US4618363A
Expired / Lapsed
US
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N-phenylsulfonyl-N'-triazinylureas
Assignee: Novartis Corp
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Filing: 1983-01-18
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Granted: 1986-10-21
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Expires: 2003-01-18
Abstract
Abstract N-Phenylsulfonyl-N'-pyrimidinylureas and -N'-triazinylureas of the general formula ##STR1## and the salts of these compounds with amines, alkali metal bases and alkaline earth metal bases or with quaternary ammonium bases, have good selective herbicidal and plant growth regulating properties when applied pre- and postemergence. In the formula R 1 is hydrogen, halogen, nitro, C 1 -C 4 haloalkyl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 2 -C 5 alkenyl or C 1 -C 4 alkoxycarbonyl, R 2 is C 1 -C 3 alkyl or C 1 -C 3 alkoxy, each unsubstituted or substituted by 1 to 3 halogen atoms, R 3 is halogen, hydrogen, --NR 4 R 5 , C 1 -C 3 alkyl, unsubstituted or substituted by 1 to 3 halogen atoms or C 1 -C 4 alkoxy, or is C 1 -C 3 alkoxy, unsubstituted or substituted by methoxy, ethoxy, or 1 to 3 halogen atoms, R 4 is hydrogen or methyl, R 5 is hydrogen, C 1 -C 2 alkyl or methoxy, A is C 1 -C 4 alkylene or C 2 -C 4 alkenylene, each unsubstituted or substituted by C 1 -C 4 alkyl, m is 0 or 1, E is nitrogen or the methine group, X is oxygen, sulfur, --SO-- or --SO 2 --, and Q is hydroxyl, cyano or radicals selected from the group consisting of 5- or 6-membered heterocyclic rings and fused homologues, amines, acetals, esters, ketones, phenyls, sulfonic acid and carboxylic acids, which radicals may be further substituted and have functional structures.
Inventors
- 👤 Karl Gass
- 👤 Werner Fory
- 👤 Willy Meyer
- 👤 Werner Topfl
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 12:13
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/643; C07D301/00; C07D301/02; C07D301/03; C07D301/14; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/22; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/12; C07D309/00; C07D309/02; C07D309/04; C07D309/06; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/22; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16; C07D521/00
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
262 words
A compound selected from the group consisting of a sulfonylurea of the formula: ##STR119## wherein R 1 is hydrogen, halo, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyl of 2 to 5 carbon atoms, or alkoxycarbonyl of 1 to 4 carbon atoms in the alkoxy group; R 2 is alkyl or alkoxy, each of 1 to 3 carbon atoms, unsubstituted or substituted with 1 to 3 halogen atoms; R 3 is halo, hydrogen, unsubstituted alkyl of 1 to 3 carbon atoms, alkyl of 1 to 3 carbon atoms substituted with alkoxy of 1 to 4 carbon atoms or with 1 to 3 halogen atoms, unsubstituted alkoxy of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms substituted with methoxy, ethoxy or 1 to 3 halogen atoms, or --NR 4 R 5 in which R 4 is hydrogen or methyl and R 5 is hydrogen, methyl, ethyl or methoxy; and Q is a heterocyclic ring selected from the group consisting of (i) a saturated ring of 3 to 6 members containing one or two nonadjacent oxygen atoms as the hetero atoms, which ring is unsubstituted or substituted with one to three alkyl groups, each of 1 to 3 carbon atoms, (ii) pyridyl, unsubstituted or substituted with chloro or methyl, or (iii) thienyl; and A is a direct bond, alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; and the alkali metal, alkaline earth metal, and organic amine salts thereof.
Claim 2
Dependent Claim
262 words
A compound selected from the group consisting of a sulfonylurea of the formula: ##STR119## wherein R 1 is hydrogen, halo, nitro, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, alkenyl of 2 to 5 carbon atoms, or alkoxycarbonyl of 1 to 4 carbon atoms in the alkoxy group; R 2 is alkyl or alkoxy, each of 1 to 3 carbon atoms, unsubstituted or substituted with 1 to 3 halogen atoms; R 3 is halo, hydrogen, unsubstituted alkyl of 1 to 3 carbon atoms, alkyl of 1 to 3 carbon atoms substituted with alkoxy of 1 to 4 carbon atoms or with 1 to 3 halogen atoms, unsubstituted alkoxy of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms substituted with methoxy, ethoxy or 1 to 3 halogen atoms, or --NR 4 R 5 in which R 4 is hydrogen or methyl and R 5 is hydrogen, methyl, ethyl or methoxy; and Q is a heterocyclic ring selected from the group consisting of (i) a saturated ring of 3 to 6 members containing one or two nonadjacent oxygen atoms as the hetero atoms, which ring is unsubstituted or substituted with one to three alkyl groups, each of 1 to 3 carbon atoms, (ii) pyridyl, unsubstituted or substituted with chloro or methyl, or (iii) thienyl; and A is a direct bond, alkylene of 1 to 4 carbon atoms or alkenylene of 2 to 4 carbon atoms; and the alkali metal, alkaline earth metal, and organic amine salts thereof.
Claim 3
Dependent Claim
40 words
A compound according to claim 1 wherein R 1 is hydrogen, methyl or chloro; R 2 is methyl or methoxy; R 3 is methyl, methoxy, chloro, difluoromethoxy, ethoxy or dimethylamino; and A is alkylene of 1 to 3 carbon atoms.
Claim 4
Dependent Claim
11 words
A compound according to claim 1, wherein R 1 is hydrogen.
Claim 5
Dependent Claim
21 words
A compound according to claim 1, wherein the substituents R 2 and R 3 together contain at most 4 carbon atoms.
Claim 6
Dependent Claim
20 words
A compound according to claim 2 wherein Q is oxiranyl; 2-methoxyoxiran-2-yl; 3-methyloxiran-2-yl; tetrahydrofuran-2-yl; tetrahydrofuran-3-yl; 1,3-dioxolan-2-yl; 2-methyl-1,3-dioxolan-2-yl; 2-isopropyl-1,3-dioxolan-2-yl; 2,2-dimethyl-1,3-dioxolan-4-yl; or 2-methyl-5-ethyl-1,3-dioxolan-2-yl.
Claim 7
Dependent Claim
15 words
A compound according to claim 2 wherein Q is pyrid-2-yl, pyrid-3-yl, pyrid-4-yl, 3,5-dichloropyrid-2-yl, or thien-2-yl.
Claim 8
Dependent Claim
9 words
The compound according to claim 5 which is N-(2-oxiranylmethoxyphenylsulfonyl)-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 9
Dependent Claim
9 words
The compound according to claim 5 which is N-(2-oxiranylmethoxyphenylsulfonyl)-N'-(4-ethoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 10
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(tetrahydrofuran-3-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 11
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(tetrahydrofuran-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 12
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2-methyl-1,3-dioxolan-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 13
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2,2-dimethyl-1,3-dioxolan-4-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 14
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2-methyl-4-ethyl-1,3-dioxolan-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 15
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2,4,5-trimethyl-1,3-dioxolan-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 16
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2-methyl-4-propyl-1,3-dioxolan-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 17
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2,2,4-trimethyl-1,3-dioxolan-4-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 18
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(3-methoxyoxiran-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 19
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(2-methyloxiran-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 20
Dependent Claim
9 words
The compound according to claim 5 which is N-[2-(pyran-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 21
Dependent Claim
9 words
The compound according to claim 6 which is N-[2-(3,5-dichloropyrid-2-yloxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 22
Dependent Claim
9 words
The compound according to claim 6 which is N-[2-(pyrid-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 23
Dependent Claim
9 words
The compound according to claim 6 which is N-[2-(pyrid-3-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 24
Dependent Claim
9 words
The compound according to claim 6 which is N-[2-(pyrid-4-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 25
Dependent Claim
9 words
The compound according to claim 6 which is N-[2-(thien-2-ylmethoxy)phenylsulfonyl]-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea.
Claim 26
Dependent Claim
20 words
A herbicidal and growth-regulating composition comprising an effective amount of a compound according to claim 1 and a carrier therefor.
Claim 27
Dependent Claim
31 words
The method of suppressing the growth of plants which comprises applying to the plants or to the environs of their growth an effective amount of a compound according to claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-10-20 | 1990-04-21 | 1990-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-10-20 | 1994-04-21 | 1994-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-10-20 | 1998-04-21 | 1998-10-21 | $7700.00 | Window Closed / Lapsed |