Synthesis, Insecticidal, Fungicidal Activities and Structure–Activity Relationships of Tschimganin Analogs

Abstract

For the first time, a novel series of tschimganin analogs were designed, synthesized, and evaluated for their insecticidal and fungicidal activities. Their structures were characterized by 1H-NMR, 13C-NMR and HRMS. Some of these compounds displayed excellent insecticidal and fungicidal activities, suggesting that they have potential to be used as bifunctional agrochemicals. Compound 3d and 3g with electron donating groups showed better inhibitory activity and growth inhibition activity towards Helicoverpa armigera (Hübner). The properties and positions of the substituents on the benzene ring have an important influence on the acaricidal activity of tschimganin analogs. Topomer comparative molecular field analysis (CoMFA) was employed to develop a three-dimensional quantitative structure-activity relationship model for the compounds against Tetranychus turkestani Ugarov et Nikolski. It was indicated that higher electronegativity was beneficial for acaricidal activity. Moreover, compound 3r having a 2-hydroxy-3,5- dinitrophenyl moiety displayed a fungicidal spectrum as broad as azoxystrobin against these phytopathogens.

Discovery of ZQ-8, a Novel Starting Point To Develop Inhibitors against the Potent Molecular Target Chitinase

“…In a previous study, we took the active substance tschimganin from Ferula samarcandica as the lead compound to obtain a compound, ZQ- 8 , which had a strong impact on the growth and development of Helicoverpa armigera (Figure ). After treatment with ZQ- 8 , the growth and development of H. armigera can be effectively regulated, resulting in blocked larval molting, formation of abnormal pupae, and death after pupation.…”

“…13−16 In a previous study, we took the active substance tschimganin from Ferula samarcandica as the lead compound to obtain a compound, ZQ-8, which had a strong impact on the growth and development of Helicoverpa armigera (Figure 1). 17 molting, formation of abnormal pupae, and death after pupation. However, the mechanism and target of ZQ-8 are not clear, which makes it difficult to optimize the structure of this compound.…”

Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners

“…These molecules can be employed for efficient control over plant pathogenic fungi, such as ascomycetes, basidiomycetes, and deuteromycetes, often found in vegetables, fruits, and grain crops. 10 , 13 − 17 However, the widespread application of some commercial pyrimidine fungicide agents led to the development of resistance. 18 − 20 For example, the destructive plant pathogen Phytophthora capsici has developed great resistance to azoxystrobin in southern China.…”

“…Pyrimidine derivatives are well known for their pharmacological activities, including antiviral, anticancer, − anti-inflammatory, acaricidal, insecticidal, herbicidal, herbicide safener, and even fungicidal activities. − Commonly used commercial pyrimidine fungicides include diflumetorim (Figure a), pyrimethanil (Figure b), and azoxystrobin (Figure c). These molecules can be employed for efficient control over plant pathogenic fungi, such as ascomycetes, basidiomycetes, and deuteromycetes, often found in vegetables, fruits, and grain crops. ,− However, the widespread application of some commercial pyrimidine fungicide agents led to the development of resistance. − For example, the destructive plant pathogen Phytophthora capsici has developed great resistance to azoxystrobin in southern China . Hence, the design and development of novel pyrimidine derivatives with promising fungicidal activities are required.…”

Isotschimgine alleviates nonalcoholic steatohepatitis and fibrosis via FXR agonism in mice

“…Therefore, novel FXR agonists that could selectively activate target genes should be developed to avoid the side effects of steroidal FXR agonists. Isotschimgine (ITG) and its isomer tschimgine are naturally occurred in genus Ferula plants and propolis (Trusheva et al, 2010;Zhou et al, 2018). Recently we and others have reported that ITG and tschimgine are FXR agonists using reporter gene assay and crystaldrug analysis, and shown the anti-obesity, anti-hepatic steatosis, and insulin resistance improving effects on diet-induced obesity (DIO) mice (Li et al, 2020;Zheng et al, 2017).…”