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US4465680A Expired / Lapsed US ⏱️ 0.0 years remaining

Combating fungi with azolylvinyldithioacetals

Assignee: Bayer AG
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Filing: 1982-11-01
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Granted: 1984-08-14
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Expires: 2002-11-01
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Abstract

Abstract New azolylvinyldithioacetals of the formula ##STR1## in which R 1 is an alkyl, optionally substituted cycloalky, optionally substituted phenyl or alkoxy group, R 2 and R 3 are identical and each is an alkyl, alkenyl, alkinyl, optionally substituted benzyl or trialkylsilyl group, R 2 and R 3 together form an alkylene chain, a dialkylsilyl bridge or a --CH═CH-- group, X is a keto group or a CH--(OH) group, and Y is a nitrogen atom or a CH group, and their acid addition salts and metal salt complexes are prepared as described and find use as fungicides.

Inventors

  • 👤 Udo Kraatz
  • 👤 Gerhard Jager
  • 👤 Karl H. Buchel
  • 👤 Paul-Ernst Frohberger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 20:57
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/12; A; A01; A01N; A01N43/00; A01N43/48; A01N43/50; A01N43/64; A01N43/647; A01N43/653; C07D233/00; C07D233/54; C07D233/56; C07D249/00; C07D249/02; C07D249/08

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 279 words
An azolylvinyldithioacetal of the formula ##STR59## in which R 1 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms and optionally substituted by alkyl having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a phenyl group optionally substituted with at least one substituent selected from halogen, alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkylthio each having 1 or 2 carbon atoms and up to 5 identical or different halogen atoms and phenoxy and phenyl optionally substituted by halogen and/or by alkyl having 1 or 2 carbon atoms; and R 2 and R 3 both are an alkyl group having 1 to 4 carbon atoms; an alkenyl or alkinyl group each having 2 to 6 carbon atoms; a benzyl group optionally substituted on the phenyl ring by at least one of halogen, alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio each having 1 or 2 carbon atoms and up to 5 identical or different halogen atoms, and phenoxy and phenyl optionally substituted by halogen and/or by alkyl having 1 or 2 carbon atoms; or a trialkylsilyl group having 1 to 4 carbon atoms in each alkyl part; or R 2 and R 3 together form an alkylene chain having 1 to 4 carbon atoms, a dialkylsilyl bridge having 1 to 4 carbon atoms in each alkyl part, or a --CH═CH-- group, X is a keto group or a CH--(OH) group, and Y is a nitrogen atom or a CH group, or an addition product thereof with an acid or metal salt.
Claim 2
Dependent Claim 279 words
An azolylvinyldithioacetal of the formula ##STR59## in which R 1 is an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms and optionally substituted by alkyl having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or a phenyl group optionally substituted with at least one substituent selected from halogen, alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkylthio each having 1 or 2 carbon atoms and up to 5 identical or different halogen atoms and phenoxy and phenyl optionally substituted by halogen and/or by alkyl having 1 or 2 carbon atoms; and R 2 and R 3 both are an alkyl group having 1 to 4 carbon atoms; an alkenyl or alkinyl group each having 2 to 6 carbon atoms; a benzyl group optionally substituted on the phenyl ring by at least one of halogen, alkyl, alkoxy and alkylthio each having 1 to 4 carbon atoms, halogenoalkyl, halogenoalkoxy and halogenoalkylthio each having 1 or 2 carbon atoms and up to 5 identical or different halogen atoms, and phenoxy and phenyl optionally substituted by halogen and/or by alkyl having 1 or 2 carbon atoms; or a trialkylsilyl group having 1 to 4 carbon atoms in each alkyl part; or R 2 and R 3 together form an alkylene chain having 1 to 4 carbon atoms, a dialkylsilyl bridge having 1 to 4 carbon atoms in each alkyl part, or a --CH═CH-- group, X is a keto group or a CH--(OH) group, and Y is a nitrogen atom or a CH group, or an addition product thereof with an acid or metal salt.
Claim 3
Dependent Claim 171 words
A compound according to claim 1, in which R 1 is a tert.-butyl or isopropyl group, a cyclopropyl, cyclopentyl or cyclohexyl group which is optionally substituted by methyl, ethyl or propyl, a methoxy, ethoxy or butoxy group, a phenyl group optionally substituted by at least one of fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, and phenoxy or phenyl which is optionally substituted by fluorine, chlorine and/or methyl; and R 2 and R 3 are identical and each is an alkyl group having 1 to 4 carbon atoms, an allyl or propargyl group or a benzyl group optionally substituted on the phenyl ring by at least one of fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, and phenoxy or phenyl which is optionally substituted by fluorine, chlorine and/or methyl, or R 2 and R 3 are identical and form a trimethylsilyl group, or R 2 and R 3 together form a methylene radical, a dimethylene or trimethylene chain, a dimethylsilyl bridge or a --CH═CH-- group.
Claim 4
Dependent Claim 26 words
A compound according to claim 1, wherein such compound is 2,2-dimethyl-5,5-dibenzylthio-4-(1,2,4-triazol-1-yl)-pent-4-en-3-one of the formula ##STR60## or an addition product thereof with an acid or metal salt.
Claim 5
Dependent Claim 26 words
A compound according to claim 1, wherein such compound is 1-phenyl-2-(1,2,4-triazol-1-yl)-2-(1,3-dithiolan-2-ylidene)-ethanol of the formula ##STR61## or an addition product thereof with an acid or metal salt.
Claim 6
Dependent Claim 26 words
A compound according to claim 1, wherein such compound is 2,2-dimethyl-5,5-dimethylthio-4-(imidazol-1-yl)-pent-4-en-3-ol of the formula ##STR62## or an addition product thereof with an acid or metal salt.
Claim 7
Dependent Claim 26 words
A compound according to claim 1, wherein such compound is 2,2-dimethyl-5,5-diallylthio-4-(imidazol-1-yl)-pent-4-en-3-ol of the formula ##STR63## or an addition product thereof with an acid or metal salt.
Claim 8
Dependent Claim 26 words
A compound according to claim 1, wherein such compound is 2,2-dimethyl-5,5-diisopropylthio-4-(imidazol-1-yl)-pent-4-en-3-ol of the formula ##STR64## or an addition product thereof with an acid or metal salt.
Claim 9
Dependent Claim 20 words
A fungicidal composition comprising a fungicidally effective amount of a compound according to claim 1 in admixture with a diluent.
Claim 10
Dependent Claim 26 words
A method of combating fungi comprising applying to the fungi, or to a habitat thereof, a fungicidally effective amount of a compound according to claim 1.
Claim 11
Dependent Claim 27 words
The method according to claim 9, wherein such compound is 2,2-dimethyl-5,5-dibenzylthio-4-(1,2,4-triazol-1-yl)-pent-4-en-3-one, 1-phenyl-2-(1,2,4-triazol-1-yl)-2-(1,3-dithiolan-2-ylidene)-ethanol, 2,2-dimethyl-5,5-dimethylthio-4-(imidazol-1-yl)-pent-4-en-3-ol, 2,2-dimethyl-5,5-diallylthio-4-(imidazol-1-yl)-pent-4-en-3-ol or 2,2-dimethyl-5,5-diisopropylthio-4-(imidazol-1-yl)-pent-4-en-3-ol, or an addition product thereof with an acid or metal salt.

References Cited (Backward Citations)

EP0001928A1 Cited
EP0040368A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1987-08-14 1988-02-13 1988-08-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1991-08-14 1992-02-13 1992-08-14 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1995-08-14 1996-02-13 1996-08-14 $7700.00 Window Closed / Lapsed

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