and lower alkylol having 1 to 4 carbon atoms, inclusive.
Claim 2
Dependent Claim
117 words
An herbicidal composition comprising an active thiocarbamate herbicidal compound and an antidote therefor corresponding to the formula ##SPC4## in which X is oxygen or sulfur, R is haloalkyl having 1 to 10 carbon atoms, inclusive, and the term halo includes chloro and bromo substitutions, alkyl having 1 to 10 carbon atoms, inclusive, or alkylthio having 1 to 4 carbon atoms, inclusive; R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl having 1 to 4 carbon atoms, inclusive, alkoxyalkyl having a total of 2 to 4 carbon atoms, inclusive, and lower alkylol having 1 to 4 carbon atoms, inclusive.
Claim 3
Dependent Claim
40 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is lower alkyl, R 2 is lower alkyl and R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 4
Dependent Claim
20 words
A composition according to claim 2 in which R is dichloromethyl, R 1 is methyl and R 2 is methyl.
Claim 5
Dependent Claim
20 words
A composition according to claim 2 in which R is monochloromethyl, R 1 is methyl and R 2 is methyl.
Claim 6
Dependent Claim
20 words
A composition according to claim 2 in which R is tribromomethyl, R 1 is methyl and R 2 is methyl.
Claim 7
Dependent Claim
20 words
A composition according to claim 2 in which R is monochloromethyl, R 1 is methyl and R 2 is ethyl.
Claim 8
Dependent Claim
20 words
A composition according to claim 2 in which R is dichloromethyl, R 1 is methyl and R 2 is ethyl.
Claim 9
Dependent Claim
20 words
A composition according to claim 2 in which R is trichloromethyl, R 1 is methyl and R 2 is ethyl.
Claim 10
Dependent Claim
20 words
A composition according to claim 2 in which R is 1-bromoethyl, R 1 is methyl and R 2 is ethyl.
Claim 11
Dependent Claim
20 words
A composition according to claim 2 in which R is tribromomethyl, R 1 is methyl and R 2 is ethyl.
Claim 12
Dependent Claim
20 words
A composition according to claim 2 in which R is monobromomethyl, R 1 is methyl and R 2 is ethyl.
Claim 13
Dependent Claim
20 words
A composition according to claim 2 in which R is 1,2,3,4-tetrabromopentyl, R 1 is methyl and R 2 is methyl.
Claim 14
Dependent Claim
20 words
A composition according to claim 2 in which R is 2-chloroethyl, R 1 is methyl and R 2 is methyl.
Claim 15
Dependent Claim
20 words
A composition according to claim 2 in which R is 1,2-dibromoethyl, R 1 is methyl and R 2 is ethyl.
Claim 16
Dependent Claim
20 words
A composition according to claim 2 in which R is 1,2-dibromoethyl, R 1 is methyl and R 2 is methyl.
Claim 17
Dependent Claim
20 words
A composition according to claim 2 in which R is 1,2-dibromoethyl, R 1 is methyl and R 2 is t-butyl.
Claim 18
Dependent Claim
20 words
A composition according to claim 2 in which R is dichloromethyl, R 1 is methyl and R 2 is t-butyl.
Claim 19
Dependent Claim
20 words
A composition according to claim 2 in which R is tribromomethyl, R 1 is methyl and R 2 is t-butyl.
Claim 20
Dependent Claim
20 words
A composition according to claim 2 in which R is dichloromethyl, R 1 is methyl and R 2 is i-propyl.
Claim 21
Dependent Claim
20 words
A composition according to claim 2 in which R is 2-bromoethyl, R 1 is methyl and R 2 is methyl.
Claim 22
Dependent Claim
20 words
A composition according to claim 2 in which R is ω-bromodecyl, R 1 is methyl and R 2 is methyl.
Claim 23
Dependent Claim
20 words
A composition according to claim 2 in which R is 3-chloropropyl, R 1 is methyl and R 2 is methyl.
Claim 24
Dependent Claim
20 words
A composition according to claim 2 in which R is 2-chloropropyl, R 1 is methyl and R 2 is methyl.
Claim 25
Dependent Claim
20 words
A composition according to claim 2 in which R is 1-bromopropyl, R 1 is methyl and R 2 is methyl.
Claim 26
Dependent Claim
20 words
A composition according to claim 2 in which R is 1-bromobutyl, R 1 is methyl and R 2 is methyl.
Claim 27
Dependent Claim
20 words
A composition according to claim 2 in which R is 5-bromopentyl, R 1 is methyl and R 2 is methyl.
Claim 28
Dependent Claim
38 words
A composition according to claim 1 wherein X is oxygen, R is alkyl, R 1 is lower alkyl, R 2 is lower alkyl and R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 29
Dependent Claim
20 words
A composition according to claim 27 in which R is hexyl, R 1 is methyl and R 2 is methyl.
Claim 30
Dependent Claim
40 words
The composition as set forth in claim 1 wherein X is sulfur, R is haloalkyl, R 1 is lower alkyl, R 2 is lower alkyl and R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 31
Dependent Claim
20 words
A composition according to claim 29 in which R is dichloromethyl, R 1 is methyl and R 2 is methyl.
Claim 32
Dependent Claim
20 words
A composition according to claim 29 in which R is trichloromethyl, R 1 is methyl and R 2 is methyl.
Claim 33
Dependent Claim
20 words
A composition according to claim 29 in which R is dibromomethyl, R 1 is methyl and R 2 is methyl.
Claim 34
Dependent Claim
20 words
A composition according to claim 29 in which R is 1-bromoethyl, R 1 is methyl and R 2 is methyl.
Claim 35
Dependent Claim
20 words
A composition according to claim 29 in which R is 2-bromoethyl, R 1 is methyl and R 2 is methyl.
Claim 36
Dependent Claim
20 words
A composition according to claim 29 in which R is 1,2-dibromoethyl, R 1 is methyl and R 2 is methyl.
Claim 37
Dependent Claim
20 words
A composition according to claim 29 in which R is 3-chloropropyl, R 1 is methyl and R 2 is methyl.
Claim 38
Dependent Claim
20 words
A composition according to claim 29 in which R is 2-chloropropyl, R 1 is methyl and R 2 is methyl.
Claim 39
Dependent Claim
20 words
A composition according to claim 29 in which R is 1-bromopropyl, R 1 is methyl and R 2 is methyl.
Claim 40
Dependent Claim
20 words
A composition according to claim 29 in which R is 1-bromobutyl, R 1 is methyl and R 2 is methyl.
Claim 41
Dependent Claim
20 words
A composition according to claim 29 in which R is 5-bromopentyl, R 1 is methyl and R 2 is methyl.
Claim 42
Dependent Claim
20 words
A composition according to claim 29 in which R is dichloromethyl, R 1 is methyl and R 2 is ethyl.
Claim 43
Dependent Claim
20 words
A composition according to claim 29 in which R is 1-bromoethyl, R 1 is methyl and R 2 is ethyl.
Claim 44
Dependent Claim
20 words
A composition according to claim 29 in which R is 2-bromoethyl, R 1 is methyl and R 2 is ethyl.
Claim 45
Dependent Claim
20 words
A composition according to claim 29 in which R is monochloromethyl, R 1 is methyl and R 2 is ethyl.
Claim 46
Dependent Claim
42 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is lower alkyl, R 2 is lower alkyl, R 5 is lower alkyl and R 3 , R 4 and R 6 are each hydrogen.
Claim 47
Dependent Claim
24 words
A composition according to claim 45 in which R is tribromomethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 48
Dependent Claim
24 words
A composition according to claim 45 in which R is monochloromethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 49
Dependent Claim
24 words
A composition according to claim 45 in which R is dichloromethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 50
Dependent Claim
24 words
A composition according to claim 45 in which R is 1-bromoethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 51
Dependent Claim
24 words
A composition according to claim 45 in which R is monobromomethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 52
Dependent Claim
24 words
A composition according to claim 45 in which R is 1,2-dibromoethyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 53
Dependent Claim
24 words
A composition according to claim 45 in which R is 2-chloropropyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 54
Dependent Claim
24 words
A composition according to claim 45 in which R is 1-bromopropyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 55
Dependent Claim
24 words
A composition according to claim 45 in which R is 1-bromobutyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 56
Dependent Claim
24 words
A composition according to claim 45 in which R is 3-chloropropyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 57
Dependent Claim
24 words
A composition according to claim 45 in which R is 5-bromopentyl, R 1 is methyl, R 2 is methyl and R 5 is methyl.
Claim 58
Dependent Claim
41 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is lower alkyl, R 2 is lower alkyl, R 3 is lower alkyl, R 4 , R 5 and R 6 are each hydrogen.
Claim 59
Dependent Claim
44 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is lower alkyl, R 2 is lower alkyl, R 3 is lower alkyl and R 4 is lower alkyl, R 5 and R 6 are each hydrogen.
Claim 60
Dependent Claim
39 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 , R 2 , R 3 , R 4 and R 5 are each independently lower alkyl and R 6 is hydrogen.
Claim 61
Dependent Claim
36 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is alkoxyalkyl, R 2 , R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 62
Dependent Claim
16 words
The composition according to claim 60 in which R is dichloromethyl and R 1 is methoxymethyl.
Claim 63
Dependent Claim
40 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 1 is lower alkyl, R 5 is lower alkyl and R 2 , R 3 , R 4 and R 6 are each hydrogen.
Claim 64
Dependent Claim
38 words
The composition as set forth in claim 1 wherein X is oxygen, R is haloalkyl, R 3 is lower alkyl and R 1 , R 2 , R 4 , R 5 and R 6 are each hydrogen.
Claim 65
Dependent Claim
36 words
The composition as set forth in claim 1 in which X is oxygen, R is dichloromethyl, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 66
Dependent Claim
37 words
The composition as set forth in claim 1 in which X is sulfur, R is dichloromethyl, R 1 is ethyl, R 2 , R 3 , R 4 , R 5 and R 6 are each hydrogen.
Claim 67
Independent Claim
80 words
The method of protecting a crop from injury due to a thiocarbamate herbicide, comprising applying to the crop seed prior to planting a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##SPC5## in which X is oxygen or sulfur; R is haloalkyl, alkyl, alkylthio; and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl, alkoxyalkyl and lower alkylol.
Claim 68
Independent Claim
80 words
The method of protecting a crop from injury due to a thiocarbamate herbicide, comprising applying to the crop seed prior to planting a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##SPC5## in which X is oxygen or sulfur; R is haloalkyl, alkyl, alkylthio; and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl, alkoxyalkyl and lower alkylol.
Claim 69
Independent Claim
85 words
The method of protecting a crop from injury due to a thiocarbamate herbicide, comprising preplant incorporation in the soil in which said crop is to be planted, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##SPC6## in which X is oxygen or sulfur; R is haloalkyl, alkyl, alkylthio; and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl, alkoxyalkyl and lower alkylol.
Claim 70
Independent Claim
85 words
The method of protecting a crop from injury due to a thiocarbamate herbicide, comprising preplant incorporation in the soil in which said crop is to be planted, a non-phytotoxic antidotally effective amount of a compound corresponding to the formula ##SPC6## in which X is oxygen or sulfur; R is haloalkyl, alkyl, alkylthio; and R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from the group consisting of hydrogen, lower alkyl, alkoxyalkyl and lower alkylol.
References Cited (Backward Citations)
US3131509A
Cited
US3719466A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-11-02 | 1980-05-03 | 1980-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-11-02 | 1984-05-03 | 1984-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-11-02 | 1988-05-03 | 1988-11-02 | $7700.00 | Window Closed / Lapsed |