36 results on '"Lixia Xiong"'
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2. Synthesis and evaluation of novel xanthine‐acrylamides and xanthine‐acrylates as insecticidal agents
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Shuyun, Zhang, Hang, Liu, Na, Yang, Lixia, Xiong, and Baolei, Wang
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Acrylamides ,Insecticides ,Structure-Activity Relationship ,Molecular Structure ,Caffeine ,Larva ,Insect Science ,Animals ,General Medicine ,Moths ,Pesticides ,Xanthine ,Agronomy and Crop Science - Abstract
The design and discovery of novel pesticidal agents according to bioactive natural products is an important aspect of agrochemical innovation. New xanthine derivatives derived from natural xanthine or methylxanthines are rich resources that possess great potential to afford new active pesticidal molecules. Herein novel xanthine derivatives were designed through a strategy of combining the methylxanthine caffeine skeleton with the acrylamide or acrylate motif of cinnamic acid derivatives.A series of novel (E)-3-(1,3,7-trimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)acrylic acid derivatives, caffeine-(E)-acrylamides and caffeine-(E)-acrylates, were synthesized and confirmed via melting points,Compounds I12, I18, I24 and I26 generated from the integration of natural methylxanthine (caffeine) and acrylate moieties could be novel insecticidal leading compounds for further structural optimization. The SAR analysis may bring a new inspiration to the extensive and deep investigations on new xanthine derivatives in the agrochemical area.
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- 2022
3. Improving Insecticidal Activity of Chlorantraniliprole by Replacing the Chloropyridinyl Moiety with a Substituted Cyanophenyl Group
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Zhenwu Yu, Xiulan Zhang, Jinzhou Ren, Haolin Yuan, Wei Gao, Lixia Xiong, Na Yang, Yuxin Li, Zhengming Li, and Zhijin Fan
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Diamide ,Insecticide Resistance ,Molecular Docking Simulation ,Insecticides ,Animals ,Ryanodine Receptor Calcium Release Channel ,ortho-Aminobenzoates ,General Chemistry ,Moths ,General Agricultural and Biological Sciences - Abstract
Insect ryanodine receptors (RyRs) are molecular targets of the anthranilic diamide insecticides. In the present study, a new series of anthranilic diamides containing a cyanophenyl pyrazole moiety were rationally designed by active-fragment assembly and computer-aided design using the 3D structure of
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- 2022
4. Design, Synthesis and Biological Evaluation of Novel Thienylpyridyl- and Thioether-Containing Acetamides and Their Derivatives as Pesticidal Agents
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Na Yang, Huan Li, Bao-Lei Wang, and Lixia Xiong
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Insecticides ,synthesis ,Stereochemistry ,Pharmaceutical Science ,Moths ,Sulfides ,Article ,thioether ,Analytical Chemistry ,Sulfone ,chemistry.chemical_compound ,Mythimna separata ,Structure-Activity Relationship ,QD241-441 ,Thioether ,Ascomycota ,pesticidal activity ,Drug Discovery ,Acetamides ,Animals ,Physical and Theoretical Chemistry ,Pesticides ,Cartap ,biology ,Chemistry ,Basidiomycota ,Organic Chemistry ,sulfone ,Plutella ,Sulfoxide ,biology.organism_classification ,Chemistry (miscellaneous) ,Molecular Medicine ,thienylpyridylthioacetamide ,Pharmacophore ,Acetamide - Abstract
Referring to the structural information of the “hit” compound A from the reported pharmacophore-based virtual screening, a series of novel thienylpyridyl- and thioether/sulfoxide/sulfone-containing acetamide derivatives have been designed and synthesized. The structures of new compounds were confirmed by 1H NMR, 13C NMR and HRMS. The single-crystal structure of A was firstly reported. All the new synthesized compounds were evaluated for insecticidal activities on Mythimna separata Walker and Plutella xylostella L. Through a step-by-step structural optimization, the high insecticidal agents, especially towards Plutella xylostella L., have been found, and thienylpyridyl- and sulfone/thioether-containing acetamides Iq, Io, Ib and A, which are comparable with the control insecticides cartap, triflumuron and chlorantraniliprole in the present study, can be used as novel lead structures for new insecticides innovation research. In addition, some of the compounds, e.g., A, Ih, Id, Io and Iq, also exhibited favourable fungicidal activities against Physalospora piricola, Rhizoctonia cerealis and Sclerotinia sclerotiorum and would provide useful guidance for the design and development of new fungicides.
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- 2021
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5. Synthesis, Insecticidal Activities, and Structure-Activity Relationship of Phenylpyrazole Derivatives Containing a Fluoro-Substituted Benzene Moiety
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Sha Zhou, Binqiao Sun, Pengwei Sun, Na Yang, Lixia Xiong, Zheng-Ming Li, Yan Zhang, Yuxin Li, Huangong Li, Yi Ma, Yangyang Zhao, Fan-Fei Meng, Yongtao Xie, and Li Gao
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0106 biological sciences ,Insecticides ,Moths ,01 natural sciences ,chemistry.chemical_compound ,Mythimna separata ,Structure-Activity Relationship ,Structure–activity relationship ,Moiety ,Bioassay ,Organic chemistry ,Animals ,Benzene ,biology ,Molecular Structure ,010401 analytical chemistry ,Plutella ,Biological activity ,Ryanodine Receptor Calcium Release Channel ,General Chemistry ,biology.organism_classification ,Calcium Channel Blockers ,0104 chemical sciences ,chemistry ,Larva ,Insect Proteins ,Pyrazoles ,General Agricultural and Biological Sciences ,Selectivity ,010606 plant biology & botany - Abstract
Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L-1, while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10-5 mg L-1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.
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- 2020
6. Synthesis, Insecticidal Evaluation, and 3D-QASR of Novel Anthranilic Diamide Derivatives Containing
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Changchun, Wu, Xiaobo, Yu, Baolei, Wang, Jingbo, Liu, Fanfei, Meng, Yangyang, Zhao, Lixia, Xiong, Na, Yang, Yuxin, Li, and Zhengming, Li
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Diamide ,Calcium Channel Agonists ,Insecticides ,Larva ,Animals ,Insect Proteins ,Quantitative Structure-Activity Relationship ,Ryanodine Receptor Calcium Release Channel ,Isoxazoles ,Moths - Abstract
To cope with the global food shortage and insect pest, there is an urgent need to discover new pesticides with novel modes of actions. Ryanodine receptor (RyR) insecticides showed great promise in integrated pest management. Herein, we report the synthesis of novel anthranilic diamide derivatives incorporating pyrrole moieties targeting at insect RyRs. The structures were confirmed by
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- 2020
7. Anthranilic diamides derivatives as potential ryanodine receptor modulators: Synthesis, biological evaluation and structure activity relationship
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Wang Yuanhong, Zheng-Ming Li, Lixia Xiong, Xiu-Lan Zhang, Yuxin Li, Liu Jingbo, Feng-Yun Li, and Jing-Yue Dong
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Insecticides ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Cockroaches ,Moths ,Pyrazole ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Structure-Activity Relationship ,chemistry.chemical_compound ,Mythimna separata ,Heart Rate ,Drug Discovery ,Animals ,Structure–activity relationship ,Molecular Biology ,Diamide ,Trifluoromethyl ,Diamondback moth ,biology ,010405 organic chemistry ,Chemistry ,Ryanodine receptor ,Organic Chemistry ,Ryanodine Receptor Calcium Release Channel ,Isoxazoles ,biology.organism_classification ,0104 chemical sciences ,Larva ,Quantum Theory ,Molecular Medicine ,American cockroach ,Periplaneta - Abstract
A series of novel anthranilic diamides derivatives (7a–s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, 1H NMR, 13C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L−1, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L−1 and 20%, 0.1 mg L−1). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L−1, superior to chlorantraniliprole (45%, 0.01 mg L−1). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o. The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.
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- 2018
8. Synthesis, biological evaluation and SAR analysis of novel poly‐heterocyclic compounds containing pyridylpyrazole group
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Hong-Wei Zhu, Lixia Xiong, Zheng-Ming Li, Bao-Lei Wang, Xiao Zhang, Hai-Bin Song, and Lizhong Wang
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Insecticides ,Alternaria solani ,Moths ,010402 general chemistry ,01 natural sciences ,Physalospora ,Structure-Activity Relationship ,chemistry.chemical_compound ,Ascomycota ,Heterocyclic Compounds ,Animals ,Organic chemistry ,biology ,010405 organic chemistry ,Biological activity ,General Medicine ,Aziridine ,Carbon-13 NMR ,biology.organism_classification ,Cercospora arachidicola ,Fungicides, Industrial ,0104 chemical sciences ,Fungicide ,chemistry ,Insect Science ,Proton NMR ,Pyrazoles ,Agronomy and Crop Science - Abstract
Background In recent years, pyridylpyrazole derivatives, such as pyridylpyrazole-containing anthranilic diamide have attracted much attention by virtue of their useful insecticidal properties and unique action mode. Moreover, some pyridylpyrazole-containing compounds have also been found to possess significant fungicidal activities. With the aim of discovering new bioactive agrochemicals for crop protection, a series of poly-heterocyclic compounds containing pyridylpyrazole and aziridine, or β-lactam, or thiazolinone moieties were synthesized. Results A series of pyridylpyrazole-containing poly-heterocyclic compounds were obtained, and confirmed through IR, 1 H NMR, 13 C NMR, HRMS and elemental analysis. The crystalline structure of 4-(3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-3-chloro-1-mesitylazetidin-2-one (compound 13f) was determined to further illustrate a trans- configuration of the β-lactam motif. In addition, bioassays showed that most of these new compounds exhibited modest insecticidal activity towards Mythimna separate Walker at 200 µg mL-1 . Some of the compounds displayed excellent fungicidal activity towards some plant fungi, including Cercospora arachidicola (13j: EC50 = 14.5 µg mL-1 ), Physalospora piricola (12d and 13d: EC50 = 10.5 and 9.70 µg mL-1 ), Alternaria solani Sorauer (13j: EC50 = 7.29 µg mL-1 ), Puccinia sorghi Schw. (13d: control efficacy 99.0 ± 2.1% at 200 µg mL-1 ) and Erysiphe graminis (14d: control efficacy 95.0 ± 1.4% at 200 µg mL-1 ). Conclusion Compounds 12b-12e, 13a, 13d, 13f, 13j, 13 k and 14d could be considered potential fungicidal lead compounds to do further structural optimization. The structure-activity relationship analysis in this study brings some new understanding to the biological activities of N-pyridylpyrazole-containing compounds, and provides important information for the research and development of novel agricultural fungicides with poly-heterocyclic structures. © 2017 Society of Chemical Industry.
- Published
- 2017
9. Synthesis, biological activities, and SAR studies of novel 1-(2-chloro-4,5-difluorophenyl)-1H-pyrazole derivatives
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Yangyang Zhao, Lixia Xiong, Pengwei Sun, Yuxin Li, Zheng-Ming Li, Jingbo Liu, Na Yang, Li Gao, Sha Zhou, and Huangong Li
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Insecticides ,Stereochemistry ,Anthranilic diamide ,Clinical Biochemistry ,Pharmaceutical Science ,chemistry.chemical_element ,Moths ,Calcium ,Pyrazole ,01 natural sciences ,Biochemistry ,Structure-Activity Relationship ,Mythimna separata ,chemistry.chemical_compound ,Drug Discovery ,Animals ,Moiety ,Molecular Biology ,Dose-Response Relationship, Drug ,Molecular Structure ,biology ,010405 organic chemistry ,Ryanodine receptor ,Chemistry ,Endoplasmic reticulum ,Organic Chemistry ,Plutella ,biology.organism_classification ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,Pyrazoles ,Molecular Medicine - Abstract
In order to search for the new ryanodine receptor (RyR) regulator, a series of 35 novel fluoro-substituted compounds introduced 1-(2-chloro-4,5-difluorophenyl)-1H-pyrazole moiety containing modified pyrazole heterocycle were designed and synthesized. Then, they were tested for the insecticidal activities against Mythimna separata and Plutella xylostella in our greenhouse. After a systematic biological screening, it was found out that IVc showed 50% larvicidal activities against Mythimna separata at 0.1 mg L−1, equivalent to that of chlorantraniliprole (36%, 0.1 mg L−1). The activity of IVc against Plutella xylostella was 90% at 10−5 mg L−1, whereas the chlorantraniliprole was 70% at the same concentration. Then, insect electrophysiology experiments were conducted to study the pattern of action of IVc and IVe. It was confirmed by the experimental results that both compounds could lead to the release of calcium from the endoplasmic reticulum of neurons as classical anthranilic diamide insecticides.
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- 2020
10. Novel Anthranilic Diamide Scaffolds Containing N-Substituted Phenylpyrazole as Potential Ryanodine Receptor Activators
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Jingbo Liu, Lixia Xiong, Yingying Wan, Xiu-Lan Zhang, Changchun Wu, Wei Wei, Dandan Cheng, Yuxin Li, Zheng-Ming Li, Xuewen Hua, Na Yang, and Hai-Bin Song
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Insecticides ,Stereochemistry ,Moths ,Helicoverpa armigera ,010402 general chemistry ,01 natural sciences ,Toxicology ,Structure-Activity Relationship ,Mythimna separata ,X-Ray Diffraction ,Animals ,Diamide ,Diamondback moth ,Molecular Structure ,biology ,010405 organic chemistry ,Ryanodine receptor ,Chemistry ,Calcium channel ,Ryanodine Receptor Calcium Release Channel ,Isoxazoles ,General Chemistry ,Carbon-13 NMR ,biology.organism_classification ,0104 chemical sciences ,Calcium Channel Agonists ,Drug Design ,Larva ,Proton NMR ,Nitro ,Insect Proteins ,General Agricultural and Biological Sciences - Abstract
To discover potent insecticides targeting ryanodine receptors (RyRs), a series of novel anthranilic diamides analogues (12a-12u) containing N-substituted phenylpyrazole were designed and synthesized. These compounds were characterized by (1)H NMR, (13)C NMR, and HRMS, and the structure of compound 12u was confirmed by X-ray diffraction. Their insecticidal activities indicated that these compounds displayed moderate to excellent activities. In particular, 12i showed 100 and 37% larvicidal activities against oriental armyworm (Mythimna separata) at 0.25 and 0.05 mg L(-1), equivalent to that of chlorantraniliprole (100%, 0.25 mg L(-1); and 33%, 0.05 mg L(-1)). The activity of 12i against diamondback moth (Plutella xylostella) was 95% at 0.05 mg L(-1), whereas the control was 100% at 0.05 mg L(-1). The calcium-imaging technique experiment results showed that the effects of 12i on the intracellular calcium ion concentration ([Ca(2+)]i) in neurons were concentration-dependent. After the central neurons of Helicoverpa armigera were dyed by loading with fluo-5N and treated with 12i, the free calcium released in endoplasmic reticulum indicated the target of compound 12i is RyRs or IP3Rs. The activation of RyRs by natural ryanodine completely blocked the calcium release induced by 12i, which indicated that RyRs in the central neurons of H. armigera third-instar larvae is the possible target of compound 12i.
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- 2016
11. Synthesis, insecticidal activities and SAR of novel phthalamides targeting calcium channel
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Na Yang, Zheng-Ming Li, Wei Chen, Youwei Chen, Yuxin Li, Hai-Bin Song, Yingying Wan, Jingbo Liu, Li Pan, and Lixia Xiong
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Insecticides ,Stereochemistry ,Clinical Biochemistry ,Molecular Conformation ,Pharmaceutical Science ,chemistry.chemical_element ,Moths ,Calcium ,Crystallography, X-Ray ,Endoplasmic Reticulum ,Biochemistry ,Structure-Activity Relationship ,Mythimna separata ,Drug Discovery ,Structural isomer ,Animals ,Molecular Biology ,Diamondback moth ,biology ,Ryanodine receptor ,Endoplasmic reticulum ,Calcium channel ,Organic Chemistry ,biology.organism_classification ,Amides ,Lepidoptera ,chemistry ,Larva ,Molecular Medicine ,Calcium Channels ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
In order to find novel and environmental friendly insecticides targeting the ryanodine receptor, three series of novel phthalamides containing heptafluoroisopropyl group, low fluorine atoms group and non-fluorine group were designed and synthesized. 35 novel structures of three series were obtained. Insecticidal activities of title compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of title compounds showed moderate to high activities at the tested concentration. The structure–activity relationship (SAR) was discussed in detail. During synthesizing title compounds B8, C7, D1, D9 and D12, their corresponding positional isomers (B8′, C7′, D1′, D9′ and D12′) were afforded, and their structures were confirmed by 2D NMR. The calcium-imaging technique was also applied to investigate the effects of compounds B2, B10, C4 and C5 on the intracellular calcium ion concentration ([Ca2+]i), which indicated that they released stored calcium ions from endoplasmic reticulum, which denoted that some compounds are potential modulators of the insect ryanodine receptor (RyR).
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- 2014
12. Chiral Dicarboxamide Scaffolds Containing a Sulfiliminyl Moiety as Potential Ryanodine Receptor Activators
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Guiping Wu, Hai-Bin Song, Sha Zhou, Lixia Xiong, Zhehui Jia, Zheng-Ming Li, Na Yang, and T.Y. Yan
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Insecticides ,Stereochemistry ,Stereoisomerism ,Diamines ,Moths ,Structure-Activity Relationship ,Animals ,Moiety ,Structure–activity relationship ,Diamondback moth ,Molecular Structure ,biology ,Chemistry ,Ryanodine Receptor Calcium Release Channel ,Biological activity ,General Chemistry ,Carbon-13 NMR ,biology.organism_classification ,Calcium Channel Agonists ,Drug Design ,Larva ,Proton NMR ,Insect Proteins ,General Agricultural and Biological Sciences ,Chirality (chemistry) - Abstract
To search for new environmentally benign insecticides with high activity, low toxicity, and low residue, novel chiral configurations introduced into dicarboxamide scaffolds containing N-cyano sulfiliminyl moieties were first studied. Four series of phthalamides with sulfur-containing side chains were designed, synthesized, and evaluated against oriental armyworm (Pseudaletia separata Walker) and diamondback moth (Plutella xylostella (L.)) for their insecticidal activities. All structures were characterized by (1)H NMR, (13)C NMR, and HRMS (or elemental analysis), and their configurations were confirmed by optical polarimetry. The biological assessment indicated that some title compounds exhibited significant insecticidal activities. For oriental armyworm, these stereoisomers exerted different impacts on biological activity following the sequence (Sc, Ss) ≥ (Sc, Rs) ≫ (Rc, Ss)(Rc, Rs), and carbon chirality influenced the activities more strongly than sulfur. Compounds Ia and IIa reached as high an activity as commercial flubendiamide, with LC50 values of 0.0504 and 0.0699 mg L(-1), respectively, lower than that of flubendiamide (0.1230 mg L(-1)). For diamondback moth, the sequence of activity was (Sc, Ss)(Sc, Rs), and the sulfur chirality influenced the activities more greatly than carbon. Compound IIe exhibited even higher activity than flubendiamide, whereas Ie and Ic,d reached the activity of the latter. The results indicated that the improvement of insecticidal activity probably required a coordination of both carbon and sulfur chirality. Comparative molecular field analysis calculation indicated that stereoisomers with Sc configurations containing strong electron-withdrawing groups such as as CN are important in maintaining the high activity. The chiral scaffolds containing the N-cyano sulfiliminyl moiety are also essential for high larvicidal activity. Some title compounds could be considered as potential candidates for ryanodine receptor activators.
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- 2014
13. Design, Synthesis, and Biological Evaluation of Various α-Substituted Benzylpyrroles Based on the Structures of Insecticidal Chlorfenapyr and Natural Pyrrolomycins
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Qiaoqiao Ma, Yuxiu Liu, Qingmin Wang, Pengxiang Zhang, Lixia Xiong, and Yongqiang Li
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Models, Molecular ,Insecticides ,Alkylation ,Stereochemistry ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,chemistry.chemical_compound ,Pyrethrins ,Animals ,Moiety ,Pyrroles ,IC50 ,Ovum ,Pyrrole ,Diamondback moth ,Trifluoromethyl ,Molecular Structure ,Mycelium ,biology ,Fungi ,General Chemistry ,Chlorfenapyr ,biology.organism_classification ,Oxime ,Fungicides, Industrial ,Lepidoptera ,Culicidae ,chemistry ,Larva ,Tetranychidae ,General Agricultural and Biological Sciences - Abstract
On the basis of the structures of chlorfenapyr and dioxapyrrolomycin, a series of 2-benzylpyrroles with a hydroxyl, an alkyloxy, an acyloxy, an alkylsulfanyl, or an oxime moiety at the α-position of benzyl were designed and synthesized. Their insecticidal, acaricidal, and fungicidal activities were extensively investigated. The structure-activity relationship showed that benzylpyrroles bearing shorter α-alkyloxy groups gave better activities against most of the insect species; the alkylation of pyrrole usually gave increased activity. Among all compounds, (4-bromo-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) (5'j) exhibited the most outstanding insecticidal activities against oriental armyworm (IC₅₀=10 mg L⁻¹), diamondback moth (0.07 mg L⁻¹), corn borer (50 mg L⁻¹), and mosquito (0.04 mg L⁻¹), which are very close to those of chlorfenapyr (5, 0.08,25, and0.025 mg L⁻¹, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.
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- 2014
14. Synthesis and biological activities of 2,3-dihydro-1,3,4-oxadiazole compounds and its derivatives as potential activator of ryanodine receptors
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Lixia Xiong, Na Yang, Bao-Lei Wang, Yongqiang Li, Yunyun Zhou, Zheng-Ming Li, Yuxin Li, and Fengjuan Di
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Insecticides ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Oxadiazole ,Moths ,Biochemistry ,Structure-Activity Relationship ,chemistry.chemical_compound ,Mythimna separata ,Calcium imaging ,Drug Discovery ,Animals ,Molecular Biology ,Oxadiazoles ,Diamondback moth ,biology ,Ryanodine receptor ,Activator (genetics) ,Endoplasmic reticulum ,Calcium channel ,Organic Chemistry ,Ryanodine Receptor Calcium Release Channel ,biology.organism_classification ,chemistry ,Drug Design ,Molecular Medicine - Abstract
A series of novel 2,3-dihydro-1,3,4-oxadiazoles containing N-pyridylpyrazole carboxamides moieties were obtained by applying a new synthetic route. Their insecticidal tests against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to excellent activities at the testing concentrations. In particular, compound 6a showed 40% larvicidal activities against oriental armyworm at 1 mg/L, while 7a against diamondback was 100% at 0.01 mg/L. Calcium imaging results demonstrated that 6a, 6d and 7a stimulated a transient elevation in [Ca2+]i in the absence of external calcium after the central neurons dye loading with fluo-3 AM, implying that these novel compounds were potential activators of the ligand-gated calcium channel on the endoplasmic reticulum.
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- 2014
15. Synthesis and Insecticidal Evaluation of Novel N-Pyridylpyrazolecarboxamides Containing an Amino Acid Methyl Ester and Their Analogues
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Zheng-Ming Li, Yunyun Zhou, Yuxin Li, Lixia Xiong, Mingzhen Mao, Fengjuan Di, Yongqiang Li, Xiu-Lan Zhang, Hai-Bin Song, and Qiao-Xia Liu
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chemistry.chemical_classification ,Insecticides ,Diamondback moth ,Molecular Structure ,biology ,Chemistry ,Plutella ,Esters ,General Chemistry ,Moths ,biology.organism_classification ,Amino acid ,Structure-Activity Relationship ,chemistry.chemical_compound ,Mythimna separata ,13c nmr spectroscopy ,Larva ,Proton NMR ,Animals ,Organic chemistry ,Bioassay ,ortho-Aminobenzoates ,Amino Acids ,General Agricultural and Biological Sciences ,Methyl acrylate - Abstract
On the basis of the commercial insecticide chlorantraniliprole, a series of novel N-pyridylpyrazolecarboxamides containing an amino acid methyl ester and their analogues were designed and synthesized. Their chemical structures were established on the basis of corresponding (1) H NMR spectroscopy, (13)C NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction analysis. The insecticidal activities of the new compounds against oriental armyworm ( Mythimna separata ) and diamondback moth ( Plutella xylostella ) were evaluated. The results of bioassays indicated that most of the compounds showed moderate to high activities at the tested concentration, of which the compounds 6 containing a methyl acrylate substructure had excellent larvicidal activity; for example, 6a displayed 100% larvicidal activity against P. xylostella at the concentration of 0.005 mg/L, whereas the activities of both compounds 6g and 6h against M. separata were 100% at 2.5 mg/L. The calcium imaging technique experiment results showed that novel compound 6 could elevate the calcium concentration in the cytoplasm. Furthermore, this study also provided evidence that compound 6h activates inositol 1,4,5-trisphosphate (IP3) sensitive intracellular calcium release channels in the endoplasmic reticulum of Spodoptera exigua third-instar larva neurons.
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- 2014
16. Synthesis, insecticidal activities and structure-activity relationship study of dual chiral sulfilimines
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Xiangde Meng, Yi Ma, Sha Zhou, Hongjian Song, Ru-Yi Jin, Zheng-Ming Li, Lixia Xiong, Yu Zhao, and Yongtao Xie
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0301 basic medicine ,Insecticides ,Flubendiamide ,Stereochemistry ,Substituent ,Chemistry Techniques, Synthetic ,Field analysis ,01 natural sciences ,Catalysis ,Inorganic Chemistry ,03 medical and health sciences ,chemistry.chemical_compound ,Structure-Activity Relationship ,Drug Discovery ,Moiety ,Structure–activity relationship ,Animals ,Physical and Theoretical Chemistry ,Benzene ,Molecular Biology ,010405 organic chemistry ,Organic Chemistry ,Biological activity ,Stereoisomerism ,General Medicine ,0104 chemical sciences ,Lepidoptera ,030104 developmental biology ,chemistry ,Imines ,Information Systems - Abstract
To investigate the “methyl” impact on bioactivity of sulfiliminyl dicarboxamides, a total of 16 novel N-cyano and N-trifluoroacetyl sulfiliminyl dicarboxamides containing m-heptafluoroisopropylated aromatic amino moiety were studied. Two series of sulfiliminyl substituents were designed, synthesized and evaluated against oriental armyworm (Pseudaletia separata Walker) for their insecticidal activities. Their chemical structures were established by corresponding $$^{1}\hbox {H}$$ NMR, HRMS and optical polarimetry. Bioassay results revealed that some of the title compounds showed potent insecticidal activities against oriental armyworm. Notably, compounds IIa, IIIa, IVa exhibited 100% activity at $$1\, \hbox {mg}\,\hbox {L}^{-1}$$ , in particular, IIa showed a comparable control efficacy to that of the commercial product flubendiamide. The SAR of these N-cyano sulfiliminyl isomers can be summarized as follows (Sc, Ss) $$\ge $$ (Sc, Rs), while the N-trifluoroacetyl sulfiliminyl isomers is (Sc, Rs) $$\ge $$ (Sc, Ss). Comparative molecular field analysis indicated that an electropositive substituent, $$\hbox {CH}_{3}$$ group in the benzene ring was very important for the improvement in biological activity. These results could hold promise for novel chiral sulfiliminyl RyR regulators.
- Published
- 2016
17. Design, Synthesis, and Insecticidal Evaluation of New Pyrazole Derivatives Containing Imine, Oxime Ether, Oxime Ester, and Dihydroisoxazoline Groups Based on the Inhibitor Binding Pocket of Respiratory Complex I
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Qingmin Wang, Hongjian Song, Yongqiang Li, Lixia Xiong, Na Yang, and Yuxiu Liu
- Subjects
Insecticides ,Insecta ,Stereochemistry ,Imine ,Helicoverpa armigera ,Pyrazole ,Structure-Activity Relationship ,chemistry.chemical_compound ,Oximes ,Animals ,Organic chemistry ,Binding site ,Tebufenpyrad ,Aphid ,Binding Sites ,Electron Transport Complex I ,Molecular Structure ,biology ,Esters ,General Chemistry ,biology.organism_classification ,Oxime ,chemistry ,Drug Design ,Insect Proteins ,Pyrazoles ,Imines ,General Agricultural and Biological Sciences ,Aphis craccivora ,Ethers - Abstract
On the basis of complex I receptor protein binding site and commercial tebufenpyrad and tolfenpyrad, four series of novel pyrazole-5-carboxamides containing imine, oxime ether, oxime ester, and dihydroisoxazoline were designed and synthesized via the key intermediate 4-chloro-3-ethyl-N-(4-formylbenzyl)-1-methyl-1H-pyrazole-5-carboxamide. The structures of target compounds were confirmed by ¹H NMR and high-resolution mass spectrum (HRMS). The results of bioassays indicated that the target compounds possessed good-to-excellent activities against a broad spectrum of insects such as cotton bollworm (Helicoverpa armigera), spider mite (Tetranychus cinnabarinus), bean aphid (Aphis craccivora), and mosquito (Culex pipiens pallens), but gave different structure-activity relationships for each species. Compounds containing imine showed high insecticidal activity against cotton bollworm. Especially, stomach activity of compounds 5-1c was 60% at 11 mg kg⁻¹. The compounds also had good activities against bean aphid and mosquito. The foliar contact activity of compounds 5-1a, 5-1b, 5-1e, 5-3c, and 5-3d against bean aphid were 90, 100, 90, 90, and 90%, respectively, at 200 mg kg⁻¹. The activity of compound containing dihydroisoxazoline moiety (5-4) against mosquito was 60% at 1 mg kg⁻¹, which was near that of tebufenpyrad. The introduction of dihydroisoxazoline structure (5-4) was advantageous to improve the activity of the compound against adult mites compared with other structures; the miticidal activity of 5-4- against adult mites was 60% at 50 mg kg⁻¹.
- Published
- 2013
18. Synthesis and insecticidal activities of 2,3-dihydroquinazolin-4(1H)-one derivatives targeting calcium channel
- Author
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Zheng-Ming Li, Yunyun Zhou, Lixia Xiong, Youwei Chen, Yuxin Li, Qiaoxiao Liu, Qi Feng, Hai-Bin Song, Fengjuan Di, and Duoyi Wang
- Subjects
Insecticides ,Patch-Clamp Techniques ,Stereochemistry ,Clinical Biochemistry ,Molecular Conformation ,Pharmaceutical Science ,chemistry.chemical_element ,Spodoptera ,Calcium ,Crystallography, X-Ray ,Biochemistry ,Structure-Activity Relationship ,Mythimna separata ,Calcium imaging ,Drug Discovery ,Exigua ,Animals ,Structure–activity relationship ,Patch clamp ,Molecular Biology ,Quinazolinones ,Neurons ,biology ,Voltage-dependent calcium channel ,Chemistry ,Calcium channel ,Organic Chemistry ,Calcium Channel Blockers ,biology.organism_classification ,Lepidoptera ,Larva ,Molecular Medicine ,Calcium Channels - Abstract
A series of compounds containing dihydroquinazolinone moiety was designed and synthesized. Amine bridge part was changed in comparison with known anthranilic diamides insecticides. Their insecticidal activities against oriental armyworm (Mythimna separata) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compounds 5a and 5k showed 80% larvicidal activities against oriental armyworm at the concentration of 5mg/L. The present study also explored the possible effects of target compounds on the high voltage-gated calcium channel and the calcium channels in the endoplasmic reticulum in the central neurons isolated from the third instar larvae of Spodoptera exigua using whole-cell patch clamp and calcium imaging technique. The results showed that compound 5a activated the high voltage-gated calcium channel in the central neurons of S. exigua weakly. The peak currents only increased by 6% of the initial value at the end of the 10-min recording after treated with 0.22μM 5a, while chlorantraniliprole has an opposite effect. The effects of 5a on the intracellular calcium ion concentration ([Ca(2+)]i) in neurons were well investigated. The experimental results indicated that these novel compounds have different mechanism compared with chlorantraniliprole.
- Published
- 2013
19. Synthesis, Insecticidal Activities, and SAR Studies of Novel Pyridylpyrazole Acid Derivatives Based on Amide Bridge Modification of Anthranilic Diamide Insecticides
- Author
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Zheng-Ming Li, Youwei Chen, Lixia Xiong, Sha Zhou, Bao-Lei Wang, Ji-Feng Zhang, Yongqiang Li, Yu Zhao, Yi Ma, and Hong-Wei Zhu
- Subjects
Diamide ,Insecticides ,Insecta ,Diamondback moth ,Molecular Structure ,biology ,Stereochemistry ,Anthranilic diamide ,Isoxazoles ,General Chemistry ,biology.organism_classification ,Structure-Activity Relationship ,chemistry.chemical_compound ,chemistry ,Thiourea ,Beet armyworm ,Drug Design ,Amide ,Proton NMR ,Animals ,Bioassay ,Structure–activity relationship ,Organic chemistry ,Biological Assay ,General Agricultural and Biological Sciences - Abstract
Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, (1)H NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
- Published
- 2013
20. Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Amide and Sulfonate Groups Based on the Sulfonylurea Receptor Protein Binding Site for Diflubenzuron and Glibenclamide
- Author
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Ziwen Wang, Yuxiu Liu, Lixia Xiong, Qingmin Wang, Yongqiang Li, and Ranfeng Sun
- Subjects
Insecticides ,Magnetic Resonance Spectroscopy ,Stereochemistry ,Benzoylurea ,Moths ,Sulfonylurea Receptors ,Glibenclamide ,Structure-Activity Relationship ,chemistry.chemical_compound ,Amide ,Glyburide ,medicine ,Animals ,Structure–activity relationship ,Organic chemistry ,Diamondback moth ,Molecular Structure ,biology ,Phenylurea Compounds ,General Chemistry ,Nuclear magnetic resonance spectroscopy ,biology.organism_classification ,Diflubenzuron ,chemistry ,Larva ,Sulfonylurea receptor ,General Agricultural and Biological Sciences ,Protein Binding ,medicine.drug - Abstract
On the basis of the sulfonylurea receptor (SUR) protein binding site for diflubenzuron and glibenclamide, 15 new benzoylphenylureas containing amide and sulfonate groups were designed and synthesized. Their structures were characterized by (1)H nuclear magnetic resonance (NMR) and elemental analysis [or high-resolution mass spectrometry (HRMS)]. The larvicidal activities of the new compounds against oriental armyworm and diamondback moth were evaluated. Compound II-3 showed nearly the same level of insecticidal activity against oriental armyworm as commercial insecticide flucycloxuron and, thus, emerged as a new lead compound for the development of new benzoylurea insecticides.
- Published
- 2013
21. Synthesis and insecticidal evaluation of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position
- Author
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Yuxin Li, Qiao-Xia Liu, Yunyun Zhou, Xiu-Lan Zhang, Mingzhen Mao, Yongqiang Li, Zheng-Ming Li, and Lixia Xiong
- Subjects
Insecticides ,Pyridines ,Stereochemistry ,Clinical Biochemistry ,Substituent ,Pharmaceutical Science ,chemistry.chemical_element ,Moths ,Calcium ,Biochemistry ,chemistry.chemical_compound ,Mythimna separata ,Calcium imaging ,Drug Discovery ,Animals ,Molecular Biology ,biology ,Ryanodine receptor ,Endoplasmic reticulum ,Calcium channel ,Organic Chemistry ,Ryanodine Receptor Calcium Release Channel ,biology.organism_classification ,Amides ,chemistry ,Cytoplasm ,Larva ,Pyrazoles ,Molecular Medicine - Abstract
In an attempt to search for potent insecticides targeting the ryanodine receptor (RyR), a series of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position were designed and synthesized. Their insecticidal activities of target compounds against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentrations. In particular, compound 6l and 6o showed 86% larvicidal activities against Plutella xylostella at the concentration of 0.1mg/L, while the activity of compound 6h against Mythimna separate was 80% at 1mg/L. The calcium imaging technique was applied to investigate the effects of some title compounds on the intracellular calcium ion concentration ([Ca(2+)](i)), experimental results demonstrated that compound 6h stimulates a transient elevation in [Ca(2+)](i) in the absence of external calcium after the central neurons dye loading with fluo-3 AM. However, when the central neurons were dyed with fluo-5N and incubated with 2-APB, [Ca(2+)]i decreased transiently by treated of compound 6h. All of the calcium imaging technique experiments demonstrated that these novel compounds deliver calcium from endoplasmic reticulum to cytoplasm, which proved that the title compounds were the possible activators of insect RyR.
- Published
- 2013
22. Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Acylthiourea and Acylurea
- Author
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Ji-Feng Zhang, Jun-Ying Xu, Yuxin Li, Yi Ma, Zheng-Ming Li, Bao-Lei Wang, Lixia Xiong, and Yongqiang Li
- Subjects
Diamide ,Insecticides ,Diamondback moth ,biology ,Culex pipiens pallens ,Chemistry ,Stereochemistry ,Anthranilic diamide ,Plutella ,General Chemistry ,Moths ,biology.organism_classification ,Culex ,Structure-Activity Relationship ,Mythimna separata ,Mosquito larvae ,Drug Design ,Larva ,Animals ,ortho-Aminobenzoates ,General Agricultural and Biological Sciences - Abstract
Two series of anthranilic diamides containing acylthiourea and acylurea linkers were designed and synthesized, with changed length and flexibility of the linkers to compare to known anthranilic diamide insecticides. In total, 26 novel compounds were synthesized, and all compounds were characterized by (1)H nuclear magnetic resonance and high-resolution mass spectrometry. Their insecticidal activities against oriental armyworm (Mythimna separata), mosquito larvae (Culex pipiens pallens), and diamondback moth (Plutella xylostella) were evaluated. The larvicidal activities against oriental armyworm indicated that the introduction of acylthiourea into some structures could retain their insecticidal activity; 8 of the 15 compounds (13a-13e, 14a-14e, and 15a-15e) exhibited 100% larvicidal activity at 10 mg/L. However, the introduction of acylurea decreased the insecticidal activity; only 3 of the 11 compounds (17a-17k) exhibited 100% larvicidal activity at 200 mg/L. The whole-cell patch-clamp technique indicated that compound 13b and chlorantraniliprole exhibited similar effects on the voltage-gated calcium channel. The calcium-imaging technique was also applied to investigate the effects of compounds 13b and 15a on the intracellular calcium ion concentration ([Ca(2+)](i)), which indicated that they released stored calcium ions from endoplasmic reticulum. Experimental results denoted that several new compounds are potential activators of the insect ryanodine receptor (RyR).
- Published
- 2012
23. Design, Synthesis, and Insecticidal Activity of Novel Pyrazole Derivatives Containing α-Hydroxymethyl-N-benzyl Carboxamide, α-Chloromethyl-N-benzyl Carboxamide, and 4,5-Dihydrooxazole Moieties
- Author
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Yuxiu Liu, Lixia Xiong, Na Yang, Hongjian Song, Qingmin Wang, and Yongqiang Li
- Subjects
Insecticides ,medicine.drug_class ,Stereochemistry ,Carboxamide ,Moths ,Pyrazole ,Helicoverpa armigera ,chemistry.chemical_compound ,Spider mite ,medicine ,Animals ,Hydroxymethyl ,Tebufenpyrad ,Diamondback moth ,Molecular Structure ,biology ,General Chemistry ,biology.organism_classification ,Lepidoptera ,Culex ,chemistry ,Aphids ,Drug Design ,Pyrazoles ,Tetranychidae ,General Agricultural and Biological Sciences ,Aphis craccivora - Abstract
On the basis of commercial insecticides tebufenpyrad and tolfenpyrad, two series of novel pyrazole-5-carboxamides containing α-hydroxymethyl-N-benzyl or α-chloromethyl-N-benzyl and pyrazoles containing 4,5-dihydrooxazole moieties were designed and synthesized via the key intermediate 2-amino-1-(4-substituted) phenyl ethanol. The structures of target compounds were confirmed by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS), and their activities against cotton bollworm (Helicoverpa armigera), diamondback moth (Plutella xylostella), bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens), and spider mite (Tetranychus cinnabarinus) were tested. The results of bioassays indicated that compounds containing α-chloromethyl-N-benzyl and compounds containing 4,5-dihydrooxazole showed high insecticidal activity against cotton bollworm. Especially, stomach activities of compounds Ij, Il, and IIe were 60% at 5 mg kg(-1). Moreover, the target compounds exhibited high selectivity between cotton bollworm and diamondback moth, although both of them belong to the order Lepidoptera. Although the activities against diamondback moth were at a low level, some of the target compounds exhibited antifeedant activity. The compounds also had good activities against bean aphid, mosquito, and spider mite. The foliar contact activity of compounds Ic, Id, Ie, and IIf against bean aphid were 95, 95, 100, and 95%, respectively, at 200 mg kg(-1). The miticidal and ovicidal activities of compound IIi against spider mite were both 95% at 200 mg kg(-1). Furthermore, a trivial change at 4-position of pyrazole ring would lead to great changes in properties and activities, which can easily be deduced by comparing the activities of compounds in series I (4-chloro-pyrazole compounds) with corresponding compounds in series II (4-hydro-pyrazole compounds), especially from the miticidal and ovicidal activities of Ii and IIi against spider mite.
- Published
- 2012
24. Design, Synthesis, and Insecticidal Evaluation of New Benzoylureas Containing Isoxazoline and Isoxazole Group
- Author
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Yuxiu Liu, Qingmin Wang, Lixia Xiong, Ranfeng Sun, and Yongqiang Li
- Subjects
Insecticides ,Diamondback moth ,biology ,Stereochemistry ,Isoxazoles ,General Chemistry ,Moths ,Pesticide ,biology.organism_classification ,Structure-Activity Relationship ,chemistry.chemical_compound ,Culicidae ,chemistry ,Design synthesis ,Flucycloxuron ,Drug Design ,Insect growth regulator ,Animals ,Urea ,Organic chemistry ,Structure–activity relationship ,Isoxazole ,General Agricultural and Biological Sciences - Abstract
Twenty-two new benzoylphenylureas containing isoxazoline and the isoxazole group were designed and synthesized, and their structures were characterized by (1)H NMR and elemental analysis (or HRMS). The larvicidal activities against Oriental armyworm, mosquito, and diamondback moth of the new compounds were evaluated. Compounds I-1 and III-1 showed nearly the same level of insecticidal activity against Oriental armyworm as commercial insecticide Flucycloxuron and surprisingly exhibited much higher larvicidal activities against diamondback moth than Flucycloxuron.
- Published
- 2011
25. Design and Synthesis of Benzoylphenylureas with Fluorinated Substituents on the Aniline Ring as Insect Growth Regulators
- Author
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Lixia Xiong, Yonglin Zhang, Qingmin Wang, Ranfeng Sun, and Yuxiu Liu
- Subjects
Insecticides ,Molecular Structure ,Stereochemistry ,Phenylurea Compounds ,media_common.quotation_subject ,General Chemistry ,Insect ,Moths ,Biology ,Ring (chemistry) ,Juvenile Hormones ,Culex ,Structure-Activity Relationship ,chemistry.chemical_compound ,Aniline ,chemistry ,Drug Design ,Larva ,Insect growth regulator ,Animals ,Structure–activity relationship ,Organic chemistry ,General Agricultural and Biological Sciences ,media_common - Abstract
Enormous numbers of synthetic fluorine-containing compounds have been widely used in a variety of fields, especially in drug and pesticide design. To find novel insect growth regulators, a series of benzoylphenylureas with fluorinated substituents were designed and synthesized. The results of larvicidal activities of those novel fluoro-substituted benzoylphenylureas against oriental armyworm and mosquito revealed that most compounds exhibited excellent activities. It is worth mentioning that compounds 3 and 6 exhibited higher activities against oriental armyworm and mosquito than commercial Hexaflumuron. It can be further seen that the insecticidal activities would increase significantly by introducing fluorinated substituents into the structure of the designed benzoylphenylureas.
- Published
- 2011
26. Synthesis and Insecticidal Activities of Novel Anthranilic Diamides Containing Modified N-Pyridylpyrazoles
- Author
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Ming-Zhong Wang, Lixia Xiong, Zheng-Ming Li, Zhili Liu, Qi Feng, and Yongqiang Li
- Subjects
Diamide ,Insecticides ,Diamondback moth ,Molecular Structure ,biology ,Stereochemistry ,Chemistry ,Chemical structure ,Plutella ,Isoxazoles ,General Chemistry ,Moths ,Carbon-13 NMR ,biology.organism_classification ,Structure-Activity Relationship ,Mythimna separata ,Proton NMR ,Animals ,Pyrazoles ,Structure–activity relationship ,General Agricultural and Biological Sciences - Abstract
In order to look for novel insecticides targeting the ryanodine receptor, four new series of anthranilic diamides containing modified N-pyridylpyrazoles were designed and synthesized. All of the compounds were characterized and confirmed by (1)H NMR, (13)C NMR, and HRMS. The single crystal structure of 10c was determined by X-ray diffraction. Their insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella) indicated that most of the compounds showed moderate to high activities at the tested concentration, while compound 19 showed comparable higher activity at the concentration of 0.125 mg/L. The preliminary structure-activity relationship (SAR) was discussed.
- Published
- 2010
27. Synthesis and Insecticidal Activities and SAR Studies of Novel Benzoheterocyclic Diacylhydrazine Derivatives
- Author
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Qingmin Wang, Zhiqiang Huang, Quanmin Cui, Kaiyun Wang, Qiqi Zhao, Fuchun Bi, Lixia Xiong, and Ziwen Wang
- Subjects
Insecticides ,General Chemistry ,Biology ,Combinatorial chemistry ,Lepidoptera ,Structure-Activity Relationship ,chemistry.chemical_compound ,Culicidae ,Hydrazines ,chemistry ,Larva ,Botany ,Animals ,Benzopyrans ,Benzofuran ,General Agricultural and Biological Sciences - Abstract
Two series of novel N'-tert-butyl-N'-substituted benzoyl-N-2,3-dihydrobenzofuran-5-carbohydrazide derivatives were synthesized, their activities and different insecticidal action modes for different Lepidopteral larvicidal assays were evaluated carefully. The results of larvicidal activities against oriental armyworm and mosquito indicate that different benzoheterocyclic analogues of diacylhydrazide have different structure-activity relationships according to the types and patterns of substitution on the benzene, and 3,5-dimethyl is the most efficient substituent for benzoheterocyclic diacylhydrazine. Among them, N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-N-2,4-dimethyl-2,3-dihydrobenzofuran-5-carbohydrazide (Ii) stood out as the best compound with high activity. Compound Ii and N'-tert-butyl-N'-(3,5-dimethylbenzoyl)-N-5-chloro-6-chromanecarbohydrazide (F) have higher contact activities against diamond-back moth and stomach toxicities against cotton bollworm than ANS-118 and JS-118. Compound F has higher contact toxicity against beet armyworm than ANS-118 and JS-118. These results indicate that different heterocycles and substitutents on the benzene rings of benzoheterocyle moiety not only influence the larvicidal activities strongly but also are very sensitive to the insecticidal action modes for different Lepidopteran larvicidal insects.
- Published
- 2009
28. Synthesis, Larvicidal Activities and Antifungal Activities of Novel Chlorantraniliprole Derivatives and Their Target in the Ryanodine Receptor
- Author
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Yonghong Li, Min Luo, Shu-Jing Yu, Dequn Sun, Xiao Zhang, Jin Wang, Changyan Hu, Qichao Chen, and Lixia Xiong
- Subjects
Antifungal ,Insecticides ,Antifungal Agents ,medicine.drug_class ,Stereochemistry ,Pharmaceutical Science ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,lcsh:Organic chemistry ,Drug Discovery ,medicine ,ryanodine receptor ,Animals ,ortho-Aminobenzoates ,anthranilic diamides ,Physical and Theoretical Chemistry ,insecticidal activities ,Binding Sites ,Indoxacarb ,Ryanodine receptor ,Organic Chemistry ,Fungi ,Ryanodine Receptor Calcium Release Channel ,molecular docking ,chlorantraniliprole ,Lepidoptera ,Fungicide ,Biochemistry ,chemistry ,Chemistry (miscellaneous) ,Larva ,Molecular Medicine ,antifungal activities - Abstract
In order to identify novel chlorantraniliprole derivatives as potential insecticides or fungicides, 25 analogues of chlorantraniliprole were synthesized. The insecticidal activities against oriental armyworm and the antifungal activities against five typical fungi of these derivatives were tested. Compounds 2u, 2x and 2y exhibited good activities against oriental armyworm, especially compounds 2u and 2x which showed higher larvicidal activities than indoxacarb. Moreover, all of the tested compounds exhibited activities against five typical fungi. The Ki values of all synthesized compounds were calculated using AutoDock4. The relationship between the Ki values and the results of insecticidal activities against oriental armyworm further indicated that the membrane-spanning domain protein of the ryanodine receptor might contain chlorantraniliprole binding sites.
- Published
- 2015
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29. Insecticidal activities of chiral N-trifluoroacetyl sulfilimines as potential ryanodine receptor modulators
- Author
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Sha Zhou, Yucheng Gu, Ming Liu, Changchun Wu, Yu Zhao, Zhehui Jia, Baolei Wang, Lixia Xiong, Na Yang, and Zhengming Li
- Subjects
Insecticides ,Diamondback moth ,Flubendiamide ,biology ,Molecular Structure ,Chemistry ,Ryanodine receptor ,Stereochemistry ,Plutella ,Ryanodine Receptor Calcium Release Channel ,Stereoisomerism ,General Chemistry ,Optically active ,Moths ,biology.organism_classification ,chemistry.chemical_compound ,Structure-Activity Relationship ,Asymmetric carbon ,Proton NMR ,Animals ,Insect Proteins ,Imines ,General Agricultural and Biological Sciences - Abstract
This is the first report of novel chiral N-trifluoroacetyl sulfilimines during research for new environmentally benign and ecologically safe novel insecticides with new modes of action. Four series of phthalamides containing 20 new structures were designed, synthesized, and evaluated against oriental armyworm (Pseudaletia separata Walker) and diamondback moth (Plutella xylostella (L.)) for their insecticidal activities. The target compounds were established by corresponding (1)H NMR, HRMS (or elemental analysis), X-ray diffraction analysis, and optical polarimetry. Introduction of chiral N-trifluoroacetyl sulfiliminyl moieties into the new scaffolds showed that some target compounds possessed impressive activities as commercial flubendiamide. These N-trifluoroacetyl sulfilimines exhibited the sequence of activity against oriental armyworm as (Sc, Ss) ≥ (Sc, Rs) ≫ (Rc, Rs)(Rc, Ss), in which the chiral carbon influenced the activities stronger than sulfur. For diamondback moth, compounds If, IIa, and IIc exhibited even stronger activity than flubendiamide; especially If displayed a death rate of 100% at 10(-6) mg L(-1), much better than that of flubendiamide (0% at 10(-4) mg L(-1)). Comparative molecular field analysis calculation indicated that stereoisomers with Sc configurations containing more electronegative group as COCF3 are favorable to the insecticidal activity. The present work demonstrated that chiral N-trifluoroacetyl sulfilimines can be considered as potential insect ryanodine receptor modulators. From the standpoint of molecular design, it was concluded that the conventional second methyl group in the aliphatic amido side chain of dicarboxamide might not be a requisite in our research on novel sulfiliminyl insecticides.
- Published
- 2014
30. Synthesis, structure and insecticidal activities of some novel amides containing N-pyridylpyrazole moeities
- Author
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Wei-Li Dong, Lixia Xiong, Zheng-Ming Li, and Jing-Ying Xu
- Subjects
Insecticides ,crystal structure ,N-pyridylpyrazole ,synthesis ,Stereochemistry ,Pharmaceutical Science ,Crystal structure ,Moths ,Article ,Analytical Chemistry ,insecticidal activity ,Mythimna separata ,chemistry.chemical_compound ,Structure-Activity Relationship ,Amide ,Drug Discovery ,Exigua ,High activity ,Organic chemistry ,Bioassay ,Animals ,Physical and Theoretical Chemistry ,Low toxicity ,biology ,Molecular Structure ,Chemistry ,Organic Chemistry ,Plutella ,biology.organism_classification ,amide ,Amides ,Chemistry (miscellaneous) ,Drug Design ,Molecular Medicine ,Pyrazoles - Abstract
In our search for environmentally benign insecticides with high activity, low toxicity and low residue, a novel series of amides containing N- pyridylpyrazole moieties were designed and synthesized. The structures of the title compounds were characterized and confirmed by 1H-NMR and elemental analysis. Furthermore, the structure of compound 7l was determined by single crystal X-ray diffraction. The preliminary bioassay tests showed that some of them exhibited good insecticidal activities against Mythimna separata Walker, Plutella xylostella (Linnaeus, 1758) and Laphygma exigua Hübner.
- Published
- 2012
31. Synthesis, crystal structure and biological activity of novel anthranilic diamide insecticide containing alkyl ether group
- Author
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Zheng-Ming Li, Fang Li, Li-na Peng, Jun Tong, Yu Zhao, Li-ping Xu, Lixia Xiong, and Yongqiang Li
- Subjects
Methyl Ethers ,Insecticides ,Magnetic Resonance Spectroscopy ,Anthranilic diamide ,Ether ,Crystal structure ,Catalysis ,Inorganic Chemistry ,chemistry.chemical_compound ,Structure-Activity Relationship ,X-Ray Diffraction ,Drug Discovery ,Exigua ,Organic chemistry ,Animals ,ortho-Aminobenzoates ,Physical and Theoretical Chemistry ,Molecular Biology ,Diamide ,biology ,Molecular Structure ,Organic Chemistry ,Maleates ,Plutella ,Biological activity ,General Medicine ,Isoxazoles ,biology.organism_classification ,Alkyl ether ,Lepidoptera ,chemistry ,Larva ,Single crystal ,Information Systems ,Ethers - Abstract
In searching for environmentally benign insecticides with high activity, low toxicity and low residue, two series of novel anthranilic diamide containing methyl ether and isopropyl ether group were designed and synthesized. All of the compounds were characterized by (1)H NMR spectroscopy, (13)C NMR spectroscopy and elemental analysis. The single crystal structure of 19j was determined by X-ray diffraction. The insecticidal activities of the new compounds were evaluated. The results showed that some compounds exhibited excellent insecticidal activities against Lepidoptera pests. Among this series, compound, 18l showed 100 % larvicidal activity against Mythimna separate Walker, Plutella xylostella Linnaeus and Laphygma exigua Hubner at the test concentration, which was equal to the available chlorantraniliprole.
- Published
- 2012
32. Design, synthesis, structure, and acaricidal/insecticidal activity of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety
- Author
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Qingmin Wang, Hai-Bin Song, Liu Zhihui, Lixia Xiong, Yongqiang Li, and Qiong Lei
- Subjects
Insecticides ,genetic structures ,Stereochemistry ,chemistry.chemical_compound ,Spider mite ,Bioassay ,Organic chemistry ,Moiety ,Animals ,Spiro Compounds ,Furans ,Acaricides ,Oxalates ,biology ,Molecular Structure ,Biological activity ,General Chemistry ,biology.organism_classification ,chemistry ,Larva ,Proton NMR ,Piperidine ,General Agricultural and Biological Sciences ,Tetronic acid ,Selectivity ,Tetranychidae - Abstract
A series of novel spirocyclic tetronic acid derivatives containing an oxalyl moiety was designed and synthesized via the key intermediate 3-(2,4,6-trimethyl)-2-oxo-1-oxaspiro[4.4]-decyl-3-en-4-ol. The target compounds were identified by (1)H NMR and elemental analysis or high-resolution mass spectrum (HRMS). The results of bioassays indicated that most of the target compounds possessed excellent acaricidal activities against carmine spider mite larvae and eggs. Especially, diisopropylamino oxalyl compound 7g and piperidine oxalyl compound 7h were 1.4- and 2.3-fold as high as the activities of commercial Spiromesifen, respectively, against spider mite eggs. Moreover, most of the target compounds exhibited insecticidal activities against Lepidoptera pest. Interestingly, compounds containing alkylamino-substituted oxalyl moiety showed obvious selectivity between spider mite larvae and eggs because the activities against spider mite eggs of 7g and 7h were 25-fold those against spider mite larvae, whereas Spiromesifen had no significant differences in these activities. This meant that the introduction of an oxalyl moiety to spirocyclic tetronic acid might lead to novel biological activity characteristics.
- Published
- 2011
33. Design, synthesis and insecticidal activity of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety
- Author
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Lixia Xiong, Qingmin Wang, Yongqiang Li, and Qiqi Zhao
- Subjects
Aphid ,Insecticides ,Diamondback moth ,Magnetic Resonance Spectroscopy ,biology ,Stereochemistry ,Imine ,Plutella ,Stereoisomerism ,General Chemistry ,Moths ,biology.organism_classification ,Toxicology ,chemistry.chemical_compound ,chemistry ,Bioassay ,Moiety ,Animals ,Pyrazoles ,General Agricultural and Biological Sciences ,Aphis craccivora - Abstract
A series of novel phenylpyrazoles containing a 2,2,2-trichloro-1-alkoxyethyl moiety were designed and synthesized via the key intermediate 5-trichloroethylideneimino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-alkylsulfenylpyrazole (5). The addition reaction of the imine 5 was closely related with the nature of the alcohol. The target compounds were confirmed by (1)H NMR and elemental analysis. The results of bioassays indicated that the target compounds possessed excellent activities against a broad spectrum of insects such as bean aphid (Aphis craccivora), mosquito (Culex pipiens pallens) and diamondback moth (Plutella xylostella). Especially, the foliar contact activity against bean aphid of compound 7h at 2.5 mg kg(-1) was 89%, the larvacidal activity against mosquito of compound 6c at 2.5 microg kg(-1) was 100%, the activity against diamondback moth of compound 7a at 5 mg kg(-1) was 87%, and all of these activities were much higher than the contrast ethiprole. The results of insecticidal activities showed that the two pairs of enantiomers 7d-1 and 7d-2 gave activities without distinctive difference, and it was the similar situation for 7e-1 and 7e-2. Interestingly, the target compounds exhibited high selectivity between diamondback moth and oriental armyworm, both of which are of the order Lepidoptera. The 2,2,2-trichloro-1-alkoxyethyl moiety was essential for high insecticidal activities.
- Published
- 2010
34. Synthesis, larvicidal activity, and SAR studies of new benzoylphenylureas containing oxime ether and oxime ester group
- Author
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Maoyun Lü, Qingmin Wang, Lixia Xiong, Yongqiang Li, and Ranfeng Sun
- Subjects
Insecticides ,Stereochemistry ,Clinical Biochemistry ,Molecular Conformation ,Pharmaceutical Science ,Moths ,Biochemistry ,Chemical synthesis ,chemistry.chemical_compound ,Structure-Activity Relationship ,Beet armyworm ,Drug Discovery ,Insect growth regulator ,Oximes ,Bioassay ,Organic chemistry ,Structure–activity relationship ,Animals ,Molecular Biology ,Diamondback moth ,biology ,Phenylurea Compounds ,fungi ,Organic Chemistry ,Esters ,Pesticide ,biology.organism_classification ,Oxime ,Culicidae ,chemistry ,Larva ,Molecular Medicine ,Ethers - Abstract
A series of new structural benzoylphenylureas (BPUs) containing oxime ether and oxime ester group were designed and synthesized. The larvicidal activities against Oriental armyworm and mosquito of these benzoylphenylureas were evaluated and the result of bioassay displayed specific structure-activity relationship (SAR). Most of the compounds exhibited excellent larvicidal activities against Oriental armyworm and mosquito. Interestingly, some compounds showed different structure-activity relationship towards diamondback moth, beet armyworm, and corn borer although three tested insects all belong to the same insect order.
- Published
- 2010
35. Novel phthalamides containing sulfiliminyl moieties and derivatives as potential ryanodine receptor modulators
- Author
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Yuanyuan Qiao, Yuxin Li, Yongqiang Li, Yu Zhao, Bao-Lei Wang, Zhehui Jia, Zheng-Ming Li, Lixia Xiong, Tao Yan, and Sha Zhou
- Subjects
Insecticides ,Stereochemistry ,Phthalic Acids ,chemistry.chemical_element ,Moths ,Spodoptera ,Calcium ,Endoplasmic Reticulum ,Biochemistry ,Calcium in biology ,Structure-Activity Relationship ,Beet armyworm ,Botany ,Animals ,Bioassay ,Sulfones ,Physical and Theoretical Chemistry ,Neurons ,Diamondback moth ,Molecular Structure ,biology ,Ryanodine receptor ,Calcium channel ,Organic Chemistry ,Ryanodine Receptor Calcium Release Channel ,biology.organism_classification ,Amides ,chemistry ,Drug Design ,Larva ,Benzamides ,Insect Proteins - Abstract
To tackle the serious challenge of insect resistance and stricter environmental regulations, innovating a new eco-friendly insecticide is urgently required. A series of new phthalamides containing sulfiliminyl and sulfoximinyl moieties were designed and synthesized. In total, 30 new structures were characterized by 1H NMR spectra and HRMS. The bioassay results indicated that some title compounds exhibited excellent insecticidal activities against oriental armyworm (Pseudaletia separata Walker) and diamondback moth (Plutella xylostella (L.)). 4a showed the same larvicidal level as that of commercial flubendiamide as a control. 7a and 9a exhibited outstanding activity against diamondback moth. The LC50 values of 7a and 9a were 8.33 × 10(−8) and 2.34 × 10(−8) mg L(−1), respectively, lower than that of flubendiamide (1.25 × 10(−7) mg L(−1)). The effects of 4a, 7a and 9a on intracellular calcium of neurons from the beet armyworm (Spodoptera exigua) indicated that these title compounds activate the receptor-operated calcium channel. The calcium ions efflux from the calcium store on endoplasmic reticulum (ER) when treated with novel compounds. The results of CoMFA calculation showed that N-cyanosulfilimines and N-trifluoroacetylsulfoximines might be of importance to the larvicidal activity. The present work demonstrated that structures containing sulfiliminyl and sulfoximinyl moieties can be considered as lead compounds for the development of new insect ryanodine receptor modulators.
- Published
- 2014
36. Synthesis, Larvicidal Activities and Antifungal Activities of Novel Chlorantraniliprole Derivatives and Their Target in the Ryanodine Receptor.
- Author
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Qichao Chen, Lixia Xiong, Min Luo, Jin Wang, Changyan Hu, Xiao Zhang, Shujing Yu, Yonghong Li, and Dequn Sun
- Subjects
- *
CHLORANTRANILIPROLE , *CHEMICAL derivatives , *RYANODINE receptors , *INSECTICIDES , *FUNGICIDES , *ARMYWORMS , *BINDING sites - Abstract
In order to identify novel chlorantraniliprole derivatives as potential insecticides or fungicides, 25 analogues of chlorantraniliprole were synthesized. The insecticidal activities against oriental armyworm and the antifungal activities against five typical fungi of these derivatives were tested. Compounds 2u, 2x and 2y exhibited good activities against oriental armyworm, especially compounds 2u and 2x which showed higher larvicidal activities than indoxacarb. Moreover, all of the tested compounds exhibited activities against five typical fungi. The Ki values of all synthesized compounds were calculated using AutoDock4. The relationship between the Ki values and the results of insecticidal activities against oriental armyworm further indicated that the membrane-spanning domain protein of the ryanodine receptor might contain chlorantraniliprole binding sites. [ABSTRACT FROM AUTHOR]
- Published
- 2015
- Full Text
- View/download PDF
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