Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1<i>H</i>-pyrazole-4-carbaldehyde-<i>O</i>-(4-trifluoromethylbenzoyl)oximes

戴红,; 李宏,; 金智超,; 刘文永,; 肖瑶,; 何海兵,; 汪清民,; 石玉军,

doi:10.6023/cjoc201508028

Cited by 4 publications

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“…On the other hand, oxime esters as an important class of bioactive compounds for agrochemical and pharmaceutical use were investigated extensively by chemists. It was reported that oxime esters exhibited insecticidal [ 16 , 17 ], herbicidal [ 18 ], antiviral [ 19 ], antitumor [ 20 , 21 , 22 ], and antibacterial activities [ 23 , 24 , 25 ]. For example, a series of 3-ethoxy-4-hydroxybenzaldehyde oxime esters were synthesized and evaluated for their in vitro antifungal activity against three pathogenic fungi and antibacterial activity against three bacterial strains, and the structure-activity relationship was also preliminarily summarized [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

et al. 2017

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A series of novel 3-caren-5-one oxime esters were designed and synthesized by multi-step reactions in an attempt to develop potent antifungal agents. Two E-Z stereoisomers of the intermediate 3-caren-5-one oxime were separated by column chromatography for the first time. The structures of all the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal activity of the target compounds was preliminarily evaluated by the in vitro method against Fusarium oxysporum f. sp. cucumerinum, Physalospora piricola, Alternaria solani, Cercospora arachidicola, Gibberella zeae, Rhizoeotnia solani, Bipolaris maydis, and Colleterichum orbicalare at 50 µg/mL. The target compounds exhibited best antifungal activity against P. piricola, in which compounds (Z)-4r (R = β-pyridyl), (Z)-4q (R = α-thienyl), (E)-4f′ (R = p-F Ph), (Z)-4i (R = m-Me Ph), (Z)-4j (R = p-Me Ph), and (Z)-4p (R = α-furyl) had inhibition rates of 97.1%, 87.4%, 87.4%, 85.0%, 81.9%, and 77.7%, respectively, showing better antifungal activity than that of the commercial fungicide chlorothanil. Also, compound (Z)-4r (R = β-pyridyl) displayed remarkable antifungal activity against all the tested fungi, with inhibition rates of 76.7%, 82.7%, 97.1%, 66.3%, 74.7%, 93.9%, 76.7% and 93.3%, respectively, showing better or comparable antifungal activity than that of the commercial fungicide chlorothanil. Besides, the E-Z isomers of the target oxime esters were found to show obvious differences in antifungal activity. These results provide an encouraging framework that could lead to the development of potent novel antifungal agents.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

et al. 2017

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“…Shi obtained 5-substituted pyrazole compounds 46 and 47 with trifluoromethylbenzoyl oxime ester (Figure 6K), which exhibited moderate aphicidal activity at 500 μg/mL. 47 Shi further modified the pyrazole oxime ester derivatives by introducing pyridine rings in 2017. 48 Among them, compounds 48 and 49 (Figure 6L) demonstrated significant insecticidal activity against pests such as thrips, aphids, and brown planthoppers.…”

Section: ■ Data Collectionmentioning

confidence: 99%

“…Enhancements to their biological potency and selectivity can be made through the integration of the oxime ester structural into molecular frameworks. Shi obtained 5-substituted pyrazole compounds 46 and 47 with trifluoromethylbenzoyl oxime ester (Figure K), which exhibited moderate aphicidal activity at 500 μg/mL . Shi further modified the pyrazole oxime ester derivatives by introducing pyridine rings in 2017 .…”

Section: Oxime Ether Derivatives With Insecticidal Activitymentioning

confidence: 99%

Recent Research Progress in Oxime Insecticides and Perspectives for the Future

Wang,

Tian

et al. 2024

J. Agric. Food Chem.

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In recent decades, the unique structural attributes and purported insecticidal properties of oximes have garnered increasing attention. A variety of insecticides, encompassing fluxametamide, fluhexafon, and lepimectin, have been synthesized, all of which incorporate oximes. This review endeavors to encapsulate the insecticidal efficacy, structure−activity correlations, and operative mechanisms of oxime-containing compounds. Furthermore, it delves into the conceptual frameworks underpinning the design of innovative oxime-based insecticides, thereby shedding light on prospective advancements in this field.

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“…Amide compounds with ideal biological activity and metabolic properties were widely used in insecticide and fungicide [ 5 , 6 ]. Additionally, in the process of creating green pesticides, heterocyclic pesticides have the characteristics of high activity and good selectivity, thus becoming one of the hot spots in the development of pesticide lead compounds [ 7 , 8 , 9 , 10 , 11 ]. Since the 20th century, many highly active amide-containing fungicidal drugs containing heterocyclic structures [ 12 , 13 , 14 , 15 ] have been developed ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos

et al. 2021

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Eight novel pyridyl–oxazole carboxamides were evaluated against fungi and displayed good fungicidal activities against Botrytis cinereal and Rhizoctonia solani. Preliminary bioassay results indicated that at 100 mg/L, compounds 6a–6e, 6g and 6h exhibited 100% fungicidal activities against Botrytis cinerea, and the compound 6b to Rhizoctonia solani at 100%. Then, the zebrafish embryo acute toxicity test was performed to assess the toxicity of 6b and 6c. A series of malformations appeared, when the zebrafish embryos were exposed to 6b and 6c, such as delayed yolk sac resorption, significant shortening of body length, pericardial edema, bending spine, lack of melanin, heart hemorrhage, head hemorrhage, delayed swim sac development, yolk malformation and head malformation. In addition, the acute toxicity of 6b to zebrafish embryo is 4.878 mg/L, and 6c is 6.257 mg/L.

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Synthesis and Bioactivity of Novel 1-Methyl-3-trifluoromethyl- 5-subsituent-1H-pyrazole-4-carbaldehyde-O-(4-trifluoromethylbenzoyl)oximes

Cited by 4 publications

References 0 publications

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

Synthesis and Antifungal Activity of Novel 3-Caren-5-One Oxime Esters

Recent Research Progress in Oxime Insecticides and Perspectives for the Future

Novel Pyridyl–Oxazole Carboxamides: Toxicity Assay Determination in Fungi and Zebrafish Embryos

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