Claims
- 1. A compound of the formula I in whichR1 and R2 each independently represent a hydrogen atom or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, haloalkyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, or R1 and R2 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring; R3, R4 and R5 each independently represent a fluorine or a chlorine atom, provided that at least one of R3, R4 and R5 is a chlorine atom; and X represents a halogen atom.
- 2. A compound according to claim 1 in whichR1 represents a straight chained or branched C1-C6-alkyl, C1-C6-haloalkyl, or C2-C6-alkenyl, or a C3-C6 cycloalkyl, or C5-C9 bicycloalkyl, and R2 represents hydrogen or C1-C6-alkyl, or R1 and R2 together with the interjacent nitrogen atom represent a heterocyclic ring having 5 or 6 carbon atoms, optionally substituted by one or two C1-C6-alkyl groups.
- 3. A compound according to claim 1 in whichR2 represents a hydrogen atom.
- 4. A compound according to claim 1 in whichone of R3, R4 and R5 is a fluorine atom and the other two are chlorine atoms.
- 5. A compound according to claim 4 in which R3 and R5 present chlorine atoms.
- 6. A compound according to claim 1 in which R3 represents a chlorine atom, and R4 and R5 represent fluorine atoms.
- 7. A compound according to claim 1 selected from the group consisting of:[5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-cyclopentyl-amine; [5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-7-(4-methyl-piperidin-1-yl)-[1,2,4]triazolo[1,5-α]pyrimidine; [5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5<]pyrimidin-7-yl]-(2,2,2-trifluoro-ethyl)-amine; [5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-(1,1,1-trifluoro-prop-2-yl)-amine; [5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-diethyl-amine; [5-Chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-isopropyl-amine; sec-butyl-[5-chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-amine; bicyclo[2.2.1]hept-2-yl-[5-chloro-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-amine; [5-Chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-cyclopentyl-amine; [5-Chloro-6-(2-chloro-4,6-difluoro-phenyl)-7-(4-methyl-piperidin-1-yl)-1,2,4]triazolo[1,5-α]pyrimidine; [5-Chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-(2,2,2-trifluoro-ethyl)-amine; [5-Chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-(1,1,1-trifluoroprop-2-yl)-amine; [5-Chloro-6(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-diethyl-amine; [5-Chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-isopropyl-amine; sec-butyl-[5-chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-amine; bicyclo[2.2.1]hept-2-yl-[5-chloro-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidin-7-yl]-amine; but-2-yl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-amine; isopropyl-15-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-amine; [5-chloro-6-(2,4,6-trichlorophenyl)-7-(3-methyl-piperidin-1-yl)-1,2,4]triazolo[1,5-α]pyrimidine; cyclopentyl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-7yl]-amine; 5-chloro-6-(2,4,6-trichloro-phenyl)-7-(4-methyl-piperidin-1-yl)-1,2,4]triazolo[1,5-α]pyrimidine; diethyl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-amine; norborn-2-yl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-7-yl]amine; cyclopropyl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-7-yl]-amine; 2,2,2-trifluoroethyl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidin-7-yl]-amine; N-ethyl-N-2-methylallyl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-amine; and 1,1,1-trifluoroprop-2-yl-[5-chloro-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]-amino.
- 8. A process for the preparation of a compound of formula I as defined in claim 1 which comprisesreacting a compound of formula II in whichR3, R4, R5 and X are as defined in claim 1, with an amine of formula III in whichR1 and R2 are as defined in claim 1.
- 9. A compound of formula II in whichR3, R4, R5 and X are as defined in claim 1.
- 10. A compound selected from 5,7-dihydroxy-6-(2,4,6-trichlorophenyl)-[1,2,4]triazolo[1,5-α]pyrimidine, 5,7-dihydroxy-6-(2,6-dichloro-4-fluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidine and 5,7-dihydroxy-6-(2-chloro-4,6-difluoro-phenyl)-[1,2,4]triazolo[1,5-α]pyrimidine.
- 11. A fungicidal composition which comprises a carrier, and as active agent, at least one compound of formula I as defined in claim 1.
- 12. A method of combating fungus at a locus which comprises treating the locus with a compound of formula I as defined in claim 1.
- 13. A method according to claim 12 wherein said fungus is Pyricularia oryzae f. sp. grisea.
Parent Case Info
This is a continuation-in-part of application Ser. No. 09/160,568 filed on Sep. 25, 1998 now U.S. Pat. No. 5,985,883, and claims benefit of Provisional No. 60/101,764, filed Sep. 25, 1998 the entire disclosure of which is hereby incorporated by reference.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
4567263 |
Eicken et al. |
Jan 1986 |
|
5593996 |
Pees et al. |
Jan 1997 |
|
5612345 |
Becher et al. |
Mar 1997 |
|
5948783 |
Pees et al. |
Sep 1999 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
05501131A2 |
Dec 1992 |
EP |
0770615A1 |
Dec 1992 |
EP |
Non-Patent Literature Citations (1)
Entry |
09/057197 (Apr. 8, 1998). |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/101764 |
Sep 1998 |
US |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
09/160568 |
Sep 1998 |
US |
Child |
09/405413 |
|
US |