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JOURNAL OF ASIA-PACIFIC ENTOMOLOGY · 2024 · IF 1.1

Knockdown of the cap ‘n’ collar isoform C gene increases the susceptibility of Agrotis ipsilon to chlorantraniliprole and phoxim

Qing-Hua Xiao,Wu-Ye Li,Jin Zhang,Jia-Min Yu,Dong-Yang Liu,Jiang-Nan Peng,Mao-Ye Li,Su Liu

In insects, the transcription factor cap ‘n’ collar isoform C (CncC) plays a critical role in the regulation of multiple genes involved in insecticide detoxification. Knockdown of CncC genes leads to increased susceptibility to different types of insecticides in several insect species. However, the CncC gene has not yet been fully characterized in the black cutworm Agrotis ipsilon , a notorious insect pest that causes severe damage to field crops. In this study, the CncC gene (designated AiCncC ) was identified from A. ipsilon . Exposure to a median lethal concentration (LC 50 ) of chlorantraniliprole (CAP) or phoxim (PHO) strongly increased the expression of AiCncC . Silencing of AiCncC by RNA interference significantly increased the susceptibility of A. ipsilon larvae to both insecticides. Moreover, CncC/Maf binding sites were predicted in the putative promoters of two glutathione S -transferase (GST) genes ( AiGSTe1 and AiGSTu1 ) involved in the detoxification of CAP and PHO. The transcription levels of AiGSTe1 and AiGSTu1 were dramatically decreased by silencing AiCncC . These findings indicate that AiCncC is associated with CAP and PHO susceptibility through the regulation of GST genes.

CAS / MDL: 50-18-0
研究领域: 昆虫学 · 分子生物学 · 害虫防治
✓ 已验证 产品关联 DOI 高影响因子
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Vietnam Journal of Chemistry · 2023 ·Vol. 61 ·期 2 ·204-209 · IF 0.9

Copper promoted, directed sulfenylation and phenoxylation of benzamide C−H bonds

Nguyen Van Vinh Ha,Nguyen Thi Thu Ha,Ong Ngoc Khanh,Dinh Truc Phuong,Ho Thanh Nhat,Nguyen Thanh Tung

Herein we reported a method for copper pivalate mediated, directed functionalization of ortho C−H bonds in (2-methylthio)aniline benzamides. Diaryl disulfides were used for thiolation, while successful phenoxylation was obtained with phenol as the coupling agent. Our report marks a rare example for flexible transformation of benzamide C(sp 2 )−H bonds into the corresponding unsymmetrical diaryl ethers and thioethers.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI 高影响因子
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INTERNATIONAL JOURNAL OF PHARMACEUTICS · 2021 · IF 5.875

Phase solubility diagrams and energy surface calculations support the solubility enhancement with low hygroscopicity of Bergenin: 4-Aminobenzamide (1: 1) cocrystal

Hongji Liu,Jinju Nie,H.C. Stephen Chan,Hailu Zhang,Liang Li,Hongqing Lin,Henry H.Y. Tong,Ande Ma,Zhengzheng Zhou

Herein, we reported a new bergenin : 4-aminobenzamide ( BGN-4AM ) cocrystal with significantly enhanced solubility and low hygroscopicity probed from two aspects such as phase solubility diagrams and theoretical calculations. Compared with anhydrous BGN , BGN-4AM solubilities in water and different buffer solutions (pH = 1.2, 4.5, 6.8) increase significantly. It is noted that BGN-4AM solubility in pH = 6.8 buffer solution presents 32.7 times higher than anhydrous BGN . Interestingly, BGN-4AM (0.31 ± 0.07%) showcases lower hygroscopicity than anhydrous BGN (9.31 ± 0.16%). The predicted and experimental solubilities agree with each other when considering solubility product ( K sp ) and solution binding constant ( K 11 ) in phase solubility diagrams, indicating the solution complexes formation occurs. Further crystal surface-water interactions and Bravais, Friedel, Donnay-Harker (BFDH) analyses based on Density Functional Theory with dispersion correction (DFT- d ) methods support the enhanced solubility. The water probe demonstrates an average interaction energy of −6.48 kcal/mol on the 002 plane of BGN-4AM , and only −5.47 kcal/mol on the 011 plane of BGN monohydrate. The lower lattice energy of BGN-4AM guarantees its lower hygroscopicity than BGN monohydrate. BGN-4AM with enhanced solubility and low hygroscopicity can be a potential candidate for further formulation development.

研究领域: 药剂学 · 理论化学
✓ 已验证 DOI 高影响因子
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Heliyon · 2024 · IF 3.4

The adsorption mechanism and optimal dosage of walnut shell biochar for chloramphenicol

Caixia Sun,Gangjun Wang,Yuhong Liu,Ke Bei,Guoguang Yu,Weiran Zheng,Yuxue Liu

Biochar derived from biomass pyrolysis has proven to be an excellent material for pesticide adsorption and can be used as soil amendment for pesticide non-point pollution. However, the adsorption and desorption mechanisms for certain biochar and pesticide are still unclear. In this study, we investigated the properties of biochar derived from walnut (Juglans regia L.) shell (WSB), and used batch equilibrium method to investigate the adsorption and desorption behavior for chlorantraniliprole (CAP). The physical-chemical analysis showed that there were mainly lignin charcoal of alkyl carbon, methoxyl carbon, aromatic carbon, and carboayl carbon as the primary carbon compounds of WSB. The π - π electron donor acceptor interaction, electrostatic interaction, and hydrogen bond were the primary adsorption mechanisms of the WSB adsorption. Batch equilibrium study under 298 K showed that WSB application in the soil significantly improved the adsorption ability for CAP, and the adsorption behavior was a mono-layer adsorption process as Langmuir model fitted the adsorption isotherm data better than the Freundlich model. While Freundlich model analysis showed that WSB addition to the soil changed the isothermal adsorption line from the S style to the L style. The spontaneous degree reaction of sorbents from strong to weak was in the following order: 5%-WSB >7%-WSB >10%-WSB >1%-WSB >3%-WSB > soil > WSB, and the maximum application effect was achieved at 5 % (m/m) WSB dosage mixed with the soil. Therefore, we considered that WSB addition in soil increased its CAP adsorption capacity, and 5 % (m/m) WSB application was the best choice for CAP pollution control. These data will contribute to the adsorption mechanism and the optimal use dosage of WSB for CAP pollution control.

研究领域: 环境科学 · 农业科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHEMICAL PHYSICS LETTERS · 2025 · IF 3.1

Pressure-induced structural phase transition of energetic material 4-aminobenzamide

Tingting Yan,Han Li,Dongyang Xi,Lei Sun,Linan Liu,Dinghan Jin

This study investigated the behavior of energetic material 4-aminobenzamide (4-AMBZA; C 7 H 8 N 2 O) under high pressure utilizing Raman spectroscopy. Notable alterations were detected in the Raman spectra within 2.6–7.8 GPa, suggesting 4-AMBZA experiences a phase transition. Continued pressure caused the crystal to show a tendency towards amorphization. When the pressure is released, the amorphization phenomenon persists. Variations of N H bending vibration (amide II), C N stretching vibration (amide III), and C O stretching vibration (amide I) indicate that phase transition arises from the twisting and rearrangement of hydrogen-bonded networks. Hirshfeld surface energy were conducted to analyze intermolecular interactions within 4-AMBZA.

研究领域: 材料科学 · 化学
✓ 已验证 DOI 高影响因子
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SYNTHESIS-STUTTGART · 2019 ·Vol. 51 ·期 21 ·4048-4065 · IF 2.867

Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide

Rui-Xiang Wang,Zhuang Fang,Guanyinsheng Qiu,Wenlin Xie,Jin-Biao Liu

The copper-catalyzed synthesis of 3-vinylisocoumarin-1-imine is reported. The transformation proceeds smoothly with good yields in THF and the regioselectivity was determined by a O-nucleo­philic 6-endo cyclization. Studies on the mechanism indicate that copper trifluoroacetate serves as a Lewis acid, and the use of vinyl-connected 2-alkynylbenzamide is important for this O-nucleophilic 6-endo cyclization.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2017 · IF 4.849

Palladium-Catalyzed Decarboxylative ortho-Acylation of Benzamides with α-Oxocarboxylic Acids

Kun Jing,Jia-Ping Yao,Zhong-Yuan Li,Qi-Li Li,Hao-Sheng Lin,Guan-Wu Wang

A palladium-catalyzed decarboxylative ortho-acylation of tertiary benzamides with α-oxocarboxylic acids by weak O-coordination has been described. This reaction proceeds smoothly with a high monoacylation selectivity, affording ortho-acylated benzamides in moderate to good yields. When secondary benzamides are employed as the substrates, the formed ortho-acylated benzamides undergo further intramolecular cyclization to provide isoindolinone derivatives. In addition, several transformations of the synthesized ortho-acylated benzamides into a diversity of synthetically valuable products have been demonstrated.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI 高影响因子
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WATER RESEARCH · 2023 · IF 12.8

Occurrence, stability and cytotoxicity of halobenzamides: A new group of nitrogenous disinfection byproducts in drinking water

Jinxiu Lou,Lu Yin,Zhu Meng,Shuangxi Fang,Xiangliang Pan

Exploring disinfection byproducts (DBPs) with adverse health effects in drinking water is a constant challenge. Halobenzamides (HBZAMs) are suspected to be a new group of nitrogenous DBPs but have not been reported in drinking water to date. In this study, by coupling SPE and UPLC‒MS/MS, a sensitive method was established to detect eight HBZAMs in drinking water with recoveries and limits of detection of 80–103% and 0.01–0.04 ng/L, respectively. Subsequently, distinct fragments of HBZAMs were extended to the development of a pseudotargeted method for the analysis of the fourteen HBZAMs that were speculated and lack chemical standards. Using the developed method, eight HBZAMs were quantified in ten drinking water samples with concentrations ranging from 2.4 to 7.2 ng/L and a detection frequency of 100%, among which five HBZAMs were stable with half-lives over 72 h under real chlorine levels. Twelve HBZAMs without standards were identified in three to ten drinking water samples with comparable levels. The cytotoxicity of eight quantified HBZAMs in CHO-K1 cells varied with disparity, in which the cytotoxicity of 3,5-DBBZAM was over 10-fold higher than that of aliphatic dichloroacetamide. Considering their diversity, toxicity and stability, the occurrence of HBZAMs in drinking water deserves attention.

研究领域: 环境科学 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PEST MANAGEMENT SCIENCE · 2023 · IF 4.1

Unclassified glutathione-S-transferase AiGSTu1 confers chlorantraniliprole tolerance in Agrotis ipsilon

Hao-Lan Yang,Jia-Min Yu,Fu Cao,Wu-Ye Li,Bin Li,Xiao Lei,Shi-Guang Li,Su Liu,Mao-Ye Li

BACKGROUND Chlorantraniliprole (CAP) is a diamide insecticide with high efficacy against many pest insects, including the black cutworm, Agrotis ipsilon . Agrotis ipsilon is a serious pest causing significant yield losses in crops. Glutathione- S -transferases (GSTs) belong to a family of metabolic enzymes that can detoxify a wide range of pesticides. However, little is known about the functions of GSTs in CAP tolerance in A. ipsilon . RESULTS A cDNA sequence (designated AiGSTu1 ) encoding an unclassified GST was identified from A. ipsilon . AiGSTu1 is highly expressed during the 3 rd -instar larval and the pupal stages. Most of the mRNA transcripts were found in larval Malpighian tubules. Exposure to CAP strongly enhanced AiGSTu1 expression, GST activity, hydrogen peroxide (H 2 O 2 ) and malondialdehyde levels in larvae. H 2 O 2 treatment upregulated the transcription level of AiGSTu1 , suggesting that CAP-induced oxidative stress may activate AiGSTu1 expression. The activity of recombinant AiGSTu1 was inhibited by CAP in a dose-dependent manner. Metabolism assay results demonstrated that AiGSTu1 is capable of depleting CAP. Overexpression of AiGSTu1 enhanced the tolerance of Escherichia coli cells to H 2 O 2 and the oxidative stress inducer, cumene hydroperoxide. Silencing of AiGSTu1 by RNA interference increased the susceptibility of A. ipsilon larvae to CAP. CONCLUSION The findings of this study provide valuable insights into the potential role of AiGSTu1 in CAP detoxification and will improve our understanding of CAP tolerance in A. ipsilon . © 2023 Society of Chemical Industry.

研究领域: 昆虫学 · 分子生物学 · 农药科学
✓ 已验证 DOI PubMed 高影响因子
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Environmental Science-Nano · 2024 · IF 5.8

Eco-friendly chitosan base chlorantraniliprole nano-pesticides for effective control of Chilo suppressalis (Walker) through bidirectional transport

Ao Liang,Yunzheng Zhang,Xiang Xu,Hao Wang,Changwei Gong,Jie Hu,Xiangsong Li,Jizhi Yang,Anchun Peng,Xuegui Wang

Chilo suppressalis is a major pest that severely impacts rice production in China. However, the widespread use of insecticides has resulted in the development of resistance in C. suppressalis. The advancement of nanotechnology offers promising prospects for enhancing insecticide formulations and improving their efficacy. This study designed a pH-responsive release system composed of γ-PGA and chitosan (CS) loaded with chlorantraniliprole (CLAP). The synthesized CLAP-loaded nanoparticles had an average particle size of approximately 39.67 nm and a loading efficiency of 38.87%. Under a pH of 8.5, 64.4% of the pesticide was released within 120 hours. The CLAP@CS/γ-PGA formulation, after loading, exhibited a significant synergistic insecticidal effect, with bioassay results showing an 82.2% mortality rate of C. suppressalis six days post-treatment. Tests of metabolic genes and enzyme activities showed that CLAP@CS/γ-PGA rendered C. suppressalis more sensitive to insecticides by inhibiting the activities of P450 and by decreasing the expression of CYP9A68. CLAP@CS/γ-PGA also demonstrated favorable transport properties within C. suppressalis and rice plants, and due to the encapsulation by the nanoparticle carrier, it reduced toxicity to zebrafish. In summary, the system we investigated not only meets the needs of pest management but also enhances the utilization of pesticides.

研究领域: 农业科学 · 环境科学 · 纳米技术
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2024 · IF 4.2

Evaluating the toxicity effects of thiamethoxam and its main metabolite clothianidin to earthworms (Eisenia fetida) from the perspective of endogenous metabolites

Zhiyuan Meng,Zixin Yan,Ruixian Yang,Xinyi Wu,Xiuli Zhang,Hui Pan,Xin Bao,Li Liu,Xiaojun Chen

The widespread application of neonicotinoid insecticides (NNIs) has attracted widespread attention to their potential ecotoxicological effects. In this study, we systematically evaluated the toxic effects of thiamethoxam (TMX) and its metabolite clothianidin (CLO) on earthworms ( Eisenia fetida ). Specifically, the antioxidant system responses and endogenous metabolite metabolism responses in earthworms were analyzed in the temporal dimension after 7, 14, 21 and 28 days of exposure to TMX and CLO. The results found that TMX and CLO could inhibit the growth phenotype of earthworms and cause significant changes in antioxidant system related indicators. More importantly, we found that TMX and CLO could cause significant changes in the metabolic profiles of earthworms through NMR-based metabolomics. From the changes in endogenous metabolites, the toxicity effects of TMX on earthworms gradually increases with prolonged exposure time. Differently, the toxicity effects of CLO on earthworms is significantly higher than that of TMX in the early stages of exposure. Meanwhile, these impacts will not weaken with prolonged exposure time. Furthermore, the results of KEGG enrichment pathway analysis indicated that TMX and CLO could significantly interfere with energy homeostasis, redox homeostasis, osmotic regulation, amino acid metabolism and protein synthesis in earthworms. These findings further deepen our understanding of the ecotoxicological effects of NNIs on soil organism.

研究领域: 环境科学 · 毒理学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY · 2025 ·Vol. 95 ·期 3 ·644-653 · IF 0.8

Design, Efficient One-Step Synthesis of Bromo-p-hydroxybenzamides and Herbicidal Activity Evaluation

Wang J.,Zhou Y.,Wu X.,Zhou X.,Sun Y.,Wu W.,Wang X.

Discovering super-efficient herbicides with novel structures is one of the effective ways to solve the increasingly severe weed resistance problem and meet ecological requirements. In this work, a series of novel bromo- p -hydroxybenzamides were designed based on the molecular hybridization strategy, and rapidly synthesized by one-step amidation reaction, and then characterized by 1 H NMR, 13 C NMR and HRMS. The herbicidal activity assay indicated that most of the target compounds exhibited good-to-excellent inhibition effects on seed germination of two model plants. At a concentration of 100 mg/L, the inhibition rate of 3,5-dibromo- N -(4-bromo-3-chlorophenyl)- p -hydroxybenzamide reached up to 98 and 96% on the roots and stalks of the monocotyledonous barnyard grass ( E. crus-galli ), respectively. 3,5-Dibromo- N -(2-bromophenyl)- p -hydroxybenzamide showed excellent inhibitory activity on the roots and stalks of dicotyledonous rape ( B. napus ) at 100 mg/L, with an inhibitory rate of more than 90%. Furthermore, the concentration was reduced to 1 mg/L, the inhibitory rate of 3,5-dibromo- N -(2-bromophenyl)- p -hydroxybenzamide on the roots of B. napus was still as high as 90%. This work provides a novel molecular scaffold for the development and research of new super-efficient herbicides.

研究领域: 农药化学 · 植物生理学
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