US4563448A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Bactericidal agents
Assignee: Bayer AG
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Filing: 1984-03-02
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Granted: 1986-01-07
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Expires: 2004-03-02
Abstract
Abstract A method of combating plant-pathogenic bacteria, comprising applying to the bacteria or to a bacteria habitat a bactericidally effective amount of a cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivative of the formula ##STR1## in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C═CH-- radical, R 1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, optionally substituted carbamoyl, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, optionally substituted carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro, or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof. The heavy metal salts are new.
Inventors
- 👤 Uwe Petersen
- 👤 Klaus Grohe
- 👤 Karl-Heinz Kuck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 09:33
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/48; C07D215/54; C07D215/56; C07D405/00; C07D405/02; C07D405/12; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6558; C07F9/65583
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
170 words
A bactericidal composition comprising a diluent and a bactericidally effective amount of a heavy metal salt of a quinolinecarboxylic acid derivative of the formula ##STR52## in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C═CH-- radical, R 1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part and R 2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro.
Claim 2
Dependent Claim
170 words
A bactericidal composition comprising a diluent and a bactericidally effective amount of a heavy metal salt of a quinolinecarboxylic acid derivative of the formula ##STR52## in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C═CH-- radical, R 1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part and R 2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro.
Claim 3
Dependent Claim
130 words
A composition according to claim 1, wherein A represents straight-chain or branched alkylene with 1 to 5 carbon atoms or the >C═CH-- group, R 1 represents alkoxycarbonyl with 1 to 5 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano, methylsulphonyl or ethylsulphonyl, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 5 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 or 2 carbon atoms or phenyl, or R 1 and R 2 together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 represent hydrogen, methyl or ethyl and X represents hydrogen, fluorine, chlorine or nitro.
Claim 4
Dependent Claim
113 words
A composition according to claim 1, in which A represents straight-chain alkylene with 1 to 5 carbon atoms or the >C═CH-- group, R 1 represents alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl, cyano or methylsulphonyl and R 2 represents hydrogen, alkoxycarbonyl with 1 to 3 carbon atoms in the alkyl part, cyano, chlorine, acetyl or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydro-3-furyl ring, R 3 represents hydrogen, methyl or ethyl, R 4 represents hydrogen, R 5 represents hydrogen or methyl, R 6 represents hydrogen and X represents hydrogen, fluorine, chlorine or nitro.
Claim 5
Dependent Claim
16 words
A composition according to claim 1, in which the heavy metal is zinc, manganese or copper.
Claim 6
Dependent Claim
28 words
A composition according to claim 1, wherein the quinoline carboxylic acid derivative is a heavy metal salt of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[2-oxo-1-(methoxycarbonyl)-1-propyl]-1-piperazinyl}-3-quinolinecarboxylic acid, 7-[4-(2-benzyloxycarbonylethyl)-1-piperazinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid, 1-cyclopropyl-6-fluoro-1-,4-dihydro-4-oxo-7-[4-(2-methoxycarbonylethyl)-1-piperazinyl]-3-quinolinecarboxylic acid, or 1-cyclopropyl-7-[4-(2,2-diethoxycarbonyl-vinylene)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid.
Claim 7
Independent Claim
197 words
A method of combating plant-pathogenic bacteria, comprising applying to a plant, seed or site where a plant is to be grown a bactericidally effective amount of a 1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivative of the formula ##STR53## in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C═CH-- radical, R 1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro, or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof.
Claim 8
Independent Claim
197 words
A method of combating plant-pathogenic bacteria, comprising applying to a plant, seed or site where a plant is to be grown a bactericidally effective amount of a 1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid derivative of the formula ##STR53## in which A represents straight-chain or branched alkylene with 1 to 6 carbon atoms or a >C═CH-- radical, R 1 represents alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano or dialkoxyphosphonyl or alkylsulphonyl with 1 to 4 carbon atoms in the alkyl part, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 6 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 to 3 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 can be identical or different and represent hydrogen, methyl, ethyl or n- or i-propyl and X represents hydrogen, halogen or nitro, or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof.
Claim 9
Dependent Claim
131 words
A method according to claim 6, in which A represents straight-chain or branched alkylene with 1 to 5 carbon atoms or the >C═CH-- group, R 1 represents alkoxycarbonyl with 1 to 5 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl which is optionally substituted by 1 or 2 methyl or ethyl radicals, cyano, methylsulphonyl or ethylsulphonyl, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 5 carbon atoms in the alkyl part, benzyloxycarbonyl, carbamoyl, cyano, chlorine, acetyl, alkyl with 1 or 2 carbon atoms or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 , R 4 , R 5 and R 6 represent hydrogen, methyl or ethyl and X represents hydrogen, fluorine or nitro.
Claim 10
Dependent Claim
113 words
A method according to claim 6, in which A represents straight-chain alkylene with 1 to 5 carbon atoms or the >C═CH-- group, R 1 represents alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl part, benzyloxycarbonyl, carboxyl, carbamoyl, cyano or methylsulphonyl, and R 2 represents hydrogen, alkoxycarbonyl with 1 to 3 carbon atoms in the alkyl part, cyano, chlorine, acetyl or phenyl, or R 1 and R 2 , together with the carbon atom which they substitute, can also form a 2-oxo-tetrahydrofuryl ring, R 3 represents hydrogen, methyl or ethyl, R 4 represents hydrogen, R 5 represents hydrogen or methyl, R 6 represents hydrogen and X represents hydrogen, fluorine, chlorine or nitro.
Claim 11
Dependent Claim
35 words
A method according to claim 6, wherein the quinolinecarboxylic acid derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-{4-[2-oxo-1-(methoxycarbonyl)-1-propyl]-1-piperazinyl}-3-quinolinecarboxylic acid of the formula ##STR54## or an acid addition, alkali metal or alkaline earth metal salt, heavy metal salt or hydrate thereof.
Claim 12
Dependent Claim
36 words
A method according to claim 6, wherein the quinolinecarboxylic acid derivative is 7-[4-(2-benzyloxycarbonylethyl)-1-piperazinyl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid of the formula ##STR55## or an acid addition, alkali metal or alkaline earth metal salt, heavy metal salt or hydrate thereof.
Claim 13
Dependent Claim
36 words
A method according to claim 6, wherein the quinolinecarboxylic acid derivative is 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[4-(2-methoxycarbonylethyl)-1-piperazinyl]-3-quinolinecarboxylic acid of the formula ##STR56## or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof.
Claim 14
Dependent Claim
36 words
A method according to claim 6, wherein the quinolinecarboxylic acid derivative is 1-cyclopropyl-7-[4-(2,2-diethoxycarbonyl-vinylene)-1-piperazinyl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid of the formula ##STR57## or an acid addition salt, alkali metal salt, alkaline earth metal salt, heavy metal salt or hydrate thereof.
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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) | 1989-01-06 | 1989-07-08 | 1990-01-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-01-06 | 1993-07-08 | 1994-01-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-01-06 | 1997-07-08 | 1998-01-07 | $7700.00 | Window Closed / Lapsed |