Fungicidal 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles
AssigneeJanssen Pharmaceutica NV
InventorsJan Heeres, Leo J. J. Backx, Joseph A. Mostmans
Life of this patent
Estimating the term…
Abstract
Novel compounds of the class of 1-(2-aryl-2-R-ethyl)-1H-1,2,4-triazoles having fungicidal and plant-growth regulating properties.
Claims43
A chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR18## and the physiologically acceptable acid addition salts thereof, wherein:
- Ar is a member selected from the group consisting of mono-, di- and tri-halophenyl and
- R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, cycloalkyl-lower alkyl, lower alkenyl, aryl-lower alkyl, and aryloxy-lower alkyl said aryl being selected from the group consisting of phenyl, and substituted phenyl, wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro and phenyl provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of cyano, nitro and phenyl.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-3-methylbutyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-4-methylpentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)hexyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[4-(4-chlorophenyl)-2-(4-methylphenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dibromophenyl)hexyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(4-fluorophenyl)-4-(4-methylphenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)heptyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula ##STR19## and the physiologically acceptable acid addition salts thereof, wherein:
- Ar' is selected from the group consisting of dichlorophenyl and dibromophenyl;
- and
- R' is selected from the group consisting of alkyl having from 1 to 8 carbon atoms, cycloalkyl and 2-propenyl.
A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective antifungal amount of a compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR20## and the physiologically acceptable acid addition salts thereof, wherein:
- Ar is a member selected from the group consisting of mono-, di- and tri-halophenyl and
- R is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, cycloalkyl-lower alkyl, lower alkenyl, aryl-lower alkyl, and aryloxy-lower alkyl, said aryl being selected from the group consisting of phenyl, and substituted phenyl, wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group consisting of halo, lower alkyl, lower alkyloxy, cyano, nitro and phenyl provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of cyano, nitro and phenyl.
A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective antifungal amount of 1-[2-(2,4-dichlorophenyl)-3-methylbutyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective antifungal amount of 1-[2-(2,4-dichlorophenyl)hexyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective antifungal amount of 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR21## and the physiologically-acceptable acid addition salts thereof, wherein:
- Ar' is selected from the group consisting of, mono- and di-halophenyl;
- and
- R' is selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, loweralkenyl, arylmethyl, and arylethyl, wherein said aryl is phenyl, halophenyl, methylphenyl, or methoxyphenyl.
A chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR22## and the physiologically-acceptable acid addition salts thereof, wherein:
- Ar' is, chlorophenyl, fluorophenyl, bromophenyl, dichlorophenyl, or dibromophenyl;
- and
- R' is alkyl having from 1 to 8 carbon atoms, cycloalkyl, or 2-propenyl.
A chemical compound selected from the group consisting of:
- 1-[2-(2,4-dichlorophenyl)butyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dibromophenyl)hexyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1H-1,2,4-triazole;
- 1[2-(2,4-dichlorophenyl)-4-methylpentyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)heptyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)decyl]-1H-1,2,4-triazole;
- 1-[2-cyclopentyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole;
- 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole;
- 1-[3-cyclohexyl-2-(2,4-dichlorophenyl)propyl]-1H-1,2,4-triazole;
- 1-[4-cyclohexyl-2-(2,4-dichlorophenyl)butyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)-4-pentenyl]-1H-1,2,4-triazole;
- and
- 1-[2-(2,4-dichlorophenyl)-5-hexenyl]-1H-1,2,4-triazole;
- and
- the pharmaceutically acceptable acid addition salts thereof.
A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective anti-fungal amount of 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole or a physiologically acceptable acid addition salt thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR23## and the physiologically acceptable acid addition salts thereof, wherein:
- Ar is a member selected from the group consisting of mono-, di- and tri-halophenyl;
- and R is alkyl having from 1 to 10 carbon atoms, cycloalkyl, cycloalkyl-lower alkyl, lower alkenyl, aryl-lower alkyl or, aryloxy-lower alkyl, said aryl being selected from the group consisting of phenyl and substituted phenyl, wherein said substituted phenyl is phenyl having from 1 to 3 substituents independently selected from the group conssisting of halo, lower alkyl, lower alkyloxy, cyano, nitro and phenyl provided that when more than 1 substituents are present only 1 thereof may be selected from the group consisting of cyano, nitro and phenyl.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-3-methylbutyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-4-methylpentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)hexyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[4-(4-chlorophenyl)-2-(4-methylphenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[4-(4-chlorophenyl)-2-(4-fluorophenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dibromophenyl)hexyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(4-fluorophenyl)-4-(4-methylphenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)heptyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR24## and the physiologically acceptable acid addition salts thereof, wherein:
- Ar' is selected from the group consisting of dichlorophenyl and dibromophenyl;
- and
- R' is selected from the group consisting of alkyl having from 1 to 8 carbon atoms, cycloalkyl and 2-propenyl.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of 1H-1,2,4-triazole derivative having the formula:
- ##STR25## and the physiologically-acceptable acid addition salts thereof, wherein:
- Ar' is selected from the group consisting of, mono- and di-halophenyl;
- and
- R' is selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, loweralkenyl, arylmethyl, and arylethyl, wherein said aryl is phenyl, halophenyl, methylphenyl, or methoxyphenyl.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula:
- ##STR26## and the physiologically-acceptable acid addition salts thereof, wherein:
- Ar' is, chlorophenyl, fluorophenyl, bromophenyl, dichlorophenyl, or dibromophenyl;
- and
- R' is alkyl having from 1 to 8 carbon atoms, cycloalkyl, or 2-propenyl.
A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound selected from the group consisting of:
- 1-[2-(2,4-dichlorophenyl)butyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dibromophenyl)hexyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)-3-methylpentyl]-1H1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)-4-methylpentyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)heptyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)decyl]-1H-1,2,4-triazole;
- 1-[2-cyclopentyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole;
- 1-[2-cyclohexyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole;
- 1-[3-cyclohexyl-2-(2,4-dichlorophenyl)propyl]-1H-1,2,4-triazole;
- 1-[4-cyclohexyl-2-(2,4-dichlorophenyl)butyl]-1H-1,2,4-triazole;
- 1-[2-(2,4-dichlorophenyl)-4-pentenyl]-1H-1,2,4-triazole;
- and
- 1-[2-(2,4-dichlorophenyl)-5-hexenyl]-1H-1,2,4-triazole;
- and
- the pharmaceutically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-cyclopentyl-2-(2,4-dichlorophenyl)ethyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-4-pentenyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)-5-hexenyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[2-(2,4-dichlorophenyl)propyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
A chemical compound selected from the group consisting of 1-[4-(4-bromophenyl)-2-(2-chlorophenyl)butyl]-1H-1,2,4-triazole and the physiologically acceptable acid addition salts thereof.
Dependencies are inferred from the claim text.