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US4154842A Expired / Lapsed US ⏱️ 0.0 years remaining

Fungicidally and bactericidally active 1-azolyl-4-hydroxy-1-phenoxy-butane derivatives

Assignee: Bayer AG
•
Filing: 1977-07-27
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Granted: 1979-05-15
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Expires: 1997-07-27
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Abstract

Abstract 1-Azolyl-4-hydroxy-1-phenoxy-butane derivatives of the formula ##STR1## in which R is hydrogen, --CO--R 1 or --SO 2 --R 2 , R 1 is cycloalkyl, alkylamino, dialkylamino, alkenyl, alkynyl, or optionally substituted alkyl, phenyl, phenoxyalkyl, phenylalkyl or phenylamino, R 2 is alkyl or optionally substituted phenyl, A is --CO--or CH(OH), X is H or --OR, X 1 is alkyl or optionally substituted phenyl, Y is CH or N, Z is halogen, alkyl, halogenoalkyl, cycloalkyl, alkoxy, alkylthio, alkoxycarbonyl, amino, cyano, nitro, or optionally substituted phenyl, phenoxy or phenylalkyl, and N is 0, 1, 2, 3, 4 or 5, Or a salt thereof, which possess fungicidal and bactericidal properties.

Inventors

  • 👤 Wolfgang Kramer
  • 👤 Karl H. Buchel
  • 👤 Paul-Ernst Frohberger
  • 👤 Peter Kraus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 12:32
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N43/00; A01N43/64; A01N43/647; A01N43/653; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 301 words
A 1-azolyl-4-hydroxy-1-phenoxy-butane derivative of the formula ##STR35## in which R is hydrogen, --CO-R 1 or --SO 2 -R 2 , R 1 is alkyl with 1 to 18 carbon atoms optionally substituted by halogen, amino, acetylamino, alkoxy with 1 to 4 carbon atoms, or alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl moiety, alkenyl or alkynyl with 2 to 6 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, phenyl or phenyl-C 1-4 -alkyl optionally substituted on the phenyl ring by halogen, amino, cyano, nitro or alkyl with 1 to 2 carbon atoms, alkylamino or dialkylamino with 1 to 4 carbon atoms in each alkyl moiety, or phenylamino optionally substituted by halogen, nitro or cyano, R 2 is alkyl with 1 to 4 carbon atoms, or phenyl optionally substituted by halogen, amino, cyano, nitro or alkyl with 1 to 2 carbon atoms, A is --CO-- or CH(OH), X is H or --OR, X 1 is alkyl with 1 or 2 carbon atoms, or phenyl optionally substituted by halogen or by alkyl with 1 to 2 carbon atoms, Y is CH or N, Z is halogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy or alkylthio each with 1 or 2 carbon atoms, alkoxycarbonyl with 1 to 5 carbon atoms in the alkoxy moiety, amino, cyano, nitro, phenyl or phenoxy optionally substituted by halogen, amino cyano, nitro or alkyl with 1 to 2 carbon atoms or phenyl-C 1-2 -alkyl optionally substituted in the alkyl moiety with alkylcarbonyl with a total of up to 3 carbon atoms and on the phenyl ring with halogen, nitro or cyano, and n is 0, 1, 2, 3, 4 or 5, or a salt thereof.
Claim 2
Dependent Claim 301 words
A 1-azolyl-4-hydroxy-1-phenoxy-butane derivative of the formula ##STR35## in which R is hydrogen, --CO-R 1 or --SO 2 -R 2 , R 1 is alkyl with 1 to 18 carbon atoms optionally substituted by halogen, amino, acetylamino, alkoxy with 1 to 4 carbon atoms, or alkoxycarbonyl with 1 to 4 carbon atoms in the alkyl moiety, alkenyl or alkynyl with 2 to 6 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, phenyl or phenyl-C 1-4 -alkyl optionally substituted on the phenyl ring by halogen, amino, cyano, nitro or alkyl with 1 to 2 carbon atoms, alkylamino or dialkylamino with 1 to 4 carbon atoms in each alkyl moiety, or phenylamino optionally substituted by halogen, nitro or cyano, R 2 is alkyl with 1 to 4 carbon atoms, or phenyl optionally substituted by halogen, amino, cyano, nitro or alkyl with 1 to 2 carbon atoms, A is --CO-- or CH(OH), X is H or --OR, X 1 is alkyl with 1 or 2 carbon atoms, or phenyl optionally substituted by halogen or by alkyl with 1 to 2 carbon atoms, Y is CH or N, Z is halogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 5 to 7 carbon atoms, halogenoalkyl with 1 or 2 carbon atoms and 1 to 5 halogen atoms, alkoxy or alkylthio each with 1 or 2 carbon atoms, alkoxycarbonyl with 1 to 5 carbon atoms in the alkoxy moiety, amino, cyano, nitro, phenyl or phenoxy optionally substituted by halogen, amino cyano, nitro or alkyl with 1 to 2 carbon atoms or phenyl-C 1-2 -alkyl optionally substituted in the alkyl moiety with alkylcarbonyl with a total of up to 3 carbon atoms and on the phenyl ring with halogen, nitro or cyano, and n is 0, 1, 2, 3, 4 or 5, or a salt thereof.
Claim 3
Dependent Claim 24 words
A compound according to claim 1, in which n is 0, 1, 2 or 3, or a salt thereof with a physiologically tolerated acid.
Claim 4
Dependent Claim 19 words
A compound according to claim 1 wherein such compound is 4-acetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula ##STR36## or a salt thereof.
Claim 5
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 4-acetoxy-1-(2,4-dichloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula ##STR37##
Claim 6
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 4-acetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(imidazol-1-y)-butan-2-one of the formula ##STR38##
Claim 7
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 1-(4-chloro-phenoxy)-4-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula ##STR39##
Claim 8
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 1-(4-chloro-phenoxy)-2-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol of the formula ##STR40##
Claim 9
Dependent Claim 15 words
A compound according to claim 1, wherein such compound is 4-dichloroacetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one of the formula ##STR41##
Claim 10
Dependent Claim 31 words
A fungicidal or bactericidal composition containing as active ingredient a fungicidally or bactericidally effective amount of a compound according to claim 1 or a salt thereof in admixture with a diluent.
Claim 11
Dependent Claim 37 words
A method of combating fungi or bacteria which comprises applying to the fungi or bacteria, or to a habitat thereof, a fungicidally or bactericidally effective amount of a compound according to claim 1 or a salt thereof.
Claim 12
Dependent Claim 22 words
The method according to claim 10 in which said compound is 4-acetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 4-acetoxy-1-(2,4-dichloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, 4-acetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(imidazol)-1-yl)-butan-2-one, (4-chloro-phenoxy)-4-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, (4-chloro-phenoxy)-2-hydroxy-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-ol, or 4-dichloroacetoxy-1-(4-chloro-phenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one, or a salt thereof.

References Cited (Backward Citations)

US3796704A Cited
US3812142A Cited
US4038404A Cited
US3952002A Cited
US4005083A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-05-14 1982-11-13 1983-05-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-05-14 1986-11-13 1987-05-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-05-14 1990-11-13 1991-05-15 $7700.00 Window Closed / Lapsed

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