Claims
- 1. A compound of formula I: whereinR1 represents an alkyl or an optionally substituted alkenyl, alkynyl, alkadienyl, aryl, heteroaryl, cycloalkyl, bicycloalkyl or heterocyclyl group, R2 represents a halogen atom or a group of formula —Y—R4, wherein Y represents O, S or NR5, R3 represents hydrogen, or an alkyl or aryl group, R4 has the meaning given for R1, R5 represents a hydrogen atom or has the meaning given for R1, or R4 and R5 together with the interjacent nitrogen atom represent a heterocyclic ring, L represents halogen, or an optionally substituted alkyl or alkoxy group, A represents N or CR6, wherein R6 has the meaning given for R3, X represents O or S, and n is 0 or an integer between 1 and 5.
- 2. A compound of the formula I: whereinR1 represents an alkyl group substituted with an alkyl, alkenyl, alkynyl, alkadienyl, cycloalkyl, bicycloalkyl or heterocyclyl group, R2 represents a halogen atom or a group of formula —Y—R4, wherein Y represents O, S or NR5, R3 represents hydrogen, or an alkyl or aryl group, R4 has the meaning given for R1, R5 represents a hydrogen atom or has the meaning given for R1, or R4 and R5 together with the interjacent nitrogen atom represent a heterocyclic ring, L represents halogen, or an optionally substituted alkyl or alkoxy group, A represents N or CR6, wherein R6 has the meaning given for R3, X represents O or S, and n is 0 or an integer between 1 and 5.
- 3. A compound of formula I: whereinR1 represents an alkyl group substituted with either an aryl or a heteroaryl group, R2 represents a halogen atom or a group of formula —Y—R4, wherein Y represents O, S or NR5, R3 represents hydrogen, or an alkyl or aryl group, R4 has the meaning given for R1, R5 represents a hydrogen atom or has the meaning given for R1, or R4 and R5 together with the interjacent nitrogen atom represent a heterocyclic ring, L represents halogen, or an optionally substituted alkyl or alkoxy group, A represents N or CR6, wherein R6 has the meaning given for R3, X represents O or S, and n is 0 or an integer between 1 and 5.
- 4. A compound of formula I: whereinR1 represents an aryl or heteroaryl group substituted with an alkyl group, R2 represents a halogen atom or a group of formula —Y—R4, wherein Y represents O, S or NR5, R3 represents hydrogen, or an alkyl or aryl group, R4 has the meaning given for R1, R represents a hydrogen atom or has the meaning given for R1, or R4 and R5 together with the interjacent nitrogen atom represent a heterocyclic ring, L represents halogen, or an optionally substituted alkyl or alkoxy group, A represents N or CR6, wherein R6 has the meaning given for R3, X represents O or S, and n is 0 or an integer between 1 and 5.
- 5. A compound according to claim 1 or 2 or 3 or 4 in which R1 represents straight or branched chained C1-C6 alkyl, C1-6 haloalkyl or C2-C6 alkenyl, C3-C8 cycloalkyl or phenyl, being optionally substituted by at least one substituent selected from the group consisting of halogen, and C1-C4alkyl and C1-C4alkoxy.
- 6. A compound according to claim 1 or 2 or 4 in which R2 represents chlorine.
- 7. A compound according to claim 1 in which A is N and R3 is hydrogen.
- 8. A compound according to claim 1 selected from the group consisting of:5-chloro-6-phenyl-7-(furfur-2-ylmethylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-phenyl-7-(3,4,5,6-tetrahydropyrimid-2-ylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(4-methoxyphenyl)-7-(furfur-2-ylmethylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-allylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-cyclopentylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(isopropylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(1-methylpropylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-propylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-methylpropylthio)-[1 2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-cyclohexylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-butylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-phenylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-benzylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-tert-butylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-methylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-ethylthio-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-chlorophenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-methylphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-methoxyphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(4-methoxyphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2-chlorophenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-ethoxy-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-cyclopentyloxy-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2-chloro-6-fluorophenyl)-7-(2,2,2-trifluoroethoxy)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-allylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine 5-chloro-7-cyclopentylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(2,2,2-trifluoroethylthio)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(isopropylthio)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(1-methylpropylthio)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-propylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-(2-methylpropylthio)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-cyclohexylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-butylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-phenylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-benzylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-tert-butylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-methylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-7-ethylthio-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-chlorophenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(2-methylphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(2-methoxyphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(4-methoxyphenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-(2-chlorophenylthio)-[1,2,4]triazolo[1,5-a]pyrimidine, 5-chloro-6-(2,4,6-trifluorophenyl)-7-ethoxy-[1,2,4]triazolo[1,5-a]pyrimidine 5-chloro-6-(2,4,6-trifluorophenyl)-7-cyclopentyloxy-[1,2,4]triazolo[1,5-a]pyrimidine, and 5-chloro-6-(2,4,6-trifluorophenyl)-7-(2,2,2-trifluoroethoxy)-[1,2,4]triazolo[1,5-a]pyrimidine.
- 9. A fungicidal composition which comprises a carrier, and as an active agent, at least one compound of formula I as defined in any of claims 1 or 5 or 6 or 7 or 8.
- 10. A process for the preparation of a compound of formula I as defined in any of claims 1 to 4, which comprises(a) reacting a compound of the general formula II in which each of R3, A, L and n have the meaning given for formula I, and Hal represents a halogen atom, with a compound of formula III R1—XH (III) in which R1 and X have the meaning given for formula I, in the presence of a base; and(b) optionally treating the resulting 5-halogentriazolopyrimidine with an alcohol, thiol or amine of formula R4—YH, in which R4 and Y have the meaning given for formula I, in the presence of a base.
- 11. A method of combating fungus at a locus which comprises treating the locus with a compound of formula I as defined in any of claims 1 or 5 or 6 or 7 or 8.
Parent Case Info
This application claims priority from copending provisional application(s) Ser. No. 60/101,689 filed on Sep. 25, 1998.
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Provisional Applications (1)
|
Number |
Date |
Country |
|
60/101689 |
Sep 1998 |
US |