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Design, Synthesis, and Fungicidal Activity of Isoxazoles/Isoxazolines Containing Dihydrobenzofuran
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ABSTRACT
In the search for new antifungal agents, a series of isoxazoles (
D
) and isoxazolines (
E
) analogs were designed and synthesized. The 2,3‐dihydro‐2,2‐dimethyl‐7‐benzofuranol was used as the raw material, and the chalcone derivatives were obtained by methylation, acetylation, and hydroxyaldol condensation. Notably, the isoxazoles (
D
) and isoxazolines (
E
) were obtained via a one‐pot [3 + 2] cycloaddition reaction for the first time, and the reaction mechanism was explored preliminarily. The synthesized compounds were verified using
1
H NMR,
13
C NMR and HRMS. The antifungal activity results showed that the isoxazoles and isoxazolines both have good activity against
Pseudoperonospora cubensis
. Among them, compounds
D2
and
E2
have excellent inhibitory activities of 80% and 95% at 100 mg/L, respectively, which are almost comparable to the positive control fluopicolide.
Title: Design, Synthesis, and Fungicidal Activity of Isoxazoles/Isoxazolines Containing Dihydrobenzofuran
Description:
ABSTRACT
In the search for new antifungal agents, a series of isoxazoles (
D
) and isoxazolines (
E
) analogs were designed and synthesized.
The 2,3‐dihydro‐2,2‐dimethyl‐7‐benzofuranol was used as the raw material, and the chalcone derivatives were obtained by methylation, acetylation, and hydroxyaldol condensation.
Notably, the isoxazoles (
D
) and isoxazolines (
E
) were obtained via a one‐pot [3 + 2] cycloaddition reaction for the first time, and the reaction mechanism was explored preliminarily.
The synthesized compounds were verified using
1
H NMR,
13
C NMR and HRMS.
The antifungal activity results showed that the isoxazoles and isoxazolines both have good activity against
Pseudoperonospora cubensis
.
Among them, compounds
D2
and
E2
have excellent inhibitory activities of 80% and 95% at 100 mg/L, respectively, which are almost comparable to the positive control fluopicolide.
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