US4339267A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal sulfonamides
Assignee: EIDP Inc
•
Filing: 1980-10-16
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Granted: 1982-07-13
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Expires: 2000-10-16
Abstract
Abstract N-(heterocyclicaminocarbonyl)aryl and pyridylsulfonamides, useful for the regulation of plant growth and as pre-emergence and post-emergence herbicides.
Inventors
- 👤 George Levitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:08
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; A01N47/40; A01N47/42; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; C07D213/71; C07D239/70; C07D239/72; C07D239/78; C07D239/84; C07D239/95; C07D491/00; C07D491/02; C07D491/04
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
526 words
A compound selected from ##STR368## R 2 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , CF 3 , COR 5 , S(O) m R 10 , SO 2 NR 10 R 11 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 or SO 2 N(OCH 3 )CH 3 ; R 3 is H, F, Cl, Br, alkyl C 1 -C 4 or CH 3 O; R 4 is H, Cl, Br, F, alkyl C 1 -C 4 , alkoxy C 1 -C 4 , NO 2 , CO 2 R 6 or R 13 --S--; R 5 is alkoxy C 1 -C 6 ; alkenyloxy C 3 -C 6 ; haloalkoxy C 2 -C 6 substituted with 1 to 3 halogens selected from Cl, F and Br; cycloalkoxy C 5 -C 6 ; O--CH 2 CH 2 O) n R 7 ; OCH 2 CH 2 CH 2 OR 7 ; NR 8 R 9 ; N(OCH 3 )CH 3 or C 1 -C 4 alkylthio; R 6 is alkyl C 1 -C 6 ; R 7 is alkyl C 1 -C 2 ; R 8 and R 9 are independently H or alkyl C 1 -C 4 or R 8 and R 9 may be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 --) 2 ; and R 8 can also be ##STR369## R 10 and R 11 are independently C 1 -C 6 alkyl or C 3 -C 4 alkenyl or R 10 and R 11 can be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 ) 2 ; R 12 is C 1 -C 12 alkyl; CH 2 CH 2 OCH 3 ; CH 2 CH 2 OCH 2 CH 3 ; CH 2 CH 2 CH 2 OCH 3 ; ##STR370## R 13 is C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or CH 3 S; R 15 is H, F, Cl, Br, CH 3 or OCH 3 ; X is H, CH 3 , CH 3 O, Cl or OCH 2 CH 3 ; Y is CH 2 or O; A is CO 2 H, CO 2 B, CONH 2 , phenyl, CN, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl substituted with one or two methyl groups or with one or two chlorines; B is C 1 -C 4 alkyl; m is 0, 1 or 2; n is 1 or 2 Z is 0 or 1; W is oxygen or sulfur; provided that (i) when R 1 is ##STR371## then R 2 is NO 2 , COR 5 , SO 2 NR 10 R 11 , SO 2 N(CH 3 )(OCH 3 ) or SO 2 R 10 ; R 4 is other than H; and X is CH 3 or OCH 3 ; (ii) when W is sulfur; when Y is oxygen and their agriculturally suitable salts.
Claim 2
Dependent Claim
526 words
A compound selected from ##STR368## R 2 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , CF 3 , COR 5 , S(O) m R 10 , SO 2 NR 10 R 11 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 or SO 2 N(OCH 3 )CH 3 ; R 3 is H, F, Cl, Br, alkyl C 1 -C 4 or CH 3 O; R 4 is H, Cl, Br, F, alkyl C 1 -C 4 , alkoxy C 1 -C 4 , NO 2 , CO 2 R 6 or R 13 --S--; R 5 is alkoxy C 1 -C 6 ; alkenyloxy C 3 -C 6 ; haloalkoxy C 2 -C 6 substituted with 1 to 3 halogens selected from Cl, F and Br; cycloalkoxy C 5 -C 6 ; O--CH 2 CH 2 O) n R 7 ; OCH 2 CH 2 CH 2 OR 7 ; NR 8 R 9 ; N(OCH 3 )CH 3 or C 1 -C 4 alkylthio; R 6 is alkyl C 1 -C 6 ; R 7 is alkyl C 1 -C 2 ; R 8 and R 9 are independently H or alkyl C 1 -C 4 or R 8 and R 9 may be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 --) 2 ; and R 8 can also be ##STR369## R 10 and R 11 are independently C 1 -C 6 alkyl or C 3 -C 4 alkenyl or R 10 and R 11 can be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 ) 2 ; R 12 is C 1 -C 12 alkyl; CH 2 CH 2 OCH 3 ; CH 2 CH 2 OCH 2 CH 3 ; CH 2 CH 2 CH 2 OCH 3 ; ##STR370## R 13 is C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or CH 3 S; R 15 is H, F, Cl, Br, CH 3 or OCH 3 ; X is H, CH 3 , CH 3 O, Cl or OCH 2 CH 3 ; Y is CH 2 or O; A is CO 2 H, CO 2 B, CONH 2 , phenyl, CN, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl substituted with one or two methyl groups or with one or two chlorines; B is C 1 -C 4 alkyl; m is 0, 1 or 2; n is 1 or 2 Z is 0 or 1; W is oxygen or sulfur; provided that (i) when R 1 is ##STR371## then R 2 is NO 2 , COR 5 , SO 2 NR 10 R 11 , SO 2 N(CH 3 )(OCH 3 ) or SO 2 R 10 ; R 4 is other than H; and X is CH 3 or OCH 3 ; (ii) when W is sulfur; when Y is oxygen and their agriculturally suitable salts.
Claim 3
Dependent Claim
9 words
A compound of claim 1 wherein W is oxygen.
Claim 4
Dependent Claim
9 words
A compound of claim 2 wherein R is ##STR372##
Claim 5
Dependent Claim
10 words
A compound of claim 3 wherein R 1 is ##STR373##
Claim 6
Dependent Claim
15 words
A compound of claim 4 wherein X is H, CH 3 or OCH 3 .
Claim 7
Dependent Claim
46 words
A compound of claim 5 wherein R 2 is NO 2 , COR 5 , SO 2 NR 10 R 11 or SO 2 N(OCH 3 )(CH 3 ) and where R 10 and R 11 are independently CH 3 or CH 3 CH 2 .
Claim 8
Dependent Claim
10 words
A compound of claim 6 wherein R 3 is H.
Claim 9
Dependent Claim
16 words
A compound of claim 7 wherein R 5 is C 1 -C 3 alkoxy or allyloxy.
Claim 10
Dependent Claim
8 words
The compound of claim 1 which is N-[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide.
Claim 11
Dependent Claim
11 words
The compound of claim 1 which is 2-[[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoic acid, methyl ester.
Claim 12
Dependent Claim
8 words
The compound of claim 1 which is N-[(6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide.
Claim 13
Dependent Claim
8 words
The compound of claim 1 which is 2-chloro-N-[(5,6-dihydro-4-methylfuro[2,3-d]-pyrimidin-2-yl)aminocarbonyl]benzenesulfonamide.
Claim 14
Dependent Claim
8 words
The compound of claim 1 which is N-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]-2-nitrobenzenesulfonamide.
Claim 15
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester.
Claim 16
Dependent Claim
8 words
The compound of claim 1 which is N'-[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide.
Claim 17
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, ethyl ester.
Claim 18
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, ethyl ester.
Claim 19
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester.
Claim 20
Dependent Claim
11 words
The compound of claim 1 which is 2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]benzenecarbothioic acid, methyl ester.
Claim 21
Dependent Claim
8 words
The compound of claim 1 which is 1-[2-[[(5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzoyl]pyrrolidine.
Claim 22
Dependent Claim
8 words
The compound of claim 1 which is 2-[[(5,6-Dihydro-4-methylfuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl]-N,N-dimethylbenzamide.
Claim 23
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(4-Chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)-aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester.
Claim 24
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(6,7-Dihydro-4-methyl-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester.
Claim 25
Dependent Claim
11 words
The compound of claim 1 which is 2-{[(6,7-Dihydro-4-methoxy-5H-pyrano[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoic acid, methyl ester.
Claim 26
Dependent Claim
40 words
A composition for the control of undesirable vegetation consisting essentially of an herbicidally effective amount of a compound of any of claims 1-24 and at least one of (a) a surface active agent, and (b) a solid or liquid diluent.
Claim 27
Independent Claim
29 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation an herbicidally effective amount of a compound of any of claims 1-24.
Claim 28
Independent Claim
27 words
A method for the control of nutsedge comprising applying to the locus of such nutsedge an herbicidally effective amount of a compound of any of claims 1-24.
Claim 29
Dependent Claim
503 words
A compound selected from: ##STR374## R 2 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , CF 3 , COR 5 , S(O) m R 10 , SO 2 NR 10 R 11 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 or SO 2 N(OCH 3 )CH 3 ; R 3 is H, F, Cl, Br, alkyl C 1 -C 4 or CH 3 O; R 4 is H, Cl, Br, F, alkyl C 1 -C 4 , alkoxy C 1 -C 4 , NO 2 , CO 2 R 6 or R 13 --S--; R 5 is alkoxy C 1 -C 6 ; alkenyloxy C 3 -C 6 ; haloalkoxy C 2 -C 6 substituted with 1 to 3 halogens selected from Cl, F and Br; cycloalkoxy C 5 -C 6 ; O--CH 2 CH 2 O) n R 7 ; OCH 2 CH 2 CH 2 OR 7 ; NR 8 R 9 ; N(OCH 3 )CH 3 or C 1 -C 4 alkylthio; R 6 is alkyl C 1 -C 6 ; R 7 is alkyl C 1 -C 2 ; R 8 and R 9 are independently H or alkyl C 1 -C 4 or R 8 and R 9 may be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 --) 2 ; and R 8 can also be ##STR375## R 10 and R 11 are independently C 1 -C 6 alkyl or C 3 -C 4 alkenyl or R 10 and R 11 can be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 ) 2 ; R 12 is C 1 -C 12 alkyl; CH 2 CH 2 OCH 3 ; CH 2 CH 2 OCH 2 CH 3 ; CH 2 CH 2 CH 2 OCH 3 ; ##STR376## R 13 is C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or CH 3 S; R 15 is H, F, Cl, Br, CH 3 or OCH 3 ; X is H, CH 3 , CH 3 O, Cl or OCH 2 CH 3 ; A is CO 2 H, CO 2 B, CONH 2 , phenyl, CN, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl substituted with one or two methyl grohups or with one or two chlorines; B is C 1 -C 4 alkyl; m is 0, 1 or 2; n is 1 or 2; and Z is 0 or 1; provided that (i) when R 1 " is ##STR377## then R 2 is NO 2 , COR 5 , SO 2 NR 10 R 11 , SO 2 N(CH 3 )(OCH 3 ) or SO 2 R 10 ; R 4 is other than H; and X is CH 3 or OCH 3 .
Claim 30
Dependent Claim
503 words
A compound selected from: ##STR374## R 2 is H, CH 3 , OCH 3 , F, Cl, Br, NO 2 , CF 3 , COR 5 , S(O) m R 10 , SO 2 NR 10 R 11 , SO 2 OCH 2 CF 3 , SO 2 OCH 2 CCl 3 or SO 2 N(OCH 3 )CH 3 ; R 3 is H, F, Cl, Br, alkyl C 1 -C 4 or CH 3 O; R 4 is H, Cl, Br, F, alkyl C 1 -C 4 , alkoxy C 1 -C 4 , NO 2 , CO 2 R 6 or R 13 --S--; R 5 is alkoxy C 1 -C 6 ; alkenyloxy C 3 -C 6 ; haloalkoxy C 2 -C 6 substituted with 1 to 3 halogens selected from Cl, F and Br; cycloalkoxy C 5 -C 6 ; O--CH 2 CH 2 O) n R 7 ; OCH 2 CH 2 CH 2 OR 7 ; NR 8 R 9 ; N(OCH 3 )CH 3 or C 1 -C 4 alkylthio; R 6 is alkyl C 1 -C 6 ; R 7 is alkyl C 1 -C 2 ; R 8 and R 9 are independently H or alkyl C 1 -C 4 or R 8 and R 9 may be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 --) 2 ; and R 8 can also be ##STR375## R 10 and R 11 are independently C 1 -C 6 alkyl or C 3 -C 4 alkenyl or R 10 and R 11 can be taken together to be (CH 2 ) 4 , (CH 2 ) 5 or O(CH 2 CH 2 ) 2 ; R 12 is C 1 -C 12 alkyl; CH 2 CH 2 OCH 3 ; CH 2 CH 2 OCH 2 CH 3 ; CH 2 CH 2 CH 2 OCH 3 ; ##STR376## R 13 is C 1 -C 3 alkyl; R 14 is H, F, Cl, Br, NO 2 , CN, CF 3 , C 1 -C 3 alkyl, OCH 3 or CH 3 S; R 15 is H, F, Cl, Br, CH 3 or OCH 3 ; X is H, CH 3 , CH 3 O, Cl or OCH 2 CH 3 ; A is CO 2 H, CO 2 B, CONH 2 , phenyl, CN, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, phenyl substituted with one or two methyl grohups or with one or two chlorines; B is C 1 -C 4 alkyl; m is 0, 1 or 2; n is 1 or 2; and Z is 0 or 1; provided that (i) when R 1 " is ##STR377## then R 2 is NO 2 , COR 5 , SO 2 NR 10 R 11 , SO 2 N(CH 3 )(OCH 3 ) or SO 2 R 10 ; R 4 is other than H; and X is CH 3 or OCH 3 .
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1985-07-12 | 1986-01-11 | 1986-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-12 | 1990-01-11 | 1990-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-12 | 1994-01-11 | 1994-07-13 | $7700.00 | Window Closed / Lapsed |