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US4560694A
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Fungicidal alkylene(cycloalkylene)-bis-heterocyclyl-biguanides
Assignee: Bayer AG
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Filing: 1983-05-20
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Granted: 1985-12-24
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Expires: 2003-05-20
Abstract
Abstract Alkylene(cycloalkylene)-bis-heterocyclyl-biguanides of the formula ##STR1## in which A and B each independently is a nitrogen-containing heterocyclic radical which is linked via a nitrogen atom, R is an optionally alkyl-substituted cycloalkylene radical, or an alkylene radical which is optionally substituted by cycloalkylene, bicycloalkylene, tricycloalkylene, oxygen, sulphur or the NR 3 group, R 1 and R 2 each independently is hydrogen, alkyl or optionally substituted aralkyl, or R 1 and R 2 together with the two nitrogen atoms on which they are located and R form a heterocyclic ring, and R 3 is hydrogen, alkyl or optionally substituted aralkyl, or salts thereof which possess fungicidal activity.
Inventors
- 👤 Siegfried Oeckl
- 👤 Hans-Georg Schmitt
- 👤 Wilhelm Brandes
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:30
CPC Classifications
C; C07; C07D; C07D233/00; C07D233/54; A; A01; A01N; A01N47/00; A01N47/40; A01N47/42; A01N47/44; C07D231/00; C07D231/02; C07D231/10; C07D231/12; C07D233/56; C07D233/66; C07D233/91; C07D233/92; C07D235/00; C07D235/02; C07D235/04; C07D235/06; C07D249/00; C07D249/02; C07D249/08; C07D249/16; C07D249/18
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
248 words
An alkylene(cycloalkylene)-bis-heterocyclyl biguanide of the formula ##STR26## in which A and B each independently is a triazole, tetrazole, pyrazole, imidazole, benzotriazole or benzimidazole radical which is linked via a nitrogen atom and which is optionally substituted by at least one member selected from the group consisting of halogen, nitro, alkyl with 1 to 18 carbon atoms, alkylthio with 1 to 10 carbon atoms, and aryl with 6 to 10 carbon atoms which is optionally mono-, di-, tri-, tetra-, penta- or hexa-substituted by at least one substituent selected from the group consisting of halogen, alkyl with 1 to 4 carbon atoms and halogenoalkyl with 1 to 3 carbon atoms and up to 5 halogen atoms, R is an optionally C 1-6 -alkyl-substituted cycloalkylene radical with 5 to 9 carbon atoms, or a C 1-20 -alkylene radical which is optionally substituted by C 5-7 -cycloalkylene, C 6-12 -bicycloalkylene, C 9-18 -tricycloalkylene, oxygen, sulphur or the NR 3 group, R 1 and R 2 each independently is hydrogen, C 1-20 -alkyl or aralkyl which has 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part and is optionally substituted by C 1-6 -alkyl or halogen, and R 3 is hydrogen, C 1-6 -alkyl or optionally substituted aralkyl which has 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part and is optionally substituted by C 1-6 -alkyl or halogen, or a salt thereof.
Claim 2
Dependent Claim
248 words
An alkylene(cycloalkylene)-bis-heterocyclyl biguanide of the formula ##STR26## in which A and B each independently is a triazole, tetrazole, pyrazole, imidazole, benzotriazole or benzimidazole radical which is linked via a nitrogen atom and which is optionally substituted by at least one member selected from the group consisting of halogen, nitro, alkyl with 1 to 18 carbon atoms, alkylthio with 1 to 10 carbon atoms, and aryl with 6 to 10 carbon atoms which is optionally mono-, di-, tri-, tetra-, penta- or hexa-substituted by at least one substituent selected from the group consisting of halogen, alkyl with 1 to 4 carbon atoms and halogenoalkyl with 1 to 3 carbon atoms and up to 5 halogen atoms, R is an optionally C 1-6 -alkyl-substituted cycloalkylene radical with 5 to 9 carbon atoms, or a C 1-20 -alkylene radical which is optionally substituted by C 5-7 -cycloalkylene, C 6-12 -bicycloalkylene, C 9-18 -tricycloalkylene, oxygen, sulphur or the NR 3 group, R 1 and R 2 each independently is hydrogen, C 1-20 -alkyl or aralkyl which has 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part and is optionally substituted by C 1-6 -alkyl or halogen, and R 3 is hydrogen, C 1-6 -alkyl or optionally substituted aralkyl which has 6 to 10 carbon atoms in the aryl part and 1 to 6 carbon atoms in the alkyl part and is optionally substituted by C 1-6 -alkyl or halogen, or a salt thereof.
Claim 3
Dependent Claim
244 words
An alkylene(cycloalkylene)-bis-heterocyclyl-biguanide or salt according to claim 1, in which A and B are identical, and each is a triazole, tetrazole, pyrazole or imidazole radical which is optionally substituted by halogen, nitro, alkyl with 1 to 9 carbon atoms or alkylthio with 1 to 4 carbon atoms or phenyl, or a benzotriazole or benzimidazole radical, the fused-on benzene ring being optionally substituted by halogen, nitro, alkyl with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms or phenyl optionally substituted by methyl, ethyl, propyl, fluorine, chlorine, trifluoromethyl or difluorochloromethyl, R is cycloalkylene with 5 to 7 carbon atoms in the ring, the rings optionally being substituted by alkyl with 1 to 4 carbon atoms, alkylene with 1 to 12 carbon atoms, or alkylene which has 1 to 4 carbon atoms per alkylene radical and is substituted by cycloalkylene, bicycloalkylene or tricycloalkylene radicals with 5 to 12 carbon atoms in the ring system or alkylene radicals with 1 to 6 carbon atoms which are interrupted by oxygen atoms, sulphur atoms or the NR 3 group, R 1 and R 2 each independently is hydrogen, alkyl with 1 to 10 carbon atoms or aralkyl, the aryl radical optionally being substituted by alkyl with 1 to 4 carbon atoms or halogen, and R 3 is hydrogen, alkyl with 1 to 4 carbon atoms or aralkyl, the aryl radical optionally being substituted by alkyl with 1 to 4 carbon atoms, fluorine, chlorine, bromine or iodine.
Claim 4
Dependent Claim
19 words
A compound according to claim 1, wherein such compound is hexamethylene-bis-triazol-1-yl-biguanide of the formula ##STR27## or a salt thereof.
Claim 5
Dependent Claim
19 words
A compound according to claim 1, wherein such compound is hexamethylene-bis-imidazol-1-yl-biguanide of the formula ##STR28## or a salt thereof.
Claim 6
Dependent Claim
19 words
A compound according to claim 1, wherein such compound is hexamethylene-bis-2-methyl-4-nitroimidazol-1-yl-biguanide of the formula ##STR29## or a salt thereof.
Claim 7
Dependent Claim
22 words
A fungicidal composition comprising a fungicidally effective amount of a compound or salt according to claim 1 in admixture with a diluent.
Claim 8
Dependent Claim
29 words
A method of combating fungi which comprises applying to said fungi or to a fungus habitat a fungicidally effective amount of a compound or salt according to claim 1.
Claim 9
Dependent Claim
18 words
The method according to claim 7, wherein such compound is hexamethylene-bis-triazol-1-yl-biguanide, hexamethylene-bis-imidazol-1-yl-biguanide or hexamethylene-bis-2-methyl-4-nitroimidazol-1-yl-biguanide, or a salt thereof.
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) | 1988-12-23 | 1989-06-24 | 1989-12-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-23 | 1993-06-24 | 1993-12-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-23 | 1997-06-24 | 1997-12-24 | $7700.00 | Window Closed / Lapsed |