US4310346A
Expired / Lapsed
US
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N(Substituted phenylsulfonyl) N'(substituted cyumidin-2-yl) ureas
Assignee: EIDP Inc
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Filing: 1980-05-30
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Granted: 1982-01-12
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Expires: 2000-05-30
Abstract
Abstract This invention relates to N(Substituted Phenylsulfonyl) N'(Substituted Pyrimidinyl) urea compounds having the formulae I and IA <IMAGE> I <IMAGE> IA to agricultural compositions containing them and to their methods of use as general as well as selective pre- and post-emergence herbicides and as plant growth regulants.
Inventors
- 👤 George Levitt
- 👤 Richard F. Sauers
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 00:13
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; C07D239/46; C07D251/00; C07D251/02; C07D251/12; C07D251/14; C07D251/16; C07D251/26; C07D251/40; C07D251/42; C07D251/46; C07D253/00; C07D253/02; C07D253/06; C07D253/065; C07D253/07
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
549 words
A compound of the formulae ##STR376## wherein A is ##STR377## where R a is H, Cl, CH 3 , OCH 3 or NO 2 and R b is H, F or C 1 -C 2 alkyl with 0-5F and R c is CH 3 or CF 3 ; R 1 is ##STR378## where R d is C 1 -C 3 alkyl, or R 1 is N(CH 3 ) 2 , CN, CH 2 S(O) n CH 3 or S(O) n CH 3 , where n is 0, 1 or 2; R 1 ' is H, Cl, F, Br, CH 3 or OCH 3 ; R 2 is H, C 1 -C 6 alkyl, C 3 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 5 -C 6 cycloalkenyl, C 3 -C 5 alkynyl, C 3 -C 6 cycloalkyl substituted with 1-2 CH 3 groups, CF 2 CF 2 H, CF 2 CHFCl, CF 2 CHFBr, CF 2 CHFCF 3 , C(CH 3 ) 2 CN, (CH 2 ) m CN, where m is 1 or 2, CH 2 CH 2 OCH 3 , CH 2 CH(CH 3 )OCH 3 , (CH 2 ) 3 OCH 3 , CHR 7 CO 2 R 8 or CHR 7 CON(R 8 ) 2 , where R 7 is H or CH 3 and R 8 is C 1 -C 3 alkyl, OCH 3 , ##STR379## where R 9 is H, CH 3 , Cl, Br or F; R 3 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH(CH) 3 OCH 3 , CH 2 CF 3 , or (CH 2 ) m CN, where m is 1 or 2, or CHR 7 CO 2 R 8 , NR 2 R 3 taken together are ##STR380## R 4 and R 5 are independently H or CH 3 , but R 4 and R 5 cannot both be CH 3 ; R 6 is ##STR381## wherein X is H, CH 3 , CH 3 O or CH 3 CH 2 O; Y is Cl, Br, H, C 1 -C 3 alkyl, CF 3 , NHCH 3 N(CH 3 ) 2 , OCH 2 CF 3 , OCH 3 , OC 2 H 5 , SCH 3 , O(CH 2 ) p OR 10 , where p is 2 or 3 and R 10 is CH 3 or C 2 H 5 , CH 2 CH 2 OCH 3 , CH 2 OCH 3 , CH 2 OCH 2 CH 3 , OCHR 7 CO 2 R 11 , OCHR 7 CON(R 8 ) 2 , CO 2 R 11 and CH 2 CO 2 R 11 , where R 11 is H or C 1 -C 3 alkyl, CH 2 CN, NCH 3 (CH 2 CN), CH 2 CH 2 CN, CH 2 Cl, N 3 , OCH 2 CH═CH 2 or OCH 2 C.tbd.CH; provided that: (1) when R 2 is OCH 3 , R 3 is CH 3 ; (2) when R 2 is CF 2 CHFCl, CF 2 CHFBr, CF 2 CF 2 H or CF 2 CHFCF 3 , then R 3 is C 1 -C 4 alkyl; and their agriculturally suitable salts.
Claim 2
Dependent Claim
549 words
A compound of the formulae ##STR376## wherein A is ##STR377## where R a is H, Cl, CH 3 , OCH 3 or NO 2 and R b is H, F or C 1 -C 2 alkyl with 0-5F and R c is CH 3 or CF 3 ; R 1 is ##STR378## where R d is C 1 -C 3 alkyl, or R 1 is N(CH 3 ) 2 , CN, CH 2 S(O) n CH 3 or S(O) n CH 3 , where n is 0, 1 or 2; R 1 ' is H, Cl, F, Br, CH 3 or OCH 3 ; R 2 is H, C 1 -C 6 alkyl, C 3 -C 4 alkenyl, C 3 -C 6 cycloalkyl, C 4 -C 7 cycloalkylalkyl, C 5 -C 6 cycloalkenyl, C 3 -C 5 alkynyl, C 3 -C 6 cycloalkyl substituted with 1-2 CH 3 groups, CF 2 CF 2 H, CF 2 CHFCl, CF 2 CHFBr, CF 2 CHFCF 3 , C(CH 3 ) 2 CN, (CH 2 ) m CN, where m is 1 or 2, CH 2 CH 2 OCH 3 , CH 2 CH(CH 3 )OCH 3 , (CH 2 ) 3 OCH 3 , CHR 7 CO 2 R 8 or CHR 7 CON(R 8 ) 2 , where R 7 is H or CH 3 and R 8 is C 1 -C 3 alkyl, OCH 3 , ##STR379## where R 9 is H, CH 3 , Cl, Br or F; R 3 is C 1 -C 4 alkyl, C 3 -C 4 alkenyl, CH 2 CH 2 OCH 3 , CH 2 CH(CH) 3 OCH 3 , CH 2 CF 3 , or (CH 2 ) m CN, where m is 1 or 2, or CHR 7 CO 2 R 8 , NR 2 R 3 taken together are ##STR380## R 4 and R 5 are independently H or CH 3 , but R 4 and R 5 cannot both be CH 3 ; R 6 is ##STR381## wherein X is H, CH 3 , CH 3 O or CH 3 CH 2 O; Y is Cl, Br, H, C 1 -C 3 alkyl, CF 3 , NHCH 3 N(CH 3 ) 2 , OCH 2 CF 3 , OCH 3 , OC 2 H 5 , SCH 3 , O(CH 2 ) p OR 10 , where p is 2 or 3 and R 10 is CH 3 or C 2 H 5 , CH 2 CH 2 OCH 3 , CH 2 OCH 3 , CH 2 OCH 2 CH 3 , OCHR 7 CO 2 R 11 , OCHR 7 CON(R 8 ) 2 , CO 2 R 11 and CH 2 CO 2 R 11 , where R 11 is H or C 1 -C 3 alkyl, CH 2 CN, NCH 3 (CH 2 CN), CH 2 CH 2 CN, CH 2 Cl, N 3 , OCH 2 CH═CH 2 or OCH 2 C.tbd.CH; provided that: (1) when R 2 is OCH 3 , R 3 is CH 3 ; (2) when R 2 is CF 2 CHFCl, CF 2 CHFBr, CF 2 CF 2 H or CF 2 CHFCF 3 , then R 3 is C 1 -C 4 alkyl; and their agriculturally suitable salts.
Claim 3
Dependent Claim
11 words
The compounds of claim 1 wherein R 4 =R 5 =H.
Claim 4
Dependent Claim
7 words
The compounds of claim 2 wherein W=O.
Claim 5
Dependent Claim
9 words
The compounds of claim 3 wherein R 1 '=H.
Claim 6
Dependent Claim
64 words
The compounds of claim 3 wherein A is OCH 2 CF 3 or NR 2 R 3 and R 2 is C 1 -C 6 alkyl, C 3 -C 4 alkenyl, OCH 3 , CH 2 CH 2 OCH 3 , CH 2 CH(CH 3 )OCH 3 or (CH 2 ) 3 OCH 3 , or NR 2 R 3 taken together are ##STR382##
Claim 7
Dependent Claim
24 words
The compounds of claim 3 wherein R 3 is C 1 -C 4 alkyl or where NR 2 R 3 taken together are ##STR383##
Claim 8
Dependent Claim
24 words
The compounds of claim 5 wherein R 3 is C 1 -C 4 alkyl or where NR 2 R 3 taken together are ##STR384##
Claim 9
Dependent Claim
23 words
The compounds of claim 7 wherein R 1 is H, Cl, CF 3 , NO 2 , CH 3 or OCH 3 .
Claim 10
Dependent Claim
23 words
The compounds of claim 8 wherein R 2 is C 1 -C 4 alkyl or NR 2 R 3 taken together are ##STR385##
Claim 11
Dependent Claim
78 words
The compounds of claim 9 in which X is CH 3 , OCH 3 or OCH 2 CH 3 ; and Y is H, CH 3 , CH 3 CH 2 , OCH 2 CF 3 , OCH 3 , OC 2 H 5 , OCH 2 CH 2 OCH 3 , CH 2 OCH 3 , CH 2 CH 2 OCH 3 , N(CH 3 )CH 2 CN, OCH 2 CH═CH 2 , or OCH 2 C.tbd.CH.
Claim 12
Dependent Claim
39 words
The compounds of claim 10 in which X is CH 3 , OCH 3 or OCH 2 CH 3 ; and Y is CH 3 , OCH 2 CF 3 , OCH 3 or OCH 2 CH 3 .
Claim 13
Dependent Claim
6 words
The compound of claim 1, N'-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide.
Claim 14
Dependent Claim
6 words
The compound of claim 1, N'-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide.
Claim 15
Dependent Claim
6 words
The compound of claim 1, N'-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide.
Claim 16
Dependent Claim
6 words
The compound of claim 1, N'-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-N,N-diethyl-1,2-benzenedisulfonamide.
Claim 17
Dependent Claim
6 words
The compound of claim 1, N'-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-N,N-diethyl-1,2-benzenedisulfonamide.
Claim 18
Dependent Claim
6 words
The compound of claim 1, N'-[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-N,N-diethyl-1,2-benzenedisulfonamide.
Claim 19
Dependent Claim
12 words
The compound of claim 1, N 2 [(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-N 1 ,N 1 -dimethyl-4-(trifluoromethyl)-1,2-benzenesulfonamide.
Claim 20
Dependent Claim
12 words
The compound of claim 1, 4-Chloro-N 2 -[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-N 1 ,N 1 -dimethyl-1,2-benzenedisulfonamide.
Claim 21
Dependent Claim
7 words
The compound of claim 1, (2,2,2-Trifluoroethyl) 2-[[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzenesulfonoate.
Claim 22
Dependent Claim
7 words
The compound of claim 1, (2,2,2-Trifluoroethyl) 2-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]benzenesulfonoate.
Claim 23
Dependent Claim
6 words
The compound of claim 1, N'[(4,6-Dimethylpyrimidin-2-yl)aminocarbonyl]-N-ethyl-N-methyl-1,2-benzenedisulfonamide.
Claim 24
Dependent Claim
6 words
The compound of claim 1, N-Ethyl-N'-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-N-methyl-1,2-benzenedisulfonamide.
Claim 25
Dependent Claim
6 words
The compound of claim 1, N'-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-N-ethyl-N-methyl-1,2-benzenedisulfonamide.
Claim 26
Dependent Claim
6 words
The compound of claim 1, N-Methyl-N(1-methylethyl)-N'-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide.
Claim 27
Dependent Claim
6 words
The compound of claim 1, N-Methyl-N(1-methylethyl)-N'-[(4-methyl-6-methoxypyrimidin-2-yl)aminocarbonyl]-1,2-benzenedisulfonamide.
Claim 28
Dependent Claim
32 words
A composition for the control of undesirable vegetation consisting essentially of a compound of claim 1 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 29
Dependent Claim
32 words
A composition for the control of undesirable vegetation consisting essentially of a compound of claim 2 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 30
Dependent Claim
32 words
A composition for the control of undesirable vegetation consisting essentially of a compound of claim 3 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 31
Dependent Claim
32 words
A composition for the control of undesirable vegetation consisting essentially of a compound of claim 4 and at least one of (a) a surface-active agent and (b) a solid or liquid diluent.
Claim 32
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 1.
Claim 33
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 2.
Claim 34
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 3.
Claim 35
Dependent Claim
27 words
A method for the control of undesirable vegetation comprising applying to the locus of such undesirable vegetation a herbicidally effective amount of a compound of claim 4.
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) | 1985-01-11 | 1985-07-13 | 1986-01-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-01-11 | 1989-07-13 | 1990-01-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-01-11 | 1993-07-13 | 1994-01-12 | $7700.00 | Window Closed / Lapsed |