Fraxinellone acylhydrazone/hydrazone/ester derivatives and application in preparation of plant source insecticides

Abstract

The invention relates to a series of novel fraxinellone acylhydrazone / hydrazone / ester derivatives. The fraxinellone acylhydrazone / hydrazone / ester derivatives have the chemical structures of a general formula as shown in the specification. The preparation method comprises the following steps of: carrying out allylic oxidation and ketoaldehyde reduction based on fraxinellone as a raw material to obtain fraxinellone ketone, aldehyde and alcohol; then respectively reacting with hydrazine, phenylhydrazine and acid to obtain the series of novel fraxinellone acylhydrazone / hydrazone / ester derivatives. Experiments show that the fraxinellone acylhydrazone / hydrazone / ester derivatives have good food refusal and poisoning activities on three-age armyworms, part of the activities are higher than those of fraxinellone, part of the insecticidal activity is higher than that of commercial plant source pesticide toosendanin, and the fraxinellone acylhydrazone / hydrazone / ester derivatives are expected to be used for preparing efficient, environment-friendly and low-toxic plant source insecticides.

Description

technical field [0001] The present invention relates to a series of alkone acylhydrazone / hydrazone / ester compounds with insecticidal activity, in particular to a preparation method of arketone acylhydrazone / hydrazone / ester derivatives, and the use of the series of derivatives in the preparation of botanical insecticides Applications. Background technique [0002] Dictamnus is a plant secondary metabolite extracted from the dry root bark of the Rutaceae plant Dictamnus dasycsrpus Turcz. It is favored for its anti-inflammatory, antibacterial, and insecticidal activities. Especially in terms of insecticidal activity, in recent years, many researchers have found that it has good antifeedant, poisonous and growth inhibitory effects on various pests. [0003] The anti-inflammatory, antibacterial and insecticidal activities of alkalone have been reported in the literature, such as: [Yang Sun, Yu Qin, Qiang Xu, et al. Selective triggering of apoptosis of concanavalin A-activated T ...

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Problems solved by technology

[0003] The anti-inflammatory, antibacterial, and insecticidal activities of alkalone have been reported in the literature, such as: [Yang Sun, Yu Qin, Qiang Xu, et al. Selective triggering of apoptosis of concanavalin A-activated T cells by fraxinellone for the treatment of T-cell-dependent hepatitis in mice. Biochemical Pharmacology 2009, 77, 1717-1724] reported that it can significantly improve cellular immune liver injury, and is expected to be applied in the treatment of various acute and chronic viral hepatitis; literature [Zhao Weimin, Wolfender J L, Hostettmann K, et al.Antifun-gal alkaloids and limonoid derivatives from Dictamnus dasycarpus[J].Phtochemistry, 1998,47(1):7-11.] and [Wang Mailing, Zhang Jiwen, Qian Yong, Li Junhao, Ji Zhiqin. Research on the bactericidal active components of Cortex Dictica. Pesticides. 2006, 45 (11), 739-741] reported that the active ingredient alkone in Cortex Dictica has certain bactericidal activity; literature [Liu Zhilong, Xu Yuanjian, Wu Jien, et al.Feeding deterrents from Dictamnus dasycarpus Turcz against two stored-product insects[J].Journary of Agriculture and Food Chemistry 2002,50:1447-1450.] and [Yuan Chunlan, Li Zongxiao. A new botanical insecticide Insecticidal activity of alkone. Plant Protection. 2005, 31 (5), 86-87.] reported that alkone has good biological activity against storage pests and third-instar armyworms, but the synthesis of alkone derivatives and Its research on insecticidal activity has not been reported yet

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