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Synthesis of Hinokitiol Sulfonate Derivatives and Their Anti-Oomycete and Nematicidal Activities. 2022

Zhiping Che, and Yibo Liu, and Luyao Chen, and Puhou Xing, and Xiangdong Li, and Xiaobo Huang, and Shengming Liu, and Genqiang Chen, and Xiaomin Lin, and Yuee Tian
Laboratory of Pesticidal Design & Synthesis, Department of Plant Protection, College of Horticultrue and Plant Protection, Henan University of Science and Technology, Luoyang, 471023, Henan Province, P. R. China.

In order to explore novel natural product-based anti-oomycete and nematicidal agents, sixteen unreported 2-sulfonyloxyhinokitiol derivatives were prepared using the principle of active splicing, and structurally confirmed by proton nuclear magnetic resonance (1 H-NMR), carbon-13 nuclear magnetic resonance (13 C-NMR), high-resolution mass spectrometry (HRMS), and melting point. Moreover, we evaluated the title compounds as anti-oomycete and nematicidal agents against two serious agricultural pests of Phytophthora capsici and Meloidogyne incongnita. Among the sixteen hinokitiol esters tested: (1) Compounds 3a and 3m exhibited the most potent anti-oomycete activity compared to zoxamide against P. capsici, and the median effective concentration (EC50 ) values of 3a, 3m, and zoxamide were 18.64, 21.11, and 23.15 mg/L, respectively; Further studies showed that the existence of seven membered ring and carbonyl group was the necessary condition for the high anti-oomycete activity of hinokitiol. (2) Compounds 3n and 3p exhibited more promising nematicidal activity than hinokitiol, and the median lethal concentration (LC50 ) values of 3n, 3p and 1 against M. incongnita were 0.2111, 0.2079, and 0.3933 mg/L, respectively. This result will pave the way for further modification of hinokitiol to develop potential new fungicides and nematicides.

UI MeSH Term Description Entries
D010838 Phytophthora A genus of destructive parasitic OOMYCETES in the family Peronosporaceae, order Peronosporales, affecting numerous fruit, vegetable, and other crops. Differentiation of zoospores usually takes place in the sporangium and no vesicle is formed. It was previously considered a fungus. Phytophthora sp. ex Parrotia persica,Sudden Oak Death Agent,Phytophthora cinnamomi,Phytophthora parasitica,Phytophthora ramorum,Phytophthora sojae
D011522 Protons Stable elementary particles having the smallest known positive charge, found in the nuclei of all elements. The proton mass is less than that of a neutron. A proton is the nucleus of the light hydrogen atom, i.e., the hydrogen ion. Hydrogen Ions,Hydrogen Ion,Ion, Hydrogen,Ions, Hydrogen,Proton
D005659 Fungicides, Industrial Chemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc. Industrial Fungicides
D000577 Amides Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amide
D000969 Antinematodal Agents Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. Nematocides,Antinematodal Drugs,Antinematodals,Agents, Antinematodal,Drugs, Antinematodal
D001688 Biological Products Complex pharmaceutical substances, preparations, or matter derived from organisms usually obtained by biological methods or assay. Biologic,Biologic Drug,Biologic Product,Biological,Biological Drug,Biological Medicine,Biological Product,Biologics,Biopharmaceutical,Natural Product,Natural Products,Biologic Drugs,Biologic Medicines,Biologic Pharmaceuticals,Biologic Products,Biological Drugs,Biological Medicines,Biologicals,Biopharmaceuticals,Products, Biological,Drug, Biologic,Drug, Biological,Drugs, Biologic,Drugs, Biological,Medicine, Biological,Medicines, Biologic,Medicines, Biological,Pharmaceuticals, Biologic,Product, Biologic,Product, Biological,Product, Natural
D014334 Tropolone A seven-membered aromatic ring compound. It is structurally related to a number of naturally occurring antifungal compounds (ANTIFUNGAL AGENTS).
D039821 Monoterpenes Compounds with a core of 10 carbons generally formed via the mevalonate pathway from the combination of 3,3-dimethylallyl pyrophosphate and isopentenyl pyrophosphate. They are cyclized and oxidized in a variety of ways. Due to the low molecular weight many of them exist in the form of essential oils (OILS, VOLATILE). Monoterpene,Monoterpenoid,Monoterpenoids

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