US4076519A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-substituted perfluoroalkanesulfonamides as herbicides
Assignee: Pbi-Gordon Corp
•
Filing: 1975-10-01
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Granted: 1978-02-28
•
Expires: 1995-10-01
Abstract
Abstract N-Substituted perfluoroalkanesulfonamides of the formula: ##STR1## WHEREIN R f is perfluoroalkyl group containing one to four carbon atoms, each Y is a non-cyclic group which can contain only carbon, hydrogen, oxygen, sulfur, nitrogen and halogen and m is 1-5, provided that all of the Y groups together contain not more than about twenty carbon atoms and that at least one of the Y groups contains a heteroatom selected from oxygen, sulfur, nitrogen and halogen. Also included are salts of these compounds, compositions containing the compounds of the present invention and processes for their preparation and use. The compounds are active as herbicides and plant growth modifiers.
Inventors
- 👤 Joseph Kenneth Harrington
- 👤 Donald C. Kvam
- 👤 Arthur Mendel
- 👤 Jerry E. Robertson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:10
CPC Classifications
A; A01; A01N; A01N41/00; A01N41/02; A01N41/04; A01N41/06; C; C07; C07C; C07C311/00; C07C311/01; C07C311/02; C07C311/09
Claims Analysis
Total Claims: 50
Claim 1
Independent Claim
130 words
The method for terminating the life cycle of plants which comprises contacting said plants with an effective amount of a compound of the formula: ##STR6## or a metal, ammonium, alkyl amine or dialkanol amine salt thereof wherein R f is a perfluoroalkyl group containing one to four carbon atoms, each Y is a non-cyclic group selected from alkyl, alkanoylamido, halo, haloalkyl, nitro, alkoxy, alkylsulfonyl, alkylsulfinyl, alkylthio, amino, sulfamoyl, carbamyl, alkoxyalkylthio and sulfamoylamino and m is 1-3, provided that all of the Y groups together contain not more than about twenty carbon atoms, at least one of the Y groups contains a heteroatom selected from oxygen, sulfur, nitrogen and halogen, no single Y contains more than six carbon atoms and at least one Y is other than alkyl, halo and haloalkyl.
Claim 2
Independent Claim
130 words
The method for terminating the life cycle of plants which comprises contacting said plants with an effective amount of a compound of the formula: ##STR6## or a metal, ammonium, alkyl amine or dialkanol amine salt thereof wherein R f is a perfluoroalkyl group containing one to four carbon atoms, each Y is a non-cyclic group selected from alkyl, alkanoylamido, halo, haloalkyl, nitro, alkoxy, alkylsulfonyl, alkylsulfinyl, alkylthio, amino, sulfamoyl, carbamyl, alkoxyalkylthio and sulfamoylamino and m is 1-3, provided that all of the Y groups together contain not more than about twenty carbon atoms, at least one of the Y groups contains a heteroatom selected from oxygen, sulfur, nitrogen and halogen, no single Y contains more than six carbon atoms and at least one Y is other than alkyl, halo and haloalkyl.
Claim 3
Dependent Claim
13 words
The method of claim 1 in which R f is CF 3 .
Claim 4
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is alkyl.
Claim 5
Dependent Claim
13 words
The method of claim 3 in which R f is CF 3 .
Claim 6
Dependent Claim
15 words
The method of claim 4 in which the compound is 5-acetamido-2-methyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 7
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is alkanoylamido.
Claim 8
Dependent Claim
13 words
The method of claim 6 in which R f is CF 3 .
Claim 9
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is halo.
Claim 10
Dependent Claim
13 words
The method of claim 8 in which R f is CF 3 .
Claim 11
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is haloalkyl.
Claim 12
Dependent Claim
13 words
The method of claim 10 in which R f is CF 3 .
Claim 13
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is alkylsulfonyl.
Claim 14
Dependent Claim
13 words
The method of claim 12 in which R f is CF 3 .
Claim 15
Dependent Claim
15 words
The method of claim 13 in which the compound is 3-methylsulfonyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 16
Dependent Claim
15 words
The method of claim 13 in which the compound is 4-methylsulfonyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 17
Dependent Claim
15 words
The method of claim 13 in which the compound is 3-ethylsulfonyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 18
Dependent Claim
15 words
The method of claim 13 in which the compound is 2-bromo-4-methylsulfonyltrifluoromethanesulfonanilide or a salt thereof.
Claim 19
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is alkylsulfinyl.
Claim 20
Dependent Claim
13 words
The method of claim 18 in which R f is CF 3 .
Claim 21
Dependent Claim
15 words
The method of claim 19 in which the compound is 3-methylsulfinyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 22
Dependent Claim
15 words
The method of claim 19 in which the compound is 4-methylsulfinyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 23
Dependent Claim
15 words
The method of claim 19 in which the compound is 3-ethylsulfinyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 24
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is alkylthio.
Claim 25
Dependent Claim
13 words
The method of claim 23 in which R f is CF 3 .
Claim 26
Dependent Claim
15 words
The method of claim 24 in which the compound is 3-methylthiotrifluoromethanesulfonanilide, or a salt thereof.
Claim 27
Dependent Claim
15 words
The method of claim 24 in which the compound is 4-methylthiotrifluoromethanesulfonanilide, or a salt thereof.
Claim 28
Dependent Claim
15 words
The method of claim 24 in which the compound is 3-ethylthiotrifluoromethanesulfonanilide, or a salt thereof.
Claim 29
Dependent Claim
15 words
The method of claim 24 in which the compound is 3-n-propylthiotrifluoromethanesulfonanilide, or a salt thereof.
Claim 30
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is carbamyl.
Claim 31
Dependent Claim
13 words
The method of claim 29 in which R f is CF 3 .
Claim 32
Dependent Claim
15 words
The method of claim 30 in which the compound is 2-carbamyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 33
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is sulfamoyl.
Claim 34
Dependent Claim
13 words
The method of claim 32 in which R f is CF 3 .
Claim 35
Dependent Claim
12 words
The method of claim 33 in which the sulfamoyl group is N-alkylsulfamoyl.
Claim 36
Dependent Claim
15 words
The method of claim 34 in which the compound is 2-methyl-4-(N-methylsulfamoyl)trifluoromethanesulfonanilide, or a salt thereof.
Claim 37
Dependent Claim
15 words
The method of claim 34 in which the compound is 3-(N-methylsulfamoyl)trifluoromethanesulfonanilide, or a salt thereof.
Claim 38
Dependent Claim
12 words
The method of claim 33 in which the sulfamoyl group is N,N-diloweralkylsulfamoyl.
Claim 39
Dependent Claim
15 words
The method of claim 37 in which the compound is 4-(N,N-dimethylsulfamoyl)-2-methyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 40
Dependent Claim
15 words
The method of claim 37 in which the compound is 3-(N,N-dimethylsulfamoyl)trifluoromethanesulfonanilide, or a salt thereof.
Claim 41
Dependent Claim
15 words
The method of claim 37 in which the compound is 5-(N,N-dimethylsulfamoyl)-2-methyltrifluoromethanesulfonanilide, or a salt thereof.
Claim 42
Dependent Claim
15 words
The method of claim 1 in which at least one Y group is lower alkoxyloweralkylthio.
Claim 43
Dependent Claim
13 words
The method of claim 41 in which R f is CF 3 .
Claim 44
Dependent Claim
15 words
The method of claim 42 in which the compound is 3-(methoxymethylthio)trifluoromethanesulfonanilide, or a salt thereof.
Claim 45
Dependent Claim
14 words
The method of claim 1 in which at least one Y group is sulfamoylamino.
Claim 46
Dependent Claim
13 words
The method of claim 44 in which R f is CF 3 .
Claim 47
Dependent Claim
12 words
The method of claim 45 in which the sulfamoylamino group is N,N-diloweralkylsulfamoylamino.
Claim 48
Dependent Claim
15 words
The method of claim 46 in which the compound is 3-(N,N-dimethylsulfamoylamino)trifluoromethanesulfonanilide, or a salt thereof.
Claim 49
Dependent Claim
131 words
A composition for terminating the life cycle of plants which comprises one or more compounds of the formula ##STR7## or a metal, ammonium, alkyl amine or dialkanol amine salt thereof wherein R f is a perfluoroalkyl group containing one to four carbon atoms, each Y is a non-cyclic group selected from alkyl, alkanoylamido, halo, haloalkyl, nitro, alkoxy, alkylsulfonyl, alkylsulfinyl, alkylthio, amino, sulfamoyl, carbamyl, alkoxyalkylthio and sulfamoylamino and m is 1-3, provided that all of the Y groups together contain not more than about twenty carbon atoms, at least one of the Y groups contains a heteroatom selected from oxygen, sulfur, nitrogen and halogen, no single Y contains more than six carbon atoms and at least one Y is other than alkyl, halo and haloalkyl, together with a horticulturally acceptable extending medium.
Claim 50
Dependent Claim
131 words
A composition for terminating the life cycle of plants which comprises one or more compounds of the formula ##STR7## or a metal, ammonium, alkyl amine or dialkanol amine salt thereof wherein R f is a perfluoroalkyl group containing one to four carbon atoms, each Y is a non-cyclic group selected from alkyl, alkanoylamido, halo, haloalkyl, nitro, alkoxy, alkylsulfonyl, alkylsulfinyl, alkylthio, amino, sulfamoyl, carbamyl, alkoxyalkylthio and sulfamoylamino and m is 1-3, provided that all of the Y groups together contain not more than about twenty carbon atoms, at least one of the Y groups contains a heteroatom selected from oxygen, sulfur, nitrogen and halogen, no single Y contains more than six carbon atoms and at least one Y is other than alkyl, halo and haloalkyl, together with a horticulturally acceptable extending medium.
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) | 1981-02-27 | 1981-08-29 | 1982-02-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-27 | 1985-08-29 | 1986-02-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-27 | 1989-08-29 | 1990-02-28 | $7700.00 | Window Closed / Lapsed |