Pentafluorophenylazolopyrimidines
AssigneeAmerican Cyanamid Company
InventorsKlaus Jurgen Pees, Peter Liers, Cornelia Karla
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Abstract
The novel compounds of formula I ##STR1## (A and R.sup.1 through R.sup.4 are defined in the specification) show selective fungicidal activity. The new compounds are obtainable by a new synthetic method and processed with carriers and adjuvants to fungicidal compositions.
Claims18
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.
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.
Dependencies are inferred from the claim text.