US4391627A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Herbicidal benzothiophene and benzofuran sulfonamides
Assignee: EIDP Inc
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Filing: 1981-06-22
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Granted: 1983-07-05
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Expires: 2001-06-22
Abstract
Abstract Novel N-(heterocyclicaminocarbonyl)carbonyl-substituted benzothiophene- and benzofuransulfonamides are useful as herbicides. The invention also includes novel sulfonamides and sulfonyl isocyanates useful in preparing such compounds.
Inventors
- 👤 George Levitt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 16:11
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; C07D491/044; C07D307/00; C07D307/77; C07D307/78; C07D307/82; C07D307/84; C07D307/85; C07D333/00; C07D333/50; C07D333/52; C07D333/62; C07D333/68; C07D333/70; C07D521/00
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
364 words
A compound of the formula: ##STR102## wherein R is H or CH 3 ; R 1 is H, Cl, Br, NO 2 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CO 2 R 2 , C(O)NR 3 R 4 , SO 2 R 5 or SO 2 NR 6 R 7 ; R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OC 2 H 5 , CH 2 CH 2 CH 2 OCH 3 or CH 2 R 8 ; R 3 is C 1 -C 4 alkyl; R 4 is H, C 1 -C 4 alkyl or OCH 3 ; or R 3 and R 4 can be taken together to form --(CH 2 ) 4 --; R 5 is C 1 -C 4 alkyl; R 6 is C 1 -C 3 alkyl or OCH 3 ; R 7 is C 1 -C 3 alkyl; R 8 is C 1 -C 3 alkyl substituted with 1-3 atoms of F, Cl, or Br; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; A is ##STR103## X is H, CH 3 , OCH 3 , OC 2 H 5 , OCH 2 CF 3 , CH 2 OCH 3 or Cl; Y is CH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 or SCH 3 ; Z is N, CH, C--Cl, C--Br, C--CN, C--CH 3 , C--C 2 H 5 , C--CH 2 CH 2 Cl or C--CH 2 CH═CH 2 ; Y 1 is H, CH 3 , OCH 3 or Cl; and Q is O or CH 2 ; provided that (1) when R 4 or R 6 is OCH 3 , then R 3 or R 7 is CH 3 ; (2) the total number of carbon atoms of either R 3 and R 4 , or R 6 and R 7 , is less than or equal to 4; and (3) when X is Cl, then Z is CH.
Claim 2
Dependent Claim
364 words
A compound of the formula: ##STR102## wherein R is H or CH 3 ; R 1 is H, Cl, Br, NO 2 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CO 2 R 2 , C(O)NR 3 R 4 , SO 2 R 5 or SO 2 NR 6 R 7 ; R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OC 2 H 5 , CH 2 CH 2 CH 2 OCH 3 or CH 2 R 8 ; R 3 is C 1 -C 4 alkyl; R 4 is H, C 1 -C 4 alkyl or OCH 3 ; or R 3 and R 4 can be taken together to form --(CH 2 ) 4 --; R 5 is C 1 -C 4 alkyl; R 6 is C 1 -C 3 alkyl or OCH 3 ; R 7 is C 1 -C 3 alkyl; R 8 is C 1 -C 3 alkyl substituted with 1-3 atoms of F, Cl, or Br; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; A is ##STR103## X is H, CH 3 , OCH 3 , OC 2 H 5 , OCH 2 CF 3 , CH 2 OCH 3 or Cl; Y is CH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 or SCH 3 ; Z is N, CH, C--Cl, C--Br, C--CN, C--CH 3 , C--C 2 H 5 , C--CH 2 CH 2 Cl or C--CH 2 CH═CH 2 ; Y 1 is H, CH 3 , OCH 3 or Cl; and Q is O or CH 2 ; provided that (1) when R 4 or R 6 is OCH 3 , then R 3 or R 7 is CH 3 ; (2) the total number of carbon atoms of either R 3 and R 4 , or R 6 and R 7 , is less than or equal to 4; and (3) when X is Cl, then Z is CH.
Claim 3
Dependent Claim
43 words
A compound of claim 1 wherein Z is N or CH; and R 1 is H, Cl, Br, NO 2 , C 1 -C 3 alkyl, CO 2 R 2 , SO 2 R 5 or SO 2 NR 6 R 7 .
Claim 4
Dependent Claim
10 words
A compound of claim 2 wherein R 9 is H.
Claim 5
Dependent Claim
9 words
A compound of claim 3 wherein R is H.
Claim 6
Dependent Claim
36 words
A compound of claim 4 wherein A is ##STR104## X is CH 3 , OCH 3 , OC 2 H 5 or CH 2 OCH 3 ; and Y is CH 3 or OCH 3 .
Claim 7
Dependent Claim
9 words
A compound of claim 5 wherein W is S.
Claim 8
Dependent Claim
31 words
A compound of claim 6 wherein R 1 is Cl, Br, NO 2 , CO 2 R 2 , SO 2 R 5 or SO 2 NR 6 R 7 .
Claim 9
Dependent Claim
16 words
A compound of claim 7 wherein R 1 is at the 2-position of the benzo[b]thiophene ring.
Claim 10
Dependent Claim
14 words
A compound of claim 8 wherein R 1 is CO 2 R 2 .
Claim 11
Dependent Claim
9 words
The compound of claim 1, 3-[[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 12
Dependent Claim
9 words
The compound of claim 1, 3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 13
Dependent Claim
9 words
The compound of claim 1, 3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 14
Dependent Claim
9 words
The compound of claim 1, 3-[[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 15
Dependent Claim
9 words
The compound of claim 1, 3-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 16
Dependent Claim
9 words
The compound of claim 1, 3-[[(4-methyl-6-methoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]thiophene-2-carboxylic acid, methyl ester.
Claim 17
Dependent Claim
9 words
The compound of claim 1, 3-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzo[b]-thiophene-2-carboxylic acid, ethyl ester.
Claim 18
Dependent Claim
199 words
A compound selected from: ##STR105## R 1 is H, Cl, Br, NO 2 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CO 2 R 2 , C(O)NR 3 R 4 , SO 2 R 5 or SO 2 NR 6 R 7 ; R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OC 2 H 5 , CH 2 CH 2 CH 2 OCH 3 or CH 2 R 8 ; R 3 is C 1 -C 4 alkyl; R 4 is H, C 1 -C 4 alkyl or OCH 3 ; or R 3 and R 4 can be taken together to form --(CH 2 ) 4 --; R 5 is C 1 -C 4 alkyl; R 6 is C 1 -C 3 alkyl or OCH 3 ; R 7 is C 1 -C 3 alkyl; R 8 is C 1 -C 3 alkyl substituted with, 1-3 atoms of F, Cl, or Br; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; and Z is N or CH.
Claim 19
Dependent Claim
199 words
A compound selected from: ##STR105## R 1 is H, Cl, Br, NO 2 , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, CO 2 R 2 , C(O)NR 3 R 4 , SO 2 R 5 or SO 2 NR 6 R 7 ; R 2 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH 2 OC 2 H 5 , CH 2 CH 2 CH 2 OCH 3 or CH 2 R 8 ; R 3 is C 1 -C 4 alkyl; R 4 is H, C 1 -C 4 alkyl or OCH 3 ; or R 3 and R 4 can be taken together to form --(CH 2 ) 4 --; R 5 is C 1 -C 4 alkyl; R 6 is C 1 -C 3 alkyl or OCH 3 ; R 7 is C 1 -C 3 alkyl; R 8 is C 1 -C 3 alkyl substituted with, 1-3 atoms of F, Cl, or Br; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; and Z is N or CH.
Claim 20
Dependent Claim
139 words
A compound selected from: ##STR106## wherein M is H or alkali metal ion; R is H or CH 3 ; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; A is ##STR107## X is H, CH 3 , OCH 3 , OC 2 H 5 , OCH 2 CF 3 , CH 2 OCH 3 ; Y is CH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 or SCH 3 ; Z is N, CH, C--Cl, C--Br, C--CN, C--CH 3 , C--C 2 H 5 , C--CH 2 CH 2 Cl or C--CH 2 CH═CH 2 ; Y 1 is H, CH 3 , OCH 3 ; and Q is O or CH 2 .
Claim 21
Dependent Claim
139 words
A compound selected from: ##STR106## wherein M is H or alkali metal ion; R is H or CH 3 ; R 9 is H, CH 3 , OCH 3 , Cl, Br or NO 2 ; W is O or S; A is ##STR107## X is H, CH 3 , OCH 3 , OC 2 H 5 , OCH 2 CF 3 , CH 2 OCH 3 ; Y is CH 3 , OCH 3 , OC 2 H 5 , NH 2 , NHCH 3 , N(CH 3 ) 2 or SCH 3 ; Z is N, CH, C--Cl, C--Br, C--CN, C--CH 3 , C--C 2 H 5 , C--CH 2 CH 2 Cl or C--CH 2 CH═CH 2 ; Y 1 is H, CH 3 , OCH 3 ; and Q is O or CH 2 .
Claim 22
Dependent Claim
32 words
A composition 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 23
Dependent Claim
32 words
A composition 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 24
Dependent Claim
32 words
A composition 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 25
Dependent Claim
32 words
A composition 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 26
Dependent Claim
32 words
A composition 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 27
Dependent Claim
32 words
A composition 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 28
Dependent Claim
32 words
A composition 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 29
Dependent Claim
32 words
A composition for controlling the growth of undesired vegetation which comprises an effective amount of the compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
Claim 30
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 31
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 32
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 33
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 34
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 35
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 36
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 37
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 the compound of claim 8.
Claim 38
Dependent Claim
29 words
A method for controlling the growth of undesired vegetation in rice which comprises applying to the locus of the rice an effective amount of the compound of claim 11.
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) | 1986-07-04 | 1987-01-03 | 1987-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-07-04 | 1991-01-03 | 1991-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-07-04 | 1995-01-03 | 1995-07-05 | $7700.00 | Window Closed / Lapsed |