US4614535A
Expired / Lapsed
US
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Herbicidal imidazolinones
Assignee: Hoechst AG
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Filing: 1984-11-08
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Granted: 1986-09-30
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Expires: 2004-11-08
Abstract
Abstract Imidazolinones of the formula ##STR1## in which A denotes N or C--R 4 ; B denotes halogenoalkyl, alkoxymethyl, cyanomethyl or thiocyanatomethyl; X denotes alkyl; and Y denotes alkyl, cycloalkyl, alkenyl, phenyl or benzyl; or X and Y, together with C, denote a spiro-cycloalkyl group; Z denotes H, (substituted) alkyl, alkenyl, propargyl or an alkyl, carboxylic acid ester or sulfonic acid ester group; and R 1 -R 4 denote H, halogen, alkyl, alkoxy, alkoxycarbonyl, halogenoalkyl, NO 2 , CN, (substituted) phenoxy or (substituted) phenyl, or in each case two adjacent radicals together denote the radical --CH═CH--CH--CH--, are active herbicides and growth regulators.
Inventors
- 👤 Roland Schmierer
- 👤 Reinhard Handte
- 👤 Rainer Liebl
- 👤 Hilmar Mildenberger
- 👤 Klaus Bauer
- 👤 Hermann Bieringer
- 👤 Helmut Burstell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 17:42
CPC Classifications
C; C07; C07D; C07D235/00; C07D235/02; C07D233/00; C07D233/54; C07D233/66; C07D233/70; C07D401/00; C07D401/02; C07D401/04
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
394 words
An imidazolinone of the formula I ##STR7## in which A denotes N or C-R 4 ; B denotes halogeno (C 1 -C 2 ) alkyl, wherein halogen means fluorine, chlorine or bromine, or (C 1 -C 4 ) alkoxymethyl, cyanomethyl or thiocyanatomethyl; X denotes (C 1 -C 4 ) alkyl; and Y denotes (C 1 -C 6 )alkyl, cyclo (C 3 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkinyl, phenyl or benzyl; or X and Y, together with the carbon atom to which they are bonded, denoted a spirocyclo (C 3 -C 6 ) alkyl group which is optionally substituted by --CH 3 ; Z denotes hydrogen, (C 1 -C 4 ) alkyl, which can be substituted by (C 1 -C 4 ) alkoxycarbonyl, or (C 3 -C 4 ) alkenyl, propargyl, --CO--R 5 or --SO 2 --R 6 ; R 1 , R 2 , R 3 and R 4 independently of one another denote hydrogen, halogen, (C 1 -C 4 ) alkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkoxycarbonyl, halogeno (C 1 -C 2 ) alkyl, nitro, cyano, phenoxy or phenyl, which can optionally be substituted by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or halogen, it also being possible for in each case two radicals R 1 , R 2 , R 3 and R 4 in the o-position relative to one another together to form the grouping --CH═CH--CH═CH--; R 5 denotes (C 1 -C 12 ) alkyl, which is optionally substituted by up to two (C 1 -C 4 ) alkoxy groups or by up to three halogen; phenyl, which can be substituted by up to two halogen or a methyl, nitro or methoxy group; or cyclo (C 3 -C 7 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 )alkoxycarbonyl, benzyloxy, phenoxy or --NR 7 R 8 ; R 6 denotes (C 1 -C 4 ) alkyl, CF 3 , CCl 3 , phenyl, chlorophenyl or methylphenyl; R 7 denotes hydrogen or (C 1 -C 4 ) alkyl; and R 8 denotes (C 1 -C 4 ) alkyl, phenyl, chlorophenyl, methylphenyl, amino or mono- or di(C 1 -C 4 ) alkylamino, or an optical isomer thereof (if X≠Y), an acid addition salt or N-oxide (if A represents N).
Claim 2
Dependent Claim
394 words
An imidazolinone of the formula I ##STR7## in which A denotes N or C-R 4 ; B denotes halogeno (C 1 -C 2 ) alkyl, wherein halogen means fluorine, chlorine or bromine, or (C 1 -C 4 ) alkoxymethyl, cyanomethyl or thiocyanatomethyl; X denotes (C 1 -C 4 ) alkyl; and Y denotes (C 1 -C 6 )alkyl, cyclo (C 3 -C 6 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkinyl, phenyl or benzyl; or X and Y, together with the carbon atom to which they are bonded, denoted a spirocyclo (C 3 -C 6 ) alkyl group which is optionally substituted by --CH 3 ; Z denotes hydrogen, (C 1 -C 4 ) alkyl, which can be substituted by (C 1 -C 4 ) alkoxycarbonyl, or (C 3 -C 4 ) alkenyl, propargyl, --CO--R 5 or --SO 2 --R 6 ; R 1 , R 2 , R 3 and R 4 independently of one another denote hydrogen, halogen, (C 1 -C 4 ) alkyl, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkoxycarbonyl, halogeno (C 1 -C 2 ) alkyl, nitro, cyano, phenoxy or phenyl, which can optionally be substituted by (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or halogen, it also being possible for in each case two radicals R 1 , R 2 , R 3 and R 4 in the o-position relative to one another together to form the grouping --CH═CH--CH═CH--; R 5 denotes (C 1 -C 12 ) alkyl, which is optionally substituted by up to two (C 1 -C 4 ) alkoxy groups or by up to three halogen; phenyl, which can be substituted by up to two halogen or a methyl, nitro or methoxy group; or cyclo (C 3 -C 7 ) alkyl, (C 1 -C 4 ) alkoxy, (C 1 -C 4 )alkoxycarbonyl, benzyloxy, phenoxy or --NR 7 R 8 ; R 6 denotes (C 1 -C 4 ) alkyl, CF 3 , CCl 3 , phenyl, chlorophenyl or methylphenyl; R 7 denotes hydrogen or (C 1 -C 4 ) alkyl; and R 8 denotes (C 1 -C 4 ) alkyl, phenyl, chlorophenyl, methylphenyl, amino or mono- or di(C 1 -C 4 ) alkylamino, or an optical isomer thereof (if X≠Y), an acid addition salt or N-oxide (if A represents N).
Claim 3
Dependent Claim
13 words
The compound as claimed in claim 1, wherein halogen means fluorine or chlorine.
Claim 4
Dependent Claim
17 words
The compound as claimed in claim 1, wherein R 5 denotes (C 1 -C 12 ) alkyl.
Claim 5
Dependent Claim
25 words
A herbicidal and plant growth-regulating agent containing an effective amount of a compound of the formula (I) as claimed in claim 1 and a carrier.
Claim 6
Dependent Claim
42 words
A method of combating undesired plants and for regulating plant growth, which comprises applying an effective amount of a compound of the formula (I) as claimed in claim 1 to an area to be treated or to the plants to be treated.
References Cited (Backward Citations)
US4125727A
Cited
US4188487A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-09-29 | 1990-03-31 | 1990-09-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-09-29 | 1994-03-31 | 1994-09-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-09-29 | 1998-03-31 | 1998-09-30 | $7700.00 | Window Closed / Lapsed |