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PEST MANAGEMENT SCIENCE · 2018 ·Vol. 75 ·期 4 ·1045-1055 · IF 3.249

Synthesis and bioactivity studies of sex pheromone analogs of the diamond back moth, Plutella xylostella

An-jia Wang,Kai-Xin Zhang,Yu-lin Gao,Ai-zhen Weng,Liu-yang Wang,Yun-hui Zhang,Zhi Zhang,Dong-mei She,Jun Ning,Xiang-dong Mei

BACKGROUND Diamondback moth, Plutella xylostella L., is a very important pest of cruciferous vegetables causing excessive economic losses worldwide. Bioactivities of halo-, diazo-, and cyclopropane acetates of P. xylostella sex pheromone have been evaluated using electrophysiology and enzyme inhibition assays. RESULTS A total of 23 sex pheromone analogs of P. xylostella were designed and synthesized and the result shows that (11 Z )-hexadec-11-en-1-yl 2,2,2-trifluoroacetate, (11 Z )-hexadec-11-en-1-yl 2,2,3,3,3-pentafluoropropanoate, and (11 Z )-hexadec-11-en-1-yl trifluoromethanesulfonate elicited potential inhibitory effects at all doses tested in the electrophysiology and enzyme inhibition assays. Interference of locating the sex pheromone source was found strongest when these three analogs were mixed with the sex pheromone at a 10:1 ratio. In addition, field test showed that the rate of mating disruption was over 90% when (11 Z )-hexadec-11-en-1-yl 2,2,2-trifluoroacetate or (11 Z )-hexadec-11-en-1-yl 2,2,3,3,3-pentafluoropropanoate was mixed with the sex pheromone at a 10:1 ratio. CONCLUSION Two sex pheromone antagonists were screen out by electrophysiology, enzyme inhibition assays, wind tunnel and field tests. We believe that these antagonists could be used to establish a novel eco-friendly measure to control P. xylostella and provide evidence for clarifying the specific functions and molecular mechanisms of sex pheromone antagonists. © 2018 Society of Chemical Industry

研究领域: 昆虫学 · 农业科学 · 有机化学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF HETEROCYCLIC CHEMISTRY · 2022 ·Vol. 60 ·期 1 ·145-155 · IF 2.035

Structural design and insecticidal activity of 1,3,4-oxadiazole-ring containing pyridylpyrazole-4-carboxamides

Abdalla Khallaf,Ping Wang,Shuping Zhuo,Hongjun Zhu,Hui Liu

The insecticidal activity of 1,3,4-oxadiazole-ring containing pyridylpyrazole-4-carboxamides against diamondback ( Plutella xylostella ) and noctuid ( Spodoptera frugiperda ) moths were evaluated. Only substitutions on the 1,3,4-oxadiazole moiety dictated bioreactivity, with 8q2 m -CF 3 Ph being the most effective against Plutella xylostella, showing 80%–93% mortality at a concentration of 0.5–500 μg ml −1 while the others remained inactive or less active (highest mortality being 63%). The larvicidal activity against Spodoptera frugiperda was inferior compared with that of Plutella xylostella , with the highest mortality being 33%. A crystal of 8q5 was obtained and analyzed, revealing the effects of intramolecular H-bonds and intermolecular π  π interactions.

研究领域: 昆虫学 · 有机化学 · 农药科学
✓ 已验证 DOI 高影响因子
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PEST MANAGEMENT SCIENCE · 2022 ·Vol. 78 ·期 12 ·5358-5365 · IF 4.462

Enhanced and sustained pesticidal activity of a graphene-based pesticide delivery system against the diamondback moth Plutella xylostella

Jianfeng Liu,Yi Luo,Xuefeng Jiang,Guangjun Sun,Saijie Song,Maofa Yang,Jian Shen

Background Traditional abamectin (Abm) formulations have several shortcomings, such as low water solubility, burst release behavior, poor photostability, and short persistence periods, which decrease their pesticidal activity and the risks they pose to the environment. Nanomaterial-based pesticide delivery systems (PDSs) provide new strategies for the efficient and safe application of pesticides. Here, we developed Abm-loaded graphene oxide (Abm/GO) as a PDS for the sustained release of Abm, which shows enhanced control efficacy against Plutella xylostella . Results The hydrophobic Abm molecule was effectively loaded on GO nanocarrier by a physisorption method, which formed a uniform and stable Abm/GO nanoformulation. GO possesses high adsorption capacity and can effectively load Abm. The Abm/GO nanoformulation shows enhanced water dispersion stability and can remain stable during a 2-year storage period in contrast to the water-insoluble Abm. In addition, the Abm/GO nanoformulation exhibits sustained pesticide release behavior and possesses significantly improved anti-ultraviolet properties. Thus, the Abm/GO nanoformulation shows superior pesticidal activity compared with Abm. Abm/GO showed negligible toxicity to maize seedlings, and its GO nanocarrier can reduce the cytotoxicity of Abm to A549 cells. Conclusion GO-based PDSs can effectively overcome the disadvantages of traditional pesticides, such as their insolubility, burst release behavior, instability, and short persistence period. GO shows much future promise in agriculture in light of its industrialization potential. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

研究领域: 农业科学 · 害虫防治 · 纳米材料应用
✓ 已验证 DOI 高影响因子
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2024 · IF 1.3

Design, Synthesis and Insecticidal Activity of Novel meta-Diamide Compounds Containing Methoxy Group

Liang Limei,Wu Minghui,Huang Pengmian,Liu Jiyong

This work is based on the precursor compound cyproflanilide and designs a series of methoxy containing meta-diamine compounds. By replacing the fluorine atom on the phenyl ring in cyproflanilide with methoxy group, 17 derivatives (12a-12q) were obtained with yields ranging from 46 to 92%, which were characterized by high-resolution mass spectrometry, and nuclear magnetic resonance (1H and 13C) spectroscopy and infrared. The insecticidal activities were evaluated against the Plutella xylostella and Spodoptera frugiperda. Compound N-(3-((2-bromopropane-4-(perfluoropropan-2-yl))-6-(trifluoromethyl)phenyl)methoxyphenyl)-N-(cyclopropylmethyl)-6-fluoronicotinamide (12q) showed significant insecticidal activity against the Plutella xylostella with a mortality rate of 97.67% at a concentration of 1 mg L-1. It also exhibited moderate activity against the Spodoptera frugiperda at a concentration of 0.1 mg L-1, which can be used as a template for structure modification to obtain higher insecticidal activity.

研究领域: 农药化学 · 有机合成 · 农业昆虫学
✓ 已验证 DOI 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2018 · IF 3.412

Synthesis of Piperine Analogs Containing Isoxazoline/Pyrazoline Scaffold and Their Pesticidal Bioactivities

Ruige Yang,Min Lv,Hui Xu

In continuation of our program to discover new potential pesticidal agents, thirty-one piperine analogs containing isoxazoline/pyrazoline scaffold were prepared, and confirmed by infrared spectra, proton/carbon-13 nuclear magnetic resonance spectra, and high-resolution mass spectra. The structures of compounds VIIb and VIIIc were further determined by 1H–1H COSY spectra. Especially the configuration of compound VIIIc was unambiguously confirmed by single-crystal X-ray diffraction. Their pesticidal activities were evaluated against three serious and typically crop-threatening agricultural pests, Tetranychus cinnabarinus Boisduval (spider mite), Mythimna separata Walker (Oriental armyworm), and Plutella xylostella Linnaeus (diamondback moth). Compounds VIIIb and VIIIc exhibited greater than 40-fold more potent acaricidal activity than the lead compound piperine against T. cinnabarinus. Notably, compounds VIa–c exhibited more pronounced oral toxicity against P. xylostella than toosendanin; compounds VIb and VIc displayed more promising growth inhibitory activity against M. separata than toosendanin. It demonstrated that the methylenedioxy and isoxazoline scaffolds were important for the oral toxicity and growth inhibitory activity against P. xylostella and M. separata, respectively; the ethylenedioxy and isoxazoline scaffolds were vital for the acaricidal activity against T. cinnabarinus. Moreover, compounds VIb, VIIf, and VIIIc showed very low toxicity against NRK-52E cells.

研究领域: 有机化学 · 农药学 · 生物化学
✓ 已验证 DOI PubMed 高影响因子
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Biology-Basel · 2025 ·Vol. 14 ·期 12 ·1746 · IF 3.5

Identification and Functional Characterization of the Leg-Enriched Chemosensory Protein PxylCSP9 in Plutella xylostella (Lepidoptera: Plutellidae)

Shuhui Fu,Fangyuan Li,Xizhong Yan,Chi Hao

Phytophagous insects rely on highly evolved chemosensory systems to recognize plant cues, which guide essential behaviors such as feeding and oviposition. While the antennal chemosensory functions of Plutella xylostella are well-studied, little is known about the role of its legs in detecting host plant chemicals. This study systematically identified and characterized chemosensory-related genes expressed in the legs of P. xylostella using transcriptome data. A total of 114 leg-expressed chemosensory genes were identified, with PxylCSP9 showing high expression in legs and strong, broad-spectrum binding to key cruciferous plant volatiles. Leg chemosensory proteins, particularly PxylCSP9, play an important role in the chemical perception. Plutella xylostella , a major pest of cruciferous vegetables, depends predominantly on chemoreception to locate host plants. Legs are crucial in insect chemical perception, particularly during close-range and contact chemoreception. However, the molecular basis underlying the chemosensory repertoire in P. xylostella legs remains elusive. To address this, we sequenced chemosensory-related genes in diamondback moth legs. Sequencing identified 32 odorant binding protein (OBP), 18 chemosensory protein (CSP), 26 odorant receptor (OR), 20 gustatory receptor (GR), 15 ionotropic receptor (IR), and 3 sensory neuron membrane protein (SNMP) genes. Comparative analysis with antennal transcriptome data revealed three CSPs, seven ORs, and two GRs newly identified in the legs. Transcriptome analysis showed higher fragments per kilobase of transcript per million mapped reads values for CSPs than for other chemosensory-related gene families. Furthermore, qRT-PCR confirmed the highest expression of PxylCSP9 in the legs, suggesting its role in perceiving external compounds. Fluorescent binding assays revealed high binding affinity of PxylCSP9 for several host plant semiochemicals. Molecular docking predicted a hydrophobic binding pocket in PxylCSP9 with Met11, Leu13, and Leu43 frequently participating in ligand interactions. Our findings indicate that leg-enriched PxylCSP9 is pivotal for host plant recognition during close-range chemoreception, suggesting its potential as a molecular target for precision management through behavior-based strategies.

CAS / MDL: 65664-81-5 67-56-1
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PEST MANAGEMENT SCIENCE · 2025 · IF 3.8

Generation of alpaca-derived nanobody fragments as potential insecticidal agents against Plutella xylostella via cadherin toxin binding region-based screening

Cheng Shen,Guochen Li,Tianyi Han,Naila Ilyas,Meng He,Ziyan Huang,Xiao Zhang,Chongxin Xu,Chengyu Chen,Wei Chen,Xianjin Liu,Qing Zhu,Yuan Liu

BACKGROUND Bacillus thuringiensis (Bt) toxins are widely used in pest control owing to their effectiveness as bioinsecticides. However, the extensive use of these toxins has resulted in the development of resistance in various pest populations, including Plutella xylostella , which is a significant pest of cruciferous crops. This increasing resistance highlights the need for alternative insecticidal strategies that can complement or replace traditional methods. RESULTS A novel approach involves using insect cadherin receptors to screen for nanobodies with potential insecticidal activity that selectively target the toxin binding region of the Plutella xylostella cadherin toxin via phage display technology. Through three rounds of panning with a natural alpaca nanobody phage display library, we identified nanobody B1, which specifically binds to the CR9-CR11 region of Plutella xylostella cadherin. This nanobody significantly inhibited the binding of Cry1Ac toxin to cadherin, a key factor in insect susceptibility to the toxin. In bioassays, the application of soluble B1 protein (80 μg/cm 2 ) resulted in 25 ± 4.5% mortality in Plutella xylostella larvae. Histological examination of the midgut tissue revealed substantial damage to the epithelial layer, supporting the bioassay findings. Enzymatic hydrolysis assays demonstrated that, while B1 exhibited some stability, it showed limited resistance to enzymatic degradation in vitro . This could be a significant contributing factor to the low insecticidal activity of B1. CONCLUSION This study proposes a novel strategy for insecticide development based on the application of nanobodies to target cadherins within the midgut of Plutella xylostella . The identification of nanobody B1 presents a novel approach to circumvent resistance mechanisms in pest populations, overcoming resistance mechanisms in pest populations, and thus advancing sustainable pest management practices. Furthermore, these findings establish a foundation for designing alternative insecticidal proteins that could diminish the reliance on traditional formulations. © 2025 Society of Chemical Industry.

CAS / MDL: 7177-48-2 8063-07-8
研究领域: 昆虫学 · 生物技术 · 害虫防治 · 分子生物学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Unraveling Key Amino Acid Residues Crucial for PxGSTs1 Conferring Benzoylurea Insecticide Resistance in Plutella xylostella

Yifan Li,Ruichi Li,Hainan Shao,Zhuoda Liu,Xueyi Gao,Zhen Tian,Yalin Zhang,Jiyuan Liu

The widespread use of benzoylurea insecticides (BUs) has led to significant resistance issues in various agricultural pests. Previous studies have demonstrated that the overexpression of sigma glutathione S-transferase 1 (PxGSTs1) can confer resistance to novaluron in Plutella xylostella; however, the underlying molecular mechanism remains unclear. This study investigates the role of glutathione S-transferase PxGSTs1 in mediating resistance to BUs in P. xylostella. Using a combination of RNA interference and transgenic Drosophila models, we demonstrated that the overexpression of PxGSTs1 significantly contributes to the resistance against BUs. Functional assays revealed that PxGSTs1 binds to these insecticides with varying affinities. Structural analysis through homology modeling and molecular docking identified the importance of hydrogen bonding and pi–pi stacking in resistance mechanisms. Site-directed mutagenesis confirmed the critical role of Ser65 and Tyr97 in these interactions. Our findings provide a molecular basis for the development of novel BUs and inform strategies for managing BU resistance in P. xylostella.

研究领域: 昆虫学 · 分子生物学 · 害虫管理
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Agricultural Science & Technology · 2022 · IF 0

Discovery of Indoloazepinone Analogues as Novel Antiviral, Antiphytopathogenic Fungus, and Insecticidal Agents

Yanke Hao,Hongfu He,Pan Zhou,Kaikai Niu,Hongjian Song,Yuxiu Liu,Jingjing Zhang,Deyu Hu,Qingmin Wang,Baoan Song

Aldisine alkaloid has a wide range of biological activities and is also the core skeleton of a variety of natural products, but its poor solubility affects its efficacy. In order to improve its solubility and biological activity, a series of indoloazepinone derivatives containing oxime ether, oxime ester, hydrazone, and ester moieties were designed and synthesized, and their antiviral, fungicidal, and larvicidal activities were evaluated. The solubility of these indoloazepinone derivatives improved in comparison with that of aldisine, and most of these compounds showed good antiviral activities against pepper mild mottle virus (PMMoV), among which the 4-chlorobenzoyl oxime ester derivative 5i showed the highest protection, curative, and inactivation activities in vivo (inhibition rate 61 ± 4.1, 60 ± 5.3, and 74 ± 4.2% at 500 mg/L, respectively), which was comparable to that of ningnanmycin (59 ± 2.2, 58 ± 0.7, and 81 ± 4.8% at 500 mg/L, respectively). Compound 5i (the rat acute oral toxicity test, LD50 > 2000 mg/kg) emerged as a promising candidate for anti-PMMoV drug. Most of these compounds have broad-spectrum fungicidal activities, and 5a and 5f showed selectively fungicidal activities against Phytophthora capsici. In addition, these compounds also showed good larvicidal activities against Plutella xylostella and Culex pipiens pallens.

研究领域: 药理学 · 化学 · 植物病理学 · 昆虫学 · 病毒学
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2021 · IF 5.268

Emamectin benzoate nanogel suspension constructed from poly(vinyl alcohol)-valine derivatives and lignosulfonate enhanced insecticidal efficacy

Da-xia Zhang,Rui Wang,Haichao Cao,Jian Luo,Tong-fang Jing,Bei-xing Li,Wei Mu,Feng Liu,Youming Hou

To reduce the negative impact of nanopesticide carriers of on the environment, a greener nanodelivery system is necessary. Nanogels are nontoxic and degradable carriers, however, the potential of nanogels for delivering pesticides has not been proven. In this study, poly(vinyl alcohol)-valine, an ecofriendly polymer, was synthesized and used to fabricate emamectin benzoate nanogel suspension (EB NS). The nanoformulation showed favorable stability at low temperature, high temperature or one year storage, and in water with different hardnesses. The retention of the EB NS solution on leaves was higher than that of an EB emulsifiable concentrate (EC) by approximately 9% at a concentration of 10 mg L −1 . The half-life of EB nanogels under Ultra Violet irradiation was prolonged by 3.3-fold. Moreover, the bioactivity of the EB NS against Plutella xylostella was higher than that of the EB EC. These advantages resulted in a relatively long duration of pest control. The response of nanogels to laccase , a digestive enzyme in the digestive tract of lepidopteran pests, enables pesticide release on demand. Nanogels have the advantages of being ecofriendly carriers, exhibiting higher utilization, and prolonged pest control periods, and they have a brilliant future in pesticide delivery.

研究领域: 农业科学 · 纳米技术 · 环境科学 · 农药化学
✓ 已验证 DOI PubMed 高影响因子
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