US4514211A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Benzofuran and benzothiophene sulfonamides
Assignee: EIDP Inc
•
Filing: 1983-04-27
•
Granted: 1985-04-30
•
Expires: 2003-04-27
Abstract
Abstract Benzofuran and benzothiophene sulfonamides show utility as herbicides and plant growth regulants.
Inventors
- 👤 Morris P. Rorer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:31
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/46; C07D239/47; A; A01; A01N; A01N47/00; A01N47/08; A01N47/28; A01N47/36; C07D307/00; C07D307/77; C07D307/78; C07D307/79; C07D333/00; C07D333/50; C07D333/52; C07D333/54; C07D335/00; C07D335/04; C07D335/06; C07D409/00; C07D409/02; C07D409/12; C07D521/00
Claims Analysis
Total Claims: 54
Claim 1
Independent Claim
552 words
A compound selected from: ##STR95## wherein Q is O, S, SO or SO 2 ; Q 1 is O, S or SO 2 ##STR96## R 1 is H or C 1 -C 4 alkyl; R 2 is H or C 1 -C 4 alkyl; R 3 is H or CH 3 ; R 4 is H, Cl, CH 3 , CF 3 , OCH 3 , Br, F, SCH 3 or OCF 2 H; R 5 is H, CH 3 , OCH 3 , Cl, Br, NO 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 , SO 2 NR 10 R 11 , F, CF 3 , SCH 3 , OCF 2 H or SO 2 N(OCH 3 )CH 3 ; R 6 is H, Cl, Br of C 1 -C 4 alkyl; R 6 ' is H, CH 3 , Cl or Br; R 7 is C 1 -C 3 alkyl, CH 2 CH═CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 8 is C 1 -C 3 alkyl; R 9 is C 1 -C 3 alkyl or CF 3 ; R 10 and R 11 are independently C 1 -C 2 alkyl; R 12 is H or CH 3 ; W is O or S; A is ##STR97## X is H, CH 3 , OCH 3 , Cl, F, OCF 2 H or SCF 2 H; Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , CH(OCH 2 CH 3 ) 2 , C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, ##STR98## CH.tbd.CCH 2 O, CF 3 CH 2 O, OCH 2 CH 2 Cl, OCH 2 CH 2 Br, OCH 2 CH 2 F, CN, CH 2 OCH 2 CH 3 , OCH 2 CH 2 OCH 3 or GCF 2 T wherein G is O or S and T is H, CHClF, CHBrF, CF 2 H or CHFCF 3 ; Z is CH, N, CCH 3 , CC 2 H 5 , CCl or CBr; Y 1 is O or CH 2 ; X 1 is CH 3 , OCH 3 , OC 2 H 5 or OCF 2 H; X 2 is CH 3 , C 2 H 5 or CH 2 CF 3 ; Y 2 is C 2 H 5 , CH 3 , OCH 3 , OC 2 H 5 , SCH 3 or SC 2 H 5 ; and X 3 is CH 3 or OCH 3 ; provided that (1) in Formulae II and II', when R 5 is NO 2 , then R 6 is C 1 -C 4 alkyl and R 6 ' is CH 3 ; (2) when X is Cl or F, then Z is CH and Y is OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H; (3) when Q is SO, then W is O; (4) when R 4 is other than H, then R 5 is H; and (5) R 1 and R 2 taken together are not more than four carbon atoms.
Claim 2
Dependent Claim
552 words
A compound selected from: ##STR95## wherein Q is O, S, SO or SO 2 ; Q 1 is O, S or SO 2 ##STR96## R 1 is H or C 1 -C 4 alkyl; R 2 is H or C 1 -C 4 alkyl; R 3 is H or CH 3 ; R 4 is H, Cl, CH 3 , CF 3 , OCH 3 , Br, F, SCH 3 or OCF 2 H; R 5 is H, CH 3 , OCH 3 , Cl, Br, NO 2 , CO 2 R 7 , SO 2 R 8 , OSO 2 R 9 , SO 2 NR 10 R 11 , F, CF 3 , SCH 3 , OCF 2 H or SO 2 N(OCH 3 )CH 3 ; R 6 is H, Cl, Br of C 1 -C 4 alkyl; R 6 ' is H, CH 3 , Cl or Br; R 7 is C 1 -C 3 alkyl, CH 2 CH═CH 2 , CH 2 CH 2 OCH 3 or CH 2 CH 2 Cl; R 8 is C 1 -C 3 alkyl; R 9 is C 1 -C 3 alkyl or CF 3 ; R 10 and R 11 are independently C 1 -C 2 alkyl; R 12 is H or CH 3 ; W is O or S; A is ##STR97## X is H, CH 3 , OCH 3 , Cl, F, OCF 2 H or SCF 2 H; Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , CH(OCH 2 CH 3 ) 2 , C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, ##STR98## CH.tbd.CCH 2 O, CF 3 CH 2 O, OCH 2 CH 2 Cl, OCH 2 CH 2 Br, OCH 2 CH 2 F, CN, CH 2 OCH 2 CH 3 , OCH 2 CH 2 OCH 3 or GCF 2 T wherein G is O or S and T is H, CHClF, CHBrF, CF 2 H or CHFCF 3 ; Z is CH, N, CCH 3 , CC 2 H 5 , CCl or CBr; Y 1 is O or CH 2 ; X 1 is CH 3 , OCH 3 , OC 2 H 5 or OCF 2 H; X 2 is CH 3 , C 2 H 5 or CH 2 CF 3 ; Y 2 is C 2 H 5 , CH 3 , OCH 3 , OC 2 H 5 , SCH 3 or SC 2 H 5 ; and X 3 is CH 3 or OCH 3 ; provided that (1) in Formulae II and II', when R 5 is NO 2 , then R 6 is C 1 -C 4 alkyl and R 6 ' is CH 3 ; (2) when X is Cl or F, then Z is CH and Y is OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H; (3) when Q is SO, then W is O; (4) when R 4 is other than H, then R 5 is H; and (5) R 1 and R 2 taken together are not more than four carbon atoms.
Claim 3
Dependent Claim
6 words
Compounds of claim 1, Formula I.
Claim 4
Dependent Claim
8 words
Compounds of claim 2 where W is O.
Claim 5
Dependent Claim
101 words
Compounds of claim 3 where R 5 is H, Cl, CH 3 , OCH 3 , CO 2 R 7 or SO 2 R 8 , R 4 is H, Cl, CH 3 or OCH 3 , and Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , ##STR99## C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, HC.tbd.CCH 2 O, CF 3 CH 2 O, OCF 2 H or SCF 2 H.
Claim 6
Dependent Claim
38 words
Compounds of claim 4 where R 3 , R 4 , R 5 and R 12 are H, R 1 is H, CH 3 or CH 2 CH 3 and R 2 is H or CH 3 .
Claim 7
Dependent Claim
23 words
Compounds of claim 5 where A is ##STR100## Z is CH or N; and X is CH 3 , OCH 3 or Cl.
Claim 8
Dependent Claim
23 words
Compounds of claim 6 where Y is CH 3 , OCH 3 , CH 2 OCH 3 or N(CH 3 ) 2 .
Claim 9
Dependent Claim
6 words
Compounds of claim 1, Formula I'.
Claim 10
Dependent Claim
14 words
Compounds of claim 8 where W is O and Q is S or O.
Claim 11
Dependent Claim
90 words
Compound of claim 9 where R 5 is H, Cl, CH 3 , OCH 3 , CO 2 R 7 or SO 2 R 8 ; and Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , ##STR101## C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, HC.tbd.CCH 2 O, CF 3 CH 2 O, OCF 2 H or SCF 2 H.
Claim 12
Dependent Claim
25 words
Compounds of claim 10 where R 5 and R 12 are H and R 1 and R 2 are independently H or CH 3 .
Claim 13
Dependent Claim
23 words
Compounds of claim 11 where A is ##STR102## Z is CH or N; and X is CH 3 , OCH 3 or Cl.
Claim 14
Dependent Claim
23 words
Compounds of claim 12 where Y is CH 3 , OCH 3 , CH 2 OCH 3 or N(CH 3 ) 2 .
Claim 15
Dependent Claim
6 words
Compounds of claim 1, Formula II.
Claim 16
Dependent Claim
25 words
Compounds of claim 14 where W is O, R 6 is H, CH 3 or CH 2 CH 3 and R 6 ' is H.
Claim 17
Dependent Claim
101 words
Compounds of claim 15 where R 5 is H, Cl, CH 3 , OCH 3 , CO 2 R 7 or SO 2 R 8 , R 4 is H, Cl, CH 3 or OCH 3 , and Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , ##STR103## C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, HC.tbd.CCH 2 O, CF 3 CH 2 O, OCF 2 H or SCF 2 H.
Claim 18
Dependent Claim
28 words
Compounds of claim 16 where R 4 , R 5 , R 6 ' and R 12 are H and R 6 is H or CH 3 .
Claim 19
Dependent Claim
23 words
Compounds of claim 17 where A is ##STR104## Z is CH or N; and X is CH 3 , OCH 3 or Cl.
Claim 20
Dependent Claim
23 words
Compounds of claim 18 where Y is CH 3 , OCH 3 , CH 2 OCH 3 or N(CH 3 ) 2 .
Claim 21
Dependent Claim
6 words
Compounds of claim 1, Formula II'.
Claim 22
Dependent Claim
30 words
Compounds of claim 20 where W is O, Q is O or S, R 6 is H or CH 3 and R 6 ' is H or CH 3 .
Claim 23
Dependent Claim
90 words
Compounds of claim 21 where R 5 is H, Cl, CH 3 , OCH 3 , CO 2 R 7 or SO 2 R 8 ; and Y is CH 3 , OCH 3 , OC 2 H 5 , CH 2 OCH 3 , NH 2 , NHCH 3 , N(CH 3 ) 2 , CH(OCH 3 ) 2 , ##STR105## C 2 H 5 , CF 3 , CH 2 ═CHCH 2 O, HC.tbd.CCH 2 O, CF 3 CH 2 O, OCF 2 H or SCF 2 H.
Claim 24
Dependent Claim
12 words
Compounds of claim 22 where R 5 and R 12 are H.
Claim 25
Dependent Claim
23 words
Compounds of claim 23 where A is ##STR106## Z is CH or N; and X is CH 3 , OCH 3 or Cl.
Claim 26
Dependent Claim
23 words
Compounds of claim 24 where Y is CH 3 , OCH 3 , CH 2 OCH 3 or N(CH 3 ) 2 .
Claim 27
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 28
Dependent Claim
9 words
The compound of claim 1 which is N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 29
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 30
Dependent Claim
9 words
The compound of claim 1 which is N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 31
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 32
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 33
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,3-dihydro-2,2-dimethyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 34
Dependent Claim
9 words
The compound of claim 1 which is N-[(4,6-dimethylpyrimidin-2-yl)methylaminocarbonyl]-2,3-dihydro-2-methyl-7-benzothiophenesulfonamide, 1,1-dioxide.
Claim 35
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
Claim 36
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
Claim 37
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
Claim 38
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
Claim 39
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
Claim 40
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
Claim 41
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
Claim 42
Dependent Claim
33 words
A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
Claim 43
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 1.
Claim 44
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 2.
Claim 45
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 3.
Claim 46
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 4.
Claim 47
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 5.
Claim 48
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 6.
Claim 49
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 7.
Claim 50
Dependent Claim
27 words
A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim 8.
Claim 51
Dependent Claim
4 words
The compound (2,3-dihydro-N-[(4-methoxy-6-methylthio-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzo[b]thiophene-7-sulfonamide, 1,1-dioxide).
Claim 52
Dependent Claim
4 words
The compound (2,3-dihydro-N-[(4-methoxy-6-methylthio-1,3,5-triazin-2-yl)aminocarbonyl]-2-methylbenzo[b]thiophene-7-sulfonamide, 1,1-dioxide).
Claim 53
Dependent Claim
6 words
The compound of claim 1, N-(2,3-dihydro-2-methylbenzo[b]furan-7-yl-sulfonyl)-N'-(4,6-dimethylpyrimidin-2-yl)urea.
Claim 54
Dependent Claim
6 words
The compound of claim 1, N-(2,3-dihydro-2-methylbenzo[b]furan-7-yl-sulfonyl)-N'-(4-methoxy-6-methylpyrimidin-2-yl)urea.
References Cited (Backward Citations)
US4339266A
Cited
US4391627A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1988-04-29 | 1988-10-29 | 1989-04-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-04-29 | 1992-10-29 | 1993-04-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-04-29 | 1996-10-29 | 1997-04-30 | $7700.00 | Window Closed / Lapsed |