US4168152A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal compositions and methods
Assignee: Zeneca Inc
•
Filing: 1977-11-07
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Granted: 1979-09-18
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Expires: 1997-11-07
Abstract
Abstract Crops are protected against injury from triazine herbicides by application of certain N-benzenesulfonyl carbamates as herbicide antidotes. The N-benzenesulfonyl carbamates have the general structural formula <IMAGE> wherein each of X1, X2, X3, X4, and X5 is independently selected from the group consisting of hydrogen, halogen and lower alkyl, with the proviso that when X3 is lower alkyl, X1 and X5 are not both hydrogen; and R is selected from the group consisting of lower alkyl, alkenyl, alkynyl and alkyl and alkenyl radicals substituted with up to five halo atoms.
Inventors
- 👤 Edmund J. Gaughan
- 👤 Martin D. Mahoney
- 👤 Ferenc M. Pallos
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:19
CPC Classifications
A; A01; A01N; A01N25/00; A01N25/32; A01N47/00; A01N47/08; A01N47/10; A01N47/24
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
156 words
A herbicidal composition consisting essentially of a herbicidally effective amount of a triazine herbicide and a non-phytotoxic antidotally effective amount to protect crops from injury by said triazine herbicide of a N-benzenesulfonyl carbamate of the formula ##STR5## wherein X 1 , X 2 , X 3 , X 4 and X 5 is independently selected from the group consisting of hydrogen, halogen, and lower alkyl containing 1 to 4 carbon atoms, with the proviso that when X 3 is lower alkyl, X 1 and X 5 are not both hydrogen; and R is selected from the group consisting of lower alkyl containing 1 to 4 carbon atoms, alkenyl containing 3 to 6 carbon atoms, alkynyl containing 3 to 6 carbon atoms and alkyl and alkenyl radicals containing 1 to 4 and 3 to 6 carbon atoms, respectively, substituted with up to five halo atoms, and wherein said N-benzenesulfonyl carbamate is antidotally active with said triazine herbicide.
Claim 2
Dependent Claim
156 words
A herbicidal composition consisting essentially of a herbicidally effective amount of a triazine herbicide and a non-phytotoxic antidotally effective amount to protect crops from injury by said triazine herbicide of a N-benzenesulfonyl carbamate of the formula ##STR5## wherein X 1 , X 2 , X 3 , X 4 and X 5 is independently selected from the group consisting of hydrogen, halogen, and lower alkyl containing 1 to 4 carbon atoms, with the proviso that when X 3 is lower alkyl, X 1 and X 5 are not both hydrogen; and R is selected from the group consisting of lower alkyl containing 1 to 4 carbon atoms, alkenyl containing 3 to 6 carbon atoms, alkynyl containing 3 to 6 carbon atoms and alkyl and alkenyl radicals containing 1 to 4 and 3 to 6 carbon atoms, respectively, substituted with up to five halo atoms, and wherein said N-benzenesulfonyl carbamate is antidotally active with said triazine herbicide.
Claim 3
Dependent Claim
11 words
A composition of claim 1 wherein said triazine herbicide is 2-chloro-4-ethylamino-6-isopropylamino-s-triazine.
Claim 4
Dependent Claim
11 words
A composition of claim 1 wherein said triazine herbicide is 2-(4-chloro-6-ethylamino-s-triazin-2-ylamino)-2-methylpropionitrile.
Claim 5
Dependent Claim
11 words
A composition of claim 1 wherein said triazine herbicide is 4-amino-6-tert.butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one.
Claim 6
Dependent Claim
29 words
A composition of claim 1 wherein each of X 1 , X 2 , X 4 and X 5 are hydrogen and X 3 is hydrogen, chlorine or bromine.
Claim 7
Dependent Claim
30 words
A composition of claim 1 wherein each of X 1 , X 3 , and X 5 are lower alkyl and each of X 2 and X 4 are hydrogen.
Claim 8
Dependent Claim
48 words
A composition of claim 1 wherein each of X 1 , X 2 , X 4 and X 5 are hydrogen, X 3 is hydrogen, chlorine or bromine and R is selected from the group consisting of methyl, ethyl, isopropyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, allyl, 2-chloroallyl, propargyl and 2-butyn-1-yl.
Claim 9
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-propargyl carbamate.
Claim 10
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesufonyl carbamate is N-(4-chlorobenzenesulfonyl)-ethyl carbamate.
Claim 11
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2,2-dichloroethyl carbamate.
Claim 12
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 13
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2-chloroallyl carbamate.
Claim 14
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2-butyn-1-yl carbamate.
Claim 15
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-propargyl carbamate.
Claim 16
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-bromobenzenesulfonyl)-propargyl carbamate.
Claim 17
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-allyl carbamate.
Claim 18
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 19
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-methyl carbamate.
Claim 20
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(2,4,6-trimethylbenzenesulfonyl)-propargyl carbamate.
Claim 21
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-isopropyl carbamate.
Claim 22
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(3-chlorobenzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 23
Dependent Claim
12 words
The composition of claim 1 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-2,2,2-trichloroethyl carbamate.
Claim 24
Independent Claim
170 words
A method of protecting crops from injury from a triazine herbicide consisting essentially of applying to the soil a herbicidally effective amount of a triazine herbicide and a non-phytotoxic antidotally effective amount to protect crops from injury by said triazine herbicide of a N-benzenesulfonyl carbamate of the formula ##STR6## wherein each of X 1 , X 2 , X 3 , X 4 and X 5 is independently selected from the group consisting of hydrogen, halogen, and lower alkyl containing 1 to 4 carbon atoms, with the proviso that when X 3 is lower alkyl, X 1 and X 5 are not both hydrogen; and R is selected from the group consisting of lower alkyl containing 1 to 4 carbon atoms, alkenyl containing 3 to 6 carbon atoms, alkynyl containing 3 to 6 carbon atoms and alkyl and alkenyl radicals containing 1 to 4 and 3 to 6 carbon atoms, respectively, substituted with up to five halo atoms, and wherein said N-benzenesulfonyl carbamate is antidotally active with said triazine herbicide.
Claim 25
Independent Claim
170 words
A method of protecting crops from injury from a triazine herbicide consisting essentially of applying to the soil a herbicidally effective amount of a triazine herbicide and a non-phytotoxic antidotally effective amount to protect crops from injury by said triazine herbicide of a N-benzenesulfonyl carbamate of the formula ##STR6## wherein each of X 1 , X 2 , X 3 , X 4 and X 5 is independently selected from the group consisting of hydrogen, halogen, and lower alkyl containing 1 to 4 carbon atoms, with the proviso that when X 3 is lower alkyl, X 1 and X 5 are not both hydrogen; and R is selected from the group consisting of lower alkyl containing 1 to 4 carbon atoms, alkenyl containing 3 to 6 carbon atoms, alkynyl containing 3 to 6 carbon atoms and alkyl and alkenyl radicals containing 1 to 4 and 3 to 6 carbon atoms, respectively, substituted with up to five halo atoms, and wherein said N-benzenesulfonyl carbamate is antidotally active with said triazine herbicide.
Claim 26
Dependent Claim
11 words
A method of claim 23 wherein said triazine herbicide is 2-chloro-4-ethylamino-6-isopropylamino-s-triazine.
Claim 27
Dependent Claim
11 words
A method of claim 23 wherein said triazine herbicide is 2-(4-chloro-6-ethylamino-s-triazin-2-ylamino)-2-methylpropionitrile.
Claim 28
Dependent Claim
11 words
A method of claim 23 wherein said triazine herbicide is 4-amino-6-tert.butyl-3-(methylthio)-1,2,4-triazin-5(4H)-one.
Claim 29
Independent Claim
29 words
A method of clam 23 wherein each of X 1 , X 2 , X 4 and X 5 are hydrogen and X 3 is hydrogen, chlorine or bromine.
Claim 30
Independent Claim
29 words
A method of clam 23 wherein each of X 1 , X 2 , X 4 and X 5 are hydrogen and X 3 is hydrogen, chlorine or bromine.
Claim 31
Dependent Claim
29 words
A method of claim 23 wherein each of X 1 , X 3 and X 5 are lower alkyl and each of X 2 and X 4 are hydrogen.
Claim 32
Dependent Claim
48 words
The method of claim 23 wherein each of X 1 , X 2 , X 4 and X 5 are hydrogen, X 3 is hydrogen, chlorine or bromine, and R is selected from the group consisting of methyl, ethyl, isopropyl, 2,2-dichloroethyl, 2,2,2-trichloroethyl, 2,2,2-trifluoroethyl, allyl, 2-chloroallyl, propargyl and 2-butyn-1-yl.
Claim 33
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-propargyl carbamate.
Claim 34
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-ethyl carbamate.
Claim 35
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2,2-dichloroethyl carbamate.
Claim 36
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 37
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2-chloroallyl carbamate.
Claim 38
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-2-butyn-1-yl carbamate.
Claim 39
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-propargyl carbamate.
Claim 40
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-bromobenzenesulfonyl)-propargyl carbamate.
Claim 41
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-allyl carbamate.
Claim 42
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 43
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(4-chlorobenzenesulfonyl)-methyl carbamate.
Claim 44
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(2,4,6-trimethylbenzenesulfonyl)-propargyl carbamate.
Claim 45
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-isopropyl carbamate.
Claim 46
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(3-chlorobenzenesulfonyl)-2,2,2-trifluoroethyl carbamate.
Claim 47
Dependent Claim
12 words
The method of claim 23 wherein said benzenesulfonyl carbamate is N-(benzenesulfonyl)-2,2,2-trichloroethyl carbamate.
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) | 1982-09-17 | 1983-03-19 | 1983-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-17 | 1987-03-19 | 1987-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-17 | 1991-03-19 | 1991-09-18 | $7700.00 | Window Closed / Lapsed |