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US4909828A
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Herbicidally active 2,5-dihydropyrroles
Assignee: Bayer AG
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Filing: 1989-04-13
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Granted: 1990-03-20
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Expires: 2009-04-13
Abstract
Abstract Herbicidal 2,5-dihydropyrroles of the formula ##STR1## wherein A represents hydroxy, halogen, an alkylcarbonyloxy group having alkyl with 1 to 4 carbon atoms optionally substituted by halogen, or an alkylsulfonyloxy group having 1 to 4 carbon atoms optionally substituted by halogen, X represents CH or N, and R 1 , R 2 and R 3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R 1 , R 2 and R 3 do not simultaneously represent hydrogen, or R 2 and R 3 , together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms. Intermediates of the formula ##STR2## are also new.
Inventors
- 👤 Toyohiko Kume
- 👤 Toshio Goto
- 👤 Atsumi Kamochi
- 👤 Akihiko Yanagi
- 👤 Hiroshi Miyauchi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 10:01
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; A; A01; A01N; A01N43/00; A01N43/72; A01N43/74; A01N43/76; A01N43/82
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
118 words
A 2,5-dihydropyrrole of the formula ##STR41## wherein A represents hydroxy, halogen, an alkylcarbonyloxy group having alkyl with 1 to 4 carbon atoms optionally substituted by halogen, or an alkylsulfonyloxy group having 1 to 4 carbon atoms optionally substituted by halogen, X represents CH or N, and R 1 , R 2 and R 3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R 1 , R 2 and R 3 do not simultaneously represent hydrogen, or R 2 and R 3 , together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms.
Claim 2
Dependent Claim
118 words
A 2,5-dihydropyrrole of the formula ##STR41## wherein A represents hydroxy, halogen, an alkylcarbonyloxy group having alkyl with 1 to 4 carbon atoms optionally substituted by halogen, or an alkylsulfonyloxy group having 1 to 4 carbon atoms optionally substituted by halogen, X represents CH or N, and R 1 , R 2 and R 3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R 1 , R 2 and R 3 do not simultaneously represent hydrogen, or R 2 and R 3 , together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms.
Claim 3
Dependent Claim
100 words
A compound according to claim 1, in which A represents hydroxy, chlorine, bromine, an alkoxycarbonyloxy having alkyl with 1 or 2 carbon atoms optionally substituted by fluorine and/or by chlorine, or an alkylsulfonyloxy having 1 or 2 carbon atoms optionally substituted by fluorine and/or by chlorine, X represents CH or N, R 1 represents methyl or ethyl, and R 2 and R 3 each represent methyl, ethyl, or chlorine- or fluorine-substituted alkyl with 1 or 2 carbon atoms, or R 2 and R 3 , together with the carbon atoms to which they are bonded, may form a cyclopropane ring.
Claim 4
Dependent Claim
37 words
A compound according to claim 1, in which A represents hydroxy, chlorine, bromine, acetyloxy, trifluoroacetyloxy or methylsulfonyloxy, X is CH or N, R 1 is methyl, and R 2 and R 3 each are methyl or fluoromethyl.
Claim 5
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is N-(5-tert-butyl-1,3-oxazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole of the formula ##STR42##
Claim 6
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is N-(5-tert-butyl-1,3-oxazol-2-yl)-3,4-dimethyl-2-acetoxy-5-oxo-2,5-dihydropyridine of the formula ##STR43##
Claim 7
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is N-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole of the formula ##STR44##
Claim 8
Dependent Claim
15 words
A compound according to claim 1, wherein such compound is N-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-chloro-3,4-dimethyl-5-oxo-2,5-dihydropyrrole of the formula: ##STR45##
Claim 9
Dependent Claim
18 words
A herbicidal composition comprising a herbicidally effective amount of a compound according to claim 1 and a diluent.
Claim 10
Dependent Claim
36 words
A method of combating unwanted vegetation which comprises applying to such vegetation or to a locus from which it is desired to exclude such vegetation a herbicidally effective amount of a compound according to claim 1.
Claim 11
Dependent Claim
15 words
The method according to claim 9, wherein such compound is N-(5-tert-butyl-1,3-oxazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole, N-(5-tert-butyl-1,3-oxazol-2-yl)-3,4-dimethyl-2-acetoxy-5-oxo-2,5-dihydropyridine, N-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole, or N-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-2-chloro-3,4-dimethyl-5-oxo-2,5-dihydropyrrole.
Claim 12
Dependent Claim
86 words
A compound of the formula ##STR46## in which X represents CH or N, and R 1 , R 2 and R 3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R 1 , R 2 and R 3 do not simultaneously represent hydrogen, or R 2 and R 3 , together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms.
Claim 13
Dependent Claim
86 words
A compound of the formula ##STR46## in which X represents CH or N, and R 1 , R 2 and R 3 each represent hydrogen, or an alkyl group having 1 to 4 carbon atoms optionally substituted by halogen, with the proviso that all of R 1 , R 2 and R 3 do not simultaneously represent hydrogen, or R 2 and R 3 , together with the carbon atom to which they are bonded, may form an alicyclic ring with 3 to 6 carbon atoms.
References Cited (Backward Citations)
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) | 1993-03-19 | 1993-09-18 | 1994-03-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-03-19 | 1997-09-18 | 1998-03-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-03-19 | 2001-09-18 | 2002-03-20 | $7700.00 | Window Closed / Lapsed |