Claims
- 1. A compound of formula I ##STR11## in which R.sup.1 and R.sup.2 each independently represent a hydrogen atom or an C.sub.1 -C.sub.10 alkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 alkadienyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.6 or C.sub.10 aryl, C.sub.6 or C.sub.10 heteroaryl containing at least one nitrogen, oxygen or sulfur ring atom, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.10 bicycloalkyl, pyrrolodinyl, pyrrazolidin, piperidinyl, piperazinyl, morpholin-4-yl or thiomorpholin-4-yl group, which group optionally may be substituted by one or more halogen atoms or nitro, cyano, hydroxy, C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cyloalkenyl, C.sub.1-6 haloalkyl, C.sub.3-6 halocycloalkyl, C.sub.1-6 alkoxy, C.sub.1-6 haloalkoxy, tri-C.sub.1-4 alkylsilyl, pheny, halo- or dihalo-phenyl or pyridyl groups, or
- R.sup.1 and R.sup.2 together with the interjacent nitrogen atom represent a C.sub.3-7 heterocyclic ring in which one CH.sub.2 group may be replaced by O or S, which ring optionally may be substituted by one or more C.sub.1-10 alkyl groups, and
- Hal represents a halogen atom.
- 2. A compound according to claim 1 in which
- R.sup.1 represents straight chained C.sub.1 -C.sub.6 -alkyl, straight chained or branched C.sub.2 -C.sub.6 -alkenyl, C.sub.3 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.9 bicyclealkyl 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 interjacent nitrogen atom represent a heterocyclic ring having four to seven carbon atoms and optionally one or two non-adjacent nitrogen, oxygen or sulfur atoms being optionally substituted with one or two C.sub.1 -C.sub.6 -alkyl groups.
- 3. A compound according to claim 2 in which R.sup.2 represents a hydrogen atom or C.sub.1 -C.sub.3 -alkyl group.
- 4. A compound according to claim 2 in which R.sup.1 and R.sup.2 together with the interjacent nitrogen atom represent a heterocyclic ring comprising 4 to 7 carbon atoms and optionally 1 sulfur atom being optionally substituted by one or two methyl group.
- 5. A compound according to claim 1, selected from the group 2 consisting of:
- 5-chloro-7-(N-ethyl-N-2-methylallylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(azocan-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidine;
- 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(thiomorpholin-4-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(azepan-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidine;
- 5-chloro-7-(N-bicyclo[2.2.1 ]heptan-2-ylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(piperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidine;
- 5-chloro-7-(2,4-dimethylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-1,2,2-trimethylpropylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-cyclopentylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(2-methylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(3-methylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-cyclohexylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-cycloheptylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-allyl-N-ethylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-3-chloropropyl-N-methylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-2-methylpropylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(4-isopropylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(2-methylpyrollidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-[N-(2,2-dichlorocyclopropyl)-methyl-N-methylamino]-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-but-2-ylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]-pyrimidine;
- 5-chloro-7-(N-cyclopropylmethyl-N-propylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-methyl-N-2-methylpropylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-butyl-N-ethyllamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N,N-di-ethylamino) -6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-isopropylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(3,3-dimethylpiperidin-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-cyclopropylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-cyclohexyl-N-methylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(1,4-diazepan-1-yl)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-(N-allyl-N-hexylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;
- 5-chloro-7-[4-(1-formylamino-2,2,2-trichloroethyl)-piperazin-1-yl]-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine; and,
- 5-chloro-7-(N-allyl-N-cyclopentylamino)-6-(2,3,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine.
- 6. A process for the preparation of a compound of formula I, as defined in claim 1, which comprises reacting a compound of formula II ##STR12## in which Hal is as defined in claim 1, with an amine of the formula III ##STR13## in which R.sup.1 and R.sup.2 are as defined in claim 1, optionally in the presence of a base.
- 7. A fungicidal composition which comprises a carrier, and as active agent, at least one compound of formula I as defined in claim 1.
- 8. A method of combating fungus at a locus which comprises treating the locus with a fungicidally effective amount of a compound of formula I as defined in claim 1.
- 9. A method of combating fungus at a locus which comprises treating the locus with a fungicidally effective amount of a composition as defined in claim 7.
Parent Case Info
This application claims priority from copending provisional application(s) Ser. No. 60/099711 filed on Sep. 10, 1998.
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