Claims
- 1. A compound of the formula ##STR7## wherein Z is phenyl or phenyl substituted with up to two halogen substituents;
- R.sup.1 is hydrogen;
- R.sup.2 is (C.sub.1 -C.sub.12)alkyl, phenyl, benzyl, phenethyl, or phenyl, benzyl or phenethyl substituted with up to two halogen substituents; and
- Q is 1-(1,2,4-triazolyl); and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes.
- 2. The compound of claim 1 wherein Z is phenyl or phenyl substituted with two chlorine substituents; and R.sup.2 is (C.sub.3 -C.sub.5)-alkyl, phenyl, benzyl, phenethyl or phenyl, benzyl or phenethyl substituted with two chlorine substituents.
- 3. The compound of claim 2 wherein R.sup.2 is (C.sub.3 -C.sub.5)alkyl.
- 4. The compound of claim 3 wherein Z is phenyl or 2,4-dichlorophenyl; and R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl, phenethyl, 2,4-dichlorophenyl, 2,4-dichlorobenzyl or 2,4-dichlorophenethyl.
- 5. A compound of the formula ##STR8## wherein Z is 2,4-dichlorophenyl;
- R.sup.1 is hydrogen;
- R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl or phenethyl; and
- Q is 1-(1,2,4-triazolyl);
- and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes.
- 6. The compound of claim 5 wherein R.sup.2 is (C.sub.3 -C.sub.5)alkyl or benzyl.
- 7. The compound of claim 5 wherein Z is 2,4-dichlorophenyl; and R.sup.2 is n-C.sub.4 H.sub.9.
- 8. A compound of the formula ##STR9## wherein Z is phenyl or phenyl substituted with up to two chlorine substituents;
- R.sup.1 is hydrogen;
- R.sup.2 is (C.sub.1 -C.sub.12)alkyl; and
- Q is 1-(1,2,4-triazolyl);
- and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes.
- 9. The compound of claim 8 wherein R.sup.2 is dodecyl.
- 10. The compound of claim 2 wherein Z is a dichlorophenyl and R.sup.2 is benzyl.
- 11. A compound of the formula ##STR10## wherein Z is unsubstituted phenyl or phenyl substituted with up to two substituents selected from the group consisting of halogen;
- R.sup.1 is hydrogen;
- R.sup.2 is selected from the group consisting of (C.sub.1 -C.sub.12)alkyl, (C.sub.5 -C.sub.6)cycloalkenyl, (C.sub.2 -C.sub.4)alkynyl, unsubstituted phenyl, benzyl or phenethyl or phenyl, benzyl or phenethyl substituted with up to two substituents selected from the group consisting of halogen, nitro, trifluoromethyl and cyano; or
- R.sup.1 and R.sup.2 are taken together to form (C.sub.4 -C.sub.7)cycloalkyl; and
- Q is 1-(1,2,4-triazolyl) optionally substituted with up to two substituents selected from the group consisting of halogen, (C.sub.1 -C.sub.4)alkyl, nitro and cyano;
- and the agronomically acceptable enantiomorphs, acid addition salts and metal salt complexes.
- 12. The compound of claim 11 wherein Z is phenyl or phenyl substituted with up to two halogen substituents; R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl, phenethyl or monochloro substituted phenyl, benzyl or phenethyl; and Q is 1-(1,2,4-triazole).
- 13. The compound of claim 12 wherein Z is phenyl or phenyl substituted with up to two chlorines, R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl or monochloro substituted phenyl or benzyl.
- 14. A fungicidal composition for controlling phytopathogenic fungi which comprises an agronomically acceptable carrier and, as the active ingredient, a fungicidally-effective amount of a compound of claim 11.
- 15. A fungicidal composition for controlling phytopathogenic fungi which comprises an agronomically acceptable carrier and, as the active ingredient, a fungicidally-effective amount of a compound of claim 7.
- 16. A method for controlling phytopathogenic fungi which comprises applying to a plant, to plant seed or to the plant habitat, a fungicidally effective amount of a compound according to claim 11.
- 17. A method for controlling phytopathogenic fungi which comprises applying to a plant, to plant seed or to the plant habitat, a fungicidally effective amount of a compound of claim 7.
- 18. The compound of claim 6 wherein R.sup.2 is (C.sub.3 -C.sub.5)alkyl.
- 19. The compound of claim 1 wherein Z is phenyl substituted with two halogen substituents; and R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl or phenethyl.
- 20. The compound of claim 2 wherein Z is phenyl substituted with two chlorine substituents; and R.sup.2 is (C.sub.3 -C.sub.5)alkyl, phenyl, benzyl or phenethyl.
- 21. A chemical compound selected from the group consisting of 1H-1,2,4-triazole derivative having the formula: ##STR11## and the physiologically acceptable acid addition salts thereof, wherein: Z is a member selected from the group consisting of mono-, di- and tri-halophenyl and
- R.sup.2 is a member selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, lower alkenyl, and aryl-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.
- 22. A chemical compound according to claim 21 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.
- 23. A chemical compound according to claim 21 selected from the group consisting of 1H-1,2,4-triazole derivative having the formula: ##STR12## and the physiologically acceptable acid addition salts thereof, wherein: Z' is selected from the group consisting of dichlorophenyl and dibromophenyl; and
- R.sup.2 is selected from the group consisting of alkyl having from 1 to 8 carbon atoms, cycloalkyl and -(C.sub.2 to C.sub.4)alkenyl-.
- 24. A composition for combatting fungi, comprising an inert carrier material and as an active ingredient an effective antifungal amount of a compound according to claim 21.
- 25. A chemical compound according to claim 21 selected from the group consisting of a 1H-1,2,4-triazole derivative having the formula: ##STR13## and the physiologically acceptable acid addition salts thereof, wherein: Z is selected from the group consisting of mono- and di-halophenyl; and
- R.sup.2 is selected from the group consisting of alkyl having from 1 to 10 carbon atoms, cycloalkyl, lower alkenyl and aralkyl, wherein the alkyl portion of said aralkyl group is C.sub.1 -C.sub.4 alkyl and the aryl portion of said aralkyl group is phenyl and may be optionally substituted with up to three substituents selected from the group consisting of halo, methyl, methoxy, nitro and cyano.
- 26. A method of combatting fungal growth on plants which comprises treating said plants with an effective fungal combatting amount of a chemical compound according to claim 21.
- 27. A method of combatting fungal growth on plants according to claim 26 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.
- 28. A method of combatting fungal growth on plants according to claim 26 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: ##STR14## and the physiologically acceptable acid addition salts thereof, wherein: Z' is selected from the group consisting of dichlorophenyl and dibromophenyl; and
- R.sup.2 is selected from the group consisting of alkyl having from 1 to 8 carbon atoms, cycloalkyl and -(C.sub.2 to C.sub.4)alkenyl-.
- 29. A method of combating fungal growth on plants according to claim 26 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: ##STR15## 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, lower alkenyl and aralkyl, wherein the alkyl portion of said aralkyl group is C.sub.1 -C.sub.4 alkyl and the aryl portion of said aralkyl group is phenyl and may be optionally substituted with up to three substituents selected from the group consisting of halo, methyl, methoxy, nitro and cyano.
CROSS REFERENCE TO RELATED APPLICATIONS
This is a continuation of U.S. application Ser. No. 252,633 filed Apr. 9, 1981, now abandoned, which is a continuation of U.S. application Ser. No. 798,716 filed May 19, 1977, now abandoned.
US Referenced Citations (7)
Non-Patent Literature Citations (1)
Entry |
Ainsworth et al., J. Med. Pharm. Chem., vol. 5, pp. 383-389 (1962) RS1J5. |
Continuations (2)
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Number |
Date |
Country |
Parent |
252633 |
Apr 1981 |
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Parent |
798716 |
May 1977 |
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