Citation: Zhao Yu, Guan Aiying, Li Wanzhen, Wang Weiwei, Liu Xinlei, Wang Ming'an. Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1344-1353. doi: 10.6023/cjoc201811041 shu

Synthesis, Fungicidal and Insecticidal Activity of Novel Tetronic Acid Hydrazinyl Derivatives

Department of Applied Chemistry, China Agricultural University, Beijing 100193

Corresponding author: Wang Ming'an, wangma@cau.edu.cn
Received Date: 30 November 2018
Revised Date: 28 January 2019
Available Online: 22 May 2019
Fund Project: the National Natural Science Foundation of China 21772229the National Natural Science Foundation of China 21172254Project supported by the National Natural Science Foundation of China (Nos. 21772229, 21172254)

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A series of novel 3-acetyl-4-hydrazinyl-5, 5-disubstitutedtetronic acid and (E/Z)-3-(1-hydrazinylethyli-dene)-5, 5-disubstitutedfuran-2, 4-dione derivatives were designed and synthesized, and four methyl 5-methyl pyrazole-4-carboxylate were obtained unexpectedly. Their structures were confirmed by high-resolution mass spectrum (HR-ESI-MS), ¹H NMR, ¹³C NMR spectral data and X-ray diffraction. The bioassay results of the hydrazinyl compounds along with the amino analogues indicated that some compounds exhibited moderate to excellent fungicidal activities against phytopathagens. For example, compounds 5G, 5H, 5I and 5i showed 100% in vivo control efficacy against Colletotrichum lagenarium, and compound 5G also exhibited 100% in vivo control efficacy against Erysiphe graminis, Puccinia polysora and Colletotrichum lagenarium at 400 μg/mL. Compounds 5b, 5E and 6F showed 100% mortality against Plutella xylostella, compounds 6A, 6g and 6H exhibited 100% mortality against Myzus persicae, and compound 6b showed 100% mortality against Tetranychus cinnabarinus at 600 μg/mL. The 5, 5-spiro cyclohexyl moiety significantly improved the fungicidal activity of the tetronic acid derivatives, and the introduction of the substituted hydrazino group to the furan-2, 4-dione skeleton led to higher insecticidal and acaricidal activities. 5G and 5i were found to have the most potential to be further modified for searching new fungicide as the lead compounds.
- hydrazine derivatives,
- spirocyclohexyl tetronic acid,
- fungicidal activity,
- insecticidal activity
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