Systemic Fungicides. The Synthesis of Pyrazolo[1,5-a]pyrimidine Analogues of Carboxin

doi:10.1071/CH9850221

Paper

Systemic Fungicides. The Synthesis of Pyrazolo[1,5-a]pyrimidine Analogues of Carboxin

Published 1985 · J. Huppatz

Australian Journal of Chemistry

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16

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Abstract

The synthesis of a series of pyrazolo [1,5-a] pyrimidine derivatives, structural analogues of the systemic fungicide carboxin, is described. A common intermediate incorporating structural features desirable for fungicidal activity, N-phenyl-3(5)-amino-5(3)-methylpyrazole-4- carboxamide (6), was used to prepare pyrazolo [1,5-a] pyrimidines variously substituted in positions 5 and 7 of the ring system. Bromination of N-phenyl-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (8) occurred preferentially in the phenyl ring and the 6-bromo derivative was prepared by bromination of the corresponding 3-ethoxycarbonyl derivative (24). Attempted nitration of the ester (24) resulted in displacement of the ethoxycarbonyl substituent by a nitro group. The simplest pyrazolo [1,5-a] pyrimidine (8) showed a high level of fungicidal acitvity in fungal growth assays of Basidiomycete species, but compounds substituted in the pyrimidine ring were inactive.

Study Snapshot

The synthesis of pyrazolo [1,5-a] pyrimidine analogues, structural analogues of carboxin, resulted in high fungicidal activity against Basidiomycete species, with the simplest derivative showing high activity.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Systemic Fungicides. The Synthesis of Pyrazolo[1,5-a]pyrimidine Analogues of Carboxin

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References

Citations

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