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EP0487155A1 Expired / Lapsed EP ⏱️ 0.0 years remaining

Substituted-2,3-dihydro-2-oxo-1,5-benzodiazepines and their use as fungicides

Assignee: Eastman Kodak Co
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Filing: 1991-11-18
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Granted: —
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Expires: 2011-11-18
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Abstract

Abstract A method of controlling fungi comprising contacting the fungi with a fungicidally effective amount of a benzodiazepine of the structure: wherein R¹ is substituted or unsubstituted, straight or branched alkyl having from 3 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R² is substituted or unsubstituted, straight or branched alkyl having from 1 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R³ is hydrogen, halogen, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, alkenyl having from 2 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, and R⁴ is hydrogen or halogen, provided that when R4 is halogen, R³ is the same halogen.

Inventors

  • 👤 John James C/O Eastman Kodak Company Delany
  • 👤 Ewell Russell C/O Eastman Kodak Company Cook

Bibliographic Details

Application Number —
Jurisdiction EP
Data Source google_patents
Last Synchronized 2026-10-29 08:30
CPC Classifications
C; C07; C07D; C07D243/00; C07D243/06; C07D243/10; C07D243/12; A; A01; A01N; A01N43/00; A01N43/48; A01N43/62

Claims Analysis

Total Claims: 21
Claim 1
Independent Claim 125 words
A method of controlling fungi comprising contacting the fungi with a fungicidally effective amount of a benzodiazepine, the benzodiazapine characterized by the structure: wherein R¹ is substituted or unsubstituted alkyl having from 3 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R² is substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R³ is hydrogen, halogen, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, alkenyl having from 2 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, and R⁴ is hydrogen or halogen,provided that when R⁴ is halogen, R³ is the same halogen.
Claim 2
Dependent Claim 13 words
The method of claim 1 wherein R¹ is tertiary butyl, phenyl, or 4-chlorophenyl.
Claim 3
Independent Claim 22 words
The method as claimed in either of claims 1 or 2 wherein R² is methyl, ethyl, n -propyl, n -butyl, or benzyl.
Claim 4
Independent Claim 23 words
The method as claimed in either of claims 2 or 3 wherein R³ is hydrogen, allyl, bromo, chloro, n -butyl, ethyl, or methyl.
Claim 5
Independent Claim 19 words
The method as claimed in either of claims 1 or 4 wherein R¹ is phenyl and R² is methyl.
Claim 6
Dependent Claim 16 words
The method of claim 1 wherein R¹ is phenyl, R² is methyl and R³ is ethyl.
Claim 7
Dependent Claim 17 words
The method of claim 1 wherein R¹ is phenyl, R² is methyl and R³ is n -butyl.
Claim 8
Dependent Claim 16 words
The method of claim 1 wherein R¹ is 4-chlorophenyl, R² is methyl and R³ is methyl.
Claim 9
Dependent Claim 16 words
The method of claim 1 wherein R¹ is phenyl, R² is methyl and R³ is bromo.
Claim 10
Dependent Claim 137 words
A substituted 1,5-benzodiazepine characterized as having the following structure: wherein R¹ is substituted or unsubstituted alkyl having from 3 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R² is substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R³ is hydrogen, bromo, chloro, iodo, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, alkenyl having from 2 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, and R⁴ is hydrogen or halogen, provided that when R⁴ is halogen, R³ is the same halogen, and when R¹ is methyl or phenyl and R² is allyl, ethyl, benzyl, propyl or butyl, then neither R³ nor R⁴ are hydrogen.
Claim 11
Dependent Claim 13 words
The compound of claim 10 wherein R¹ is tertiary butyl, phenyl, or 4-chlorophenyl.
Claim 12
Dependent Claim 20 words
The compound of either of claims 10 or 11 wherein R² is methyl, ethyl, n -propyl, n -butyl, or benzyl.
Claim 13
Dependent Claim 22 words
The compound of either of claims 10, 11 or 12 wherein R³ is hydrogen, allyl, bromo, chloro, n -butyl, ethyl, or methyl.
Claim 14
Dependent Claim 13 words
The compound of claim 10 wherein R¹ is phenyl and R² is methyl.
Claim 15
Dependent Claim 16 words
The compound of claim 10 wherein R¹ is phenyl, R² is methyl and R³ is ethyl.
Claim 16
Dependent Claim 17 words
The compound of claim 10 wherein R¹ is phenyl, R² is methyl and R³ is n -butyl.
Claim 17
Dependent Claim 16 words
The compound of claim 10 wherein R¹ is 4-chlorophenyl, R² is methyl and R³ is methyl.
Claim 18
Dependent Claim 16 words
The compound of claim 10 wherein R¹ is phenyl, R² is methyl and R³ is bromo.
Claim 19
Dependent Claim 121 words
A fungicidal composition comprising a fungicidally effective amount of a benzodiazepine, the benzodiazepine characterized by the following structure: wherein R¹ is substituted or unsubstituted alkyl having from 3 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R² is substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R³ is hydrogen, halogen, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, alkenyl having from 2 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, and R⁴ is hydrogen or halogen, provided that when R⁴ is halogen, R³ is the same halogen.
Claim 20
Dependent Claim 43 words
A fungicidal composition comprising a fungicidally effective amount of at least one benzodiazepine, the benzodiazepine characterized as follows: 1- n -butyl-2,3-dihydro-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 1-benzyl-4- t -butyl-2,3-dihydro-2-oxo-1H-1,5-benzodiazepine; 3-bromo-2,3-dihydro-1-methyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 3-ethyl-2,3-dihydro-1-methyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 3- n -butyl-2,3-dihydro-1-methyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 4- t -butyl-2,3-dihydro-3-ethyl-1-methyl-2-oxo-1H-1,5-benzodiazepine; 2,3-dihydro-1,3-dimethyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 2,3-dihydro-1-ethyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 2,3-dihydro-2-oxo-4-phenyl-1-propyl-1H-1,5-benzodiazepine; 2,3-dihydro-1-ethyl-3-methyl-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 1,3-diethyl-2,3-dihydro-2-oxo-4-phenyl-1H-1,5-benzodiazepine; 2,3-dihydro-3-methyl-2-oxo-4-phenyl-1- n -propyl-1H-1,5-benzodiazepine; 4-(4-chlorophenyl)-2,3-dihydro-1,3-dimethyl-2-oxo-1H-1,5-benzodiazepine; or 4-(4-chlorophenyl)-2,3-dihydro-3-ethyl-1-methyl-2-oxo-1H-1,5-benzo-diazepine.
Claim 21
Dependent Claim 120 words
The use of a substituted 1,5-benzodizaepine as a fungicide, the benzodiazepine characterized as having the following structure: wherein R¹ is substituted or unsubstituted alkyl having from 3 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R² is substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, R³ is hydrogen, halogen, substituted or unsubstituted alkyl having from 1 to 10 carbon atoms, alkenyl having from 2 to 10 carbon atoms, or substituted or unsubstituted aryl having from 6 to 20 carbon atoms, and R⁴ is hydrogen or halogen, provided that when R⁴ is halogen, R³ is the same halogen.

References Cited (Backward Citations)

US2957867A Cited
EP0133322A1 Cited
JPS62174062A Cited

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