Claims
- 1. A compound of the general formula ##STR14## in which R.sup.1 and R.sup.2 each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, bicycloalkyl or heterocyclyl group, in which each optionally substituted group independently is substituted by one or more halogen atoms or nitro, cyano, alkyl, cycloalkyl, cycloalkenyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, phenyl, halo- or dihalo-phenyl or pyridyl groups, or
- R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C.sub.1 -C.sub.6 -alkyl groups,
- R.sup.3 represents a halogen atom or a group --NR.sup.5 R.sup.6, wherein R.sup.5 and R.sup.6 each independently have one of the meanings given for R.sup.1 and R.sup.2,
- R.sup.4 represents hydrogen or an alkyl or phenyl group, and
- A represents N.
- 2. A compound according to claim 1 in which R.sup.3 represents a bromine or chlorine atom.
- 3. A compound according to claim 1 in which R.sup.1 represents straight chained or branched C.sub.1 -C.sub.6 -alkyl or straight chained or branched C.sub.2 -C.sub.6 -alkenyl, and R.sup.2 represents hydrogen or C.sub.1 -C.sub.6 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C.sub.1 -C.sub.6 -alkyl groups.
- 4. A compound according to claim 1 in which R.sup.4 is hydrogen.
- 5. A compound according to claim 4 in which R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic group selected from the group consisting of 4-methyl-piperidin-1-yl, 2-methyl-piperidin-1-yl, 3,6-dihydro-2H-pyridin-1-yl, 2-ethyl-piperidin-1-yl and azepan-1-yl.
- 6. A compound according to claim 1, wherein the compound is selected from the group consisting of:
- 5-chloro-6-(pentafluorophenyl)-7-(4-methyl-piperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyrimidine
- 5-chloro-6-(pentafluorophenyl)-7-(N-isopropylamino)-[1,2,4]triazolo[1,5-a]pyrimidine
- 5-chloro-6-(pentafluorophenyl)-7-(N-ethyl,N-2-methylallylamino)-[1,2,4]triazolo[1,5-a]pyrimidine.
- 7. A process for the preparation of a compound of formula I ##STR15## in which R.sup.1 and R.sup.2 each independently represent hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, aryl, bicycloalkyl or heterocyclyl group, in which each optionally substituted group independently is substituted by one or more halogen atoms or nitro, cyano, alkyl, cycloalkyl, cycloalkenyl, haloalkyl halocycloalkyl, alkoxy, haloalkoxy, phenyl, halo- or dihalo-phenyl or pyridyl groups, or
- R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C.sub.1 -C.sub.6 -alkyl groups,
- R.sup.3 represents a bromine or chlorine atom,
- R.sup.4 represents hydrogen or an alkyl or phenyl group, and
- A represents N,
- which process comprises
- (a) reacting hexafluorobenzene with a dialkylmalonate in the presence of a base,
- (b) treating the resulting 2-pentafluorophenylmalonate of formula II, ##STR16## in which R is alkyl, aryl or benzyl, with a compound of formula III, ##STR17## in which R.sup.4 and A have the meaning given above, in the presence of a base,
- (c) treating the resulting dihydroxyazolopyrimidine of formula IV, ##STR18## with a halogenating agent, and (d) treating the resulting compound of formula V ##STR19## in which Hal represents a chlorine or bromine atom, with an amine of formula VI ##STR20## in which R.sup.1 and R.sup.2 are as defined above.
- 8. A process according to claim 7 further comprising reacting the compound of formula I with a fluorinating agent to produce a compound of formula I wherein R.sup.3 is a fluorine atom.
- 9. A process according to claim 7 further comprising reacting the compound of formula I with ammonia and, subsequently, diiodomethane in the presence of a diazotising agent to produce a compound of formula I wherein R.sup.3 is an iodine atom.
- 10. A process according to claim 7 further comprising reacting the compound of formula I with an amine of the formula HNR.sup.5 R.sup.6, wherein R.sup.5 and R.sup.6 are as defined above, to produce a compound of formula I wherein R.sup.3 is --NR.sup.5 R.sup.6.
- 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 of combating fungus at a locus which comprises treating the locus with a composition as defined in claim 11.
- 14. A method according to claim 12 in which R.sup.3 represents a bromine or chlorine atom.
- 15. A method according to claim 12 in which R.sup.1 represents straight chained or branched C.sub.1 -C.sub.6 -alkyl or straight chained or branched C.sub.2 -C.sub.6 -alkenyl, and R.sup.2 represents hydrogen or C.sub.1 -C.sub.6 -alkyl, or R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic ring with 5 or 6 carbon atoms being optionally substituted with one or two C.sub.1 -C.sub.6 -alkyl groups.
- 16. A method according to claim 12 in which R.sup.4 is hydrogen.
- 17. A method according to claim 16 in which R.sup.1 and R.sup.2 together with the adjacent nitrogen atom represent a saturated heterocyclic group selected from the group consisting of 4-methyl-piperidin-1-yl; 2-methyl-piperidin-1-yl; 3,6-dihydro-2H-pyridin-1-yl; 2-ethyl-piperidin-1-yl; and azepan-1-yl.
- 18. A method according to claim 12, wherein the compound is selected from the group consisting of
- 5-chloro-6-(pentafluorophenyl)-7-(4-methyl-piperidin-1-yl)-[1,2,4]triazolo-[1,5-a]pyrimidine;
- 5-chloro-6-(pentafluorophenyl)-7-(N-isopropylamino)-[1,2,4]triazolo[1,5-a]pyrimidine; and
- 5-chloro-6-(pentafluorophenyl)-7-(N-ethyl, N-2-methylallylamino)-[1,2,4]triazolo-[1,5-a]pyrimidine.
Parent Case Info
This is a Continuation-In-Part of application Ser. No. 08/729,704, filed Oct. 7, 1996.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4567263 |
Eicken |
Jan 1986 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
550113 |
Jul 1993 |
EPX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
729704 |
Oct 1996 |
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