Semi‐synthesis and characterization of some new matrine derivatives as insecticidal agents

Abstract

BACKGROUNDMatrine is an important traditional plant‐derived insecticide with broad‐spectrum activity. However, due to its moderate activity, matrine is mainly applied in combination with other pesticides. In order to discover new potential natural‐product‐based crop protection agents, a series of matrine derivatives characterized by cyclohexylamine group were synthesized to screen their insecticidal activity against seven typically agricultural pests.RESULTSThe structural configurations of compounds were characterized by IR, 1H NMR, 13C NMR, MS and XRD, with the pure yields of 42%, 65% and 71%, respectively. Although all compounds showed poor insecticidal activity against five lepidoptera pests, the compounds 2 and 4 displayed remarkable insecticidal activities against Lipaphis erysimi and Mulberry Root‐Knot Nematode with a concentration‐dependent manner within 0.5~1.5 mg/ mL. Compared with matrine (60%), compounds 2 and 4 exhibited potent insecticidal activities against L. erysimi, with a corrected mortality of 83.3% and 89.7%, respectively. They also showed excellent control effects on Mulberry Root‐Knot Nematode, with corrected mortality as high as 88% and 80%, respectively.CONCLUSIONAll four synthesized matrine derivatives showed poor insecticidal activity against five lepidoptera pests, but the compounds 2 and 4 exhibited much stronger insecticidal activities against L. erysimi and Mulberry Root‐Knot Nematode than matrine. Combined with the structural characteristics of compounds 1~4, we conclude that 4‐methylcyclohexylamine, not the carbon disulfide group or cyclohexylamine group alone, mainly contributed to the improvement of insecticidal activities of matrine derivatives against these two agricultural pests. This work provides a direction and foundation for structural optimization of the matrine pesticides in the future. © 2020 Society of Chemical Industry

Antifeedant activities of L-arabinose to caterpillars of the cotton bollwormHelicoverpa armigera(Hübner)

“…As one of plant specific primary metabolites, the metabolic pathway of LA may be of importance to plant pollen development (Kotake et al 2016). Then its physiological functions in plants may be quite different from most reported antifeedants, such as azadirachtin, rotenone, matrine, nicotine, pyrethrins, servicing as defense compounds (Cheng et al 2020; Isman 2020; Pavela 2016; Siegwart et al 2015; Walia et al 2017).…”

“…Examples of manipulating activities of insect pests include repellent, antifeedant, deterrent, as well as growth inhibition and negative effects on both fecundity and longevity of the target species (Dancewicz et al 2020; Hasheminia et al 2013; Karkanis and Athanassiou 2021; Koul et al 2003; Mao et al 2019). Lots of substances originated from plants such as azadirachtin, rotenone, matrine, nicotine, pyrethrins have been well developed and commercially registered in some countries (Cheng et al 2020; Isman 2020; Pavela 2016; Siegwart et al 2015; Walia et al 2017). But there should still be more botanical substances deserved to be explored for biological control of insect pests.…”

Synthesis of Halopyrazole Matrine Derivatives and Their Insecticidal and Fungicidal Activities

“…Using Lawson reagent to replace the oxygen atom on the carbonyl group of matrine with a sulfur atom and undergo a nucleophilic addition reaction with the active group at position C13, a series of thiomatrine derivatives were synthesized, which have antiliver fibrosis and antihepatitis activities [ 16 , 17 ]. Additionally, the introduction of nitrogen-containing and sulfur-containing derivatives synthesized at the C13 position of matrine has good insecticidal activity against Lipaphis erysimi , root knot nematode and Spodoptera frugiperda [ 18 , 19 , 20 ]. The derivative that was obtained by introducing dimethyl carbonate group condensed ester at the C14 position of matrine, and then reduced to alcohols and decarbonylated by lithium aluminum hydride has a significantly higher antitobacco mosaic virus and plant fungicidal activities than matrine [ 21 ].…”

Uncommon Bis-Amide Matrine-type Alkaloids From Sophora alopecuroides With Anti-inflammatory Effects

“…Chemically, matrine-type alkaloids are considered as ideal lead compounds for further structure modifications because of special chemical structure, widespread biological activities, high safety threshold, as well as available commercial sources. In order to improve the activities and amplify their applicants, many matrine-type derivatives have been synthesized and reported in the recent years ( Huang et al, 2017 ; Cai et al, 2018 ; Cheng et al, 2018 ; Lv et al, 2018 ; Cheng et al, 2020 ; Xu et al, 2020 ). Interestingly, we have noticed that almost all structural modifications were concentrated in the variations of D ring, such as introducing substituents to C-13 and C-14 sites, opening D ring, fusing D ring and further molecular simplification.…”